cinnamaldehyde profile

3-phenylprop-2-enal : A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

(E)-cinnamaldehyde : The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	637511
CHEMBL ID	293492
CHEBI ID	16731
CHEBI ID	142921
SCHEMBL ID	3441
MeSH ID	M0060175

Synonym
gtpl2423
trans-cinnamic aldehyde
(3e)-3-phenylprop-2-enal
(e)-cinnamaldehyde
(e)-3-phenyl-2-propenal
CHEBI:16731 ,
(e)-cinnamic aldehyde
(e)-3-phenylpropenal
nsc40346
nsc-40346
trans-cinnamaldehyde
(e)-3-phenylprop-2-enal
14371-10-9
cnma
caswell no. 221a
3-phenyl-2-propen-1-al
hefty dog and cat repellent
cinnamic aldehyde (natural)
aldehyd skoricovy [czech]
fema no. 2286
ccris 6222
einecs 203-213-9
hsdb 209
abion ca
epa pesticide chemical code 040506
fema number 2286
beta-phenylcrolein
cinnemaldehyde
ai3-00473
brn 0605737
cinnamyl aldehyde
3-fenylpropenal [czech]
nsc-16935
3-phenyl-2-propenaldehyde
cinnamylaldehyde
nsc16935
nci-c56111
3-phenylacrolein
benzylideneacetaldehyde
wln: vh1u1r
acrolein, 3-phenyl-
3-phenylpropenal
3-phenyl-2-propenal
cinnamaldehyde, (e)-
inchi=1/c9h8o/c10-8-4-7-9-5-2-1-3-6-9/h1-8h/b7-4
(2e)-3-phenylacrylaldehyde
2-propenal, 3-phenyl-, (2e)-
cinnamaldehyde (trans)
NCGC00091512-01
NCGC00091512-02
trans-cinnamylaldehyde
trans-3-phenyl-2-propenal
brn 1071571
ai3-33275
2-propenal, 3-phenyl-, (e)-
ccris 3189
(e)-cinnamaldehyde (incorrect)
cinnamic aldehyde
C00903
cassia aldehyde
2-propenal, 3-phenyl-
phenylacrolein
cinnamal
zimtaldehyde
trans-cinnamaldehyde (incorrect)
CINNAMALDEHYDE ,
3-phenylacrylaldehyde
104-55-2
cinnamaldehyde, natural, >=95%, fg
trans-cinnamaldehyde, >=98%, fcc, fg
trans-cinnamaldehyde, 99%
NCGC00091512-04
trans-cinnamaldehyde, >=99%
cinnamaldehyde (trans), neat
STK397371
(2e)-3-phenylprop-2-enal
MLS002454394
smr000112334
B99DD6C7-1C6D-4FE3-A172-54BFDB987683
cinnamaldehyde, trans-
trans-3-phenylacrylaldehyde
trans-3-phenylacrolein
xc-800
.beta.-phenylacrolein
CHEMBL293492 ,
(e)-3-phenyl-2-propenal(e)-cinnamaldehyde
BMSE010257
bdbm50203065
3-phenylprop-2-enal
CHEBI:142921
AKOS000119171
A801001
NCGC00091512-07
NCGC00091512-06
NCGC00091512-05
cinnamaldehyde [nf]
3-fenylpropenal
2-07-00-00273 (beilstein handbook reference)
ec 203-213-9
unii-sr60a3xg0f
sr60a3xg0f ,
4-07-00-00984 (beilstein handbook reference)
dtxsid6024834 ,
tox21_303271
NCGC00257017-01
cas-14371-10-9
dtxcid504834
tox21_201804
NCGC00259353-01
NCGC00257826-01
dtxcid904835
cas-104-55-2
tox21_200272
(e)-3-phenyl-acrylaldehyde
tox21_111144
HMS2268O08
S3763
AM20060482
cinnamaldehyde [fcc]
trans-cinnamaldehyde (constituent of cinnamomum cassia bark) [dsc]
cinnamaldehyde [hsdb]
cinnamaldehyde [fhfi]
cinnamaldehyde [who-dd]
cinnamaldehyde [usp-rs]
cinnamaldehyde (constituent of cinnamomum verum bark) [dsc]
cinnamal [inci]
cinnamaldehyde [mi]
cinnamaldehyde [ii]
(e)-3-phenyl-propenal
(e)-phenylvinyl aldehyde
EPITOPE ID:150921
trans-cinnamaldehyde; trans-3-phenylacrylaldehyde
SCHEMBL3441
trans cinnamaldehyde
trans cinnamic aldehyde
transcinnamaldehyde
(e)-3-phenylacrylaldehyde
(trans)-cinnamaldehyde
e-cinnamaldehyde
W-205597
(2e)-3-phenyl-2-propenal
cinnamaldehyde, united states pharmacopeia (usp) reference standard
mfcd00007000
trans-cinnamaldehyde, analytical standard
cinnamaldehyde, vetec(tm) reagent grade, 93%
CS-0009609
DB14184
cinnamaldehyde min. 98%, for synthesis
trans-cinnamaldehyde ,(s)
\|a-phenylacrolein
AS-12078
Q204036
A14480
EN300-19160
HMS3885E04
CCG-266119
cinnamaldehyde 100 microg/ml in toluene
D72477
trans-3-phenyl-propenal
HY-N0609
AS-75456
EN300-735819
Z3219847383

Excerpt	Reference	Relevance
"Cinnamaldehyde is an essential oil extracted from the leaves, bark, roots and flowers of cinnamon plants (genus "	( Encapsulation of cinnamaldehyde: an insight on delivery systems and food applications. Harindintwali, JD; Koko, MYF; Li, Y; Muhoza, B; Qi, B; Zhang, S, 2023)	2.69
"Cinnamaldehyde (Cin) is a natural product obtained from cinnamon and is reported to have a potential anti-fungal, anti-oxidant, anti-inflammatory and anticancer effect. "	( Evaluation of prophylactic efficacy of cinnamaldehyde in murine model against Paradendryphiella arenariae mycotoxin tenuazonic acid-induced oxidative stress and organ toxicity. Kumari, A; Singh, K, 2021)	2.33
"Cinnamaldehyde is a natural antimicrobial food preservative. "	( Antibacterial Mechanism of Cinnamaldehyde: Modulation of Biosynthesis of Phosphatidylethanolamine and Phosphatidylglycerol in Huang, Z; Li, E; Li, Q; Liao, S; Pang, D; Wang, E; Wang, W; Zou, Y, 2021)	2.36
"Cinnamaldehyde is an important component of cinnamon and has an effect on blood glucose."	( Effects of cinnamaldehyde on glucose-6-phosphate dehydrogenase activity, some biochemical and hematological parameters in diabetic rats. Çelik, R; Comba, B; Mert, H; Mert, N, 2022)	1.83
"Cinnamaldehyde is a major component of cinnamon bark oil."	( Evaluation of cinnamaldehyde mucoadhesive patches on minor recurrent aphthous stomatitis: a randomized, double-blind, placebo-controlled clinical trial. Malekzadeh Shafaroudi, A; Molania, T; Moosazadeh, M; Rostamkalaei, SS; Saeedi, M; Salehabadi, N; Salehi, M; Valipour, F, 2022)	1.8
"Cinnamaldehyde (CNM) is a cyclic terpene alcohol found as the major compound of essential oils from some plants of the genus Cinnamomum (Lauraceae). "	( Cinnamaldehyde for the Treatment of Microbial Infections: Evidence Obtained from Experimental Models. da Silva, LCN; de Carvalho Galvão, LC; de Holanda, RA; de Oliveira, PV; de Santana do Nascimento, M; de Sousa, TJD; Dos Reis Ferreira, L; Dos Santos, JRA; Silva E Silva Figueiredo, CS; Zagmignan, A, 2023)	3.8
"Cinnamaldehyde (CA) is a bioactive phytochemical isolated from the stem bark of Chinese herbal medicine Cinnamon and has been suggested to possess curative roles against the development of CVDs."	( The Therapeutic Roles of Cinnamaldehyde against Cardiovascular Diseases. Liu, G; Lu, L; Mi, B; Wang, G; Xiong, Y; Zhou, J, 2022)	1.75
"Cinnamaldehyde is a natural product with anti-inflammatory and immune-modulatory properties, known to regulate host responses to bacterial stimuli. "	( Cinnamaldehyde modulates host immunoinflammatory responses in rat ligature-induced periodontitis and peripheral blood mononuclear cell models. Aguiar-da-Silva, LD; Branco-de-Almeida, LS; Cardoso, CRB; de Oliveira, ICV; Duarte-Silva, M; Fernandes, ES; Galvão-Moreira, LV; Lima-Neto, LG; Pereira, CAA; Pereira, DMS; Pinheiro, AJMCR; Vilela, JL, 2023)	3.8
"Cinnamaldehyde (CIN) is an active ingredient of Cinnamomum cassia with immunomodulatory and anti-inflammatory properties."	( Cinnamaldehyde Ameliorates Dextran Sulfate Sodium-Induced Colitis in Mice by Modulating TLR4/NF-κB Signaling Pathway and NLRP3 Inflammasome Activation. Chen, F; Han, Z; Ma, K; Peng, J; Su, X; Tan, X; Wang, C; Wang, T; Wang, Y; Wen, Y, 2023)	3.07
"Cinnamaldehyde (CA) is an active ingredient of Wenyang Tongluo capsule. "	( Cinnamaldehyde Induces the Expression of MicroRNA-1285-5p and MicroRNA-140-5p in Chondrocytes to Ameliorate the Apoptosis and Inflammatory Response. Li, G; Song, Y, 2023)	3.8
"Cinnamaldehyde is an excellent natural antioxidant with high antioxidant activity, but its function in food or human digestive tract under acidic conditions remains to be studied. "	( Cinnamaldehyde Alleviates the Oxidative Stress of Caenorhabditis elegans in the Presence of Lactic Acid. Bai, J; Darwesh, OM; Eweys, AS; Xiao, M; Xiao, X; Zhao, Y, 2023)	3.8
"Cinnamaldehyde (CIN) is a major constituent of the cinnamon and it possesses potent antioxidative activity; however, it is unclear whether CIN is capable of inhibiting the adverse effects of UVB."	( Antioxidant cinnamaldehyde attenuates UVB-induced photoaging. Furue, M; Tanaka, Y; Uchi, H, 2019)	1.61
"Cinnamaldehyde is a predominant constituent and key flavour compound of cinnamon essential oil. "	( Antifungal activity of cinnamaldehyde against Fusarium sambucinum involves inhibition of ergosterol biosynthesis. Bi, Y; Prusky, D; Wang, Y; Wei, J; Xue, H; Zong, Y, 2020)	2.31
"Cinnamaldehyde (CIN) is a promising replacement for chemical synthetic preservatives, which has exhibited effective antimicrobial activities in food applications. "	( The antifungal effects of cinnamaldehyde against Aspergillus niger and its application in bread preservation. Chen, Q; Le, T; Li, J; Sun, Q; Sun, Y; Zhang, L, 2020)	2.3
"Cinnamaldehyde (CA) is a spice compound in cinnamon that enhances the antioxidant defense against reactive oxygen species (ROS) by activating nuclear factor erythroid-related factor 2 (Nrf2), which has been shown to have a cardioprotection effect."	( Cinnamaldehyde Ameliorates Vascular Dysfunction in Diabetic Mice by Activating Nrf2. Liu, S; Wan, J; Wang, D; Wang, P; Yang, Q; Yang, Y; Zhou, P, 2020)	2.72
"Cinnamaldehyde (CA) is a natural compound from Cinnamomum cassia, and its anticancer, antimicrobial and anti‑inflammatory activities have been widely investigated."	( Cinnamaldehyde protects against oxidative stress and inhibits the TNF‑α‑induced inflammatory response in human umbilical vein endothelial cells. Ahn, SG; Kim, NY; Kim, SA; Trinh, NT, 2020)	2.72
"Cinnamaldehyde (CA) is an essential component of cinnamon (Cinnamomum cassia Presland), which is often used as a flavoring condiment in beverages, pastries, perfumes, etc. "	( Cinnamaldehyde suppresses NLRP3 derived IL-1β via activating succinate/HIF-1 in rheumatoid arthritis rats. Chen, H; Fu, Y; Huang, JH; Liu, P; Pan, T; Wang, F; Wang, J; Wen, W; Xu, S, 2020)	3.44
"Cinnamaldehyde, which is a major constituent in the essential oil of cinnamon, has been previously reported to reduce xanthine oxidase activity, in addition to its anti-inflammatory, anti-oxidant, and anti-proliferative activities."	( The modulatory effects of cinnamaldehyde on uric acid level and IL-6/JAK1/STAT3 signaling as a promising therapeutic strategy against benign prostatic hyperplasia. Abdel-Rahman, HM; Abo-Youssef, AM; Afify, H; Allam, S; Azouz, AA, 2020)	1.58
"Cinnamaldehyde (CA) is an essential component of cinnamon that has been shown to exhibit anti-tumor effects through growth inhibition and induction of apoptosis in cancer cells. "	( Cinnamaldehyde induces endogenous apoptosis of the prostate cancer-associated fibroblasts via interfering the Glutathione-associated mitochondria function. Gu, Z; Han, L; Li, J; Lou, X; Ma, J; Mei, J; Qin, Z; Tao, N; Wang, F; Yao, X; Zeng, Y; Zhang, Z, 2020)	3.44
"Cinnamaldehyde (CA) is a major active compound from cinnamon, is known as its anti-inflammatory and antibacterial."	( Suppression of Th17 cell differentiation via sphingosine-1-phosphate receptor 2 by cinnamaldehyde can ameliorate ulcerative colitis. Chen, L; Lu, ZJ; Qu, SL; Wang, XY; Wen, XS; Yang, YF; Zuo, JP, 2021)	1.57
"Cinnamaldehyde (CA) is a food additive that has potential use in controlling postharvest disease of fruits and vegetables."	( Effect of applying cinnamaldehyde incorporated in wax on green mould decay in citrus fruits. Duan, X; OuYang, Q; Tao, N, 2018)	1.53
"Cinnamaldehyde is a main ingredient of cinnamon oils from the stem bark of Cinnamomum cassia, which has been widely used in food and traditional herbal medicine in Asia. "	( Protective effect of cinnamaldehyde against glutamate-induced oxidative stress and apoptosis in PC12 cells. Liu, RH; Lv, C; Yuan, X; Zeng, HW; Zhang, WD, 2017)	2.22
"Cinnamaldehyde (CA) is a food compound that has previously been observed to be protective against obesity and hyperglycemia in mouse models. "	( Cinnamaldehyde induces fat cell-autonomous thermogenesis and metabolic reprogramming. Emont, MP; Jiang, J; Jun, H; Kim, DI; Liao, J; Qiao, X; Wu, J, 2017)	3.34
"Cinnamaldehyde is a major constituent of cinnamon essential oils produced by aromatic cinnamon plants. "	( Chemistry, Antimicrobial Mechanisms, and Antibiotic Activities of Cinnamaldehyde against Pathogenic Bacteria in Animal Feeds and Human Foods. Friedman, M, 2017)	2.13
"Cinnamaldehyde is a flavor isolated from the bark of Cinnamomum cassia Presl and exerts anti-inflammation effects in various diseases. "	( Cinnamaldehyde attenuates atherosclerosis via targeting the IκB/NF-κB signaling pathway in high fat diet-induced ApoE Li, W; Liu, F; Niu, X; Zang, L; Zhao, J; Zhi, W, 2019)	3.4
"Cinnamaldehyde is an active component of some plant essential oils, which has broad antibacterial activity. "	( Modulation effect of core-wall ratio on the stability and antibacterial activity of cinnamaldehyde liposomes. Chen, W; Cheng, F; Swing, CJ; Xia, S; Zhang, X, 2019)	2.18
"Cinnamaldehyde is an active monomer isolated from the stem bark of Cinnamomum cassia, a traditional oriental medicinal herb, which is known to possess marked antitumor effects in vitro and in vivo. "	( Cinnamaldehyde/chemotherapeutic agents interaction and drug-metabolizing genes in colorectal cancer. Liu, SL; Qi, MH; Yu, C; Zou, X, 2014)	3.29
"Cinnamaldehyde is a major and a bioactive compound isolated from the leaves of Cinnamomum osmophloeum kaneh. "	( Cinnamaldehyde and nitric oxide attenuate advanced glycation end products-induced the Jak/STAT signaling in human renal tubular cells. Chuang, LY; Guh, JY; Huang, JS; Hwang, JY; Lee, YH, 2015)	3.3
"Cinnamaldehyde (CA) is a key flavor compound in cinnamon essential oil that can enhance the antioxidant defense against reactive oxygen species (ROS) by activating NF-E2-related factor 2 (Nrf2), which has been shown to have a cardiovascular protective effect, but its role in endothelial dysfunction induced by high glucose is unknown."	( Cinnamaldehyde prevents endothelial dysfunction induced by high glucose by activating Nrf2. Hao, X; Hu, Y; Li, B; Liang, D; Pu, C; Wang, F; Wang, P; Wang, Q; Zhou, P, 2015)	2.58
"Cinnamaldehyde is a diterpene with a wide range of anti-inflammatory effects thus may be advantageous in the treatment of cerebral ischaemia."	( Cinnamaldehyde inhibits inflammation and brain damage in a mouse model of permanent cerebral ischaemia. Chen, R; Dong, L; He, T; Li, L; Li, Y; Wen, Y; Zhang, C; Zhang, X; Zhang, Y; Zhao, J; Zheng, X; Zhu, X, 2015)	2.58
"Cinnamaldehyde (CIN) is a promising natural preservative and generally recognized as safe for commodities as well as consumers. "	( Cinnamaldehyde inhibits fungal growth and aflatoxin B1 biosynthesis by modulating the oxidative stress response of Aspergillus flavus. Liu, Y; Lu, Z; Shang, B; Sun, Q; Wang, L, 2016)	3.32
"Cinnamaldehyde (CA) is a bioactive compound isolated from the stem bark of Cinnamomum cassia, that has been identified as an antiproliferative substance with pro-apoptotic effects on various cancer cell lines in vitro. "	( Cinnamaldehyde affects the biological behavior of human colorectal cancer cells and induces apoptosis via inhibition of the PI3K/Akt signaling pathway. Chen, Y; Li, J; Liu, S; Teng, Y; Wang, R; Wang, Z; Xi, S; Xu, S; Zhang, Y; Zou, X, 2016)	3.32
"Cinnamaldehyde analogues are a class of chemical substances originated from derivatization of cinnamaldehyde, and are structurally characterized by the presence of cinnamoyl moiety. "	( Cinnamaldehyde Analogues as Potential Therapeutic Agents. Chen, BJ; Fu, CS; Li, GH; Lou, HX; Ren, DM; Shen, T; Wang, XN, 2017)	3.34
"Cinnamaldehyde is a major bioactive compound isolated from the leaves of Cinnamomum osmophloeum. "	( Cinnamaldehyde attenuates pressure overload-induced cardiac hypertrophy. Bian, ZY; Hu, ZF; Liu, Y; Tang, QZ; Wu, QQ; Yang, L, 2015)	3.3
"Cinnamaldehyde is a natural essential oil suggested to possess anti-bacterial and anti-inflammatory properties; and to activate transient receptor potential ankyrin 1 (TRPA1) channels expressed on neuronal and non-neuronal cells. "	( Cinnamaldehyde modulates LPS-induced systemic inflammatory response syndrome through TRPA1-dependent and independent mechanisms. Costa, SKP; da Costa, R; Fernandes, ES; Ferro, TAF; Grisotto, MAG; Mendes, SJF; Monteiro-Neto, V; Mouchrek, AQS; Nascimento, JLM; Pereira, DMS; Pereira, ICP; Pinheiro, AJMCR; Silva, BLR; Sousa, FIAB, 2016)	3.32
"Cinnamaldehyde (CIN) is a natural antibacterial ingredient found in the bark and leaves of cinnamon trees."	( An in vitro investigation of the inhibitory mechanism of β-galactosidase by cinnamaldehyde alone and in combination with carvacrol and thymol. Gong, DM; Huang, YB; Wang, LH; Wang, MS; Zeng, XA, 2017)	1.41
"Cinnamaldehyde is a major and a bioactive compound isolated from the leaves of Cinnamomum osmophloeum kaneh. "	( Cinnamaldehyde impairs high glucose-induced hypertrophy in renal interstitial fibroblasts. Chang, WT; Chao, LK; Huang, JS; Shih, YW, 2010)	3.25
"Cinnamaldehyde (1) is a pharmacologically active ingredient isolated from cassia twig (Ramulus Cinnamomi), which is commonly used in herbal remedies to treat fever-related diseases. "	( Cinnamaldehyde up-regulates the mRNA expression level of TRPV1 receptor potential ion channel protein and its function in primary rat DRG neurons in vitro. Du, XL; Guo, JY; Guo, SY; Huo, HR; Jiang, TL; Li, LF; Lin, N; Liu, HB; Sui, F; Yang, N; Zhang, CB; Zhao, BS, 2010)	3.25
"Cinnamaldehyde is a naturally occurring α,β-unsaturated aldehyde. "	( Functional properties of bioplastics made from wheat gliadins modified with cinnamaldehyde. Balaguer, MP; Gavara, R; Gómez-Estaca, J; Hernandez-Munoz, P, 2011)	2.04
"Cinnamaldehyde is a well-established natural antimicrobial compound. "	( The antimicrobial activities of the cinnamaldehyde adducts with amino acids. Jiang, H; Wei, QY; Xiong, JJ; Zhang, C, 2011)	2.09
"Cinnamaldehyde is a natural antimicrobial that has been found to be effective against many food-borne pathogens, including Escherichia coli O157:H7. "	( Examination of the genome-wide transcriptional response of Escherichia coli O157:H7 to cinnamaldehyde exposure. Hernandez-Doria, JD; Holley, RA; Visvalingam, J, 2013)	2.06
"Cinnamaldehyde is an active compound isolated from the stem bark of Cinnamomum cassia, a traditional oriental medicinal herb, which has been shown to inhibit tumor cell proliferation. "	( Cinnamaldehyde induces apoptosis by ROS-mediated mitochondrial permeability transition in human promyelocytic leukemia HL-60 cells. Cho, KS; Choi, JW; Ha, J; Jung, HJ; Ka, H; Lee, KT; Park, HJ, 2003)	3.2
"Cinnamaldehyde is a principle compound isolated from Guizhi-Tang, which is a famous traditional Chinese medical formula used to treat influenza, common cold and other pyretic conditions. "	( Cinnamaldehyde reduces IL-1beta-induced cyclooxygenase-2 activity in rat cerebral microvascular endothelial cells. Guo, JY; Guo, SY; Huo, HR; Jiang, TL; Li, LF; Liu, HB; Ma, YY; Zhao, BS, 2006)	3.22
"Cinnamaldehyde is a natural product from spices that inhibits cell separation in Bacillus cereus. "	( Inhibition of bacterial cell division protein FtsZ by cinnamaldehyde. Bhunia, A; Dasgupta, D; Domadia, P; Sivaraman, J; Swarup, S, 2007)	2.03
"Cinnamaldehyde is a principle compound isolated from Guizhi-Tang (GZT), which is a famous traditional Chinese medical formula used to treat influenza, common cold and other pyretic conditions. "	( Effects of cinnamaldehyde on PGE2 release and TRPV4 expression in mouse cerebral microvascular endothelial cells induced by interleukin-1beta. Guo, SY; Huo, HR; Jiang, TL; Li, CH; Li, LF; Ma, YY; Sui, F; Zhao, BS, 2008)	2.18
"Cinnamaldehyde is a more potent skin sensitizer than cinnamic alcohol."	( Human skin absorption and metabolism of the contact allergens, cinnamic aldehyde, and cinnamic alcohol. Elahi, EN; Hotchkiss, SA; Moore, CA; Smart, AT; Smith, CK, 2000)	1.03

Excerpt	Reference	Relevance
"Cinnamaldehyde has a potent anti-oxidant property."	( Behavioral, histopathological, and biochemical evaluations on the effects of cinnamaldehyde, naloxone, and their combination in morphine-induced cerebellar toxicity. Farshid, AA; Imani, M; Mahmoudi, S; Noroozinia, F; Tamaddonfard, E, 2022)	1.67
"Cinnamaldehyde has a potential to replace the synthetic antimicrobial and/or antibiofilm agent as well as has a positive influence on consumer concern for the food safety issues of the poultry industries."	( Investigating the antimicrobial and antibiofilm effects of cinnamaldehyde against Campylobacter spp. using cell surface characteristics. Lee, NK; Paik, HD; Song, YJ; Yu, HH; Yu, HS, 2020)	1.52
"Cinnamaldehyde (CM) has a molecular structure with the main reaction center of an aromatic ring which the bioactivity can be modified as an anticancer agent by substituting the groups in the ortho (o), meta (m), and para (p) position. "	( Molecular Docking Compounds of Cinnamaldehyde Derivatives as Anticancer Agents. Azzahra, VO; Murlistyarini, S; Sucahyo, A; Suratmo, S; Warsito, W, 2021)	2.35
"Cinnamaldehyde (CA) has a protective effect in endotoxin poisoning of mice, but there is no direct evidence for the protective effect of CA through inhibition of NLRP3 inflammasome activation in endotoxin poisoning of mice."	( Inhibition of NLRP3 inflammasome: a new protective mechanism of cinnamaldehyde in endotoxin poisoning of mice. Sang, W; Wang, D; Wang, F; Wen, T; Xu, F; Zeng, N, 2017)	2.14
"Cinnamaldehyde has been shown to exhibit multiple tumour-suppressing activities, but its role in human osteosarcoma is not yet completely defined."	( Cinnamaldehyde decreases the invasion and u-PA expression of osteosarcoma by down-regulating the FAK signalling pathway. Chen, PN; Chu, SC; Hsieh, YS; Hsu, LS; Lai, YA; Lin, CY, 2022)	2.89
"Cinnamaldehyde (Ci) has many biological properties that include anti-inflammatory and antioxidant activities."	( Cinnamaldehyde Mitigates Atherosclerosis Induced by High-Fat Diet Abdel-Reheim, ES; Ali, TM; Elesawy, BH; Ismail, BS; Mahmoud, B; Soliman, HA; Zaky, MY, 2022)	2.89
"Cinnamaldehyde has been successfully used for the short-term disinfection of dentures; however, its long-term effects on the surface and color properties of denture base materials remain unknown."	( Effects of long-term cinnamaldehyde immersion on the surface roughness and color of heat-polymerized denture base resin. Batista, AUD; Campos, DES; Carreiro, ADFP; da Nóbrega Alves, D; de Castro, RD; Macêdo, LO, 2022)	2.48
"Cinnamaldehyde (CA) has demonstrated anti-inflammatory, anti-tumor and anti-cancer activities; Its antimicrobial and antibiofilm actions against Shigella flexneri, on the other hand, have not been investigated. "	( Effects of cinnamaldehyde against planktonic bacteria and biofilm formation of Shigella flexneri. Chang, Y; Cheng, X; Guo, D; Shi, C; Su, R; Tan, Y; Wang, M; Wang, R; Xia, X; Zhan, X, 2022)	2.55
"Cinnamaldehyde has been widely applied in various fields due to its special flavor and various pharmacological activities, such as antioxidant, anti-inflammatory and antibacterial properties. "	( Enrichment of cinnamaldehyde from Cinnamomum cassia by electroosmotic coupled particle-assisted solvent flotation. Li, N; Wei, Y; Yan, C; Zhang, Y, 2023)	2.71
"Cinnamaldehyde has a potent anti-oxidant property."	( Behavioral, histopathological, and biochemical evaluations on the effects of cinnamaldehyde, naloxone, and their combination in morphine-induced cerebellar toxicity. Farshid, AA; Imani, M; Mahmoudi, S; Noroozinia, F; Tamaddonfard, E, 2022)	1.67
"Cinnamaldehyde has a potential to replace the synthetic antimicrobial and/or antibiofilm agent as well as has a positive influence on consumer concern for the food safety issues of the poultry industries."	( Investigating the antimicrobial and antibiofilm effects of cinnamaldehyde against Campylobacter spp. using cell surface characteristics. Lee, NK; Paik, HD; Song, YJ; Yu, HH; Yu, HS, 2020)	1.52
"Cinnamaldehyde has previously been shown to activate sensory neurons via the selective gating of TRPA1."	( Differential sensitivity of cinnamaldehyde-evoked calcium fluxes to ruthenium red in guinea pig and mouse trigeminal sensory neurons. Bahia, PK; Taylor-Clark, TE, 2021)	1.64
"Cinnamaldehyde (CIN) has been shown to inhibit the proliferation and inflammatory response of primary and immortalized immune cells."	( Cinnamaldehyde inhibits psoriasis‑like inflammation by suppressing proliferation and inflammatory response of keratinocytes via inhibition of NF‑κB and JNK signaling pathways. Ding, Z; Liu, J; Lv, M; Qian, H; Wu, L, 2021)	2.79
"Cinnamaldehyde (CM) has a molecular structure with the main reaction center of an aromatic ring which the bioactivity can be modified as an anticancer agent by substituting the groups in the ortho (o), meta (m), and para (p) position. "	( Molecular Docking Compounds of Cinnamaldehyde Derivatives as Anticancer Agents. Azzahra, VO; Murlistyarini, S; Sucahyo, A; Suratmo, S; Warsito, W, 2021)	2.35
"Cinnamaldehyde (CA) has been reported to exhibit anti-diabetic and anti-inflammatory properties."	( Cinnamaldehyde Ameliorates Diet-Induced Obesity in Mice by Inducing Browning of White Adipose Tissue. Fang, X; Gao, S; Liu, H; Ma, R; Ma, Y; Mo, F; Mu, Q; Wang, L; Wu, R; Yu, N; Zhang, D; Zhao, D; Zhu, R; Zuo, J, 2017)	2.62
"Cinnamaldehyde (CA) has a protective effect in endotoxin poisoning of mice, but there is no direct evidence for the protective effect of CA through inhibition of NLRP3 inflammasome activation in endotoxin poisoning of mice."	( Inhibition of NLRP3 inflammasome: a new protective mechanism of cinnamaldehyde in endotoxin poisoning of mice. Sang, W; Wang, D; Wang, F; Wen, T; Xu, F; Zeng, N, 2017)	2.14
"Cinnamaldehyde (CA) has various functional properties, such as anti-cancer, anti-microbial, anti-inflammatory, and anti-oxidant activities. "	( Cinnamaldehyde protects human dental pulp cells against oxidative stress through the Nrf2/HO-1-dependent antioxidant response. Ahn, SG; Kim, NY; Kim, SA, 2017)	3.34
"Cinnamaldehyde (CIN) has been shown to exert chemopreventive activity against several types of human cancer cells. "	( Cinnamaldehyde-induced apoptosis in human hepatoma PLC/PRF/5 cells involves the mitochondrial death pathway and is sensitive to inhibition by cyclosporin A and z-VAD-fmk. Chang, SP; Chen, JL; Lin, CC; Lin, LT; Tai, CJ; Wu, SJ, 2013)	3.28
"Cinnamaldehyde (CA) has been widely applied in medicine and food preservation. "	( Cinnamaldehyde promotes root branching by regulating endogenous hydrogen sulfide. Chen, J; Li, YQ; Qi, ZQ; Shi, Z; Xue, YF; Zhang, M, 2016)	3.32
"Cinnamaldehyde has been reported to inhibit bacteria, yeasts, and filamentous molds via the inhibition of ATPases, cell wall biosynthesis, and alteration of membrane structure and integrity."	( Cinnamaldehyde and its derivatives, a novel class of antifungal agents. Ali, I; Behbehani, JM; Hun, LT; Irshad, M; Karched, M; Raja, V; Shreaz, S; Siddiqi, WA; Wani, WA, 2016)	2.6
"Cinnamaldehyde has two independent biological activities; namely, an inhibitory action on AHR activation and an antioxidant effect mediated by NRF2/HO1 signaling. "	( Inhibition of aryl hydrocarbon receptor signaling and induction of NRF2-mediated antioxidant activity by cinnamaldehyde in human keratinocytes. Furue, M; Mitoma, C; Morino-Koga, S; Uchi, H; Yasumatsu, M, 2017)	2.11
"Cinnamaldehyde (CA) has been known to exhibit anti-inflammatory and anticancer effects. "	( Regulatory effect of cinnamaldehyde on monocyte/macrophage-mediated inflammatory responses. Cho, JY; Kim, BH; Lee, J; Lee, JY; Lee, YG, 2010)	2.12
"Cinnamaldehyde has previously been shown to inhibit QS-regulated virulence by decreasing the DNA-binding ability of the QS response regulator LuxR."	( Structure-activity relationship of cinnamaldehyde analogs as inhibitors of AI-2 based quorum sensing and their effect on virulence of Vibrio spp. Brackman, G; Celen, S; Coenye, T; Cos, P; Hillaert, U; Maes, L; Nelis, HJ; Van Calenbergh, S, 2011)	1.37
"Cinnamaldehyde has been demonstrated to stimulate glutathione production and the expression of phase II detoxifying enzymes in HepG2 cells. "	( Cinnamaldehyde enhances Nrf2 nuclear translocation to upregulate phase II detoxifying enzyme expression in HepG2 cells. Chuang, SM; Chung, YL; Huang, TC; Wu, ML, 2011)	3.25
"Cinnamaldehyde and camphor have been reported to be the major components of volatile oils from stem bark and root bark, respectively."	( Chemistry, biogenesis, and biological activities of Cinnamomum zeylanicum. Jayaprakasha, GK; Rao, LJ, 2011)	1.09
"Cinnamaldehydes have been shown to have inhibitory effects on farnesyl protein transferase (FPTase; EC 2.5.1.29) in vitro, angiogenesis, cell-cell adhesion, and tumor cell growth and to be immunomodulators. "	( Antitumor effect of the cinnamaldehyde derivative CB403 through the arrest of cell cycle progression in the G2/M phase. Ha, JH; Han, DC; Han, MY; Jeong, HW; Kim, HC; Kim, HM; Kwon, BM; Lee, CW; Lim, JS; Son, KH, 2003)	2.07
"Cinnamaldehyde has been used as a filtering agent and a rubber reinforcing agent and is used as a brightener in electroplating processes, as an animal repellent, as an insect attractant, and as an antifungal agent."	( NTP toxicology and carcinogenesis studies of trans-cinnamaldehyde (CAS No. 14371-10-9) in F344/N rats and B6C3F1 mice (feed studies). , 2004)	1.3
"1. Cinnamaldehyde has been shown to be effective in inducing cell apoptosis in a number of human cancer cells. "	( Effects of vitamin E on the cinnamaldehyde-induced apoptotic mechanism in human PLC/PRF/5 cells. Lin, CC; Ng, LT; Wu, SJ, 2004)	1.24
"Cinnamaldehyde (Cin) has been shown to be effective in inducing apoptotic cell death in a number of human cancer cells. "	( Cinnamaldehyde-induced apoptosis in human PLC/PRF/5 cells through activation of the proapoptotic Bcl-2 family proteins and MAPK pathway. Lin, CC; Ng, LT; Wu, SJ, 2005)	3.21
"Cinnamaldehyde (CA) has been reported to inhibit in vitro aggregation in human and rabbit platelets; however, little is known about the antithrombotic activities of CA in vivo."	( Cinnamaldehyde reduction of platelet aggregation and thrombosis in rodents. Huang, J; Luo, X; Shi, X; Wang, S; Xie, Y, 2007)	3.23

Excerpt	Reference	Relevance
"Cinnamaldehyde can suppress CAF T-cell inhibition."	( Cinnamaldehyde Treatment of Prostate Cancer-Associated Fibroblasts Prevents Their Inhibitory Effect on T Cells Through Toll-Like Receptor 4. Hu, M; Ma, F; Ma, J; Mei, J; Qin, Z; Tao, N; Wang, Y; Xu, Y; Xue, R, 2020)	2.72
"Cinnamaldehyde could inhibit invasive capabilities of human breast cancer cell line MDA-MB-435S. "	( [Inhibitory effect of cinnamaldehyde on invasion capacities of human breast cancer cell line MDA-MB-435S and its relation with regulating the expression of miR-27a]. Sun, QM; Wang, G; Wang, RP; Wu, J; Zou, X, 2014)	2.16
"Cinnamaldehyde and nicotine activate the transient receptor potential subtype A1 (TRPA1) channel, which may cause burning sensations. "	( Interaction between intra-oral cinnamaldehyde and nicotine assessed by psychophysical and physiological responses. Andersen, MV; Arendt-Nielsen, L; Boudreau, SA; Jensen, TK; Nielsen, KA, 2016)	2.16
"Cinnamaldehyde did not inhibit the activation of NFkappaB or IRF3 induced by MyD88-dependent (MyD88, IKKbeta) or TRIF-dependent (TRIF, TBK1) downstream signaling components."	( Cinnamaldehyde suppresses toll-like receptor 4 activation mediated through the inhibition of receptor oligomerization. Choi, YJ; Hwang, DH; Lee, JK; Lee, JY; Miyake, K; Saitoh, SI; Youn, HS, 2008)	2.51
"cinnamaldehyde, an exceeding increase in this parameter was obtained during the later period of time course."	( Pharmacological studies on Chinese cinnamon. V. Catecholamine releasing effect of cinnamaldehyde in dogs. Harada, M; Hirayama, Y; Yamazaki, R, 1982)	1.21

Excerpt	Reference	Relevance
"Cinnamaldehyde or curcumin treatment increased Akt2 phosphorylation at multiple sites including T450 and Y475, but had no effect on Akt2 phosphorylation at S474, which is critical for Akt2 activation."	( Cinnamaldehyde and Curcumin Prime Akt2 for Insulin-Stimulated Activation. Le, TT; Urasaki, Y, 2022)	2.89
"Cinnamaldehyde treatment reduced periodontal bone loss, and downregulated key inflammatory mediators and human PBMC responses, pointing to novel potential therapeutic effects of this compound."	( Cinnamaldehyde modulates host immunoinflammatory responses in rat ligature-induced periodontitis and peripheral blood mononuclear cell models. Aguiar-da-Silva, LD; Branco-de-Almeida, LS; Cardoso, CRB; de Oliveira, ICV; Duarte-Silva, M; Fernandes, ES; Galvão-Moreira, LV; Lima-Neto, LG; Pereira, CAA; Pereira, DMS; Pinheiro, AJMCR; Vilela, JL, 2023)	3.07
"Cinnamaldehyde-treated adolescent rats showed less weight gain (P = 0.041), improved OGTT (P = 0.004), increased expression of phosphorylated IRS-1 (P = 0.015), and a trend to increase phosphorylated IRS-1 (P = 0.063) in the liver of adolescent rats in the basal state. "	( Cinnamaldehyde supplementation acts as an insulin mimetic compound improving glucose metabolism during adolescence, but not during adulthood, in healthy male rats. Bento-Bernardes, T; Boechat, SK; Gaique, TG; Medeiros, RF; Neto, JGO; Oliveira, KJ; Pazos-Moura, CC, 2023)	3.8
"Cinnamaldehyde-treated microcultures showed impaired cellular development, with an expression of rare pseudo-hyphae and absence of chlamydoconidia."	( Docking Prediction, Antifungal Activity, Anti-Biofilm Effects on Abílio, GMF; Andrade, PN; Castro, RD; da Nóbrega Alves, D; Guerra, FQS; Lazarini, JG; Monteiro, AFM; Rosalen, PL; Scotti, L; Scotti, MT, 2020)	1.28
"Cinnamaldehyde treatment reduced the number of attached cells in polypropylene, reflected by colony count and scanning electron microscopy."	( Cinnamaldehyde induces changes in the protein profile of Salmonella Typhimurium biofilm. Cardoso, RF; Coelho Trevisan, DA; de Abreu Filho, BA; de Souza, EM; Dos Santos, AR; Estivalet Svidzinski, TI; Graton Mikcha, JM; Junior, MM; Kukolj, C; Ribeiro, AB; Silva, AF; Zanetti Campanerut-Sá, PA, 2018)	2.64
"Cinnamaldehyde treatment significantly decreased inflammatory cytokine (TNF-α, IL-6, NO and MCP-1) overproduction and the serum lipid level."	( Cinnamaldehyde attenuates atherosclerosis via targeting the IκB/NF-κB signaling pathway in high fat diet-induced ApoE Li, W; Liu, F; Niu, X; Zang, L; Zhao, J; Zhi, W, 2019)	2.68
"Cinnamaldehyde treatment of gliadin films provided a means of decreasing their solubility, increasing their molecular weight profile, and reducing their overall migration into food simulants as a consequence of the high degree of polymerization achieved. "	( Retention and release of cinnamaldehyde from wheat protein matrices. Balaguer, MP; Borne, M; Chalier, P; Gavara, R; Gontard, N; Hernandez-Munoz, P; Morel, MH; Peyron, S, 2013)	2.14
"Cinnamaldehyde treatment induced the generation of peroxynitrite that was blocked by the peroxynitrite scavenger FeTPPS and shown to be dependent on TRPA1, as reflected by an increase in protein tyrosine nitration in the skin of WT, but not in TRPA1 KO mice."	( TRPA1 activation leads to neurogenic vasodilatation: involvement of reactive oxygen nitrogen species in addition to CGRP and NO. Abdul-Kader, N; Aubdool, AA; Bevan, S; Brain, SD; Fernandes, ES; Heads, R; Kodji, X, 2016)	1.16
"Cinnamaldehyde treatment inhibited the browning of cut lettuce during cold storage. "	( Cinnamaldehyde inhibits enzymatic browning of cut lettuce by repressing the induction of phenylalanine ammonia-lyase without promotion of microbial growth. Hosaka, H; Murata, M; Okumura, S; Shimamura, Y; Takamiya, R; Tanaka, E, 2011)	3.25
"Cinnamaldehyde treatment of E."	( Disruption of Escherichia coli, Listeria monocytogenes and Lactobacillus sakei cellular membranes by plant oil aromatics. Gill, AO; Holley, RA, 2006)	1.06
"Treatment with cinnamaldehyde was effective in providing neuroprotection and attenuating cerebral vasospasm after subarachnoid hemorrhage in rabbits."	( The effects of Cinnamaldehyde on early brain injury and cerebral vasospasm following experimental subarachnoid hemorrhage in rabbits. Arıkök, AT; Bozkurt, H; Çelikoğlu, E; Gürer, B; Karakoç, A; Kertmen, H; Kuru Bektaşoğlu, P; Öztürk, ÖÇ, 2019)	1.21
"Treatment with cinnamaldehyde led to inhibition of cell viability, proliferation and induced apoptosis in a dose-dependent manner in primary and immortalized immune cells."	( Immune suppressive effect of cinnamaldehyde due to inhibition of proliferation and induction of apoptosis in immune cells: implications in cancer. Diaz-Perales, A; Fuchs, HC; Gomez-Casado, C; Jensen-Jarolim, E; Kinaciyan, T; Moskovskich, A; Oida, K; Roth-Walter, F; Singer, J, 2014)	1.03
"Treatment with cinnamaldehyde not only attenuated caspase-3 activation and the caspase cleavage cascade in DRG neurons, but also lowered the elevated IL-6, TNF-α, cyclo-oxygenase and inducible nitric oxide synthase levels, indicating a reduction in inflammatory damage."	( Anti-oxidative and anti-inflammatory effects of cinnamaldehyde on protecting high glucose-induced damage in cultured dorsal root ganglion neurons of rats. Liang, XC; Liu, D; Liu, W; Shi, Y; Sun, Q; Yang, D; Zhang, H, 2016)	1.03
"Pretreatment of cinnamaldehyde with thiol-containing compounds, such as β-mercaptoethanol or cysteine, blocked the inhibitory activity of cinnamaldehyde."	( Effects of cinnamaldehyde on the glucose transport activity of GLUT1. Bushhouse, KT; Cok, A; Louters, LL; Opejin, A; Plaisier, C; Salie, MJ; Scott, J, 2011)	1.09
"Treatment with cinnamaldehyde could improve the sensory properties and extend the shelf life of Pacific white shrimp to 8 days. "	( Effect of cinnamaldehyde on melanosis and spoilage of Pacific white shrimp (Litopenaeus vannamei) during storage. Chen, H; Fang, X; Gao, H; Mao, J; Mu, H, 2012)	1.13
"When treated with cinnamaldehyde for 10 weeks, hepatic tumor development was delayed with 2'-benzoyloxycinnamaldehyde (BCA) compared with control hepatocellular carcinoma formation."	( Delayed occurrence of H-ras12V-induced hepatocellular carcinoma with long-term treatment with cinnamaldehydes. Kim, HC; Kim, HM; Kim, JM; Kwon, BM; Lee, JH; Lee, MR; Moon, EY; Wang, AG; Yu, DY, 2006)	0.88

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" The related aldehyde, alcohol and esters are all more toxic than cinnamic acid."	( The occurrence, metabolism and toxicity of cinnamic acid and related compounds. Hoskins, JA, 1984)	0.27
" These results demonstrate that microencapsulation in feed can present a useful alternative to gavage dosing for repeated-dose or prolonged-exposure studies, in that (1) the toxic effects of CNMA were similar after gavage dosing and after administration in microencapsulated form in feed, (2) ingestion of chemical in the feed more closely approximates human exposures, and (3) microencapsulation allows the delivery of higher net doses of chemical, while avoiding the acutely toxic effects of a bolus dose."	( Comparison of the toxicity of cinnamaldehyde when administered by microencapsulation in feed or by corn oil gavage. Dieter, MP; Hébert, CD; Yuan, J, 1994)	0.58
" In conclusion, the considered in vitro cytotoxicity assays have shown to be sensitive enough to highlight a variety of toxic effects at the cellular level, which can be rather different between chemically closely related compounds, such as isomers."	( Toxicity of selected plant volatiles in microbial and mammalian short-term assays. Alakomi, HL; Bonsi, P; Moezelaar, R; Stammati, A; von Wright, A; Zucco, F, 1999)	0.3
" Based on 48-h LD50 values, the toxicity of allyl cinnmate (0."	( Toxicity of cassia and cinnamon oil compounds and cinnamaldehyde-related compounds to Sitophilus oryzae (Coleoptera: Curculionidae). Ahn, YJ; Choi, DR; Kim, JR; Lee, EJ, 2008)	0.6
" Based on 24-h LC50 values, binary mixtures of Bti and CA, AN, or EU were significantly more toxic against Ae."	( Enhanced toxicity of binary mixtures of Bacillus thuringiensis subsp. israelensis and three essential oil major constituents to wild Anopheles sinensis (Diptera: Culicidae) and Aedes albopictus (Diptera: Culicidae). Ahn, YJ; Chang, KS; Shin, EH; Yoo, DH, 2014)	0.4
" At LC50, CINA was the most toxic (0."	( In vitro safety assessment of food ingredients in canine renal proximal tubule cells. Jeffery, B; Koči, J; Monteiro-Riviere, NA; Riviere, JE, 2015)	0.42
" The LD50 values of CA and SME-CA in mice were 74."	( Cinnamaldehyde in a Novel Intravenous Submicrometer Emulsion: Pharmacokinetics, Tissue Distribution, Antitumor Efficacy, and Toxicity. Cao, W; Wang, S; Xie, Y; Yang, Q; Yuan, J; Zhao, H, 2015)	1.86
"Aflatoxins (AF) are toxic metabolites produced by molds, Aspergillus flavus and Aspergillus parasiticus, which frequently contaminate poultry feed ingredients."	( Phytochemicals reduce aflatoxin-induced toxicity in chicken embryos. Chen, CH; Darre, MJ; Donoghue, AM; Donoghue, DJ; Venkitanarayanan, K; Yin, HB, 2017)	0.46
" Several studies have suggested opioid antagonist and antioxidant therapy for reducing adverse effects of morphine."	( Behavioral, histopathological, and biochemical evaluations on the effects of cinnamaldehyde, naloxone, and their combination in morphine-induced cerebellar toxicity. Farshid, AA; Imani, M; Mahmoudi, S; Noroozinia, F; Tamaddonfard, E, 2022)	0.95
" In the final step, samples and single-aroma standards were tested for their toxicity to HUVEC/Tert2 cells, where some single-flavoring chemicals such as cinnamic aldehyde revealed significant toxic effects."	( Quantification of selected aroma compounds in e-cigarette products and toxicity evaluation in HUVEC/Tert2 cells. Bonn, G; Gstir, R; Noël, JC; Rainer, D; Rainer, M, 2020)	0.56
"Cinnamaldehyde was effective and safe in treating immunosuppressed BALB/c mice with invasive pulmonary candidiasis."	( Effect and Safety of Cinnamaldehyde on Immunosuppressed Mice with Invasive Pulmonary Candidiasis. Deng, JH; Li, JH; Wang, GS; Zhao, YL, 2021)	2.38
"The ointment is safe and tolerable for use on healthy oral mucosa."	( Safety and tolerability of cinnamaldehyde in orabase for oral candidiasis treatment: phase I clinical trial. Alves, AF; da Nóbrega Alves, D; da Silva Araújo, R; de Araújo, MRC; de Castro, RD; Melo, AKV, 2022)	1.02
"The ointment proved to be safe and tolerable for use on oral mucosa, encouraging studies to evaluate its clinical efficacy in patients with oral candidiasis, and contributing to a new therapeutic proposal for the treatment of fungal infections caused by Candida spp."	( Safety and tolerability of cinnamaldehyde in orabase for oral candidiasis treatment: phase I clinical trial. Alves, AF; da Nóbrega Alves, D; da Silva Araújo, R; de Araújo, MRC; de Castro, RD; Melo, AKV, 2022)	1.02
" Moreover, they were not toxic to the non-target fishes."	( Ovicidal toxicity of plant essential oils and their major constituents against two mosquito vectors and their non-target aquatic predators. Aungtikun, J; Moungthipmalai, T; Puwanard, C; Sittichok, S; Soonwera, M, 2023)	0.91

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" Furthermore, the sensitivity of gas chromatography-mass spectrometry revealed sufficient lower limit of quantitation and detection of 20ng/ml and 5ng/ml, respectively, in the pharmacokinetic analysis."	( Pharmacokinetic study of cinnamaldehyde in rats by GC-MS after oral and intravenous administration. Cao, W; Cao, Y; Tu, H; Wang, S; Xie, Y; Yang, Q; Zhao, H, 2014)	0.71
" The new formulation exhibited lower toxicity, higher antitumor activity, and a more satisfactory pharmacokinetic property, which displayed great potential for future pharmacological application."	( Cinnamaldehyde in a Novel Intravenous Submicrometer Emulsion: Pharmacokinetics, Tissue Distribution, Antitumor Efficacy, and Toxicity. Cao, W; Wang, S; Xie, Y; Yang, Q; Yuan, J; Zhao, H, 2015)	1.86
" In order to characterize their pharmacokinetic profiles and aptitude to permeate in the central nervous system after intravenous and oral administration to rats, new analytical procedures, easily achievable with HPLC-UV techniques, were developed."	( Pharmacokinetic and Permeation Studies in Rat Brain of Natural Compounds Led to Investigate Eugenol as Direct Activator of Dopamine Release in PC12 Cells. Bianchi, A; Botti, G; Dalpiaz, A; Ferraro, L; Pavan, B; Spisni, E; Valerii, MC, 2023)	0.91

Excerpt	Reference	Relevance
"The cell-inactivating effect induced by cinnamaldehyde in combination with cis-diamminedichloroplatinum(II) (cis-DDP) on human NHIK 3025 cells in culture was investigated."	( Synergistic cell inactivation of human NHIK 3025 cells by cinnamaldehyde in combination with cis-diamminedichloroplatinum(II). Dornish, JM; Oftebro, R; Pettersen, EO, 1988)	0.79
"We examined the therapeutic effects of cinnamaldehyde and the potentiation of those effects with cassia and cinnamaldehyde when combined with the food additive methylcellulose against murine oral candidiasis."	( Therapeutic effects of cinnamaldehyde and potentiation of its efficacy in combination with methylcellulose on murine oral candidiasis. Abe, S; Arai, R; Hayama, K; Okada, M; Sagawa, T; Taguchi, Y, 2011)	0.95
" In combination with HPLC-HRMS-SPE-NMR, this provides an analytical platform that allows simultaneous chemical and biological profiling of α-amylase inhibitors in plant extracts."	( High-resolution α-amylase assay combined with high-performance liquid chromatography-solid-phase extraction-nuclear magnetic resonance spectroscopy for expedited identification of α-amylase inhibitors: proof of concept and α-amylase inhibitor in cinnamon. Jäger, AK; Kongstad, KT; Okutan, L; Staerk, D, 2014)	0.4
" The aim of this study was to investigate the ability of semipurified preparations (SPP) containing either nisin A or an enhanced bioengineered derivative, nisin V, alone and in combination with low concentrations of the essential oils thymol, carvacrol, and trans-cinnamaldehyde, to control Listeria monocytogenes in both laboratory media and model food systems."	( Efficacies of nisin A and nisin V semipurified preparations alone and in combination with plant essential oils for controlling Listeria monocytogenes. Cotter, PD; Daly, K; Field, D; Hill, C; O'Connor, PM; Ross, RP, 2015)	0.6
" Cinnamon bark oil and cinnamaldehyde combined with colistin demonstrated synergistic rates at 16."	( Efficacy of cinnamon bark oil and cinnamaldehyde on anti-multidrug resistant Pseudomonas aeruginosa and the synergistic effects in combination with other antimicrobial agents. Chomnawang, MT; Jaturanpinyo, M; Khuntayaporn, P; Surassmo, S; Utchariyakiat, I, 2016)	1.02
"The antimicrobial activity of cinnamon essential oil and cinnamaldehyde against bacterial and fungal pathogens associated with canine otitis externa, as well as the effect of their combination with EDTA were investigated."	( Antimicrobial effects of cinnamon essential oil and cinnamaldehyde combined with EDTA against canine otitis externa pathogens. Deo, P; Khazandi, M; Pi, H; Sim, JXF; Trott, DJ; Venter, H, 2019)	1.01
"Cinnamon essential oil and cinnamaldehyde, either used alone or in combination with EDTA, were effective against the causative micro-organisms of canine otitis externa."	( Antimicrobial effects of cinnamon essential oil and cinnamaldehyde combined with EDTA against canine otitis externa pathogens. Deo, P; Khazandi, M; Pi, H; Sim, JXF; Trott, DJ; Venter, H, 2019)	1.06
"This study shows that cinnamon essential oil and cinnamaldehyde, especially the latter, could be used in combination with EDTA as novel treatment for sensitive and resistant bacterial and fungal pathogens involved in canine otitis externa."	( Antimicrobial effects of cinnamon essential oil and cinnamaldehyde combined with EDTA against canine otitis externa pathogens. Deo, P; Khazandi, M; Pi, H; Sim, JXF; Trott, DJ; Venter, H, 2019)	1.02
"Effects of lysozyme (LYS) combined with cinnamaldehyde (CA) on quality enhancement of olive flounder (Paralichthys olivaceus) fillets during refrigerated storage at 4 °C for 20 days were assessed."	( Effects of lysozyme combined with cinnamaldehyde on storage quality of olive flounder (Paralichthys olivaceus) fillets. Li, J; Li, T; Li, X; Sun, T; Xu, Y; Yin, Y; Zhao, H, 2020)	1.1

Excerpt	Reference	Relevance
" The estimated oral bioavailability of CNMA was less than 20% for both the 250 and 500 mg/kg doses."	( Toxicokinetics of cinnamaldehyde in F344 rats. Bucher, JR; Dieter, MP; Jameson, CW; Yuan, JH, 1992)	0.62
"The choice of vehicle for patch test materials is important for the bioavailability and stability of the allergens."	( Aspects of pharmaceutical and chemical standardization of patch test materials. Hansen, J; Kreilgård, B, 1989)	0.28
"The bioavailability of microencapsulated cinnamaldehyde (CNMA) was investigated in male F344 rats."	( Application of microencapsulation for toxicology studies. III. Bioavailability of microencapsulated cinnamaldehyde. Bucher, JR; Dieter, MP; Jameson, CW; Yuan, J, 1993)	0.77
" However, its hydrophobic nature invites attention for efficient drug delivery systems that would enhance the bioavailability of cinnamaldehyde without affecting its bioactivity."	( Synthesis, characterization and in vitro study of biocompatible cinnamaldehyde functionalized magnetite nanoparticles (CPGF Nps) for hyperthermia and drug delivery applications in breast cancer. Chikate, RC; Deore, AV; Dhole, SD; Gupta, P; Kadu, BS; Kaul-Ghanekar, R; Mansara, P; Poddar, P; Wani, KD, 2014)	0.85
"Using ultrasonic technology, trans-cinnamaldehyde as a natural antibacterial compound was used to prepare nano size emulsions to increase its bioavailability and therefore bactericidal action."	( Ultrasonic nanoemulsification of food grade trans-cinnamaldehyde: 1,8-Cineol and investigation of the mechanism of antibacterial activity. Aliahmadi, A; Moghimi, R; Rafati, H, 2017)	0.99
" Microencapsulation of BEOs has shown to improve their stability, bioavailability and to control their release rate once they are added to the feedstuff."	( Determination of cinnamaldehyde, carvacrol and thymol in feedstuff additives by pressurized liquid extraction followed by gas chromatography-mass spectrometry. Jiménez-Salcedo, M; Tena, MT, 2017)	0.79
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."	( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)	0.51
"The oral bioavailability of tangeretin, a poly(methoxyflavone) found in citrus fruits, is typically very low because of its extremely limited solubility."	( Biopolymer Additives Enhance Tangeretin Bioavailability in Emulsion-Based Delivery Systems: An Hu, Y; Li, B; Li, Y; Liu, F; McClements, DJ; Pang, J; Zhou, Z, 2021)	0.62
"The current investigation explores the possible mechanism of the microemulsion drug delivery system to improve the oral bioavailability of cinnamaldehyde (CA), an important food spice, from the perspective of the microemulsion-mucus system."	( In vitro and in vivo evaluation of cinnamaldehyde Microemulsion-Mucus interaction. Cai, Y; Chen, J; Chu, X; Dong, B; Wu, W, 2022)	1.2
"The purpose of this experiment was to explore the effect of Solid lipid nanoparticles (SLNs) on improving the oral absorption and bioavailability of cinnamaldehyde (CA)."	( Improved uptake and bioavailability of cinnamaldehyde Chu, X; Meng, Y; Wu, L; Xu, Y, 2022)	1.19
"It was concluded that CA-SLNs improved the absorption across Caco-2 cell model and improved the oral administration bioavailability of CA in rats."	( Improved uptake and bioavailability of cinnamaldehyde Chu, X; Meng, Y; Wu, L; Xu, Y, 2022)	0.99

Excerpt	Relevance	Reference
" No CNMA was present in blood at any time in rats dosed with 50 mg CNMA/kg body weight."	( Toxicokinetics of cinnamaldehyde in F344 rats. Bucher, JR; Dieter, MP; Jameson, CW; Yuan, JH, 1992)	0.62
"Rats dosed with cinnamic aldehyde (I) excreted two mercapturic acids in the urine."	( Isolation and identification of mercapturic acids of cinnamic aldehyde and cinnamyl alcohol from urine of female rats. Delbressine, LP; Klippert, PJ; Reuvers, JT; Seuttler-Berlage, F, 1981)	0.26
"The toxicity of cinnamaldehyde (CNMA) was compared after administration by gavage and in dosed feed."	( Comparison of the toxicity of cinnamaldehyde when administered by microencapsulation in feed or by corn oil gavage. Dieter, MP; Hébert, CD; Yuan, J, 1994)	0.92
" At all dose levels, a small amount of the dose was distributed to the fat and was easily measured in animals killed 3 days after dosing at the 50 or 500 mg/kg dose levels."	( Tissue distribution and excretion of 14C-labelled cinnamic aldehyde following single and multiple oral administration in male Fischer 344 rats. Dailey, RE; Ikeda, GJ; Lin, CS; Plummer, SL; Sapienza, PP; Warr, PI, 1993)	0.29
" No increase in the frequency of micronucleated erythrocytes was observed in peripheral blood of male or female mice administered trans-cinnamaldehyde in dosed feed for 3 months."	( NTP toxicology and carcinogenesis studies of trans-cinnamaldehyde (CAS No. 14371-10-9) in F344/N rats and B6C3F1 mice (feed studies). , 2004)	0.78
" All rats survived to the end of the study but some male mice in the highest dose groups died due to inanition from unpalatability of the dosed feed."	( Toxicology and carcinogenesis studies of microencapsulated trans-cinnamaldehyde in rats and mice. Bucher, JR; Burka, LT; Fuciarelli, AF; Graves, SW; Haseman, JK; Hooth, MJ; Johnson, JD; Orzech, DP; Sills, RC; Witt, KL, 2004)	0.56
" A time-course series of tissues from tuberculosis infected/INH dosed animals were assayed and the MALDI MS/MS response correlates well with the amount of INH determined to be in the tissues by high-performance liquid chromatography (HPLC)-MS/MS."	( Reagent precoated targets for rapid in-tissue derivatization of the anti-tuberculosis drug isoniazid followed by MALDI imaging mass spectrometry. Barry, CE; Caprioli, RM; Dartois, V; Goh, A; Manier, ML; Reyzer, ML; Via, LE, 2011)	0.37
" Trans-cinnamaldehyde was chosen as test substance and applied in a suitable dosing vehicle on dermatomed human skin sections."	( Application of liquid chromatography-direct-electron ionization-MS in an in vitro dermal absorption study: quantitative determination of trans-cinnamaldehyde. Cappiello, A; Famiglini, G; Jacquoilleot, S; Radici, L; Saib, O; Termopoli, V; Trufelli, H; Zazzeroni, R, 2011)	1.03
" At d 1, before placement, half of the birds from each pen were tagged and dosed with Salmonella enterica serovar Heidelberg (5 × 10(5) cfu/mL)."	( Effect of xylanase and a blend of essential oils on performance and Salmonella colonization of broiler chickens challenged with Salmonella Heidelberg. Amerah, AM; Hofacre, CL; Mathis, G, 2012)	0.38
" With the aim of exploring combinatorial options that could increase the antibacterial potency of silver nanoparticles and reduce the effective dosage of silver, we evaluated the extent of synergy that a combination of silver nanoparticles and an essential oil representative (cinnamaldehyde) could offer."	( Synergistic action of cinnamaldehyde with silver nanoparticles against spore-forming bacteria: a case for judicious use of silver nanoparticles for antibacterial applications. Ghosh, IN; Navani, NK; Pathania, R; Patil, SD; Sharma, TK; Srivastava, SK, 2013)	0.88
" To assess interaction of skin sensitizers in a mixture, a dose-response modeling approach is applied."	( A Dose-Response Modeling Approach Shows That Effects From Mixture Exposure to the Skin Sensitizers Isoeugenol and Cinnamal Are in Line With Dose Addition and Not With Synergism. Ezendam, J; Gremmer, ER; Kienhuis, AS; Slob, W; Vermeulen, JP, 2015)	0.42
" A greater therapeutic role was observed for the 4 mg/kgBW dosage of the methanolic extract (p < 0."	( Immunomodulatory and therapeutic role of Cinnamomum verum extracts in collagen-induced arthritic BALB/c mice. Anjum, S; Ashraf, MU; Bhatti, A; John, P; Qadir, MMF; Sandhu, MA, 2018)	0.48
" hBE cells were subsequently exposed to various concentrations of cinnamaldehyde to establish a dose-response relationship for effects on CBF."	( Cinnamaldehyde in flavored e-cigarette liquids temporarily suppresses bronchial epithelial cell ciliary motility by dysregulation of mitochondrial function. Carson, JL; Clapp, PW; Jaspers, I; Lavrich, KS; Lazarowski, ER; van Heusden, CA, 2019)	2.19
" albicans infection were given an oral dosage of CA (240 mg."	( Effect of Cinnamaldehyde on C. albicans cell wall and (1,3)- β - D-glucans in vivo. Deng, JH; Li, YL; Luo, JN; Qi, XM; Wang, GS; Wang, J; Zhang, XG, 2022)	1.12
" Based on muscle crude protein content, optimal CIN supplementation dosage was 88."	( Dietary cinnamaldehyde improves muscle protein content by promoting muscle fiber growth via PTP1B/IGF1/PI3K/AKTs-TOR/FOXO3a signaling pathway in grass carp (Ctenopharyngodon idella). Feng, L; Jiang, WD; Kuang, SY; Li, SW; Liu, Y; Peng, Y; Tang, L; Wu, P; Zhou, XQ; Zhou, Y, 2023)	1.34
" These results partly explain the advantages of using whole essential oils over isolated ingredients, and therefore support the application of traditional dosage forms for bacterial infections in ethnomedicine."	( Short communication: Antibacterial effects of essential oils from Cinnamomum cassia bark and Eucalyptus globulus leaves-The involvements of major constituents. Hoang, HT; Miyamoto, A; Nguyen, HT; Nguyen, HTT; Pham, HT; Tong, NTM; Truong, LTN, 2023)	0.91

Role	Description
hypoglycemic agent	A drug which lowers the blood glucose level.
EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor	An EC 4.3.* (C-N lyase) inhibitor that interferes with the action of phenylalanine ammonia-lyase (EC 4.3.1.24).
vasodilator agent	A drug used to cause dilation of the blood vessels.
antifungal agent	An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
flavouring agent	A food additive that is used to added improve the taste or odour of a food.
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
sensitiser	A chemical compound that causes a substantial proportion of exposed people or animals to develop an allergic reaction in normal tissue after repeated exposure to the compound.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
cinnamaldehydes	An enal based on a cinnamaldehyde skeleton and its substituted derivatives.
3-phenylprop-2-enal	A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Luciferase	Photinus pyralis (common eastern firefly)	Potency	44.7853	0.0072	15.7588	89.3584	AID1224835
interleukin 8	Homo sapiens (human)	Potency	70.9011	0.0473	49.4806	74.9780	AID651758
acetylcholinesterase	Homo sapiens (human)	Potency	49.9825	0.0025	41.7960	15,848.9004	AID1347397; AID1347398
RAR-related orphan receptor gamma	Mus musculus (house mouse)	Potency	25.8212	0.0060	38.0041	19,952.5996	AID1159521; AID1159523
GLI family zinc finger 3	Homo sapiens (human)	Potency	10.8005	0.0007	14.5928	83.7951	AID1259369; AID1259392
AR protein	Homo sapiens (human)	Potency	32.4312	0.0002	21.2231	8,912.5098	AID1259243; AID1259247; AID743036; AID743040; AID743053
aldehyde dehydrogenase 1 family, member A1	Homo sapiens (human)	Potency	7.5506	0.0112	12.4002	100.0000	AID1030
nuclear receptor subfamily 1, group I, member 3	Homo sapiens (human)	Potency	45.7029	0.0010	22.6508	76.6163	AID1224838; AID1224839; AID1224893
retinoic acid nuclear receptor alpha variant 1	Homo sapiens (human)	Potency	34.5925	0.0030	41.6115	22,387.1992	AID1159552; AID1159553; AID1159555
estrogen-related nuclear receptor alpha	Homo sapiens (human)	Potency	29.7882	0.0015	30.6073	15,848.9004	AID1224841; AID1259401; AID1259403
pregnane X nuclear receptor	Homo sapiens (human)	Potency	61.8710	0.0054	28.0263	1,258.9301	AID1346982
estrogen nuclear receptor alpha	Homo sapiens (human)	Potency	35.9065	0.0002	29.3054	16,493.5996	AID1259244; AID743069; AID743075; AID743079; AID743080; AID743091
67.9K protein	Vaccinia virus	Potency	22.3872	0.0001	8.4406	100.0000	AID720579
shiga toxin 1 variant A subunit	Escherichia coli O157:H7	Potency	10.0239	5.0354	16.1932	32.6037	AID2318; AID2320
shiga toxin 1 B subunit	Escherichia coli O157:H7	Potency	10.0239	5.0354	13.8488	22.4921	AID2318; AID2320
peroxisome proliferator-activated receptor delta	Homo sapiens (human)	Potency	43.6465	0.0010	24.5048	61.6448	AID743215
IDH1	Homo sapiens (human)	Potency	29.0929	0.0052	10.8652	35.4813	AID686970
aryl hydrocarbon receptor	Homo sapiens (human)	Potency	64.8601	0.0007	23.0674	1,258.9301	AID743085; AID743122
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a	Homo sapiens (human)	Potency	28.6206	0.0017	23.8393	78.1014	AID743083
parathyroid hormone/parathyroid hormone-related peptide receptor precursor	Homo sapiens (human)	Potency	112.2020	3.5481	19.5427	44.6684	AID743266
mitogen-activated protein kinase 1	Homo sapiens (human)	Potency	39.8107	0.0398	16.7842	39.8107	AID995
nuclear factor erythroid 2-related factor 2 isoform 1	Homo sapiens (human)	Potency	62.9335	0.0006	27.2152	1,122.0200	AID651741; AID720636; AID743202
nuclear receptor ROR-gamma isoform 1	Mus musculus (house mouse)	Potency	12.5893	0.0079	8.2332	1,122.0200	AID2546
geminin	Homo sapiens (human)	Potency	0.1458	0.0046	11.3741	33.4983	AID624297
peripheral myelin protein 22	Rattus norvegicus (Norway rat)	Potency	18.1056	0.0056	12.3677	36.1254	AID624032
lamin isoform A-delta10	Homo sapiens (human)	Potency	0.6310	0.8913	12.0676	28.1838	AID1487
Voltage-dependent calcium channel gamma-2 subunit	Mus musculus (house mouse)	Potency	30.6379	0.0015	57.7890	15,848.9004	AID1259244
Cellular tumor antigen p53	Homo sapiens (human)	Potency	42.1234	0.0023	19.5956	74.0614	AID651631
Glutamate receptor 2	Rattus norvegicus (Norway rat)	Potency	30.6379	0.0015	51.7393	15,848.9004	AID1259244
Nuclear receptor ROR-gamma	Homo sapiens (human)	Potency	37.5780	0.0266	22.4482	66.8242	AID651802
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Polyphenol oxidase 2	Agaricus bisporus	IC50 (µMol)	520.0000	0.0340	3.9871	10.0000	AID467606
Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)	IC50 (µMol)	35.0000	0.0001	1.6847	9.3200	AID1603728
Cell division protein FtsZ	Escherichia coli K-12	IC50 (µMol)	6.3350	5.8100	7.5567	10.0000	AID1201462; AID1201463
Prostaglandin G/H synthase 2	Homo sapiens (human)	IC50 (µMol)	245.0000	0.0001	0.9950	10.0000	AID403340
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)	EC50 (µMol)	18.8823	0.0003	3.1662	10.0000	AID1549771; AID329099; AID452237; AID482140
Transient receptor potential cation channel subfamily A member 1	Mus musculus (house mouse)	EC50 (µMol)	61.0000	0.4000	2.7714	10.0000	AID1549782
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)	Activity	10.0000	0.0990	8.0198	10.0000	AID500219
Cell division protein FtsZ	Escherichia coli K-12	INH	6.3100	5.8100	8.1250	10.0000	AID1628114; AID1628120
Cell division protein FtsZ	Escherichia coli K-12	Ka	1.0000	1.0000	1.0000	1.0000	AID1628121
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
monoatomic ion transport	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
intracellular calcium ion homeostasis	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
cell surface receptor signaling pathway	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
response to cold	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
response to xenobiotic stimulus	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
response to organic substance	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
response to organic cyclic compound	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
sensory perception of pain	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
calcium-mediated signaling	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
response to pain	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
thermoception	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
detection of mechanical stimulus involved in sensory perception of pain	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
detection of chemical stimulus involved in sensory perception of pain	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
protein homotetramerization	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
cellular response to hydrogen peroxide	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
calcium ion transmembrane transport	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
cellular response to organic substance	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
negative regulation of cell population proliferation	Cellular tumor antigen p53	Homo sapiens (human)
regulation of cell cycle	Cellular tumor antigen p53	Homo sapiens (human)
regulation of cell cycle G2/M phase transition	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response	Cellular tumor antigen p53	Homo sapiens (human)
ER overload response	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to glucose starvation	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
regulation of apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of miRNA transcription	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Cellular tumor antigen p53	Homo sapiens (human)
mitophagy	Cellular tumor antigen p53	Homo sapiens (human)
in utero embryonic development	Cellular tumor antigen p53	Homo sapiens (human)
somitogenesis	Cellular tumor antigen p53	Homo sapiens (human)
release of cytochrome c from mitochondria	Cellular tumor antigen p53	Homo sapiens (human)
hematopoietic progenitor cell differentiation	Cellular tumor antigen p53	Homo sapiens (human)
T cell proliferation involved in immune response	Cellular tumor antigen p53	Homo sapiens (human)
B cell lineage commitment	Cellular tumor antigen p53	Homo sapiens (human)
T cell lineage commitment	Cellular tumor antigen p53	Homo sapiens (human)
response to ischemia	Cellular tumor antigen p53	Homo sapiens (human)
nucleotide-excision repair	Cellular tumor antigen p53	Homo sapiens (human)
double-strand break repair	Cellular tumor antigen p53	Homo sapiens (human)
regulation of DNA-templated transcription	Cellular tumor antigen p53	Homo sapiens (human)
regulation of transcription by RNA polymerase II	Cellular tumor antigen p53	Homo sapiens (human)
protein import into nucleus	Cellular tumor antigen p53	Homo sapiens (human)
autophagy	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediator resulting in cell cycle arrest	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediator resulting in transcription of p21 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
transforming growth factor beta receptor signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
Ras protein signal transduction	Cellular tumor antigen p53	Homo sapiens (human)
gastrulation	Cellular tumor antigen p53	Homo sapiens (human)
neuroblast proliferation	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of neuroblast proliferation	Cellular tumor antigen p53	Homo sapiens (human)
protein localization	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of DNA replication	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of cell population proliferation	Cellular tumor antigen p53	Homo sapiens (human)
determination of adult lifespan	Cellular tumor antigen p53	Homo sapiens (human)
mRNA transcription	Cellular tumor antigen p53	Homo sapiens (human)
rRNA transcription	Cellular tumor antigen p53	Homo sapiens (human)
response to salt stress	Cellular tumor antigen p53	Homo sapiens (human)
response to inorganic substance	Cellular tumor antigen p53	Homo sapiens (human)
response to X-ray	Cellular tumor antigen p53	Homo sapiens (human)
response to gamma radiation	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of gene expression	Cellular tumor antigen p53	Homo sapiens (human)
cardiac muscle cell apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of cardiac muscle cell apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
glial cell proliferation	Cellular tumor antigen p53	Homo sapiens (human)
viral process	Cellular tumor antigen p53	Homo sapiens (human)
glucose catabolic process to lactate via pyruvate	Cellular tumor antigen p53	Homo sapiens (human)
cerebellum development	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of cell growth	Cellular tumor antigen p53	Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of transforming growth factor beta receptor signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
mitotic G1 DNA damage checkpoint signaling	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of telomere maintenance via telomerase	Cellular tumor antigen p53	Homo sapiens (human)
T cell differentiation in thymus	Cellular tumor antigen p53	Homo sapiens (human)
tumor necrosis factor-mediated signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
regulation of tissue remodeling	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to UV	Cellular tumor antigen p53	Homo sapiens (human)
multicellular organism growth	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of mitochondrial membrane permeability	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to glucose starvation	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
entrainment of circadian clock by photoperiod	Cellular tumor antigen p53	Homo sapiens (human)
mitochondrial DNA repair	Cellular tumor antigen p53	Homo sapiens (human)
regulation of DNA damage response, signal transduction by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of neuron apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
transcription initiation-coupled chromatin remodeling	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of proteolysis	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of DNA-templated transcription	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of DNA-templated transcription	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of RNA polymerase II transcription preinitiation complex assembly	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Cellular tumor antigen p53	Homo sapiens (human)
response to antibiotic	Cellular tumor antigen p53	Homo sapiens (human)
fibroblast proliferation	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of fibroblast proliferation	Cellular tumor antigen p53	Homo sapiens (human)
circadian behavior	Cellular tumor antigen p53	Homo sapiens (human)
bone marrow development	Cellular tumor antigen p53	Homo sapiens (human)
embryonic organ development	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of peptidyl-tyrosine phosphorylation	Cellular tumor antigen p53	Homo sapiens (human)
protein stabilization	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of helicase activity	Cellular tumor antigen p53	Homo sapiens (human)
protein tetramerization	Cellular tumor antigen p53	Homo sapiens (human)
chromosome organization	Cellular tumor antigen p53	Homo sapiens (human)
neuron apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
regulation of cell cycle	Cellular tumor antigen p53	Homo sapiens (human)
hematopoietic stem cell differentiation	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of glial cell proliferation	Cellular tumor antigen p53	Homo sapiens (human)
type II interferon-mediated signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
cardiac septum morphogenesis	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of programmed necrotic cell death	Cellular tumor antigen p53	Homo sapiens (human)
protein-containing complex assembly	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to endoplasmic reticulum stress	Cellular tumor antigen p53	Homo sapiens (human)
thymocyte apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of thymocyte apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
necroptotic process	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to hypoxia	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to xenobiotic stimulus	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to ionizing radiation	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to gamma radiation	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to UV-C	Cellular tumor antigen p53	Homo sapiens (human)
stem cell proliferation	Cellular tumor antigen p53	Homo sapiens (human)
signal transduction by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
reactive oxygen species metabolic process	Cellular tumor antigen p53	Homo sapiens (human)
cellular response to actinomycin D	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of release of cytochrome c from mitochondria	Cellular tumor antigen p53	Homo sapiens (human)
cellular senescence	Cellular tumor antigen p53	Homo sapiens (human)
replicative senescence	Cellular tumor antigen p53	Homo sapiens (human)
oxidative stress-induced premature senescence	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
oligodendrocyte apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of execution phase of apoptosis	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of mitophagy	Cellular tumor antigen p53	Homo sapiens (human)
regulation of mitochondrial membrane permeability involved in apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
regulation of intrinsic apoptotic signaling pathway by p53 class mediator	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of miRNA transcription	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of G1 to G0 transition	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of miRNA processing	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of glucose catabolic process to lactate via pyruvate	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of pentose-phosphate shunt	Cellular tumor antigen p53	Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to hypoxia	Cellular tumor antigen p53	Homo sapiens (human)
regulation of fibroblast apoptotic process	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of reactive oxygen species metabolic process	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of reactive oxygen species metabolic process	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of stem cell proliferation	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of cellular senescence	Cellular tumor antigen p53	Homo sapiens (human)
positive regulation of intrinsic apoptotic signaling pathway	Cellular tumor antigen p53	Homo sapiens (human)
negative regulation of endothelial cell proliferation	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukocyte chemotaxis involved in inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukocyte migration involved in inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukotriene production involved in inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukotriene metabolic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
humoral immune response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of angiogenesis	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukotriene biosynthetic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
lipoxygenase pathway	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
positive regulation of bone mineralization	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
dendritic cell migration	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
glucose homeostasis	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
long-chain fatty acid biosynthetic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of fat cell differentiation	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of insulin secretion	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of vascular wound healing	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of wound healing	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of inflammatory response to wounding	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of cytokine production involved in inflammatory response	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of cellular response to oxidative stress	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
leukotriene A4 biosynthetic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
regulation of reactive oxygen species biosynthetic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of response to endoplasmic reticulum stress	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
negative regulation of sprouting angiogenesis	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
positive regulation of leukocyte adhesion to arterial endothelial cell	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
lipoxin biosynthetic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
arachidonic acid metabolic process	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
lipid oxidation	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
protein polymerization	Cell division protein FtsZ	Escherichia coli K-12
cell division	Cell division protein FtsZ	Escherichia coli K-12
division septum assembly	Cell division protein FtsZ	Escherichia coli K-12
FtsZ-dependent cytokinesis	Cell division protein FtsZ	Escherichia coli K-12
protein polymerization	Cell division protein FtsZ	Escherichia coli K-12
cell division	Cell division protein FtsZ	Escherichia coli K-12
cell septum assembly	Cell division protein FtsZ	Escherichia coli K-12
prostaglandin biosynthetic process	Prostaglandin G/H synthase 2	Homo sapiens (human)
angiogenesis	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to oxidative stress	Prostaglandin G/H synthase 2	Homo sapiens (human)
embryo implantation	Prostaglandin G/H synthase 2	Homo sapiens (human)
learning	Prostaglandin G/H synthase 2	Homo sapiens (human)
memory	Prostaglandin G/H synthase 2	Homo sapiens (human)
regulation of blood pressure	Prostaglandin G/H synthase 2	Homo sapiens (human)
negative regulation of cell population proliferation	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to xenobiotic stimulus	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to nematode	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to fructose	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to manganese ion	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of vascular endothelial growth factor production	Prostaglandin G/H synthase 2	Homo sapiens (human)
cyclooxygenase pathway	Prostaglandin G/H synthase 2	Homo sapiens (human)
bone mineralization	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of prostaglandin biosynthetic process	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of fever generation	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of synaptic plasticity	Prostaglandin G/H synthase 2	Homo sapiens (human)
negative regulation of synaptic transmission, dopaminergic	Prostaglandin G/H synthase 2	Homo sapiens (human)
prostaglandin secretion	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to estradiol	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to lipopolysaccharide	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of peptidyl-serine phosphorylation	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to vitamin D	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular response to heat	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to tumor necrosis factor	Prostaglandin G/H synthase 2	Homo sapiens (human)
maintenance of blood-brain barrier	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of protein import into nucleus	Prostaglandin G/H synthase 2	Homo sapiens (human)
hair cycle	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of apoptotic process	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of nitric oxide biosynthetic process	Prostaglandin G/H synthase 2	Homo sapiens (human)
negative regulation of cell cycle	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of vasoconstriction	Prostaglandin G/H synthase 2	Homo sapiens (human)
negative regulation of smooth muscle contraction	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of smooth muscle contraction	Prostaglandin G/H synthase 2	Homo sapiens (human)
decidualization	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of smooth muscle cell proliferation	Prostaglandin G/H synthase 2	Homo sapiens (human)
regulation of inflammatory response	Prostaglandin G/H synthase 2	Homo sapiens (human)
brown fat cell differentiation	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to glucocorticoid	Prostaglandin G/H synthase 2	Homo sapiens (human)
negative regulation of calcium ion transport	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of synaptic transmission, glutamatergic	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to fatty acid	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular response to mechanical stimulus	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular response to lead ion	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular response to ATP	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular response to hypoxia	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular response to non-ionic osmotic stress	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular response to fluid shear stress	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of transforming growth factor beta production	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of cell migration involved in sprouting angiogenesis	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of fibroblast growth factor production	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of brown fat cell differentiation	Prostaglandin G/H synthase 2	Homo sapiens (human)
positive regulation of platelet-derived growth factor production	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular oxidant detoxification	Prostaglandin G/H synthase 2	Homo sapiens (human)
regulation of neuroinflammatory response	Prostaglandin G/H synthase 2	Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to osmotic stress	Prostaglandin G/H synthase 2	Homo sapiens (human)
cellular response to homocysteine	Prostaglandin G/H synthase 2	Homo sapiens (human)
response to angiotensin	Prostaglandin G/H synthase 2	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Nuclear receptor ROR-gamma	Homo sapiens (human)
xenobiotic metabolic process	Nuclear receptor ROR-gamma	Homo sapiens (human)
regulation of glucose metabolic process	Nuclear receptor ROR-gamma	Homo sapiens (human)
regulation of steroid metabolic process	Nuclear receptor ROR-gamma	Homo sapiens (human)
intracellular receptor signaling pathway	Nuclear receptor ROR-gamma	Homo sapiens (human)
circadian regulation of gene expression	Nuclear receptor ROR-gamma	Homo sapiens (human)
cellular response to sterol	Nuclear receptor ROR-gamma	Homo sapiens (human)
positive regulation of circadian rhythm	Nuclear receptor ROR-gamma	Homo sapiens (human)
regulation of fat cell differentiation	Nuclear receptor ROR-gamma	Homo sapiens (human)
positive regulation of DNA-templated transcription	Nuclear receptor ROR-gamma	Homo sapiens (human)
adipose tissue development	Nuclear receptor ROR-gamma	Homo sapiens (human)
T-helper 17 cell differentiation	Nuclear receptor ROR-gamma	Homo sapiens (human)
regulation of transcription by RNA polymerase II	Nuclear receptor ROR-gamma	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
calcium channel activity	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
channel activity	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
intracellularly gated calcium channel activity	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
identical protein binding	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
temperature-gated cation channel activity	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
transcription cis-regulatory region binding	Cellular tumor antigen p53	Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Cellular tumor antigen p53	Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specific	Cellular tumor antigen p53	Homo sapiens (human)
cis-regulatory region sequence-specific DNA binding	Cellular tumor antigen p53	Homo sapiens (human)
core promoter sequence-specific DNA binding	Cellular tumor antigen p53	Homo sapiens (human)
TFIID-class transcription factor complex binding	Cellular tumor antigen p53	Homo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specific	Cellular tumor antigen p53	Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specific	Cellular tumor antigen p53	Homo sapiens (human)
protease binding	Cellular tumor antigen p53	Homo sapiens (human)
p53 binding	Cellular tumor antigen p53	Homo sapiens (human)
DNA binding	Cellular tumor antigen p53	Homo sapiens (human)
chromatin binding	Cellular tumor antigen p53	Homo sapiens (human)
DNA-binding transcription factor activity	Cellular tumor antigen p53	Homo sapiens (human)
mRNA 3'-UTR binding	Cellular tumor antigen p53	Homo sapiens (human)
copper ion binding	Cellular tumor antigen p53	Homo sapiens (human)
protein binding	Cellular tumor antigen p53	Homo sapiens (human)
zinc ion binding	Cellular tumor antigen p53	Homo sapiens (human)
enzyme binding	Cellular tumor antigen p53	Homo sapiens (human)
receptor tyrosine kinase binding	Cellular tumor antigen p53	Homo sapiens (human)
ubiquitin protein ligase binding	Cellular tumor antigen p53	Homo sapiens (human)
histone deacetylase regulator activity	Cellular tumor antigen p53	Homo sapiens (human)
ATP-dependent DNA/DNA annealing activity	Cellular tumor antigen p53	Homo sapiens (human)
identical protein binding	Cellular tumor antigen p53	Homo sapiens (human)
histone deacetylase binding	Cellular tumor antigen p53	Homo sapiens (human)
protein heterodimerization activity	Cellular tumor antigen p53	Homo sapiens (human)
protein-folding chaperone binding	Cellular tumor antigen p53	Homo sapiens (human)
protein phosphatase 2A binding	Cellular tumor antigen p53	Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor binding	Cellular tumor antigen p53	Homo sapiens (human)
14-3-3 protein binding	Cellular tumor antigen p53	Homo sapiens (human)
MDM2/MDM4 family protein binding	Cellular tumor antigen p53	Homo sapiens (human)
disordered domain specific binding	Cellular tumor antigen p53	Homo sapiens (human)
general transcription initiation factor binding	Cellular tumor antigen p53	Homo sapiens (human)
molecular function activator activity	Cellular tumor antigen p53	Homo sapiens (human)
promoter-specific chromatin binding	Cellular tumor antigen p53	Homo sapiens (human)
arachidonate 5-lipoxygenase activity	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
arachidonate 12(S)-lipoxygenase activity	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
iron ion binding	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
protein binding	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
hydrolase activity	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
arachidonate 8(S)-lipoxygenase activity	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
GTPase activity	Cell division protein FtsZ	Escherichia coli K-12
protein binding	Cell division protein FtsZ	Escherichia coli K-12
GTP binding	Cell division protein FtsZ	Escherichia coli K-12
identical protein binding	Cell division protein FtsZ	Escherichia coli K-12
peroxidase activity	Prostaglandin G/H synthase 2	Homo sapiens (human)
prostaglandin-endoperoxide synthase activity	Prostaglandin G/H synthase 2	Homo sapiens (human)
protein binding	Prostaglandin G/H synthase 2	Homo sapiens (human)
enzyme binding	Prostaglandin G/H synthase 2	Homo sapiens (human)
heme binding	Prostaglandin G/H synthase 2	Homo sapiens (human)
protein homodimerization activity	Prostaglandin G/H synthase 2	Homo sapiens (human)
metal ion binding	Prostaglandin G/H synthase 2	Homo sapiens (human)
oxidoreductase activity, acting on single donors with incorporation of molecular oxygen, incorporation of two atoms of oxygen	Prostaglandin G/H synthase 2	Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Nuclear receptor ROR-gamma	Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specific	Nuclear receptor ROR-gamma	Homo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specific	Nuclear receptor ROR-gamma	Homo sapiens (human)
DNA-binding transcription factor activity	Nuclear receptor ROR-gamma	Homo sapiens (human)
protein binding	Nuclear receptor ROR-gamma	Homo sapiens (human)
oxysterol binding	Nuclear receptor ROR-gamma	Homo sapiens (human)
zinc ion binding	Nuclear receptor ROR-gamma	Homo sapiens (human)
ligand-activated transcription factor activity	Nuclear receptor ROR-gamma	Homo sapiens (human)
sequence-specific double-stranded DNA binding	Nuclear receptor ROR-gamma	Homo sapiens (human)
nuclear receptor activity	Nuclear receptor ROR-gamma	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
plasma membrane	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
stereocilium bundle	Transient receptor potential cation channel subfamily A member 1	Homo sapiens (human)
nuclear body	Cellular tumor antigen p53	Homo sapiens (human)
nucleus	Cellular tumor antigen p53	Homo sapiens (human)
nucleoplasm	Cellular tumor antigen p53	Homo sapiens (human)
replication fork	Cellular tumor antigen p53	Homo sapiens (human)
nucleolus	Cellular tumor antigen p53	Homo sapiens (human)
cytoplasm	Cellular tumor antigen p53	Homo sapiens (human)
mitochondrion	Cellular tumor antigen p53	Homo sapiens (human)
mitochondrial matrix	Cellular tumor antigen p53	Homo sapiens (human)
endoplasmic reticulum	Cellular tumor antigen p53	Homo sapiens (human)
centrosome	Cellular tumor antigen p53	Homo sapiens (human)
cytosol	Cellular tumor antigen p53	Homo sapiens (human)
nuclear matrix	Cellular tumor antigen p53	Homo sapiens (human)
PML body	Cellular tumor antigen p53	Homo sapiens (human)
transcription repressor complex	Cellular tumor antigen p53	Homo sapiens (human)
site of double-strand break	Cellular tumor antigen p53	Homo sapiens (human)
germ cell nucleus	Cellular tumor antigen p53	Homo sapiens (human)
chromatin	Cellular tumor antigen p53	Homo sapiens (human)
transcription regulator complex	Cellular tumor antigen p53	Homo sapiens (human)
protein-containing complex	Cellular tumor antigen p53	Homo sapiens (human)
extracellular region	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
extracellular space	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nuclear envelope	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nuclear envelope lumen	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nucleoplasm	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
cytosol	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nuclear matrix	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nuclear membrane	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
secretory granule lumen	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
perinuclear region of cytoplasm	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
ficolin-1-rich granule lumen	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
nuclear envelope	Polyunsaturated fatty acid 5-lipoxygenase	Homo sapiens (human)
cytoplasm	Cell division protein FtsZ	Escherichia coli K-12
cell division site	Cell division protein FtsZ	Escherichia coli K-12
plasma membrane	Cell division protein FtsZ	Escherichia coli K-12
divisome complex	Cell division protein FtsZ	Escherichia coli K-12
cytoplasm	Cell division protein FtsZ	Escherichia coli K-12
cell division site	Cell division protein FtsZ	Escherichia coli K-12
plasma membrane	Glutamate receptor 2	Rattus norvegicus (Norway rat)
nuclear inner membrane	Prostaglandin G/H synthase 2	Homo sapiens (human)
nuclear outer membrane	Prostaglandin G/H synthase 2	Homo sapiens (human)
cytoplasm	Prostaglandin G/H synthase 2	Homo sapiens (human)
endoplasmic reticulum	Prostaglandin G/H synthase 2	Homo sapiens (human)
endoplasmic reticulum lumen	Prostaglandin G/H synthase 2	Homo sapiens (human)
endoplasmic reticulum membrane	Prostaglandin G/H synthase 2	Homo sapiens (human)
caveola	Prostaglandin G/H synthase 2	Homo sapiens (human)
neuron projection	Prostaglandin G/H synthase 2	Homo sapiens (human)
protein-containing complex	Prostaglandin G/H synthase 2	Homo sapiens (human)
neuron projection	Prostaglandin G/H synthase 2	Homo sapiens (human)
cytoplasm	Prostaglandin G/H synthase 2	Homo sapiens (human)
nucleus	Nuclear receptor ROR-gamma	Homo sapiens (human)
nucleoplasm	Nuclear receptor ROR-gamma	Homo sapiens (human)
nuclear body	Nuclear receptor ROR-gamma	Homo sapiens (human)
chromatin	Nuclear receptor ROR-gamma	Homo sapiens (human)
nucleus	Nuclear receptor ROR-gamma	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (135)

Assay ID	Title	Year	Journal	Article
AID504749	qHTS profiling for inhibitors of Plasmodium falciparum proliferation	2011	Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043	Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID336481	Inhibition of COX2 at 10 uM by scintillation proximity assay	2002	Journal of natural products, Nov, Volume: 65, Issue:11	Screening of ubiquitous plant constituents for COX-2 inhibition with a scintillation proximity based assay.
AID1272754	Antibacterial activity against Escherichia coli at 0.25 mol/L after 12 to 24 hrs by paper disc method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.
AID1066639	Antagonist at TRPM8 isolated from mouse dorsal root ganglion cells expressed in HEK T-REx cells assessed as inhibition of icilin-induced intracellular Ca2+ influx at >500 uM by fluorescence-based assay	2014	Journal of natural products, Feb-28, Volume: 77, Issue:2	Activation and inhibition of thermosensitive TRP channels by voacangine, an alkaloid present in Voacanga africana, an African tree.
AID329102	Activation of mouse TRPA1 C415S mutant expressed in CHO cells at 100 uM by calcium imaging FLIPR assay	2007	Nature, Feb-01, Volume: 445, Issue:7127	Noxious compounds activate TRPA1 ion channels through covalent modification of cysteines.
AID1082481	Nematicidal activity against second juvenile stage (J2) of Meloidogyne incognita (root-knot nematode) assessed as mortality incubated in the dark at 28 degC after 2 days by light microscopy (benficial crop Tomato)	2011	Journal of agricultural and food chemistry, Oct-26, Volume: 59, Issue:20	Nematicidal and antifungal activities of annonaceous acetogenins from Annona squamosa against various plant pathogens.
AID1549771	Agonist activity at human TRPA1 expressed in HEK293 cells assessed as increase in calcium influx by Fluo-4-AM dye based fluorescence assay	2019	European journal of medicinal chemistry, May-15, Volume: 170	N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites.
AID1755487	Half life in human at 0.7 mg/kg, po	2020	Journal of medicinal chemistry, 12-10, Volume: 63, Issue:23	Curse or Cure? A Perspective on the Developability of Aldehydes as Active Pharmaceutical Ingredients.
AID329099	Activation of TRPA1	2007	Nature, Feb-01, Volume: 445, Issue:7127	Noxious compounds activate TRPA1 ion channels through covalent modification of cysteines.
AID1066644	Antagonist at TRPM8 isolated from mouse dorsal root ganglion cells expressed in HEK T-REx cells assessed as inhibition of icilin-induced intracellular Ca2+ influx by fluorescence-based assay	2014	Journal of natural products, Feb-28, Volume: 77, Issue:2	Activation and inhibition of thermosensitive TRP channels by voacangine, an alkaloid present in Voacanga africana, an African tree.
AID1398239	Antiproliferative activity against human HCT8 cells after 72 hrs in presence of aspirin by MTT assay	2018	Bioorganic & medicinal chemistry letters, 09-15, Volume: 28, Issue:17	Novel cinnamaldehyde-based aspirin derivatives for the treatment of colorectal cancer.
AID1549812	Agonist activity at human TRPA1 Phe909Ala mutant expressed in HEK293 cells assessed as Ca2+ influx at 30 uM by fluorescence assay	2019	European journal of medicinal chemistry, May-15, Volume: 170	N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites.
AID1581190	Agonist activity at mouse TRPA1 expressed in HEK293 cells assessed as increase in calcium influx at 1 uM incubated for 1 min by Fluo-4-AM dye based FLIPR assay	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Discovery of Nonpungent Transient Receptor Potential Vanilloid 1 (TRPV1) Agonist as Strong Topical Analgesic.
AID1398207	Antiproliferative activity against human HCT8 cells after 72 hrs by MTT assay	2018	Bioorganic & medicinal chemistry letters, 09-15, Volume: 28, Issue:17	Novel cinnamaldehyde-based aspirin derivatives for the treatment of colorectal cancer.
AID482140	Activation of TRPA1 channel expressed in CHO cells assessed as increase in intracellular calcium levels	2010	Journal of medicinal chemistry, Jul-22, Volume: 53, Issue:14	Transient receptor potential ankyrin 1 (TRPA1) channel as emerging target for novel analgesics and anti-inflammatory agents.
AID299876	Antiinflammatory activity against xylene-induced ear edema in Kunming mouse assessed as edema weight at 20 mg/kg, po after 2 hrs relative to control	2007	Bioorganic & medicinal chemistry, Jul-15, Volume: 15, Issue:14	Toward the development of chemoprevention agents. Part 1: Design, synthesis, and anti-inflammatory activities of a new class of 2,5-disubstituted-dioxacycloalkanes.
AID362785	Inhibition of human recombinant PDE5A1 expressed in COS7 cells	2008	Journal of natural products, Sep, Volume: 71, Issue:9	Potent inhibition of human phosphodiesterase-5 by icariin derivatives.
AID1755485	Oral bioavailability in human at 0.7 mg/kg	2020	Journal of medicinal chemistry, 12-10, Volume: 63, Issue:23	Curse or Cure? A Perspective on the Developability of Aldehydes as Active Pharmaceutical Ingredients.
AID1699025	Inhibition of quorum sensing system in Pseudomonas aeruginosa PAO1	2020	Bioorganic & medicinal chemistry, 11-01, Volume: 28, Issue:21	Next generation quorum sensing inhibitors: Accounts on structure activity relationship studies and biological activities.
AID1201466	Antimicrobial activity against methicillin-resistant Staphylococcus aureus	2015	European journal of medicinal chemistry, May-05, Volume: 95	Advances in the discovery of novel antimicrobials targeting the assembly of bacterial cell division protein FtsZ.
AID1066645	Antagonist at TRPM8 isolated from mouse dorsal root ganglion cells expressed in HEK T-REx cells assessed as inhibition of menthol-induced intracellular Ca2+ influx by fluorescence-based assay	2014	Journal of natural products, Feb-28, Volume: 77, Issue:2	Activation and inhibition of thermosensitive TRP channels by voacangine, an alkaloid present in Voacanga africana, an African tree.
AID467606	Inhibition of mushroom tyrosinase after 10 mins by spectrophotometry	2009	Journal of natural products, Jun, Volume: 72, Issue:6	Tyrosinase-inhibitory constituents from the twigs of Cinnamomum cassia.
AID1544945	Inhibition of NO711 binding to mouse GAT1 expressed in HEK293 cell membranes assessed as residual binding at 1 uM incubated for 4 hrs in presence of NO711 by LC-ESI-MS/MS analysis relative to control	2019	Bioorganic & medicinal chemistry, 07-01, Volume: 27, Issue:13	Application of the concept of oxime library screening by mass spectrometry (MS) binding assays to pyrrolidine-3-carboxylic acid derivatives as potential inhibitors of γ-aminobutyric acid transporter 1 (GAT1).
AID386014	Induction of neurogenic inflammation in rat esophagus assessed as CGRP release per 20 mins at 50 uM	2007	Proceedings of the National Academy of Sciences of the United States of America, Aug-14, Volume: 104, Issue:33	4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1.
AID385778	Induction of neurogenic inflammation in capsaicin desensitized rat dorsal spinal cord assessed as substance P release per 20 mins at 10 uM	2007	Proceedings of the National Academy of Sciences of the United States of America, Aug-14, Volume: 104, Issue:33	4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1.
AID1628116	Antimicrobial activity against Staphylococcus aureus	2016	Journal of medicinal chemistry, Aug-11, Volume: 59, Issue:15	Targeting the Bacterial Division Protein FtsZ.
AID1326324	Antibacterial activity against Bacillus subtilis by broth dilution method	2016	Bioorganic & medicinal chemistry, 12-15, Volume: 24, Issue:24	Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.
AID1755484	Bioavailability in human at 10.3 mg	2020	Journal of medicinal chemistry, 12-10, Volume: 63, Issue:23	Curse or Cure? A Perspective on the Developability of Aldehydes as Active Pharmaceutical Ingredients.
AID385775	Induction of neurogenic inflammation in rat dorsal spinal cord assessed as substance P release per 20 mins at 10 uM	2007	Proceedings of the National Academy of Sciences of the United States of America, Aug-14, Volume: 104, Issue:33	4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1.
AID1326307	Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC BAA-41 after 18 hrs by broth microdilution method	2016	Bioorganic & medicinal chemistry, 12-15, Volume: 24, Issue:24	Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.
AID670363	Inhibition of xanthine oxidase- mediated uric acid formation at 50 ug/mL after 5 mins by spectrophotometry	2012	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14	Xanthine oxidase inhibitory activity of constituents of Cinnamomum cassia twigs.
AID1120510	Induction of transmembrane potential loss in Bacillus subtilis subsp. subtilis str. 168 at 1 times MIC pre-treated for 5 mins and measured 15 mins post dye addition by DiOC2 dye based flow cytometry	2013	MedChemComm, Jan-01, Volume: 4, Issue:1	Inhibitors of bacterial tubulin target bacterial membranes
AID1272755	Antibacterial activity against Escherichia coli at 0.13 mol/L after 12 to 24 hrs by paper disc method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.
AID1120513	Antimicrobial activity against Bacillus subtilis subsp. subtilis str. 168 after 18 hrs by macro-dilution method	2013	MedChemComm, Jan-01, Volume: 4, Issue:1	Inhibitors of bacterial tubulin target bacterial membranes
AID452237	Agonist activity at human TRPA1 expressed in HEK293 cells assessed as [45]Ca2+ influx by microbeta plate count	2010	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 20, Issue:1	Oxime derivatives related to AP18: Agonists and antagonists of the TRPA1 receptor.
AID1272756	Antibacterial activity against Escherichia coli at 0.06 mol/L after 12 to 24 hrs by paper disc method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.
AID1603728	Inhibition of human PMNL 5-LOX using arachidonic acid as substrate after 5 mins by HPLC method	2019	Bioorganic & medicinal chemistry, 09-01, Volume: 27, Issue:17	5-Lipoxygenase as a drug target: A review on trends in inhibitors structural design, SAR and mechanism based approach.
AID386016	Induction of neurogenic inflammation in capsaicin desensitized rat esophagus assessed as CGRP release per 20 mins at 50 uM	2007	Proceedings of the National Academy of Sciences of the United States of America, Aug-14, Volume: 104, Issue:33	4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1.
AID670364	Inhibition of xanthine oxidase- mediated uric acid formation after 5 mins by spectrophotometry	2012	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14	Xanthine oxidase inhibitory activity of constituents of Cinnamomum cassia twigs.
AID642414	Estrogenic activity at ERalpha in human MVLN cells at 100 ug/mL after 24 hrs by luciferase reporter gene assay relative to E2	2012	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1	Discovery of estrogen receptor α modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells.
AID377983	Cytotoxicity against Salmonella Typhimurium TA100 assessed as maximun non-toxic concentrations after 15 hrs by ELISA	1999	Journal of natural products, Jan, Volume: 62, Issue:1	Structure-antimutagenic activity relationship study of plicatin B.
AID349484	Inhibition of NF-kappaB transfected in LPS-stimulated mouse RAW264.7 cells	2008	Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20	Aldehydic components of cinnamon bark extract suppresses RANKL-induced osteoclastogenesis through NFATc1 downregulation.
AID1082480	Nematicidal activity against second juvenile stage (J2) of Meloidogyne incognita (root-knot nematode) assessed as mortality incubated in the dark at 28 degC after 3 days by light microscopy (benficial crop Tomato)	2011	Journal of agricultural and food chemistry, Oct-26, Volume: 59, Issue:20	Nematicidal and antifungal activities of annonaceous acetogenins from Annona squamosa against various plant pathogens.
AID1272752	Antifungal activity against Penicillium citrinum at 0.06 mol/L after 2 to 4 days by paper disc method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.
AID329103	Activation of mouse TRPA1 C422S mutant expressed in CHO cells at 100 uM by calcium imaging FLIPR assay	2007	Nature, Feb-01, Volume: 445, Issue:7127	Noxious compounds activate TRPA1 ion channels through covalent modification of cysteines.
AID1628114	Inhibition of Escherichia coli FtsZ assessed as reduction in GTPase activity by malachite green assay	2016	Journal of medicinal chemistry, Aug-11, Volume: 59, Issue:15	Targeting the Bacterial Division Protein FtsZ.
AID1272749	Antifungal activity against Aspergillus niger at 0.03 mol/L after 2 to 4 days by paper disc method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.
AID1628120	Inhibition of Escherichia coli FtsZ assessed as reduction in polymerization by light scattering method	2016	Journal of medicinal chemistry, Aug-11, Volume: 59, Issue:15	Targeting the Bacterial Division Protein FtsZ.
AID592088	Antihemorrhagic activity in ddY mouse assessed as inhibition of Protobothrops flavoviridis venom-induced hemorrhage incubated with compound for 10 mins measured after 24 hrs	2011	Bioorganic & medicinal chemistry, Apr-01, Volume: 19, Issue:7	Contribution of cinnamic acid analogues in rosmarinic acid to inhibition of snake venom induced hemorrhage.
AID385770	Induction of neurogenic inflammation in rat esophagus assessed as substance P release per 20 mins at 50 uM in calcium free medium	2007	Proceedings of the National Academy of Sciences of the United States of America, Aug-14, Volume: 104, Issue:33	4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1.
AID1201465	Antimicrobial activity against Escherichia coli relative to control	2015	European journal of medicinal chemistry, May-05, Volume: 95	Advances in the discovery of novel antimicrobials targeting the assembly of bacterial cell division protein FtsZ.
AID1201463	Inhibition of Escherichia coli FtsZ polymerization	2015	European journal of medicinal chemistry, May-05, Volume: 95	Advances in the discovery of novel antimicrobials targeting the assembly of bacterial cell division protein FtsZ.
AID1100922	Insecticidal activity against Mechoris ursulus assessed as mortality at 2.5 mg/paper at 25 +/- 1 degC measured after 48 hr by filter paper diffusion method	2000	Journal of agricultural and food chemistry, Jun, Volume: 48, Issue:6	Insecticidal and fumigant activities of Cinnamomum cassia bark-derived materials against Mechoris ursulus (Coleoptera: attelabidae).
AID1326317	Antimicrobial activity against vancomycin-resistant Enterococcus faecalis after 18 hrs by broth microdilution method	2016	Bioorganic & medicinal chemistry, 12-15, Volume: 24, Issue:24	Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.
AID642415	Estrogenic activity at ERalpha in human MVLN cells at 20 ug/mL after 24 hrs by luciferase reporter gene assay relative to E2	2012	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1	Discovery of estrogen receptor α modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells.
AID1201467	Antimicrobial activity against Bacillus subtilis	2015	European journal of medicinal chemistry, May-05, Volume: 95	Advances in the discovery of novel antimicrobials targeting the assembly of bacterial cell division protein FtsZ.
AID385779	Induction of neurogenic inflammation in rat dorsal spinal cord assessed as CGRP release per 20 mins at 10 uM in calcium free medium	2007	Proceedings of the National Academy of Sciences of the United States of America, Aug-14, Volume: 104, Issue:33	4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1.
AID403340	Inhibition of COX2	2005	Journal of natural products, Jul, Volume: 68, Issue:7	Expanding the ChemGPS chemical space with natural products.
AID1326319	Antibacterial activity against Klebsiella pneumoniae ATCC BAA-1144 after 18 hrs by broth microdilution method	2016	Bioorganic & medicinal chemistry, 12-15, Volume: 24, Issue:24	Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.
AID1272748	Antifungal activity against Aspergillus niger at 0.06 mol/L after 2 to 4 days by paper disc method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.
AID1191756	Inhibition of human purified MPG pre-incubated with compound for 10 mins followed by addition of 1,N6 ethenoadenine containing 32P-labeled duplex oligonucleotide substrates at 20 uM by gel-based excision activity assay	2015	Bioorganic & medicinal chemistry, Mar-01, Volume: 23, Issue:5	Naturally occurring polyphenol, morin hydrate, inhibits enzymatic activity of N-methylpurine DNA glycosylase, a DNA repair enzyme with various roles in human disease.
AID1272758	Antibacterial activity against Staphylococcus aureus at 0.25 mol/L after 12 to 24 hrs by paper disc method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.
AID1082482	Nematicidal activity against second juvenile stage (J2) of Meloidogyne incognita (root-knot nematode) assessed as mortality incubated in the dark at 28 degC after 1 day by light microscopy (benficial crop Tomato)	2011	Journal of agricultural and food chemistry, Oct-26, Volume: 59, Issue:20	Nematicidal and antifungal activities of annonaceous acetogenins from Annona squamosa against various plant pathogens.
AID385773	Induction of neurogenic inflammation in rat dorsal spinal cord assessed as substance P release per 20 mins at 10 uM in calcium free medium	2007	Proceedings of the National Academy of Sciences of the United States of America, Aug-14, Volume: 104, Issue:33	4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1.
AID1755486	Drug excretion in human urine at 0.7 mg/kg, po measured after 8 to 24 hrs	2020	Journal of medicinal chemistry, 12-10, Volume: 63, Issue:23	Curse or Cure? A Perspective on the Developability of Aldehydes as Active Pharmaceutical Ingredients.
AID1167300	Antioxidant activity assessed as DPPH radical scavenging activity incubated at room temperature for 20 mins by UV-visible spectrophotometry	2014	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 24, Issue:21	Design, synthesis and exploring the quantitative structure-activity relationship of some antioxidant flavonoid analogues.
AID1549805	Agonist activity at human TRPA1 Cys261Ala mutant expressed in HEK293 cells assessed as Ca2+ influx at 30 uM by fluorescence assay	2019	European journal of medicinal chemistry, May-15, Volume: 170	N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites.
AID1120509	Increase in bacterial membrane permeability in Bacillus subtilis subsp. subtilis str. 168 at 1 times MIC pre-treated for 5 mins and measured 30 mins post dye addition by propidium iodide dye based flow cytometry	2013	MedChemComm, Jan-01, Volume: 4, Issue:1	Inhibitors of bacterial tubulin target bacterial membranes
AID1272759	Antibacterial activity against Staphylococcus aureus at 0.13 mol/L after 12 to 24 hrs by paper disc method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.
AID1272760	Antibacterial activity against Staphylococcus aureus at 0.06 mol/L after 12 to 24 hrs by paper disc method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.
AID1326306	Antibacterial activity against Escherichia coli ATCC 25922 after 18 hrs by broth microdilution method	2016	Bioorganic & medicinal chemistry, 12-15, Volume: 24, Issue:24	Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.
AID1184716	Negative allosteric modulation of recombinant HA-tagged GB1 subunit/Flag-tagged GB2 subunit receptor (unknown origin) expressed in HEK293 cells co-expressing Gqi9 G-protein assessed as inhibition of GABA-induced IP production at 100 uM by liquid scintilla	2014	ACS medicinal chemistry letters, Jul-10, Volume: 5, Issue:7	Discovery of a Negative Allosteric Modulator of GABAB Receptors.
AID329104	Activation of mouse TRPA1 C622S mutant expressed in CHO cells at 100 uM by calcium imaging FLIPR assay	2007	Nature, Feb-01, Volume: 445, Issue:7127	Noxious compounds activate TRPA1 ion channels through covalent modification of cysteines.
AID1100921	Insecticidal activity against Mechoris ursulus assessed as mortality at 1 mg/paper at 25 +/- 1 degC measured after 48 hr by filter paper diffusion method	2000	Journal of agricultural and food chemistry, Jun, Volume: 48, Issue:6	Insecticidal and fumigant activities of Cinnamomum cassia bark-derived materials against Mechoris ursulus (Coleoptera: attelabidae).
AID1469806	Cysteamine reactivity of the compound in TRIS-HCL assessed as second order rate constant at 40 uM and pH 7.4	2017	Journal of medicinal chemistry, 02-09, Volume: 60, Issue:3	Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions.
AID1120502	Protonophore activity in Bacillus subtilis subsp. subtilis str. 168 assessed as induction of rapid equlibration of delta-pH at 1 times MIC	2013	MedChemComm, Jan-01, Volume: 4, Issue:1	Inhibitors of bacterial tubulin target bacterial membranes
AID349480	Inhibition of bone resorption by mature osteoclast in RANKL-stimulated mouse RAW264.7 cells pretreated for 1 hr measured after 8 days	2008	Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20	Aldehydic components of cinnamon bark extract suppresses RANKL-induced osteoclastogenesis through NFATc1 downregulation.
AID385774	Induction of neurogenic inflammation in rat dorsal spinal cord assessed as CGRP peptide release per 20 mins at 10 uM	2007	Proceedings of the National Academy of Sciences of the United States of America, Aug-14, Volume: 104, Issue:33	4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1.
AID349478	Inhibition of NFATc1 expression in RANKL-stimulated mouse RAW264.7 cells after 48 hrs by immunoblotting	2008	Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20	Aldehydic components of cinnamon bark extract suppresses RANKL-induced osteoclastogenesis through NFATc1 downregulation.
AID1439502	Antiparasitic activity against L3 and L4 larval stages of Ascaris suum	2017	European journal of medicinal chemistry, Mar-31, Volume: 129	Medicinal plants used as anthelmintics: Ethnomedical, pharmacological, and phytochemical studies.
AID385772	Induction of neurogenic inflammation in capsaicin desensitized rat dorsal spinal cord assessed as CGRP peptide release per 20 mins at 10 uM	2007	Proceedings of the National Academy of Sciences of the United States of America, Aug-14, Volume: 104, Issue:33	4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1.
AID1201468	Antimicrobial activity against Escherichia coli	2015	European journal of medicinal chemistry, May-05, Volume: 95	Advances in the discovery of novel antimicrobials targeting the assembly of bacterial cell division protein FtsZ.
AID1204253	Antibacterial activity against Bacillus subtilis	2015	European journal of medicinal chemistry, Jun-05, Volume: 97	Design, synthesis and antibacterial activity of cinnamaldehyde derivatives as inhibitors of the bacterial cell division protein FtsZ.
AID1100923	Insecticidal activity against Mechoris ursulus assessed as mortality at 5 mg/paper at 25 +/- 1 degC measured after 48 hr by filter paper diffusion method	2000	Journal of agricultural and food chemistry, Jun, Volume: 48, Issue:6	Insecticidal and fumigant activities of Cinnamomum cassia bark-derived materials against Mechoris ursulus (Coleoptera: attelabidae).
AID377982	Antimutagenic activity in Salmonella Typhimurium TA100 assessed as inhibition of ethyl methanesulfonate-induced mutation at 25 ug/mL treated for 30 mins and measured after 2 days by modified Ames test	1999	Journal of natural products, Jan, Volume: 62, Issue:1	Structure-antimutagenic activity relationship study of plicatin B.
AID174708	Gastric cytoprotective activity in male wistar rat	1997	Journal of medicinal chemistry, Jun-06, Volume: 40, Issue:12	Structure-cytoprotective activity relationship of simple molecules containing an alpha,beta-unsaturated carbonyl system.
AID1272750	Antifungal activity against Penicillium citrinum at 0.25 mol/L after 2 to 4 days by paper disc method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.
AID386015	Induction of neurogenic inflammation in rat esophagus assessed as CGRP release per 20 mins at 50 uM in in calcium free medium	2007	Proceedings of the National Academy of Sciences of the United States of America, Aug-14, Volume: 104, Issue:33	4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1.
AID386013	Induction of neurogenic inflammation in capsaicin desensitized rat esophagus assessed as substance P release per 20 mins at 50 uM	2007	Proceedings of the National Academy of Sciences of the United States of America, Aug-14, Volume: 104, Issue:33	4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1.
AID1517970	Inhibition of human FBPase expressed in Escherichia coli BL21 (DE3) at 500 uM using FBP as substrate incubated for 5 mins by malachite green dye based spectrophotometry relative to control	2019	European journal of medicinal chemistry, Dec-15, Volume: 184	Discovery of novel allosteric site and covalent inhibitors of FBPase with potent hypoglycemic effects.
AID1628115	Antimicrobial activity against Bacillus subtilis	2016	Journal of medicinal chemistry, Aug-11, Volume: 59, Issue:15	Targeting the Bacterial Division Protein FtsZ.
AID1204252	Antibacterial activity against Escherichia coli	2015	European journal of medicinal chemistry, Jun-05, Volume: 97	Design, synthesis and antibacterial activity of cinnamaldehyde derivatives as inhibitors of the bacterial cell division protein FtsZ.
AID336478	Inhibition of COX2 at 100 uM by scintillation proximity assay	2002	Journal of natural products, Nov, Volume: 65, Issue:11	Screening of ubiquitous plant constituents for COX-2 inhibition with a scintillation proximity based assay.
AID1326318	Antimicrobial activity against vancomycin-sensitive Enterococcus faecalis after 18 hrs by broth microdilution method	2016	Bioorganic & medicinal chemistry, 12-15, Volume: 24, Issue:24	Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.
AID1272757	Antibacterial activity against Escherichia coli at 0.03 mol/L after 12 to 24 hrs by paper disc method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.
AID1120500	Induction of membrane associated proteins mislocalization in Bacillus subtilis subsp. subtilis str. 168 assessed as reduction in GFP-MinD protein localization by fluorescence assay	2013	MedChemComm, Jan-01, Volume: 4, Issue:1	Inhibitors of bacterial tubulin target bacterial membranes
AID1628117	Antimicrobial activity against Escherichia coli	2016	Journal of medicinal chemistry, Aug-11, Volume: 59, Issue:15	Targeting the Bacterial Division Protein FtsZ.
AID1326323	Antibacterial activity against Escherichia coli by broth dilution method	2016	Bioorganic & medicinal chemistry, 12-15, Volume: 24, Issue:24	Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.
AID1272746	Antifungal activity against Aspergillus niger at 0.25 mol/L after 2 to 4 days by paper disc method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.
AID1272761	Antibacterial activity against Staphylococcus aureus at 0.03 mol/L after 12 to 24 hrs by paper disc method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.
AID1326320	Antibacterial activity against methicillin-sensitive Staphylococcus aureus after 18 hrs by broth microdilution method	2016	Bioorganic & medicinal chemistry, 12-15, Volume: 24, Issue:24	Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.
AID647545	Inhibition of beta (1,3) glucan synthase in Candida albicans cell membrane using UDP-Glc as substrate assessed as aniline blue-glucan complex formation by microtiter-based fluorescence method	2012	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 22, Issue:3	Novel dendrimeric lipopeptides with antifungal activity.
AID1272751	Antifungal activity against Penicillium citrinum at 0.13 mol/L after 2 to 4 days by paper disc method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.
AID1201464	Antimicrobial activity against Bacillus subtilis relative to control	2015	European journal of medicinal chemistry, May-05, Volume: 95	Advances in the discovery of novel antimicrobials targeting the assembly of bacterial cell division protein FtsZ.
AID762798	Inhibition of Wnt/beta-catenin (unknown origin) signaling pathway expressed in HEK293 cells assessed as inhibition of TCF4 transcriptional activity at 5 to 40 uM after 24 hrs by TOPflash reporter gene assay	2013	Journal of natural products, Jul-26, Volume: 76, Issue:7	Antitumor activity of 2-hydroxycinnamaldehyde for human colon cancer cells through suppression of β-catenin signaling.
AID500219	Agonist activity at TRPA1	2005	Nature chemical biology, Jul, Volume: 1, Issue:2	Sensing with TRP channels.
AID1201462	Inhibition of Escherichia coli FtsZ GTPase activity	2015	European journal of medicinal chemistry, May-05, Volume: 95	Advances in the discovery of novel antimicrobials targeting the assembly of bacterial cell division protein FtsZ.
AID1581189	Agonist activity at human TRPA1 expressed in HEK293 cells assessed as increase in calcium influx at 100 uM incubated for 1 min by Fluo-4-AM dye based FLIPR assay	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Discovery of Nonpungent Transient Receptor Potential Vanilloid 1 (TRPV1) Agonist as Strong Topical Analgesic.
AID385771	Induction of neurogenic inflammation in rat esophagus assessed as substance P release per 20 mins at 50 uM	2007	Proceedings of the National Academy of Sciences of the United States of America, Aug-14, Volume: 104, Issue:33	4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1.
AID1549782	Agonist activity at mouse TRPA1 expressed in CHO cells assessed as increase in calcium influx by Fluo-3 based FLIPR analysis	2019	European journal of medicinal chemistry, May-15, Volume: 170	N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites.
AID349479	Inhibition of multinucleated cell formation in RANKL-stimulated mouse RAW264.7 cells at 0.5 to 2 uM after 3 days by TRAP staining	2008	Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20	Aldehydic components of cinnamon bark extract suppresses RANKL-induced osteoclastogenesis through NFATc1 downregulation.
AID1326325	Antibacterial activity against methicillin-resistant Staphylococcus aureus by broth dilution method	2016	Bioorganic & medicinal chemistry, 12-15, Volume: 24, Issue:24	Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.
AID1272753	Antifungal activity against Penicillium citrinum at 0.03 mol/L after 2 to 4 days by paper disc method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.
AID1272747	Antifungal activity against Aspergillus niger at 0.13 mol/L after 2 to 4 days by paper disc method	2016	Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3	Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.
AID1628121	Binding affinity to Escherichia coli FtsZ	2016	Journal of medicinal chemistry, Aug-11, Volume: 59, Issue:15	Targeting the Bacterial Division Protein FtsZ.
AID1296008	Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening	2020	SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1	Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986	P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987	P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID504810	Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812	Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID1347086	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1347082	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347083	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1346567	Mouse TRPA1 (Transient Receptor Potential channels)	2004	Neuron, Mar-25, Volume: 41, Issue:6	Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	57 (4.35)	18.7374
1990's	71 (5.42)	18.2507
2000's	222 (16.95)	29.6817
2010's	625 (47.71)	24.3611
2020's	335 (25.57)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	34 (2.54%)	5.53%
Reviews	46 (3.44%)	6.00%
Case Studies	27 (2.02%)	4.05%
Observational	0 (0.00%)	0.25%
Other	1,230 (92.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Trial	Enrollment	Study Type	Start Date	Status
In-vivo Effects of E-cigarette Aerosol on Innate Lung Host Defense [NCT03700892]	19 participants (Actual)	Interventional	2018-10-19	Terminated(stopped due to Covid-19 has been shown to increase risk associated with vaping. To increase participant safety and use real world vaping habits, the investigators plan to continue studying vaping effects on the airways in an observational format.)
Characterization of the Toll-like Receptor 7-agonist Imiquimod 3.75% as a New Surrogate Model of Itch [NCT03943407]	0 participants (Actual)	Interventional	2019-11-30	Withdrawn(stopped due to The Imiquimod 3.75% was ineffective)
Temporal Profile of the Nociceptive Desensitization Induced by 8% Topical Capsaicin and the Functional Independence of Transient Receptor Potential Ankyrin 1 (TPRA1)- and Vanilloid 1 (TRPV1)-Expressing Nociceptive Afferents [NCT03132142]	22 participants (Anticipated)	Interventional	2017-04-30	Recruiting
The Role of Transient Receptor Potential Channels in Chemotherapy-Induced Peripheral Neuropathic Pain. [NCT04415892]	240 participants (Anticipated)	Interventional	2019-10-01	Recruiting
Subacute Effect of Pharmacological Sensory Stimulation of the Oropharynx by Agonists of TRP Receptors in Swallowing Neurophysiology in the Elderly With Oropharyngeal Dysphagia. [NCT04741620]	150 participants (Actual)	Interventional	2019-01-17	Completed
The Effect of Capsaicin and Cinnamaldehyde on Intestinal Permeability, Gallbladder Motility and Satiety [NCT01667523]	13 participants (Actual)	Interventional	2011-02-28	Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial	Outcome
NCT03700892 (4) [back to overview]	Absolute Values of Whole Lung MCC for Each Group
NCT03700892 (4) [back to overview]	CA-induced Changes in Whole Lung MCC
NCT03700892 (4) [back to overview]	Percent Polymorphonuclear Leukocytes (PMN) in Induced Sputum
NCT03700892 (4) [back to overview]	CA-induced Changes in Regional Lung MCC

Intervention	percent clearance (Mean)
E-cigarette Users	17
Non-smoker/Non-vaper Healthy Controls	14

Intervention	percent clearance (Mean)
Cinnamaldehyde	41
PG/VG	27

Intervention	percent PMN (Mean)
Cinnamaldehyde	3.6
PG/VG	89.4

Intervention	percent clearance (Mean)
	Central Lung	Peripheral Lung
Cinnamaldehyde	43	33
PG/VG	25	24

Substance	Relationship Strength	Studies	Trials	Classes	Roles
dinitrochlorobenzene Dinitrochlorobenzene: A skin irritant that may cause dermatitis of both primary and allergic types. Contact sensitization with DNCB has been used as a measure of cellular immunity. DNCB is also used as a reagent for the detection and determination of pyridine compounds.. 1-chloro-2,4-dinitrobenzene : A C-nitro compound that is chlorobenzene carrying a nitro substituent at each of the 2- and 4-positions.	3.91	12	0	C-nitro compound; monochlorobenzenes	allergen; epitope; sensitiser
protocatechuic acid protocatechuic acid: RN given refers to parent cpd; structure. 3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.	3.88	3	0	catechols; dihydroxybenzoic acid	antineoplastic agent; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; human xenobiotic metabolite; plant metabolite
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	3.08	4	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
4-hydroxybenzaldehyde [no description available]	2.21	1	0	hydroxybenzaldehyde	EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor; mouse metabolite; plant metabolite
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	3.71	9	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	2.83	3	0	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	3	4	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
adipic acid adipic acid : An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.	2.25	1	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	food acidity regulator; human xenobiotic metabolite
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	3.85	2	1	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
benzaldehyde [no description available]	9.19	16	0	benzaldehydes	EC 3.1.1.3 (triacylglycerol lipase) inhibitor; EC 3.5.5.1 (nitrilase) inhibitor; flavouring agent; fragrance; odorant receptor agonist; plant metabolite
benzene [no description available]	2.03	1	0	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
benzoic acid Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.	3.93	13	0	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
benzyl alcohol Benzyl Alcohol: A colorless liquid with a sharp burning taste and slight odor. It is used as a local anesthetic and to reduce pain associated with LIDOCAINE injection. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutic aid, and in perfumery and flavoring.. hydroxytoluene : Any member of the class of toluenes carrying one or more hydroxy substituents.. benzyl alcohol : An aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.. aromatic alcohol : Any alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.. aromatic primary alcohol : Any primary alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.	2.03	1	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	2.48	2	0	halide anion; monoatomic bromine
2,3-butylene glycol 2,3-butylene glycol: RN given refers to cpd without isomeric designation. butane-2,3-diol : A butanediol in which hydroxylation is at C-2 and C-3.	2.15	1	0	butanediol; glycol; secondary alcohol
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	2.03	1	0	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	3.48	1	1	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	11.61	8	2	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	3.36	6	0	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.9	2	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	2.25	1	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	11.19	16	0	coumarins	fluorescent dye; human metabolite; plant metabolite
cuminaldehyde cuminaldehyde : A member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities.	8.12	4	0	benzaldehydes	insecticide; plant metabolite; volatile oil component
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	3.96	3	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	3.78	10	0	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant metabolite
hydrogen sulfide Hydrogen Sulfide: A flammable, poisonous gas with a characteristic odor of rotten eggs. It is used in the manufacture of chemicals, in metallurgy, and as an analytical reagent. (From Merck Index, 11th ed). hydrogen sulfide : A sulfur hydride consisting of a single sulfur atom bonded to two hydrogen atoms. A highly poisonous, flammable gas with a characteristic odour of rotten eggs, it is often produced by bacterial decomposition of organic matter in the absence of oxygen.. thiol : An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.	9.71	6	1	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
4-aminophenol 4-aminophenol: RN given refers to parent cpd. 4-aminophenol : An amino phenol (one of the three possible isomers) which has the single amino substituent located para to the phenolic -OH group.	2.11	1	0	aminophenol	allergen; metabolite
trimethylenediamine trimethylenediamine: RN given refers to parent cpd; structure. trimethylenediamine : An alkane-alpha,omega-diamine comprising a propane skeleton with amino substituents at positions 1 and 3.	2.08	1	0	alkane-alpha,omega-diamine	human metabolite; mouse metabolite; reagent
hippuric acid hippuric acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #4591. N-benzoylglycine : An N-acylglycine in which the acyl group is specified as benzoyl.	3.76	3	0	N-acylglycine	human blood serum metabolite; uremic toxin
propionaldehyde propionaldehyde: may cause respiratory irritation; RN given refers to parent cpd; structure. propanal : An aldehyde that consists of ethane bearing a formyl substituent. The parent of the class of propanals.	2.03	1	0	alpha-CH2-containing aldehyde; propanals	Escherichia coli metabolite
4-nitrobenzaldehyde 4-nitrobenzaldehyde: RN given refers to parent cpd. 4-nitrobenzaldehyde : A C-nitro compound that is benzaldehyde substituted at the para-position with a nitro group.	2.49	2	0	benzaldehydes; C-nitro compound
fosmidomycin fosmidomycin: from Streptomyces lavendulae; RN given refers to parent cpd; structure in second source. fosmidomycin : Propylphosphonic acid in which one of the hydrogens at position 3 is substituted by a formyl(hydroxy)amino group. An antibiotic obtained from Streptomyces lavendulae, it specifically inhibits DXP reductoisomerase (EC 1.1.1.267), a key enzyme in the non-mevalonate pathway of isoprenoid biosynthesis.	2.06	1	0	hydroxamic acid; phosphonic acids	antimicrobial agent; bacterial metabolite; EC 1.1.1.267 (1-deoxy-D-xylulose-5-phosphate reductoisomerase) inhibitor
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	8.46	7	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
3,4-dihydrocoumarin melilotol: structure in first source. 3,4-dihydrocoumarin : A chromanone that is the 3,4-dihydro derivative of coumarin.	1.99	1	0	chromanone	plant metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	3.23	6	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	4.6	8	0	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
glycine [no description available]	2.75	3	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	7.81	3	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
hydrogen carbonate Bicarbonates: Inorganic salts that contain the -HCO3 radical. They are an important factor in determining the pH of the blood and the concentration of bicarbonate ions is regulated by the kidney. Levels in the blood are an index of the alkali reserve or buffering capacity.. hydrogencarbonate : The carbon oxoanion resulting from the removal of a proton from carbonic acid.	2.31	1	0	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
histamine [no description available]	4.49	4	1	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	7.76	3	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	2.43	2	0	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
hydroxylamine amino alcohol : An alcohol containing an amino functional group in addition to the alcohol-defining hydroxy group.	2.08	1	0	hydroxylamines	algal metabolite; bacterial xenobiotic metabolite; EC 1.1.3.13 (alcohol oxidase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor; nitric oxide donor; nucleophilic reagent
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	2.04	1	0	imidazole
indole [no description available]	2.03	1	0	indole; polycyclic heteroarene	Escherichia coli metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	2.08	1	0	diatomic iodine	nutrient
pipecolic acid pipecolic acid: RN given refers to cpd without isomeric designation. pipecolic acid : A piperidinemonocarboxylic acid in which the carboxy group is located at position C-2.. pipecolate : A piperidinecarboxylate that is the conjugate base of pipecolic acid.	2.01	1	0	piperidinemonocarboxylic acid
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	2.99	4	0	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	4.92	8	1	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	8.42	7	0	metal allergen; nickel group element atom	epitope; micronutrient
niacin Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.	2.01	1	0	pyridine alkaloid; pyridinemonocarboxylic acid; vitamin B3	antidote; antilipemic drug; EC 3.5.1.19 (nicotinamidase) inhibitor; Escherichia coli metabolite; human urinary metabolite; metabolite; mouse metabolite; plant metabolite; vasodilator agent
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.03	1	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitric acid Nitric Acid: Nitric acid (HNO3). A colorless liquid that is used in the manufacture of inorganic and organic nitrates and nitro compounds for fertilizers, dye intermediates, explosives, and many different organic chemicals. Continued exposure to vapor may cause chronic bronchitis; chemical pneumonitis may occur. (From Merck Index, 11th ed). nitric acid : A nitrogen oxoacid of formula HNO3 in which the nitrogen atom is bonded to a hydroxy group and by equivalent bonds to the remaining two oxygen atoms.	2.1	1	0	nitrogen oxoacid	protic solvent; reagent
nitroxyl nitroxyl: hydroxamic acid oxidized to nitroxyl free radical. nitroxyl : A nitrogen oxoacid consisting of an oxygen atom double-bonded to an NH group.	2.08	1	0	nitrogen oxoacid
1-octanol 1-Octanol: A colorless, slightly viscous liquid used as a defoaming or wetting agent. It is also used as a solvent for protective coatings, waxes, and oils, and as a raw material for plasticizers. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). octan-1-ol : An octanol carrying the hydroxy group at position 1.	1.98	1	0	octanol; primary alcohol	antifungal agent; bacterial metabolite; fuel additive; kairomone; plant metabolite
oxalic acid Oxalic Acid: A strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent.. oxalic acid : An alpha,omega-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2.	2.13	1	0	alpha,omega-dicarboxylic acid	algal metabolite; human metabolite; plant metabolite
4-aminobenzoic acid 4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.	2.03	1	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
phenol [no description available]	2.21	1	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phenylacetaldehyde [no description available]	2.61	2	0	alpha-CH2-containing aldehyde; phenylacetaldehydes	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
propylene glycol Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.	3.09	4	0	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
1-propanol 1-Propanol: A colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate.. propan-1-ol : The parent member of the class of propan-1-ols that is propane in which a hydrogen of one of the methyl groups is replaced by a hydroxy group.	4.87	11	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	2.41	2	0	saturated fatty acid; short-chain fatty acid	antifungal drug
pteridines [no description available]	2.05	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; pteridines
pyridoxal [no description available]	3.35	1	0	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; pyridinecarbaldehyde; vitamin B6	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyridoxine 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol: structure in first source. vitamin B6 : Any member of the group of pyridines that exhibit biological activity against vitamin B6 deficiency. Vitamin B6 deficiency is associated with microcytic anemia, electroencephalographic abnormalities, dermatitis with cheilosis (scaling on the lips and cracks at the corners of the mouth) and glossitis (swollen tongue), depression and confusion, and weakened immune function. Vitamin B6 consists of the vitamers pyridoxine, pyridoxal, and pyridoxamine and their respective 5'-phosphate esters (and includes their corresponding ionized and salt forms).	3.35	1	0	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; vitamin B6	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyrogallol benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.	2.72	3	0	benzenetriol; phenolic donor	plant metabolite
pyruvic acid Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.	2.41	1	0	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
sulfites Sulfites: Inorganic salts of sulfurous acid.. sulfites : Any sulfurous acid derivative that is a salt or an ester of sulfurous acid.. organosulfonate oxoanion : An organic anion obtained by deprotonation of the sufonate group(s) of any organosulfonic acid.. sulfite : A sulfur oxoanion that is the conjugate base of hydrogen sulfite (H2SO3).	2.25	1	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	2.25	1	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
sulfur dioxide Sulfur Dioxide: A highly toxic, colorless, nonflammable gas. It is used as a pharmaceutical aid and antioxidant. It is also an environmental air pollutant.	2.03	1	0	sulfur oxide	Escherichia coli metabolite; food bleaching agent; refrigerant
taurine [no description available]	2.13	1	0	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	2.39	2	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	7.5	2	0	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	2.05	1	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
vanillin Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).	5.07	13	0	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
isopentenyl pyrophosphate isopentenyl pyrophosphate: substrate for isopentenyl pyrophosphate isomerase; RN given refers to unlabeled cpd; a nonpeptide mycobacterial antigen that stimulates gamma delta T cells. isopentenyl diphosphate : A prenol phosphate comprising 3-methylbut-3-en-1-ol having an O-diphosphate substituent.	2.06	1	0	prenol phosphate	antigen; antioxidant; epitope; Escherichia coli metabolite; mouse metabolite; phosphoantigen
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	11.73	38	6	p-menthane monoterpenoid; secondary alcohol	volatile oil component
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	2.05	1	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
beta-resorcylic acid beta-resorcylic acid: RN given refers to parent cpd; structure	2.78	3	0
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine: mutagen from fried ground beef; structure given in first source. PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, amino, and phenyl groups, respectively. It is the most abundant of the mutagenic heterocyclic amines found in cooked meat and fish.	1.99	1	0	imidazopyridine; primary amino compound	carcinogenic agent; mutagen
2-aminoethoxydiphenyl borate 2-aminoethoxydiphenyl borate: is a novel membrane-penetrable modulator and transient receptor potential channel blocker; structure in first source; do not confuse with 2-APB cpd. 2-aminoethoxydiphenylborane : An organoboron compound that is diphenylborane in which the borane hydrogen is replaced by a 2-aminoethoxy group.	3.12	1	0	organoboron compound; primary amino compound	calcium channel blocker; IP3 receptor antagonist; potassium channel opener
oxyquinoline Oxyquinoline: An antiseptic with mild fungistatic, bacteriostatic, anthelmintic, and amebicidal action. It is also used as a reagent and metal chelator, as a carrier for radio-indium for diagnostic purposes, and its halogenated derivatives are used in addition as topical anti-infective agents and oral antiamebics.. quinolin-8-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes.	2.25	1	0	monohydroxyquinoline	antibacterial agent; antifungal agrochemical; antiseptic drug; iron chelator
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	3	4	0	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
acetazolamide Acetazolamide: One of the CARBONIC ANHYDRASE INHIBITORS that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)	2.41	1	0	monocarboxylic acid amide; sulfonamide; thiadiazoles	anticonvulsant; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor
theophylline [no description available]	2.01	1	0	dimethylxanthine	adenosine receptor antagonist; anti-asthmatic drug; anti-inflammatory agent; bronchodilator agent; drug metabolite; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; fungal metabolite; human blood serum metabolite; immunomodulator; muscle relaxant; vasodilator agent
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	8.39	7	0	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
aurintricarboxylic acid Aurintricarboxylic Acid: A dye which inhibits protein biosynthesis at the initial stages. The ammonium salt (aluminon) is a reagent for the colorimetric estimation of aluminum in water, foods, and tissues.. aurintricarboxylic acid : A member of the class of quinomethanes that is 3-methylidene-6-oxocyclohexa-1,4-diene-1-carboxylic acid in which the methylidene hydrogens are replaced by 4-carboxy-3-hydroxyphenyl groups. The trisodium salt is the biological stain 'chrome violet CG' while the triammonium salt is 'aluminon'.	2.11	1	0	monohydroxybenzoic acid; quinomethanes; tricarboxylic acid	fluorochrome; histological dye; insulin-like growth factor receptor 1 antagonist
azelastine azelastine: azeptin is azelastine hydrochloride; structure; eye drop formulation effective in relieving symptoms of allergic conjunctivitis; do not confuse with 5-loxin which is an extract of Boswellia. azelastine : A phthalazine compound having an oxo substituent at the 1-position, a 1-methylazepan-4-yl group at the 2-position and a 4-chlorobenzyl substituent at the 4-position.	2.13	1	0	monochlorobenzenes; phthalazines; tertiary amino compound	anti-allergic agent; anti-asthmatic drug; bronchodilator agent; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; H1-receptor antagonist; platelet aggregation inhibitor
bay-k-8644 3-Pyridinecarboxylic acid, 1,4-dihydro-2,6-dimethyl-5-nitro-4-(2-(trifluoromethyl)phenyl)-, Methyl ester: A dihydropyridine derivative, which, in contrast to NIFEDIPINE, functions as a calcium channel agonist. The compound facilitates Ca2+ influx through partially activated voltage-dependent Ca2+ channels, thereby causing vasoconstrictor and positive inotropic effects. It is used primarily as a research tool.. Bay-K-8644 : A racemate comprising equimolar amounts of (R)- and (S)-Bay-K-8644. methyl 2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylate : A pentasubstituted dihydropyridine carrying methoxycarbonyl, 2-(trifluoromethyl)phenyl and nitro substituents at positions 3, 4 and 5 respectively as well as two methyl substituents at positions 2 and 6.	3.15	1	0	(trifluoromethyl)benzenes; C-nitro compound; dihydropyridine; methyl ester
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	2.15	1	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
benzocaine Benzocaine: A surface anesthetic that acts by preventing transmission of impulses along NERVE FIBERS and at NERVE ENDINGS.. dextran sulfate sodium : An organic sodium salt of dextran sulfate. It induces colitis in mice.. benzocaine : A benzoate ester having 4-aminobenzoic acid as the acid component and ethanol as the alcohol component. A surface anaesthetic, it is used to suppress the gag reflex, and as a lubricant and topical anaesthetic on the larynx, mouth, nasal cavity, respiratory tract, oesophagus, rectum, urinary tract, and vagina.	2.66	3	0	benzoate ester; substituted aniline	allergen; antipruritic drug; sensitiser; topical anaesthetic
benzyl isothiocyanate benzyl isothiocyanate: inhibits carcinogen-induced neoplasia; structure in Negwer, 5th ed, #715; also promotes urinary bladder carcinoma	3.61	2	0	benzenes; isothiocyanate	antibacterial drug
berberine [no description available]	5.5	11	0	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
caffeine [no description available]	2.4	2	0	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
camphor, (+-)-isomer [no description available]	3.69	9	0	bornane monoterpenoid; cyclic monoterpene ketone	plant metabolite
carbonyl cyanide m-chlorophenyl hydrazone Carbonyl Cyanide m-Chlorophenyl Hydrazone: A proton ionophore. It is commonly used as an uncoupling agent and inhibitor of photosynthesis because of its effects on mitochondrial and chloroplast membranes.. CCCP : A member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death.	2.51	2	0	hydrazone; monochlorobenzenes; nitrile	antibacterial agent; geroprotector; ionophore
celecoxib [no description available]	3.99	1	1	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug
cetyltrimethylammonium ion Cetrimonium: Cetyltrimethylammonium compound whose salts and derivatives are used primarily as topical antiseptics.. cetyltrimethylammonium ion : A quaternary ammonium ion in which the substituents on nitrogen are one hexadecyl and three methyl groups.	2.25	1	0	quaternary ammonium ion
cetylpyridinium Cetylpyridinium: Cationic bactericidal surfactant used as a topical antiseptic for skin, wounds, mucous membranes, instruments, etc.; and also as a component in mouthwash and lozenges.	2.1	1	0	pyridinium ion
eucalyptol [no description available]	4.85	10	0
ciprofloxacin Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.	2.84	3	0	aminoquinoline; cyclopropanes; fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone; zwitterion	antibacterial drug; antiinfective agent; antimicrobial agent; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; environmental contaminant; topoisomerase IV inhibitor; xenobiotic
4-cresol 4-cresol: RN given refers to parent cpd. p-cresol : A cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals.	2.04	1	0	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
dapi DAPI: RN given refers to parent cpd.	3.54	2	0	indoles	fluorochrome
nonivamide nonivamide: has effect on sensory neurons. nonivamide : A capsaicinoid that is the carboxamide resulting from the formal condensation of the amino group of 4-hydroxy-3-methoxybenzylamine with the carboxy group of nonanoic acid. It is the active ingredient in many pepper sprays.	2.15	1	0	capsaicinoid; phenols	lachrymator
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	2.46	2	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
dibucaine Dibucaine: A local anesthetic of the amide type now generally used for surface anesthesia. It is one of the most potent and toxic of the long-acting local anesthetics and its parenteral use is restricted to spinal anesthesia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1006). cinchocaine : A monocarboxylic acid amide that is the 2-(diethylamino)ethyl amide of 2-butoxyquinoline-4-carboxylic acid. One of the most potent and toxic of the long-acting local anesthetics, its parenteral use was restricted to spinal anesthesia. It is now generally only used (usually as the hydrochloride) in creams and ointments and in suppositories for temporary relief of pain and itching associated with skin and anorectal conditions.	1.97	1	0	aromatic ether; monocarboxylic acid amide; tertiary amino compound	topical anaesthetic
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	2.42	2	0	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
dichlorophen Dichlorophen: Nontoxic laxative vermicide effective for taenia infestation. It tends to produce colic and nausea. It is also used as a veterinary fungicide, anthelmintic, and antiprotozoan. (From Merck, 11th ed.)	2.08	1	0	bridged diphenyl fungicide; diarylmethane
disulfiram [no description available]	3.53	2	0	organic disulfide; organosulfur acaricide	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 3.1.1.1 (carboxylesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; ferroptosis inducer; fungicide; NF-kappaB inhibitor
doxepin Doxepin: A dibenzoxepin tricyclic compound. It displays a range of pharmacological actions including maintaining adrenergic innervation. Its mechanism of action is not fully understood, but it appears to block reuptake of monoaminergic neurotransmitters into presynaptic terminals. It also possesses anticholinergic activity and modulates antagonism of histamine H(1)- and H(2)-receptors.. doxepin : A dibenzooxepine that is 6,11-dihydrodibenzo[b,e]oxepine substituted by a 3-(dimethylamino)propylidene group at position 11. It is used as an antidepressant drug.	3.53	1	1	dibenzooxepine; tertiary amino compound	antidepressant
erythrosine Fluoresceins: A family of spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one derivatives. These are used as dyes, as indicators for various metals, and as fluorescent labels in immunoassays.	2.46	2	0
ethacrynic acid Ethacrynic Acid: A compound that inhibits symport of sodium, potassium, and chloride primarily in the ascending limb of Henle, but also in the proximal and distal tubules. This pharmacological action results in excretion of these ions, increased urinary output, and reduction in extracellular fluid. This compound has been classified as a loop or high ceiling diuretic.. etacrynic acid : An aromatic ether that is phenoxyacetic acid in which the phenyl ring is substituted by chlorines at positions 2 and 3, and by a 2-methylidenebutanoyl group at position 4. It is a loop diuretic used to treat high blood pressure resulting from diseases such as congestive heart failure, liver failure, and kidney failure. It is also a glutathione S-transferase (EC 2.5.1.18) inhibitor.	7.71	3	0	aromatic ether; aromatic ketone; dichlorobenzene; monocarboxylic acid	EC 2.5.1.18 (glutathione transferase) inhibitor; ion transport inhibitor; loop diuretic
etodolac Etodolac: A non-steroidal anti-inflammatory agent and cyclooxygenase-2 (COX-2) inhibitor with potent analgesic and anti-arthritic properties. It has been shown to be effective in the treatment of OSTEOARTHRITIS; RHEUMATOID ARTHRITIS; ANKYLOSING SPONDYLITIS; and in the alleviation of postoperative pain (PAIN, POSTOPERATIVE).. etodolac : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl moiety. A preferential inhibitor of cyclo-oxygenase 2 and non-steroidal anti-inflammatory, it is used for the treatment of rheumatoid arthritis and osteoarthritis, and for the alleviation of postoperative pain. Administered as the racemate, only the (S)-enantiomer is active.	3.99	1	1	monocarboxylic acid; organic heterotricyclic compound	antipyretic; cyclooxygenase 2 inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
fluconazole Fluconazole: Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS.. fluconazole : A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.	8.33	6	0	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
flufenamic acid Flufenamic Acid: An anthranilic acid derivative with analgesic, anti-inflammatory, and antipyretic properties. It is used in musculoskeletal and joint disorders and administered by mouth and topically. (From Martindale, The Extra Pharmacopoeia, 30th ed, p16). flufenamic acid : An aromatic amino acid consisting of anthranilic acid carrying an N-(trifluoromethyl)phenyl substituent. An analgesic and anti-inflammatory, it is used in rheumatic disorders.	2.21	1	0	aromatic amino acid; organofluorine compound	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	7.86	3	0	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
fomepizole Fomepizole: A pyrazole and competitive inhibitor of ALCOHOL DEHYDROGENASE that is used for the treatment of poisoning by ETHYLENE GLYCOL or METHANOL.. fomepizole : A member of the class of pyrazoles that is 1H-pyrazole substituted by a methyl group at position 4.	2.01	1	0	pyrazoles	antidote; EC 1.1.1.1 (alcohol dehydrogenase) inhibitor; protective agent
gabapentin Gabapentin: A cyclohexane-gamma-aminobutyric acid derivative that is used for the treatment of PARTIAL SEIZURES; NEURALGIA; and RESTLESS LEGS SYNDROME.. gabapentin : A gamma-amino acid that is cyclohexane substituted at position 1 by aminomethyl and carboxymethyl groups. Used for treatment of neuropathic pain and restless legs syndrome.	2.25	1	0	gamma-amino acid	anticonvulsant; calcium channel blocker; environmental contaminant; xenobiotic
gentamicin Gentamicins: A complex of closely related aminoglycosides obtained from MICROMONOSPORA purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit PROTEIN BIOSYNTHESIS.	7.41	1	0
glutaral Glutaral: One of the protein CROSS-LINKING REAGENTS that is used as a disinfectant for sterilization of heat-sensitive equipment and as a laboratory reagent, especially as a fixative.. glutaraldehyde : A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.	2.82	2	0	dialdehyde	cross-linking reagent; disinfectant; fixative
glyburide Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.	2.17	1	0	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent
gossypol Gossypol: A dimeric sesquiterpene found in cottonseed (GOSSYPIUM). The (-) isomer is active as a male contraceptive (CONTRACEPTIVE AGENTS, MALE) whereas toxic symptoms are associated with the (+) isomer.	3.66	2	0
guanethidine Guanethidine: An antihypertensive agent that acts by inhibiting selectively transmission in post-ganglionic adrenergic nerves. It is believed to act mainly by preventing the release of norepinephrine at nerve endings and causes depletion of norepinephrine in peripheral sympathetic nerve terminals as well as in tissues.. guanethidine : A member of the class of guanidines in which one of the hydrogens of the amino group has been replaced by a 2-azocan-1-ylethyl group.. guanethidine sulfate : A organic sulfate salt composed of two molecules of guanethidine and one of sulfuric acid.	2	1	0	azocanes; guanidines	adrenergic antagonist; antihypertensive agent; sympatholytic agent
guanidine Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.	2.15	1	0	carboxamidine; guanidines; one-carbon compound
hexamethonium Hexamethonium: A nicotinic cholinergic antagonist often referred to as the prototypical ganglionic blocker. It is poorly absorbed from the gastrointestinal tract and does not cross the blood-brain barrier. It has been used for a variety of therapeutic purposes including hypertension but, like the other ganglionic blockers, it has been replaced by more specific drugs for most purposes, although it is widely used a research tool.	2.05	1	0	quaternary ammonium salt
hycanthone Hycanthone: Potentially toxic, but effective antischistosomal agent, it is a metabolite of LUCANTHONE.. hycanthone : A thioxanthen-9-one compound having a hydroxymethyl substituent at the 1-position and a 2-[(diethylamino)ethyl]amino substituent at the 4-position. It was formerly used (particularly as the monomethanesulfonic acid salt) as a schistosomicide for individual or mass treatement of infection with Schistosoma haematobium and S. mansoni, but due to its toxicity and concern about possible carcinogenicity, it has been replaced by other drugs such as praziquantel.	1.96	1	0	thioxanthenes	mutagen; schistosomicide drug
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	7.47	2	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic
lidocaine Lidocaine: A local anesthetic and cardiac depressant used as an antiarrhythmia agent. Its actions are more intense and its effects more prolonged than those of PROCAINE but its duration of action is shorter than that of BUPIVACAINE or PRILOCAINE.. lidocaine : The monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline.	1.98	1	0	benzenes; monocarboxylic acid amide; tertiary amino compound	anti-arrhythmia drug; drug allergen; environmental contaminant; local anaesthetic; xenobiotic
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	3.15	5	0	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
iodoacetamide [no description available]	2.77	3	0
isoniazid Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).	2.4	2	0	carbohydrazide	antitubercular agent; drug allergen
2-propanol 2-Propanol: An isomer of 1-PROPANOL. It is a colorless liquid having disinfectant properties. It is used in the manufacture of acetone and its derivatives and as a solvent. Topically, it is used as an antiseptic.. propan-2-ol : A secondary alcohol that is propane in which one of the hydrogens attached to the central carbon is substituted by a hydroxy group.	2.47	2	0	secondary alcohol; secondary fatty alcohol	protic solvent
isoproterenol Isoproterenol: Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.. isoprenaline : A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.	2.08	1	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
juglone juglone: structure. juglone : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogen at position 5 has been replaced by a hydroxy group. A plant-derived 1,4-naphthoquinone with confirmed antibacterial and antitumor activities.	2.07	1	0	hydroxy-1,4-naphthoquinone	geroprotector; herbicide; reactive oxygen species generator
ketoprofen Ketoprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.. ketoprofen : An oxo monocarboxylic acid that consists of propionic acid substituted by a 3-benzoylphenyl group at position 2.	7.97	4	0	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
kojic acid [no description available]	2.05	1	0	4-pyranones; enol; primary alcohol	Aspergillus metabolite; EC 1.10.3.1 (catechol oxidase) inhibitor; EC 1.10.3.2 (laccase) inhibitor; EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; EC 1.4.3.3 (D-amino-acid oxidase) inhibitor; NF-kappaB inhibitor; skin lightening agent
lauric acid dodecanoic acid : A straight-chain, twelve-carbon medium-chain saturated fatty acid with strong bactericidal properties; the main fatty acid in coconut oil and palm kernel oil.	8.99	1	1	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antibacterial agent; plant metabolite
letrozole [no description available]	8.97	2	0	nitrile; triazoles	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
mefenamic acid Mefenamic Acid: A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase.. mefenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to be minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis.	2.21	1	0	aminobenzoic acid; secondary amino compound	analgesic; antipyretic; antirheumatic drug; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
methenamine Methenamine: An anti-infective agent most commonly used in the treatment of urinary tract infections. Its anti-infective action derives from the slow release of formaldehyde by hydrolysis at acidic pH. (From Martindale, The Extra Pharmacopoeia, 30th ed, p173). hexamethylenetetramine : A polycyclic cage that is adamantane in which the carbon atoms at positions 1, 3, 5 and 7 are replaced by nitrogen atoms.	2.04	1	0	polyazaalkane; polycyclic cage; tetramine	antibacterial drug
methyl salicylate methyl salicylate: used in over-the-counter liniments, ointments, lotions for relief of musculoskeletal aches and pains; has hemolytic effect on human & sheep erythrocytes; RN given refers to parent cpd; structure in Merck Index, 9th ed, #5990. methyl salicylate : A benzoate ester that is the methyl ester of salicylic acid.	8.12	5	0	benzoate ester; methyl ester; salicylates	flavouring agent; insect attractant; metabolite
methyl methanesulfonate [no description available]	6.98	1	0	methanesulfonate ester	alkylating agent; apoptosis inducer; carcinogenic agent; genotoxin; mutagen
miconazole Miconazole: An imidazole antifungal agent that is used topically and by intravenous infusion.. 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole : A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 2,4-dichlorobenzyl group.. miconazole : A racemate composed of equimolar amounts of (R)- and (S)-miconazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections. It inhibits the synthesis of ergosterol, a critical component of fungal cell membranes.	2.17	1	0	dichlorobenzene; ether; imidazoles
myristicin myristicin: asaricin is an isomer; structure; a methylene dioxy version of elemicin;	7.08	1	0	organic molecular entity	metabolite
deet N,N-diethyl-m-toluamide : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of m-toluic acid with the nitrogen of diethylamine. First developed by the U.S. Army in 1946 for use by military personnel in insect-infested areas, it is the most widely used insect repellent worldwide.	2.21	1	0	benzamides; monocarboxylic acid amide	environmental contaminant; insect repellent; xenobiotic
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	2.15	1	0	maleimides	anticoronaviral agent; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.1.1 (hexokinase) inhibitor
nicardipine Nicardipine: A potent calcium channel blockader with marked vasodilator action. It has antihypertensive properties and is effective in the treatment of angina and coronary spasms without showing cardiodepressant effects. It has also been used in the treatment of asthma and enhances the action of specific antineoplastic agents.. nicardipine : A racemate comprising equimolar amounts of (R)- and (S)-nicardipine. It is a calcium channel blocker which is used to treat hypertension.. 2-[benzyl(methyl)amino]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate : A dihydropyridine that is 1,4-dihydropyridine substituted by a methyl, {2-[benzyl(methyl)amino]ethoxy}carbonyl, 3-nitrophenyl, methoxycarbonyl and methyl groups at positions 2, 3, 4, 5 and 6, respectively.	3.15	1	0	benzenes; C-nitro compound; diester; dihydropyridine; methyl ester; tertiary amino compound
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	3.15	1	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
nimesulide nimesulide: structure. nimesulide : An aromatic ether having phenyl and 2-methylsulfonamido-5-nitrophenyl as the two aryl groups.	2.02	1	0	aromatic ether; C-nitro compound; sulfonamide	cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
nimodipine Nimodipine: A calcium channel blockader with preferential cerebrovascular activity. It has marked cerebrovascular dilating effects and lowers blood pressure.. nimodipine : A dihydropyridine that is 1,4-dihydropyridine which is substituted by methyl groups at positions 2 and 6, a (2-methoxyethoxy)carbonyl group at position 3, a m-nitrophenyl group at position 4, and an isopropoxycarbonyl group at position 5. An L-type calcium channel blocker, it acts particularly on cerebral circulation, and is used both orally and intravenously for the prevention and treatment of subarachnoid hemorrhage from ruptured intracranial aneurysm.	3.15	1	0	2-methoxyethyl ester; C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; isopropyl ester	antihypertensive agent; calcium channel blocker; cardiovascular drug; vasodilator agent
nitrendipine Nitrendipine: A calcium channel blocker with marked vasodilator action. It is an effective antihypertensive agent and differs from other calcium channel blockers in that it does not reduce glomerular filtration rate and is mildly natriuretic, rather than sodium retentive.. nitrendipine : A dihydropyridine that is 1,4-dihydropyridine substituted by methyl groups at positions 2 and 6, a 3-nitrophenyl group at position 4, a ethoxycarbonyl group at position 3 and a methoxycarbonyl group at position 5. It is a calcium-channel blocker used in the treatment of hypertension.	3.15	1	0	C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; ethyl ester; methyl ester	antihypertensive agent; calcium channel blocker; geroprotector; vasodilator agent
no 711 [no description available]	2.21	1	0	diarylmethane
masoprocol nordihydroguaretic acid: antioxidant compound found in the creosote bush (Larrea tridentata)	2.21	1	0	catechols; lignan; tetrol	antioxidant; ferroptosis inhibitor; geroprotector; plant metabolite
nortriptyline Nortriptyline: A metabolite of AMITRIPTYLINE that is also used as an antidepressive agent. Nortriptyline is used in major depression, dysthymia, and atypical depressions.. nortriptyline : An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(methylamino)propylidene group at position 5. It is an active metabolite of amitriptyline.	2.1	1	0	organic tricyclic compound; secondary amine	adrenergic uptake inhibitor; analgesic; antidepressant; antineoplastic agent; apoptosis inducer; drug metabolite
5-nitro-2-(3-phenylpropylamino)benzoic acid 5-nitro-2-(3-phenylpropylamino)benzoic acid: structure given in first source; chloride channel antagonist	2.21	1	0	nitrobenzoic acid
n-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide N-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide: structure given in first source. NS-398 : A C-nitro compound that is N-methylsulfonyl-4-nitroaniline bearing an additional cyclohexyloxy substituent at position 2.	2.42	2	0	aromatic ether; C-nitro compound; sulfonamide	antineoplastic agent; cyclooxygenase 2 inhibitor
oxonic acid Oxonic Acid: Antagonist of urate oxidase.	2.04	1	0	1,3,5-triazines; monocarboxylic acid
oxidopamine Oxidopamine: A neurotransmitter analogue that depletes noradrenergic stores in nerve endings and induces a reduction of dopamine levels in the brain. Its mechanism of action is related to the production of cytolytic free-radicals.. oxidopamine : A benzenetriol that is phenethylamine in which the hydrogens at positions 2, 4, and 5 on the phenyl ring are replaced by hydroxy groups. It occurs naturally in human urine, but is also produced as a metabolite of the drug DOPA (used for the treatment of Parkinson's disease).	2.54	2	0	benzenetriol; catecholamine; primary amino compound	drug metabolite; human metabolite; neurotoxin
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	2.06	1	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
fenclonine Fenclonine: A selective and irreversible inhibitor of tryptophan hydroxylase, a rate-limiting enzyme in the biosynthesis of serotonin (5-HYDROXYTRYPTAMINE). Fenclonine acts pharmacologically to deplete endogenous levels of serotonin.	2.05	1	0	phenylalanine derivative
pd168393 PD 168393 : A member of the class of quinazolines carrying bromoanilino and acrylamido substituents at positions 4 and 6 respectively.	2.15	1	0	acrylamides; bromobenzenes; quinazolines; secondary carboxamide; substituted aniline	epidermal growth factor receptor antagonist
oxophenylarsine oxophenylarsine: inhibits protein-tyrosine-phosphatase. phenylarsine oxide : An arsine oxide derived from phenylarsine.	2.78	3	0	arsine oxides	antineoplastic agent; apoptosis inducer; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
phenylbutazone Phenylbutazone: A butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. It has been used in ANKYLOSING SPONDYLITIS; RHEUMATOID ARTHRITIS; and REACTIVE ARTHRITIS.. phenylbutazone : A member of the class of pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position.	2.02	1	0	pyrazolidines	antirheumatic drug; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
o-phthalaldehyde o-Phthalaldehyde: A reagent that forms fluorescent conjugation products with primary amines. It is used for the detection of many biogenic amines, peptides, and proteins in nanogram quantities in body fluids.. phthalaldehyde : A dialdehyde in which two formyl groups are attached to adjacent carbon centres on a benzene ring.	2.08	1	0	benzaldehydes; dialdehyde	epitope
pioglitazone Pioglitazone: A thiazolidinedione and PPAR GAMMA agonist that is used in the treatment of TYPE 2 DIABETES MELLITUS.. pioglitazone : A member of the class of thiazolidenediones that is 1,3-thiazolidine-2,4-dione substituted by a benzyl group at position 5 which in turn is substituted by a 2-(5-ethylpyridin-2-yl)ethoxy group at position 4 of the phenyl ring. It exhibits hypoglycemic activity.	2.81	3	0	aromatic ether; pyridines; thiazolidinediones	antidepressant; cardioprotective agent; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; geroprotector; hypoglycemic agent; insulin-sensitizing drug; PPARgamma agonist; xenobiotic
potassium chloride Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.	2.52	2	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
prazosin Prazosin: A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.. prazosin : A member of the class of piperazines that is piperazine substituted by a furan-2-ylcarbonyl group and a 4-amino-6,7-dimethoxyquinazolin-2-yl group at positions 1 and 4 respectively.	2.05	1	0	aromatic ether; furans; monocarboxylic acid amide; piperazines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
probenecid Probenecid: The prototypical uricosuric agent. It inhibits the renal excretion of organic anions and reduces tubular reabsorption of urate. Probenecid has also been used to treat patients with renal impairment, and, because it reduces the renal tubular excretion of other drugs, has been used as an adjunct to antibacterial therapy.. probenecid : A sulfonamide in which the nitrogen of 4-sulfamoylbenzoic acid is substituted with two propyl groups.	2.21	1	0	benzoic acids; sulfonamide	uricosuric drug
resorcinol resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951. resorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.	2.15	1	0	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser
rofecoxib [no description available]	2.42	2	0	butenolide; sulfone	analgesic; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
safrole Safrole: A member of the BENZODIOXOLES that is a constituent of several VOLATILE OILS, notably SASSAFRAS oil. It is a precursor in the synthesis of the insecticide PIPERONYL BUTOXIDE and the drug N-methyl-3,4-methylenedioxyamphetamine (MDMA).. safrole : A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted by an allyl group at position 5. It is found in several plants, including black pepper, cinnamon and nutmeg, and is present in several essential oils, notably that of sassafras. It has insecticidal properties and has been used as a topical antiseptic. Although not thought to pose a significant carcinogenic risk to humans, findings of weak carcinogenicity in rats have resulted in the banning of its (previously widespread) use in perfumes and soaps, and as a food additive.	7.47	2	0	benzodioxoles	flavouring agent; insecticide; metabolite; plant metabolite
sanguinarine benzophenanthridine alkaloid : A specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family.	2.08	1	0	alkaloid antibiotic; benzophenanthridine alkaloid; botanical anti-fungal agent
sodium fluoride [no description available]	2.31	1	0	fluoride salt	mutagen
sulfamethoxazole Sulfamethoxazole: A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208). sulfamethoxazole : An isoxazole (1,2-oxazole) compound having a methyl substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 3-position.	2.05	1	0	isoxazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial agent; antiinfective agent; antimicrobial agent; drug allergen; EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; epitope; P450 inhibitor; xenobiotic
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	3.01	4	0	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
temefos Temefos: An organothiophosphate insecticide.. temephos : An organic sulfide that is diphenyl sulfide in which the hydrogen at the para position of each of the phenyl groups has been replaced by a (dimethoxyphosphorothioyl)oxy group.	2.6	1	0	organic sulfide; organic thiophosphate; organothiophosphate insecticide	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; ectoparasiticide
tetracaine Tetracaine: A potent local anesthetic of the ester type used for surface and spinal anesthesia.. tetracaine : A benzoate ester in which 4-N-butylbenzoic acid and 2-(dimethylamino)ethanol have combined to form the ester bond; a local ester anaesthetic (ester caine) used for surface and spinal anaesthesia.	1.97	1	0	benzoate ester; tertiary amino compound	local anaesthetic
thiram Thiram: A dithiocarbamate chemical, used commercially in the rubber processing industry and as a fungicide. In vivo studies indicate that it inactivates the enzyme GLUTATHIONE REDUCTASE. It has mutagenic activity and may induce chromosomal aberrations.. thiram : An organic disulfide that results from the formal oxidative dimerisation of N,N-dimethyldithiocarbamic acid. It is widely used as a fungicidal seed treatment.	2.04	1	0	organic disulfide	antibacterial drug; antifungal agrochemical; antiseptic drug
2,3-bis(2-methoxy-4-nitro-5-sulfophenyl)-5-((phenylamino)carbonyl)-2h-tetrazolium hydroxide 2,3-bis(2-methoxy-4-nitro-5-sulfophenyl)-5-((phenylamino)carbonyl)-2H-tetrazolium hydroxide: structure given in first source	2.48	2	0
corticosterone [no description available]	2.41	1	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	2.25	1	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
thymidine [no description available]	2.01	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	2.47	2	0	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
dehydroepiandrosterone Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.	2.05	1	0	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
penicillin g Penicillin G: A penicillin derivative commonly used in the form of its sodium or potassium salts in the treatment of a variety of infections. It is effective against most gram-positive bacteria and against gram-negative cocci. It has also been used as an experimental convulsant because of its actions on GAMMA-AMINOBUTYRIC ACID mediated synaptic transmission.. benzylpenicillin : A penicillin in which the substituent at position 6 of the penam ring is a phenylacetamido group.	2.07	1	0	penicillin allergen; penicillin	antibacterial drug; drug allergen; epitope
dimethylphenylpiperazinium iodide Dimethylphenylpiperazinium Iodide: A selective nicotinic cholinergic agonist used as a research tool. DMPP activates nicotinic receptors in autonomic ganglia but has little effect at the neuromuscular junction.	1.96	1	0	N-arylpiperazine; organic iodide salt; piperazinium salt; quaternary ammonium salt	nicotinic acetylcholine receptor agonist
pentylenetetrazole Pentylenetetrazole: A pharmaceutical agent that displays activity as a central nervous system and respiratory stimulant. It is considered a non-competitive GAMMA-AMINOBUTYRIC ACID antagonist. Pentylenetetrazole has been used experimentally to study seizure phenomenon and to identify pharmaceuticals that may control seizure susceptibility.. pentetrazol : An organic heterobicyclic compound that is 1H-tetrazole in which the hydrogens at positions 1 and 5 are replaced by a pentane-1,5-diyl group. A central and respiratory stimulant, it was formerly used for the treatment of cough and other respiratory tract disorders, cardiovascular disorders including hypotension, and pruritis.	7.25	1	0	organic heterobicyclic compound; organonitrogen heterocyclic compound
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	2	1	0	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.41	1	0	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
4-nitroquinoline-1-oxide 4-nitroquinoline N-oxide : A quinoline N-oxide carrying a nitro substituent at position 4.	2.88	4	0	C-nitro compound; quinoline N-oxide	carcinogenic agent
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	2.05	1	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	7.61	2	0	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
allyl isothiocyanate allyl isothiocyanate: used in the manufacture of flavors, war gases; medical use as a counterirritant; structure. allyl isothiocyanate : An isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152degreeC, it is responsible for the pungent taste of mustard, horseradish, and wasabi.	6.7	41	0	alkenyl isothiocyanate; isothiocyanate	antimicrobial agent; antineoplastic agent; apoptosis inducer; lachrymator; metabolite
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	4.16	3	1	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2.45	2	0	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
phenylephrine Phenylephrine: An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.. phenylephrine : A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.	7.41	1	0	phenols; phenylethanolamines; secondary amino compound	alpha-adrenergic agonist; cardiotonic drug; mydriatic agent; nasal decongestant; protective agent; sympathomimetic agent; vasoconstrictor agent
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	2.07	1	0	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	2.21	1	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
phenylethyl alcohol Phenylethyl Alcohol: An antimicrobial, antiseptic, and disinfectant that is used also as an aromatic essence and preservative in pharmaceutics and perfumery.. 2-phenylethanol : A primary alcohol that is ethanol substituted by a phenyl group at position 2.	3.3	5	0	benzenes; primary alcohol	Aspergillus metabolite; fragrance; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	1.99	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	2.21	1	0	adenosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	adenosine A1 receptor agonist; cofactor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.11 (fructose-bisphosphatase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	2.1	1	0	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	2.49	2	0	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
berlition berlition: antioxidant preparation containing alpha-lipoic acid, used in the neuroprotective therapy of chronic brain ischemia for correction of free-radical processes. (R)-lipoic acid : The (R)-enantiomer of lipoic acid. A vitamin-like, C8 thia fatty acid with anti-oxidant properties.. lipoic acid : A heterocyclic thia fatty acid comprising pentanoic acid with a 1,2-dithiolan-3-yl group at the 5-position.	2.01	1	0	dithiolanes; heterocyclic fatty acid; lipoic acid; thia fatty acid	cofactor; nutraceutical; prosthetic group
ethyl methanesulfonate Ethyl Methanesulfonate: An antineoplastic agent with alkylating properties. It also acts as a mutagen by damaging DNA and is used experimentally for that effect.. ethyl methanesulfonate : A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol.	7.41	2	0	methanesulfonate ester	alkylating agent; antineoplastic agent; carcinogenic agent; genotoxin; mutagen; teratogenic agent
methacholine chloride Methacholine Chloride: A quaternary ammonium parasympathomimetic agent with the muscarinic actions of ACETYLCHOLINE. It is hydrolyzed by ACETYLCHOLINESTERASE at a considerably slower rate than ACETYLCHOLINE and is more resistant to hydrolysis by nonspecific CHOLINESTERASES so that its actions are more prolonged. It is used as a parasympathomimetic bronchoconstrictor agent and as a diagnostic aid for bronchial asthma. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1116)	2.25	1	0	quaternary ammonium salt
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	3.04	1	0	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
n-hexanal [no description available]	2.15	1	0	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	human urinary metabolite
1-naphthaldehyde 1-naphthaldehyde: structure. naphthaldehyde : An aldehyde in which the organyl group is a naphthyl group.. 1-naphthaldehyde : A naphthaldehyde with a formyl group at position 1.	2.21	1	0	naphthaldehyde	mouse metabolite
cycloheximide Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.	1.98	1	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
ficusin Ficusin: A naturally occurring furocoumarin, found in PSORALEA. After photoactivation with UV radiation, it binds DNA via single and double-stranded cross-linking.. psoralen : The simplest member of the class of psoralens that is 7H-furo[3,2-g]chromene having a keto group at position 7. It has been found in plants like Psoralea corylifolia and Ficus salicifolia.	3.25	1	0	psoralens	plant metabolite
2-naphthaldehyde 2-naphthaldehyde: structure. 2-naphthaldehyde : A naphthaldehyde that is naphthalene substituted by a formyl group at position 2.	2.21	1	0	naphthaldehyde	mouse metabolite
sodium citrate, anhydrous Sodium Citrate: Sodium salts of citric acid that are used as buffers and food preservatives. They are used medically as anticoagulants in stored blood, and for urine alkalization in the prevention of KIDNEY STONES.. sodium citrate : The trisodium salt of citric acid.	2.21	1	0	organic sodium salt	anticoagulant; flavouring agent
ampicillin Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.	2.78	3	0	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
dinitrofluorobenzene Dinitrofluorobenzene: Irritants and reagents for labeling terminal amino acid groups.. 1-fluoro-2,4-dinitrobenzene : The organofluorine compound that is benzene with a fluoro substituent at the 1-position and two nitro substituents in the 2- and 4-positions.	2.46	2	0	C-nitro compound; organofluorine compound	agrochemical; allergen; chromatographic reagent; EC 2.7.3.2 (creatine kinase) inhibitor; protein-sequencing agent; spectrophotometric reagent
2-thiomalic acid [no description available]	2.41	1	0	C4-dicarboxylic acid
n-pentanol n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.	1.97	1	0	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
threonine Threonine: An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins.. threonine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 1-hydroxyethyl group.	2.15	1	0	amino acid zwitterion; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid; threonine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
alizarin [no description available]	7.6	1	0	dihydroxyanthraquinone	chromophore; dye; plant metabolite
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	7.82	3	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
bromochloromethane bromochloromethane: inhibitor of ruminal methane production. bromochloromethane : A halomethane that is chloromethane in which one of the hydrogens has been replaced by a bromine atom.	3.47	1	1	halomethane
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	2.47	2	0	alkane; gas molecular entity	food propellant
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	2.02	1	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
acetyl chloride [no description available]	2.6	1	0	acyl chloride
tromethamine Tromethamine: An organic amine proton acceptor. It is used in the synthesis of surface-active agents and pharmaceuticals; as an emulsifying agent for cosmetic creams and lotions, mineral oil and paraffin wax emulsions, as a biological buffer, and used as an alkalizer. (From Merck, 11th ed; Martindale, The Extra Pharmacopoeia, 30th ed, p1424)	2.11	1	0	primary amino compound; triol	buffer
linalool linalool: RN given refers to parent cpd without isomeric designation; structure. linalool : A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.	9.69	8	0	monoterpenoid; tertiary alcohol	antimicrobial agent; fragrance; plant metabolite; volatile oil component
isoprene isoprene: used in manufacture of ''synthetic'' rubber, butyl rubber; copolymer in production of elastomers; structure. isoprene : A hemiterpene with the formula CH2=C(CH3)CH=CH2; the monomer of natural rubber and a common structure motif to the isoprenoids, a large class of other naturally occurring compounds.	2.67	3	0	alkadiene; hemiterpene; volatile organic compound	plant metabolite
methacrylaldehyde [no description available]	2.15	1	0	enal
3-buten-2-one buten-2-one : A methyl ketone that is butan-2-one with an unsaturation at position 3.	2.15	1	0	enone; methyl ketone
acrylamide [no description available]	2.15	1	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
alpha-pinene [no description available]	2.6	1	0	pinene	plant metabolite
methylmethacrylate Methylmethacrylate: The methyl ester of methacrylic acid. It polymerizes easily to form POLYMETHYL METHACRYLATE. It is used as a bone cement.. methyl methacrylate : An enoate ester having methacrylic acid as the carboxylic acid component and methanol as the alcohol component.	2.74	3	0	enoate ester; methyl ester	allergen; polymerisation monomer
musk ambrette (artificial) musk ambrette (artificial): widely used fragrance implicated in contact photosensitivity; structure	3.06	1	0	C-nitro compound
diethyl phthalate diethyl phthalate: structure. diethyl phthalate : The diethyl ester of benzene-1,2-dicarboxylic acid.	1.98	1	0	diester; ethyl ester; phthalate ester	neurotoxin; plasticiser; teratogenic agent
isoamyl salicylate [no description available]	1.97	1	0	benzoate ester; phenols
xylitol xylooligosaccharide: structure in first source. pentitol : An alditol obtained by reduction of any pentose.. xylooligosaccharide : An oligosaccharide comprised of xylose residues.	2.52	2	0
n-vinyl-2-pyrrolidinone N-vinyl-2-pyrrolidinone: monomer of POVIDONE; structure given in first source	1.97	1	0	pyrrolidin-2-ones
versalide versalide: musk fragrance in soaps & cosmetics; structure	3.06	1	0
2-nitroaniline [no description available]	3.35	1	0
guaiene guaiene: RN given refers to (1S-cis)-isomer	2.6	1	0	sesquiterpene
thymol Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.	8.48	59	1	monoterpenoid; phenols	volatile oil component
2-chlorobenzaldehyde [no description available]	2.21	1	0
salicylaldehyde o-hydroxybenzaldehyde: structure in first source	8.32	6	0	hydroxybenzaldehyde	nematicide; plant metabolite
1-naphthylphenylamine N-phenyl-1-naphthylamine: RN given refers to 1-naphthylamine cpd; structure	2.07	1	0	naphthalenes
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	2.15	1	0	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
quinoline [no description available]	2.08	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
uvitex swn Uvitex SWN: optical brightner from Ciba; structure	3.25	1	0	7-aminocoumarins	fluorochrome
6-methylcoumarin 6-methylcoumarin: synthetic fragrance causing contact photoallergy. 6-methylcoumarin : A member of the class of coumarins that is coumarin in which the hydrogen at position 6 is replaced by a methyl group.	3.5	2	0	coumarins	allergen; fragrance
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.03	1	0	xanthene
methyleugenol methyleugenol: structure	3.89	3	0	phenylpropanoid
acetyleugenol acetyleugenol: from cloves; inhibits arachidonate-, adrenaline-, & collagen-induced platelet aggregation	2.02	1	0	benzoate ester; phenols
hydratropic aldehyde 2-phenylpropanal : A member of the class of phenylacetaldehydes that is phenylacetaldehyde in which a hydrogen alpha to the aldehyde carbonyl group has been replaced by a methyl group. The major species at pH 7.3.	2.21	1	0	phenylacetaldehydes
methyl nicotinate methyl nicotinate: erythema provoked is basis of a methylnicotinate test of anti-inflammatories	2.89	4	0	aromatic carboxylic acid; pyridines
propylparaben Parabens: Methyl, propyl, butyl, and ethyl esters of p-hydroxybenzoic acid. They have been approved by the FDA as antimicrobial agents for foods and pharmaceuticals. (From Hawley's Condensed Chemical Dictionary, 11th ed, p872)	2.67	3	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
dilactide dilactide: structure given in first source	2.41	1	0	dioxanes
styrene oxide styrene oxide: structure. styrene oxide : An epoxide that is oxirane in which one of the hydrogens has been replaced by a phenyl group.	2.21	1	0	epoxide	human xenobiotic metabolite
methyl acrylate [no description available]	2.15	1	0	enoate ester
n-methylpyrrole [no description available]	2	1	0	pyrroles
2,4-di-tert-butylphenol 2,4-di-tert-butylphenol: structure given in first source. 2,4-di-tert-butylphenol : A member of the class of phenols carrying two tert-butyl substituents at positions 2 and 4.	2.07	1	0	alkylbenzene; phenols	antioxidant; bacterial metabolite; marine metabolite
ethylene dimethacrylate ethylene glycol dimethacrylate : The enoate ester that is the 1,2-bis(methacryloyl) derivative of ethylene glycol.	2.31	1	0	enoate ester	allergen; cross-linking reagent; polymerisation monomer
furaldehyde Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.	3.16	5	0	aldehyde; furans	Maillard reaction product; metabolite
thiophene-2-carboxaldehyde thiophene-2-carboxaldehyde: structure in first source. formylthiophene : An aldehyde that is thiophene substituted by a formyl group at position 2.	2.21	1	0	aldehyde; thiophenes	metabolite
carveol carveol: structure given in first source; prolongs tumor latency and decreases tumor yield. carveol : A limonene monoterpenoid that is cyclohex-2-en-1-ol substituted by a methyl group at position 2 and a prop-1-en-2-yl group at position 5.	2.05	1	0	limonene monoterpenoid	plant metabolite; volatile oil component
carvone carvone: an oxidized derivative of limonene; RN given refers to cpd without isomeric designation; L-carvone has spearmint flavor, D-carvone has dill/caraway flavor. carvone : A p-menthane monoterpenoid that consists of cyclohex-2-enone having methyl and isopropenyl substituents at positions 2 and 5, respectively.	8.12	5	0	botanical anti-fungal agent; carvones	allergen
3-nitrobenzaldehyde [no description available]	2.49	2	0
4-cymene 4-cymene: structure. p-cymene : A monoterpene that is toluene substituted by an isopropyl group at position 4.	4.17	4	0	monoterpene; toluenes	human urinary metabolite; plant metabolite; volatile oil component
4-(dimethylamino)benzaldehyde p-dimethylaminobenzaldehyde: structure in first source. 4-(dimethylamino)benzaldehyde : A member of the class of benzaldehydes that is benzaldehyde carrying a dimethylamino substituent at position 4. Used as an indicator for detection of indoles and hydrazine.	2.21	1	0	benzaldehydes; substituted aniline; tertiary amino compound	chromogenic compound
terephthalic acid terephthalic acid: RN given refers to 1,4-benzenedicarboxylic acid. terephthalic acid : A benzenedicarboxylic acid carrying carboxy groups at positions 1 and 4. One of three possible isomers of benzenedicarboxylic acid, the others being phthalic and isophthalic acids.	2.25	1	0	benzenedicarboxylic acid
benzyl bromide benzyl bromide: structure given in first source. benzyl bromide : A member of the class of benzyl bromides that is toluene substituted on the alpha-carbon with bromine.	3.15	1	0	benzyl bromides	lachrymator
styrene Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.	2.47	2	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
benzyl chloride benzyl chloride: RN given refers to unlabeled cpd. chlorophenylmethane : A chlorohydrocarbon that is phenylmethane substituted by a chloro group at unspecified position.. benzyl chloride : A member of the class of benzyl chlorides that is toluene substituted on the alpha-carbon with chlorine.	2.03	1	0	benzyl chlorides
benzylamine aminotoluene : Any member of the class of toluenes carrying one or more amino groups.	1.98	1	0	aralkylamine; primary amine	allergen; EC 3.5.5.1 (nitrilase) inhibitor; plant metabolite
anisole anisole : A monomethoxybenzene that is benzene substituted by a methoxy group.	2.07	1	0	monomethoxybenzene	plant metabolite
3-phenylpropanal 3-phenylpropanal : A benzene which is substituted by a 3-oxopropyl group at position 1.	2.06	1	0	aldehyde; benzenes	flavouring agent; plant metabolite
4-methylbenzaldehyde p-tolualdehyde : A tolualdehyde compound with the methyl substituent at the 4-position.	2.49	2	0	tolualdehyde	plant metabolite
4-chlorobenzaldehyde [no description available]	2.49	2	0
ethyl bromoacetate [no description available]	3.15	1	0
citronellal citronellal: aldehyde of citronellol; found in citronella oil. citronellal : A monoterpenoid, the main component of citronella oil which gives it its distinctive lemon aroma.	3.54	7	0	aldehyde; monoterpenoid	antifungal agent; metabolite
4-phenylenediamine 4-phenylenediamine: agent hair dye responsible for contact dermatitis; RN given refers to parent cpd. 1,4-phenylenediamine : A phenylenediamine in which the amino functions are at positions 1 and 4 of the benzene nucleus.	2.71	3	0	phenylenediamine	allergen; dye; hapten; reagent
acrolein [no description available]	25.42	1,193	31	enal	herbicide; human xenobiotic metabolite; toxin
acrylonitrile [no description available]	7.42	2	0	aliphatic nitrile; volatile organic compound	antifungal agent; carcinogenic agent; fungal metabolite; mutagen; polar aprotic solvent
allyl alcohol allyl alcohol: structure. allylic alcohol : An alcohol where the hydroxy group is attached to a saturated carbon atom adjacent to a double bond (R groups may be H, organyl, etc.).. allyl alcohol : A propenol in which the C=C bond connects C-2 and C-3. It is has been found in garlic (Allium sativum). Formerly used as a herbicide for the control of various grass and weed seeds.	2.05	1	0	primary allylic alcohol; propenol	antibacterial agent; fungicide; herbicide; insecticide; plant metabolite
hydroxycitronellal hydroxycitronellal : The tertiary alcohol arising from addition of water across the C=C double bond of citronellal.	5.19	6	0	tertiary alcohol	allergen; fragrance
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.74	3	0	alkane
cyclohexanol Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.	3.65	9	0	cyclohexanols; secondary alcohol	solvent
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	2	1	0	pyrrole; secondary amine
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.47	2	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
isopropyl myristate isopropyl myristate: used for microemulsions; structure	1.98	1	0	fatty acid ester
n-hexane hexane : An unbranched alkane containing six carbon atoms.	2.31	1	0	alkane; volatile organic compound	neurotoxin; non-polar solvent
piperidine [no description available]	2.04	1	0	azacycloalkane; piperidines; saturated organic heteromonocyclic parent; secondary amine	base; catalyst; human metabolite; non-polar solvent; plant metabolite; protic solvent; reagent
1-hexanol 1-hexanol: RN given refers to parent cpd. hexanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of six carbon atoms.. hexan-1-ol : A primary alcohol that is hexane substituted by a hydroxy group at position 1.	2.59	2	0	hexanol; primary alcohol	alarm pheromone; antibacterial agent; fragrance; plant metabolite
n-decyl alcohol n-decyl alcohol: RN given refers to parent cpd. decanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of ten carbon atoms.. decan-1-ol : A fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of ten carbon atoms.	2.02	1	0	decanol; primary alcohol	metabolite; pheromone; protic solvent
desaspidin desaspidin: structure	3.25	1	0
propylene propylene: structure	2.05	1	0	alkene; gas molecular entity	refrigerant; xenobiotic
ethyl salicylate ethyl salicylate: causes erythema after topical application as an aerosol; found in blood	1.97	1	0	hydroxybenzoic acid
2'-hydroxyacetophenone 2-acetylphenol : A monohydroxyacetophenone that is acetophenone in which one of the hydrogens ortho to the acetyl group has been replaced by a hydroxy group.	2.1	1	0	monohydroxyacetophenone; phenols	flavouring agent
framycetin Framycetin: A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). framycetin : A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.	2.41	2	0	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
piperonal piperonal: has been used as a pediculicide; structure. piperonal : An arenecarbaldehyde that is 1,3-benzodioxole substituted by a formyl substituent at position 5. It has been isolated from Piper nigrum.	2.54	2	0	arenecarbaldehyde; benzodioxoles	fragrance; insect repellent; plant metabolite
cyclopentanone [no description available]	2.06	1	0	cyclopentanones	Maillard reaction product
3-tert-butyl-4-hydroxyanisole 3-tert-butyl-4-hydroxyanisole : An aromatic ether that is 4-methoxyphenol in which one of the hydrogens ortho- to the phenolic hydroxy group is replaced by a tert-butyl group.	2.1	1	0	aromatic ether; phenols	antioxidant; human xenobiotic metabolite
ethyl vanillin ethyl vanillin : A member of the class of benzaldehydes that is vanillin in which the methoxy group is replaced by an ethoxy group.	2.21	1	0	aromatic ether; benzaldehydes; phenols	antioxidant; flavouring agent
vanillic acid Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.	2.07	1	0	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
1-naphthylamine 1-Naphthylamine: A suspected industrial carcinogen (and listed as such by OSHA). Its N-hydroxy metabolite is strongly carcinogenic and mutagenic.. naphthylamine : A primary arylamine that is naphthalene substituted by an amino group at unspecified position.. 1-naphthylamine : A naphthylamine that is naphthalene substituted by an amino group at position 1.	2.07	1	0	naphthylamine	human xenobiotic metabolite
syringaldehyde syringaldehyde: isolated from nonfermented fiber fractions of oat hulls and cottonseed hulls. syringaldehyde : A hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity.	2.21	1	0	dimethoxybenzene; hydroxybenzaldehyde	hypoglycemic agent; plant metabolite
2-Methoxybenzaldehyde [no description available]	2.21	1	0	carbonyl compound
shikimic acid Shikimic Acid: A tri-hydroxy cyclohexene carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is named after it.. shikimic acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microorganisms.	2.01	1	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid; hydroxy monocarboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
estragole estragole : A phenylpropanoid that is chavicol in which the hydroxy group is replaced by a methoxy group.	3.69	2	0	alkenylbenzene; monomethoxybenzene; phenylpropanoid	carcinogenic agent; flavouring agent; genotoxin; insect attractant; plant metabolite
ethyl acrylate [no description available]	2.44	2	0	enoate ester
citronellol citronellol: alcohol form of citronellal; found in rose oil; RN given refers to parent cpd without isomeric designation; structure. citronellol : A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.. insect repellent : An insecticide that acts as a repellent to insects.	2.96	4	0	monoterpenoid	plant metabolite
n-butyl acrylate butyl acrylate : An acrylate ester obtained by the formal condensation of the hydroxy group of butan-1-ol with the carboxy group of acrylic acid.	2.15	1	0	acrylate ester
mesityl oxide mesityl oxide: solvent for extraction of nitrocellulose, many resins, & tellurium; structure	2.15	1	0	olefinic compound
hexanoic acid hexanoic acid : A C6, straight-chain saturated fatty acid.	2.03	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	human metabolite; plant metabolite
pregnenolone [no description available]	2.08	1	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
diphenhydramine hydrochloride Antitussive Agents: Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.. diphenhydramine hydrochloride : The hydrochloride salt of diphenhydramine.	2.46	2	0	hydrochloride; organoammonium salt	anti-allergic agent; antiemetic; antiparkinson drug; antipruritic drug; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; sedative
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	5.29	6	0	catechin	antioxidant; plant metabolite
dibenz(b,f)(1,4)oxazepine [no description available]	3.15	1	0
azulene [no description available]	2.21	1	0	azulenes; mancude carbobicyclic parent; ortho-fused bicyclic arene	plant metabolite; volatile oil component
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	2.46	2	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
thiazoles [no description available]	3.53	8	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
methylphenazonium methosulfate Methylphenazonium Methosulfate: Used as an electron carrier in place of the flavine enzyme of Warburg in the hexosemonophosphate system and also in the preparation of SUCCINIC DEHYDROGENASE.	2.03	1	0	azaheterocycle sulfate salt; phenazines
ephedrine Ephedrine: A phenethylamine found in EPHEDRA SINICA. PSEUDOEPHEDRINE is an isomer. It is an alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used for asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists.. (-)-ephedrine : A phenethylamine alkaloid that is 2-phenylethanamine substituted by a methyl group at the amino nitrogen and a methyl and a hydroxy group at position 2 and 1 respectively.	1.98	1	0	phenethylamine alkaloid; phenylethanolamines	bacterial metabolite; environmental contaminant; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
azacitidine Azacitidine: A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.. 5-azacytidine : An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via an N-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia.	1.97	1	0	N-glycosyl-1,3,5-triazine; nucleoside analogue	antineoplastic agent
betamethasone Betamethasone: A glucocorticoid given orally, parenterally, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. Its lack of mineralocorticoid properties makes betamethasone particularly suitable for treating cerebral edema and congenital adrenal hyperplasia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p724)	2.05	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	anti-asthmatic agent; anti-inflammatory drug; immunosuppressive agent
hydantoins Hydantoins: Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS.. imidazolidine-2,4-dione : An imidazolidinone with oxo groups at position 2 and 4.	2.05	1	0	imidazolidine-2,4-dione
propadiene [no description available]	2.11	1	0	allenes
limestone Calcium Carbonate: Carbonic acid calcium salt (CaCO3). An odorless, tasteless powder or crystal that occurs in nature. It is used therapeutically as a phosphate buffer in hemodialysis patients and as a calcium supplement.. calcium carbonate : A calcium salt with formula CCaO3.	2.13	1	0	calcium salt; carbonate salt; inorganic calcium salt; one-carbon compound	antacid; fertilizer; food colouring; food firming agent
plumbagin plumbagin: a superoxide anion generator. plumbagin : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.	3.23	1	0	hydroxy-1,4-naphthoquinone; phenols	anticoagulant; antineoplastic agent; immunological adjuvant; metabolite
thymoquinone thymoquinone: constituent of cedarwood; can cause dermatitis; structure. thymoquinone : A member of the class of 1,4-benzoquinones that is 1,4-bezoquinone in which the hydrogens at positions 2 and 5 are replaced by methyl and isopropyl groups, respectively. It is a natural compound isolated from Nigella sativa which has demonstrated promising chemotherapeutic activity.	3.65	2	0	1,4-benzoquinones	adjuvant; anti-inflammatory agent; antidepressant; antineoplastic agent; antioxidant; cardioprotective agent; plant metabolite
1,4-benzodioxan 1,4-benzodioxan: structure in first source	7.1	1	0
2-methyl-2-butenal 2-methyl-2-butenal: structure in first source	2.55	2	0
carvacrol carvacrol : A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).	9.89	101	5	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
3-pyridinaldehyde pyridine-3-carbaldehyde : A pyridinecarbaldehyde that is pyridine substituted by a formyl group at position 3.	2.21	1	0	pyridinecarbaldehyde
alpha-aminopyridine alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.	2.11	1	0
thiazolidines Thiazolidines: Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES.	2.13	1	0	thiazolidine
oleanolic acid [no description available]	3.83	3	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
abietic acid abietic acid : An abietane diterpenoid that is abieta-7,13-diene substituted by a carboxy group at position 18.	2.01	1	0	abietane diterpenoid; monocarboxylic acid	plant metabolite
podophyllotoxin Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.	2.01	1	0	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
hesperidin Hesperidin: A flavanone glycoside found in CITRUS fruit peels.. hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.31	1	0	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
flavone flavone: RN given refers to unlabeled cpd; structure given in first source. flavone : The simplest member of the class of flavones that consists of 4H-chromen-4-one bearing a phenyl substituent at position 2.	2.1	1	0	flavones	metabolite; nematicide
azomycin azomycin: RN given refers to parent cpd with specified locant; structure	2.31	1	0	C-nitro compound; imidazoles	antitubercular agent
trimellitic acid trimellitic acid: RN given refers to parent cpd; structure. trimellitic acid : Benzene substituted at the 1,2, and 4 positions by carboxy groups.	2.11	1	0	tricarboxylic acid
2-methylbenzaldehyde 2-methylbenzaldehyde: structure in first source. o-tolualdehyde : A tolualdehyde compound with the methyl substituent at the 2-position.	2.21	1	0	tolualdehyde	plant metabolite
dicyclohexylcarbodiimide 1,3-dicyclohexylcarbodiimide : A carbodiimide compound having a cyclohexyl substituent on both nitrogen atoms.	2.08	1	0	carbodiimide	ATP synthase inhibitor; cross-linking reagent; peptide coupling reagent
muscone muscone: structure in first source	2.41	2	0
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	3.72	9	0	dialdehyde	biomarker
trinitrobenzenesulfonic acid Trinitrobenzenesulfonic Acid: A reagent that is used to neutralize peptide terminal amino groups.. 2,4,6-trinitrobenzenesulfonic acid : The arenesulfonic acid that is benzenesulfonic acid with three nitro substituents in the 2-, 4- and 6-positions.	3.14	5	0	arenesulfonic acid; C-nitro compound	epitope; explosive; reagent
gentian violet Gentian Violet: A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.. crystal violet : An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.	2.41	1	0	organic chloride salt	anthelminthic drug; antibacterial agent; antifungal agent; antiseptic drug; histological dye
paeonol paeonol: structure	7.73	3	0	methoxybenzenes; phenols	metabolite
2-nitrobenzaldehyde 2-nitrobenzaldehyde: structure given in first source. 2-nitrobenzaldehyde : Benzaldehyde substituted at the ortho-position with a nitro group.	2.21	1	0	benzaldehydes; C-nitro compound
neutral red Neutral Red: A vital dye used as an indicator and biological stain. Various adverse effects have been observed in biological systems.. neutral red : A hydrochloride obtained by combining the free base of neutral red with one equivalent of hydrochloric acid. Neutral red acts as a pH indicator, changing from red to yellow between pH 6.8 and 8.0.	2	1	0	hydrochloride	acid-base indicator; dye; two-colour indicator
beta-phellandrene [no description available]	2.02	1	0	phellandrene	plant metabolite
4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol 4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol: structure in first source. 4-terpineol : A terpineol that is 1-menthene carrying a hydroxy substituent at position 4.	3.58	2	0	terpineol; tertiary alcohol	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiparasitic agent; apoptosis inducer; plant metabolite; volatile oil component
3-hydroxyflavone 3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.	3.61	2	0	flavonols; monohydroxyflavone
toluene 2,4-diisocyanate Toluene 2,4-Diisocyanate: Skin irritant and allergen used in the manufacture of polyurethane foams and other elastomers.. toluene 2,4-diisocyanate : A toluene meta-diisocyanate in which the isocyanato groups are at positions 2 and 4 relative to the methyl group on the benzene ring.	3.15	1	0	toluene meta-diisocyanate	allergen; hapten
nitrosobenzene [no description available]	2.05	1	0	benzenes; nitroso compound	xenobiotic metabolite
3-methoxybenzaldehyde 3-methoxybenzaldehyde : A member of the class of benzaldehydes in which the hydrogen at position 3 of benzaldehyde has been replaced by a methoxy group.	2.21	1	0	benzaldehydes; monomethoxybenzene	Brassica napus metabolite
levulinic acid levulinic acid: inhibits 5-aminolevulinic acid dehydratase; RN given refers to parent cpd; structure in Merck Index, 9th ed, #5316. 4-oxopentanoic acid : An oxopentanoic acid with the oxo group in the 4-position.	2.01	1	0	oxopentanoic acid; straight-chain saturated fatty acid	plant metabolite
allyl sulfide allyl sulfide: essence of garlic; inhibits CYP2E1	4.59	4	0	organic sulfide
bromoacetone bromoacetone : An alpha-bromoketone that is acetone in which one of the hydrogens is replaced by a bromine atom. A poweful lachrymator, it was formerly used as a chemical weapon.	3.15	1	0	alpha-bromoketone	lachrymator
triphenylphosphine triphenylphosphine: RN given refers to parent cpd. triphenylphosphine : A member of the class of tertiary phosphines that is phosphane in which the three hydrogens are replaced by phenyl groups.	7.41	1	0	benzenes; tertiary phosphine	NMR chemical shift reference compound; reducing agent
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.7	3	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
3-methylbenzaldehyde 3-methylbenzaldehyde: structure in first source. m-tolualdehyde : A tolualdehyde compound with the methyl substituent at the 3-position.	2.21	1	0	tolualdehyde	plant metabolite
ethyl propiolate ethyl propiolate : The ethyl ester of prop-2-ynoic acid.	2.44	2	0	ethyl ester; terminal acetylenic compound; ynoate ester
Berberine chloride (TN) [no description available]	4.41	3	0	organic molecular entity
isovanillic acid 3-hydroxy-4-methoxybenzoic acid : A methoxybenzoic acid that is 4-methoxybenzoic acid bearing a hydroxy substituent at position 3.	2.01	1	0	methoxybenzoic acid; monohydroxybenzoic acid	antibacterial agent; plant metabolite
homoserine homoserine : An alpha-amino acid that is glycine substituted at the alpha-position by a 2-hydroxyethyl group.. L-homoserine : The L-enantiomer of homoserine.	2.06	1	0	amino acid zwitterion; homoserine	algal metabolite; Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite
methylnitrosourea Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-methyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by methyl and nitroso groups.	1.98	1	0	N-nitrosoureas	alkylating agent; carcinogenic agent; mutagen; teratogenic agent
ethylnitrosourea Ethylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-ethyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by ethyl and nitroso groups.	1.97	1	0	N-nitrosoureas	alkylating agent; carcinogenic agent; genotoxin; mutagen
hydroxyethyl methacrylate hydroxyethyl methacrylate: many of cited refs are for gel which refers to polymeric form of above cpd: POLYHYDROXYETHYL METHACRYLATE. 2-hydroxyethyl methacrylate : An enoate ester that is the monomethacryloyl derivative of ethylene glycol.	2.07	1	0	enoate ester	allergen; polymerisation monomer
cyclopentenone 2-cyclopenten-1-one : An enone that is cyclopentanone having a C=C double bond at position 2.	2.76	3	0	alicyclic ketone; enone	Hsp70 inducer
2-cyclohexen-1-one 2-cyclohexen-1-one: RN given refers to unlabeled cpd with specified locant for double bond. cyclohexenone : The parent compound of the cyclohexenones, composed of cyclohexanone having one double bond in the ring.. cyclohex-2-enone : A cyclohexenone having its C=C double bond at the 2-position.	2.69	3	0	cyclohexenone
2-aminobenzimidazole 2-aminobenzimidazole: metabolite of benomyl; RN given refers to parent cpd. 2-aminobenzimidazole : A member of the class of benzimidazoles that is benzimidazole in which the hydrogen at position 2 is replaced by an amino group.	2.31	1	0	benzimidazoles	marine xenobiotic metabolite
diphenylacetaldehyde diphenylacetaldehyde: structure in first source	2.21	1	0
pyrrole-2-carboxaldehyde 2-pyrrolecarboxaldehyde: structure in first source. pyrrole-2-carboxaldehyde : A pyrrole carrying a formyl substituent at the 2-position.	2.21	1	0	1,3-thiazole-2-carbaldehyde; pyrroles
pyridine-2-carboxaldehyde pyridine-2-carboxaldehyde: structure in first source. 2-formylpyridine : A pyridinecarbaldehyde that is pyridine in which the hydrogen at position 2 is replaced by a formyl group.	2.21	1	0	pyridinecarbaldehyde
germanium oxide germanium oxide: has antimutagenic effects; RN given refers to cpd with MF GeO2	1.96	1	0
zinc oxide Zinc Oxide: A mild astringent and topical protectant with some antiseptic action. It is also used in bandages, pastes, ointments, dental cements, and as a sunblock.	2.98	3	0	zinc molecular entity
monolaurin monolaurin: RN given refers to cpd with unspecified monolaurin locant. 1-monolauroylglycerol : A 1-monoglyceride with dodecanoyl (lauroyl) as the acyl group.. rac-1-monolauroylglycerol : A rac-1-monoacylglycerol comprising equal amounts of 1-lauroyl-sn-glycerol and 3-lauroyl-sn-glycerol	2.41	1	0	1-monoglyceride; dodecanoate ester; rac-1-monoacylglycerol
beta-pinene beta-pinene: alpha-pinene is also available. beta-pinene : An isomer of pinene with an exocyclic double bond. It is a component of essential oils from many plants.	2.6	1	0	pinene	plant metabolite
glycyrrhizic acid glycyrrhizinic acid : A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.	2.7	3	0	enone; glucosiduronic acid; pentacyclic triterpenoid; tricarboxylic acid; triterpenoid saponin	EC 3.4.21.5 (thrombin) inhibitor; plant metabolite
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	2.75	3	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
allyl isocyanate allyl isocyanate: a glycosinolate degradation product that has insectidical activity	2.15	1	0	isocyanates
1,2,3,4-butanetetracarboxylic acid 1,2,3,4-butanetetracarboxylic acid: structure in first source	2.31	1	0
2-tert-butylhydroquinone 2-tert-butylhydroquinone: an anticarcinogenic and chemopreventive agent. 2-tert-butylhydroquinone : A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.	2.08	1	0	hydroquinones	food antioxidant
dronabinol Dronabinol: A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound.. Delta(9)-tetrahydrocannabinol : A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy.	4.05	2	0	benzochromene; diterpenoid; phytocannabinoid; polyketide	cannabinoid receptor agonist; epitope; hallucinogen; metabolite; non-narcotic analgesic
amiloride Amiloride: A pyrazine compound inhibiting SODIUM reabsorption through SODIUM CHANNELS in renal EPITHELIAL CELLS. This inhibition creates a negative potential in the luminal membranes of principal cells, located in the distal convoluted tubule and collecting duct. Negative potential reduces secretion of potassium and hydrogen ions. Amiloride is used in conjunction with DIURETICS to spare POTASSIUM loss. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p705). amiloride : A member of the class of pyrazines resulting from the formal monoacylation of guanidine with the carboxy group of 3,5-diamino-6-chloropyrazine-2-carboxylic acid.	2.06	1	0	aromatic amine; guanidines; organochlorine compound; pyrazines	diuretic; sodium channel blocker
diallyl trisulfide [no description available]	3.5	2	0	organic trisulfide	anti-inflammatory agent; antilipemic drug; antineoplastic agent; antioxidant; antiprotozoal drug; apoptosis inducer; estrogen receptor antagonist; insecticide; platelet aggregation inhibitor; vasodilator agent
perillaldehyde perillaldehyde: from oil of Perillae herba; has neuropharmacological actions; RN given refers to cpd without isomeric designation; structure in Merck Index, 9th ed, #6956. perillyl aldehyde : An aldehyde that is cyclohex-1-ene-1-carbaldehyde substituted by a prop-1-en-2-yl group at position 4.	9.07	4	0	aldehyde; olefinic compound	human metabolite; mouse metabolite; volatile oil component
diallyl disulfide diallyl disulfide: major constituent of garlic oil. diallyl disulfide : An organic disulfide where the organic group specified is allyl. It has been isolated from garlic and other species of the genus Allium.	5.44	4	1	organic disulfide	antifungal agent; antineoplastic agent; plant metabolite
menthol (+-)-menthol : A racemate comprising equimolar amounts of (+)- and (-)-menthol. Both (+-)- and (-)-menthol are used to relieve symptoms of conditions such as bronchitis and sinusitis. When applied to the skin, menthol dilates the blood vessels, giving a sensation of coldness followed by an analgesic effect that relieves itching. It is therefore used in creams and ointments for the relief of pruritis and urticaria.. (-)-menthol : A p-menthan-3-ol which has (1R,2S,5R)-stereochemistry. It is the most common naturally occurring enantiomer.	2.42	2	0	p-menthan-3-ol	antipruritic drug; antispasmodic drug; antitussive
phenethyl isothiocyanate phenethyl isothiocyanate: a dietary liver aldehyde dehydrogenase inhibitor; promotes urinary bladder carcinoma. phenethyl isothiocyanate : An isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties.	3.15	1	0	isothiocyanate	antineoplastic agent; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; metabolite
thioflavin t thioflavin T: RN given refers to chloride; structure. thioflavine T : An organic chloride salt having 2-[4-(dimethylamino)phenyl]-3,6-dimethyl-1,3-benzothiazol-3-ium as the counterion. It is widely used to visualise and quantify the presence of amyloids, both in vitro and in vivo.	2.31	1	0	organic chloride salt	fluorochrome; geroprotector; histological dye
benzyl acetone benzyl acetone: a dominant floral attractant	2.53	2	0	ketone
hexadecanethiol [no description available]	2.1	1	0
dithianone dithianone: structure. dithianon : A naphthodithiin that is 5,10-dioxo-5,10-dihydronaphtho[2,3-b][1,4]dithiin which is substituted by nitrile groups at positions 2 and 3. It is a broad spectrum fungicide used to control scab, downy mildew, rust, and leaf spot in the commercial growing of grapes and other fruit, citrus, coffee, and vegetables.	2.06	1	0	dinitrile; naphthodithiin; p-quinones	antifungal agrochemical
dithiothreitol 1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.	2.03	1	0	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
palmatine burasaine: structure in first source	7.02	1	0	berberine alkaloid; organic heterotetracyclic compound	plant metabolite
azo rubin s azo rubin S: RN given refers to parent cpd; structure	2.31	1	0
tranylcypromine Tranylcypromine: A propylamine formed from the cyclization of the side chain of amphetamine. This monoamine oxidase inhibitor is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in panic and phobic disorders. (From AMA Drug Evaluations Annual, 1994, p311). tranylcypromine : A racemate comprising equal amounts of (1R,2S)- and (1S,2R)-2-phenylcyclopropan-1-amine. An irreversible monoamine oxidase inhibitor that is used as an antidepressant (INN tranylcypromine).. (1R,2S)-tranylcypromine : A 2-phenylcyclopropan-1-amine that is the (1R,2S)-enantiomer of tranylcypromine.	1.96	1	0	2-phenylcyclopropan-1-amine
streptomycin [no description available]	7.48	2	0	antibiotic antifungal drug; antibiotic fungicide; streptomycins	antibacterial drug; antifungal agrochemical; antimicrobial agent; antimicrobial drug; bacterial metabolite; protein synthesis inhibitor
fructosamine Fructosamine: An amino sugar formed when glucose non-enzymatically reacts with the N-terminal amino group of proteins. The fructose moiety is derived from glucose by the classical Amadori rearrangement.	2.52	2	0
ethyl maltol ethyl maltol: structure given in first source	2.21	1	0	pyranone
chlordantoin chlordantoin: structure	3.15	1	0	imidazolidine-2,4-dione
limonene Limonene: A naturally-occurring class of MONOTERPENES which occur as a clear colorless liquid at room temperature. Limonene is the major component in the oil of oranges which has many uses, including as flavor and fragrance. It is recognized as safe in food by the Food and Drug Administration (FDA).. limonene : A monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively.	8.74	10	0	cycloalkene; p-menthadiene	human metabolite
n-methylaspartate N-Methylaspartate: An amino acid that, as the D-isomer, is the defining agonist for the NMDA receptor subtype of glutamate receptors (RECEPTORS, NMDA).. N-methyl-D-aspartic acid : An aspartic acid derivative having an N-methyl substituent and D-configuration.	2.52	2	0	amino dicarboxylic acid; D-alpha-amino acid; D-aspartic acid derivative; secondary amino compound	neurotransmitter agent
lanthanum [no description available]	2.08	1	0	f-block element atom; lanthanoid atom; scandium group element atom
molybdenum Molybdenum: A metallic element with the atomic symbol Mo, atomic number 42, and atomic weight 95.95. It is an essential trace element, being a component of the enzymes xanthine oxidase, aldehyde oxidase, and nitrate reductase.	2.05	1	0	chromium group element atom	micronutrient
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	8.16	5	0	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	2.49	2	0	elemental platinum; nickel group element atom; platinum group metal atom
rhodium Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.	2.44	2	0	cobalt group element atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	7.78	3	0	iron group element atom; platinum group metal atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	2.57	2	0	copper group element atom; elemental silver	Escherichia coli metabolite
titanium Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.	2.57	2	0	titanium group element atom
chromium Chromium: A trace element that plays a role in glucose metabolism. It has the atomic symbol Cr, atomic number 24, and atomic weight 52. According to the Fourth Annual Report on Carcinogens (NTP85-002,1985), chromium and some of its compounds have been listed as known carcinogens.. chromium ion : An chromium atom having a net electric charge.. chromium atom : A chromium group element atom that has atomic number 24.	3.12	1	0	chromium group element atom; metal allergen	micronutrient
gadolinium Gadolinium: An element of the rare earth family of metals. It has the atomic symbol Gd, atomic number 64, and atomic weight 157.25. Its oxide is used in the control rods of some nuclear reactors.	2.08	1	0	f-block element atom; lanthanoid atom
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	7.81	3	0	copper group element atom; elemental gold
vanadium Vanadium: A metallic element with the atomic symbol V, atomic number 23, and atomic weight 50.94. It is used in the manufacture of vanadium steel. Prolonged exposure can lead to chronic intoxication caused by absorption usually via the lungs.	2.05	1	0	elemental vanadium; vanadium group element atom	micronutrient
aluminum chloride Aluminum Chloride: A compound with the chemical formula AlCl3; the anhydrous salt is used as a catalyst in organic chemical synthesis, and hydrated salts are used topically as antiperspirants, and for the management of HYPERHYDROSIS.	2.25	1	0	aluminium coordination entity	Lewis acid
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	2.59	2	0	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
phosphine phosphane : The simplest phosphine, consisting of a single phosphorus atom with three hydrogens attached.. phosphine : Phosphane (PH3) and compounds derived from it by substituting one, two or three hydrogen atoms by hydrocarbyl groups: RPH2, R2PH, R3P (R =/= H) are called primary, secondary and tertiary phosphines, respectively. A specific phosphine is preferably named as a substituted phosphane.	2.08	1	0	mononuclear parent hydride; phosphanes; phosphine	carcinogenic agent; fumigant insecticide
tricalcium phosphate tricalcium phosphate: a form of tricalcium phosphate used as bioceramic bone replacement material; see also records for alpha-tricalcium phosphate, beta-tricalcium phosphate, calcium phosphate; apatitic tricalcium phosphate Ca9(HPO4)(PO4)5(OH) is the calcium orthophosphate leading to beta tricalcium phosphate Ca3(PO4)2 (b-TCP). calcium phosphate : A calcium salt composed of calcium and phosphate/diphosphate ions; present in milk and used for the mineralisation of calcified tissues.	2.21	1	0	calcium phosphate
silver nitrate Silver Nitrate: A silver salt with powerful germicidal activity. It has been used topically to prevent OPHTHALMIA NEONATORUM.	2.6	1	0	inorganic nitrate salt; silver salt	astringent
potassium dichromate Potassium Dichromate: Chromic acid (H2Cr2O7), dipotassium salt. A compound having bright orange-red crystals and used in dyeing, staining, tanning leather, as bleach, oxidizer, depolarizer for dry cells, etc. Medically it has been used externally as an astringent, antiseptic, and caustic. When taken internally, it is a corrosive poison.. potassium dichromate : A potassium salt that is the dipotassium salt of dichromic acid.	2.04	1	0	potassium salt	allergen; oxidising agent; sensitiser
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2.43	2	0	dihydrogen
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	2.05	1	0	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	3.05	4	0	diatomic chlorine; gas molecular entity	bleaching agent
nickel sulfate nickel sulfate: RN given refers to cpd with MF of Ni(2+)-H2SO4. nickel sulfate : A metal sulfate having nickel(2+) as the metal ion.	2.93	4	0	metal sulfate	allergen
sulfur trioxide sulfur trioxide: RN given refers to parent cpd	2.31	1	0	sulfur oxide
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	2.43	2	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
cadmium chloride Cadmium Chloride: A cadmium halide in the form of colorless crystals, soluble in water, methanol, and ethanol. It is used in photography, in dyeing, and calico printing, and as a solution to precipitate sulfides. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). cadmium dichloride : A cadmium coordination entity in which cadmium(2+) and Cl(-) ions are present in the ratio 2:1. Although considered to be ionic, it has considerable covalent character to its bonding.	2.13	1	0	cadmium coordination entity
titanium dioxide titanium dioxide: used medically as protectant against externally caused irritation & sunlight; high concentrations of dust may cause irritation to respiratory tract; RN given refers to titanium oxide (TiO2); structure. titanium dioxide : A titanium oxide with the formula TiO2. A naturally occurring oxide sourced from ilmenite, rutile and anatase, it has a wide range of applications.	2.41	1	0	titanium oxides	food colouring
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	3.12	5	0
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2.43	2	0	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
sodium bisulfide sodium bisulfide: RN given refers to sodium sulfide (Na(SH)); see also record for sodium sulfide (Na2S)	2.48	2	0
fluorides [no description available]	2.44	2	0	halide anion; monoatomic fluorine
benomyl [no description available]	2.06	1	0	aromatic amide; benzimidazole fungicide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	acaricide; anthelminthic drug; antifungal agrochemical; microtubule-destabilising agent; tubulin modulator
cannabichromene [no description available]	3.15	1	0	1-benzopyran
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.73	3	0	benzenes; phenyl acetates
3-phenyl-1-propanol [no description available]	2.49	2	0	monocyclic arene
4-anisaldehyde 4-anisaldehyde: RN given refers to cpd with specified locants for methoxy moieties; structure in Merck, 9th ed, #696. p-methoxybenzaldehyde : A member of the class of benzaldehydes consisting of benzaldehyde itself carrying a methoxy substituent at position 4.	2.93	4	0	benzaldehydes	bacterial metabolite; human urinary metabolite; insect repellent; plant metabolite
isoamyl acetate isoamyl acetate: structure in Merck, 9th ed, #4958. isoamyl acetate : The acetate ester of isoamylol.	1.97	1	0	acetate ester	metabolite; Saccharomyces cerevisiae metabolite
nonanal nonanal : A saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism.	2.21	1	0	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	human metabolite; plant metabolite
chloroprene Chloroprene: Toxic, possibly carcinogenic, monomer of neoprene, a synthetic rubber; causes damage to skin, lungs, CNS, kidneys, liver, blood cells and fetuses. Synonym: 2-chlorobutadiene.	2.31	1	0	chloroolefin
8-bromo cyclic adenosine monophosphate 8-Bromo Cyclic Adenosine Monophosphate: A long-acting derivative of cyclic AMP. It is an activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.. 8-Br-cAMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic AMP bearing an additional bromo substituent at position 8 on the adenine ring. An activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.	2	1	0	3',5'-cyclic purine nucleotide; adenyl ribonucleotide; organobromine compound	antidepressant; protein kinase agonist
alkenes [no description available]	2.8	3	0
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	3.23	5	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
azoxymethane Azoxymethane: A potent carcinogen and neurotoxic compound. It is particularly effective in inducing colon carcinomas.	7.11	1	0
5-chloro-2-methyl-4-isothiazolin-3-one 5-chloro-2-methyl-4-isothiazolin-3-one: RN given refers to parent cpd; structure. chloromethylisothiazolinone : A 1,2-thiazole that is 4-isothiazolin-3-one bearing a methyl group on the nitrogen atom and a chlorine at C-5. It is a powerful biocide and preservative and is the major active ingredient in the commercial product Kathon(TM).	2.43	2	0	1,2-thiazoles; organochlorine compound	antimicrobial agent; environmental contaminant; xenobiotic
sodium azide Sodium Azide: A cytochrome oxidase inhibitor which is a nitridizing agent and an inhibitor of terminal oxidation. (From Merck Index, 12th ed). sodium azide : The sodium salt of hydrogen azide (hydrazoic acid).	2.52	2	0	inorganic sodium salt	antibacterial agent; explosive; mitochondrial respiratory-chain inhibitor; mutagen
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	2.08	1	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
amitraz amitraz: ixodicide (tick control); structure. amitraz : A tertiary amino compound that is 1,3,5-triazapenta-1,4-diene substituted by a methyl group at position 3 and 2,4-dimethylphenyl groups at positions 1 and 5.	2.41	1	0	formamidines; tertiary amino compound	acaricide; environmental contaminant; insecticide; xenobiotic
substance p [no description available]	2.97	4	0	peptide	neurokinin-1 receptor agonist; neurotransmitter; vasodilator agent
amikacin Amikacin: A broad-spectrum antibiotic derived from KANAMYCIN. It is reno- and oto-toxic like the other aminoglycoside antibiotics.. amikacin : An amino cyclitol glycoside that is kanamycin A acylated at the N-1 position by a 4-amino-2-hydroxybutyryl group.	3.68	2	0	alpha-D-glucoside; amino cyclitol glycoside; aminoglycoside; carboxamide	antibacterial drug; antimicrobial agent; nephrotoxin
isovelleral isovelleral: structure given in first source	3.15	1	0	aldehyde
3-phenoxybenzaldehyde [no description available]	2.21	1	0
n-acetyl-4-benzoquinoneimine N-acetyl-4-benzoquinoneimine: reactive arylating intermediate from acetaminophen & N-hydroxyacetaminophen; structure given in first source	2.77	3	0	ketoimine; quinone imine
2-methyl-4-isothiazolin-3-one 2-methyl-4-isothiazolin-3-one: RN given refers to parent cpd; structure. methylisothiazolinone : A 1,2-thazole that is 4-isothiazolin-3-one bearing a methyl group on the nitrogen atom. It is a powerful biocide and preservative and is the minor active ingredient in the commercial product Kathon(TM).	1.99	1	0	1,2-thiazoles	antifouling biocide; antifungal agent; antimicrobial agent
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	3.03	4	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
permethrin hemoglobin Atlanta-Coventry: Leu replaced by Pro at beta75 and Leu deleted at beta141	2.21	1	0	cyclopropanecarboxylate ester; cyclopropanes	agrochemical; ectoparasiticide; pyrethroid ester acaricide; pyrethroid ester insecticide; scabicide
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	2.1	1	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
kathon cg Kathon 886: industrial biocide & cosmetic preservative formulation; contains methylcholoro-isothiazolinone and methylcholoroisothiazolinone	2.38	2	0
colforsin Colforsin: Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant COLEUS FORSKOHLII. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.	1.98	1	0	acetate ester; cyclic ketone; labdane diterpenoid; organic heterotricyclic compound; tertiary alpha-hydroxy ketone; triol	adenylate cyclase agonist; anti-HIV agent; antihypertensive agent; plant metabolite; platelet aggregation inhibitor; protein kinase A agonist
2-amino-6-methyldipyrido(1,2-a-3',2'-d)imidazole 2-amino-6-methyldipyrido(1,2-a-3',2'-d)imidazole: structure	2.17	1	0	imidazopyridine
pimonidazole pimonidazole: structure given in first source	2.31	1	0
mitoxantrone hydrochloride [no description available]	2.11	1	0	hydrochloride	antineoplastic agent
2-amino-3-methylimidazo(4,5-f)quinoline 2-amino-3-methylimidazo(4,5-f)quinoline: mutagen found in broiled food; RN given refers to parent cpd; structure given in first source; frequently abbreviated as IQ in the literature. 3-methyl-3H-imidazo[4,5-f]quinolin-2-amine : An imidazoquinoline that is 3H-imidazo[4,5-f]quinoline substituted by a methyl group at position 3 and an amino group at position 2.	1.99	1	0	imidazoquinoline	carcinogenic agent
tucaresol tucaresol: causes a dose-dependent left-shift of the oxygen saturation curve of hemoglobin S by stabilization of its oxy-(R)-conformation; an anti-sickling agent	3.35	1	0
fura-2 Fura-2: A fluorescent calcium chelating agent which is used to study intracellular calcium in tissues.	2.48	2	0
tiagabine Tiagabine: A nipecotic acid derivative that acts as a GABA uptake inhibitor and anticonvulsant agent. It is used in the treatment of EPILEPSY, for refractory PARTIAL SEIZURES.. tiagabine : A piperidinemonocarboxylic acid that is (R)-nipecotic acid in which the hydrogen attached to the nitrogen has been replaced by a 1,1-bis(3-methyl-2-thienyl)but-1-en-4-yl group. A GABA reuptake inhibitor, it is used (generally as the hydrochloride salt) for the treatment of epilepsy.	2.21	1	0	beta-amino acid; piperidinemonocarboxylic acid; tertiary amino compound; thiophenes	anticonvulsant; GABA reuptake inhibitor
3-methyl-2-butenal 3-methylbut-2-enal : An enal consisting of but-2-ene with a methyl substituent at position 3 and an oxo group at position 1.	2.15	1	0	enal	metabolite
octyl gallate [no description available]	7.49	2	0	gallate ester	food antioxidant; hypoglycemic agent; plant metabolite
ruthenium chloride (rucl3) ruthenium chloride: RN given refers to unlabeled cpd	2.07	1	0
2-amino-3,4-dimethylimidazo(4,5-f)quinoline 2-amino-3,4-dimethylimidazo(4,5-f)quinoline: strong mutagens found in broiled food; structure given in first source	2.44	2	0	aminoquinoline
musk xylene musk xylene : A C-nitro compound that is m-xylene bearing three nitro substituents at positions 2, 4 and 6 as well as a tert-butyl group at position 5.	1.98	1	0	C-nitro compound	carcinogenic agent; explosive; fragrance
ketoisophorone ketoisophorone: structure in first source	2.48	2	0	cyclohexenones
isothiocyanic acid [no description available]	2.52	2	0	hydracid; one-carbon compound
trichlorophene trichlorophene: contains 20 carbon atoms; do not confuse with trichlorophene as name for trichloro derivs of 2,2'-methylenebisphenol (contain 13 carbon atoms)	2.08	1	0
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	3.27	6	0	D-glucopyranose	epitope; mouse metabolite
ursolic acid [no description available]	3.55	2	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	geroprotector; plant metabolite
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	2.75	3	0	organic bromide salt	colorimetric reagent; dye
betulinic acid [no description available]	3.25	1	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-HIV agent; anti-inflammatory agent; antimalarial; antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; plant metabolite
baicalin [no description available]	2.47	2	0	dihydroxyflavone; glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative	antiatherosclerotic agent; antibacterial agent; anticoronaviral agent; antineoplastic agent; antioxidant; cardioprotective agent; EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; ferroptosis inhibitor; neuroprotective agent; non-steroidal anti-inflammatory drug; plant metabolite; prodrug
allicin [no description available]	4.71	3	0	botanical anti-fungal agent; sulfoxide	antibacterial agent
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	2.02	1	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
gallocatechol gallocatechol: structure give in first source; RN given for (trans-(+-))-omer; inhibits DNA-dependent DNA & RNA polymerases. (+)-gallocatechin : A gallocatechin that has (2R,3S)-configuration. It is found in green tea and bananas.. gallocatechin : A catechin that is a flavan substituted by hydroxy groups at positions 3, 3', 4', 5, 5' and 7 (the trans isomer). It is isolated from Acacia mearnsii.	2.02	1	0	gallocatechin	antioxidant; metabolite; radical scavenger
rutecarpine rutacarpine: from Evodia rutaecarpa; an ingredient in zhuyu hewei zhitong capsules	2.02	1	0	beta-carbolines
4-cyanobenzaldehyde [no description available]	2.21	1	0	benzaldehydes
boron nitride [no description available]	7.6	1	0	nitride
1,2,4-trimethoxybenzene 1,2,4-trimethoxybenzene: a volatile organic compound	2.03	1	0	methoxybenzenes
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	3.4	2	0	1,2,3-triazole
4-(trifluoromethyl)benzaldehyde [no description available]	2.21	1	0	benzaldehydes
4-fluorobenzaldehyde [no description available]	2.21	1	0
pinocembrin pinocembrin : A dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea.	3.62	2	0	(2S)-flavan-4-one; dihydroxyflavanone	antineoplastic agent; antioxidant; metabolite; neuroprotective agent; vasodilator agent
tangeretin tangeretin: structure given in first source; from citrus plants; inhibits invasion of MO4 mouse cells into embryonic chick heart in vitro. tangeretin : A pentamethoxyflavone flavone with methoxy groups at positions 4', 5, 6 , 7 and 8.. pentamethoxyflavone : A methoxyflavone that is flavone substituted by a five methoxy groups.	2.31	1	0	pentamethoxyflavone	antineoplastic agent; plant metabolite
delphinidin Paraffin: A mixture of solid hydrocarbons obtained from petroleum. It has a wide range of uses including as a stiffening agent in ointments, as a lubricant, and as a topical anti-inflammatory. It is also commonly used as an embedding material in histology.. delphinidin chloride : An anthocyanidin chloride that has delphinidin as the cationic counterpart.	2.04	1	0	anthocyanidin chloride
alpha-methylene gamma-butyrolactone alpha-methylene gamma-butyrolactone : A butan-4-olide having a methylene group at the 3-position.	2.44	2	0	butan-4-olide	anti-ulcer drug; gastrointestinal drug
perilla ketone perilla ketone: potent lung toxin from Perilla frutescens; structure	3.15	1	0	aromatic ketone
methyl acetylsalicylic acid methyl acetylsalicylic acid: has less gastrointestinal side effects than aspirin; structure in Merck Index, 9th ed, #5886	2.17	1	0
9-anthraldehyde [no description available]	2.21	1	0
2-hydroxy-4-methoxybenzaldehyde 2-hydroxy-4-methoxybenzaldehyde: from African medicinal plants: Mondia whitei (Apocynaceae), Rhus vulagaris (Anacardiaceae), Sclerocarya caffra (Anacardiaceae)	7.15	1	0	methoxybenzenes; phenols
methyl syringate methyl syringate : A benzoate ester obtained by the formal condensation of carboxy group of syringic acid with methanol.	2.08	1	0	benzoate ester; dimethoxybenzene; phenols	plant metabolite
n-methylmaleimide N-methylmaleimide: structure in first source	2.11	1	0
2,5-dihydroxybenzaldehyde 2,5-dihydroxybenzaldehyde: structure in first source. 2,5-dihydroxybenzaldehyde : A dihydroxybenzaldehyde carrying hydroxy groups at positions 2 and 5.	2.1	1	0	dihydroxybenzaldehyde	human metabolite; mouse metabolite; Penicillium metabolite
acetylisoniazid acetylisoniazid: Antitubercular Agent. N'-acetylisoniazid : A carbohydrazide resulting from the formal condensation of the carboxy group of isonicotinic acid with hydrazine and subsequent acetylation of the monosubstituted nitrogen atom.	1.96	1	0	carbohydrazide	metabolite
bw 12c79 5-(2-formyl-3-hydroxyphenoxy)pentanoic acid: aromatic aldehyde; aldehyde group interacts with N-terminal amino group of both alpha-globin chains	3.35	1	0
avarol avarol: RN given refers to parent cpd; extract from Dysidea avara(sea sponge)	2.02	1	0
epicatechin (-)-epicatechin : A catechin with (2R,3R)-configuration.	2.02	1	0	catechin; polyphenol	antioxidant
hesperetin [no description available]	7.31	1	0	3'-hydroxyflavanones; 4'-methoxyflavanones; monomethoxyflavanone; trihydroxyflavanone	antineoplastic agent; antioxidant; plant metabolite
tetrahydropalmatine [no description available]	2.07	1	0	an (S)-7,8,13,14-tetrahydroprotoberberine; berberine alkaloid; organic heterotetracyclic compound	adrenergic agent; dopaminergic antagonist; non-narcotic analgesic
betulin betulin: isolated from various white birch bark (BETULA). betulin : A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents.	2.01	1	0	diol; pentacyclic triterpenoid	analgesic; anti-inflammatory agent; antineoplastic agent; antiviral agent; metabolite
polygodial [no description available]	3.15	1	0	aldehyde
alantolactone alantolactone: allergenic sesquiterpene lactone; crystalline mixture of alantolactones from group of sesquiterpenes; structure. alantolactone : A sesquiterpene lactone that is 3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2-one bearing two methyl substituents at positions 5 and 8a as well as a methylidene substituent at position 3.	2.07	1	0	naphthofuran; olefinic compound; sesquiterpene lactone	antineoplastic agent; apoptosis inducer; plant metabolite
voacamine [no description available]	2.1	1	0	alkaloid ester; methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; plant metabolite
isoalantolactone isoalantolactone: RN given refers to (3aR-(3aalpha,4aalpha,8abeta,9aalpha))-isomer; structure. isoalantolactone : A sesquiterpene lactone of the eudesmanolide group. It has been isolated from Inula helenium.	2.07	1	0	eudesmane sesquiterpenoid; sesquiterpene lactone	antifungal agent; apoptosis inducer; plant metabolite
magnoflorine magnoflorine: opium alkaloid having the aporphine configuration; RN given refers to parent cpd(S)-isomer; structure. (S)-magnoflorine : An aporphine alkaloid that is (S)-corytuberine in which the nitrogen has been quaternised by an additional methyl group.	2.17	1	0	aporphine alkaloid; quaternary ammonium ion	plant metabolite
fangchinoline [no description available]	2.02	1	0	aromatic ether; bisbenzylisoquinoline alkaloid; macrocycle	anti-HIV-1 agent; anti-inflammatory agent; antineoplastic agent; antioxidant; neuroprotective agent; plant metabolite
tryptanthrine tryptanthrine: minor constituent of traditional Chinese medicine qing dai	2.02	1	0	alkaloid antibiotic; organic heterotetracyclic compound; organonitrogen heterocyclic compound
flusilazole flusilazole: structure given in first source. flusilazole : An organosilicon compound that is dimethylsilane in which the hydrogens attached to the silicon are replaced by p-fluorophenyl groups and a hydrogen attached to one of the methyl groups is replaced by a 1H-1,2,4-triazol-1-yl group. It is a broad-sepctrum fungicide used to protect a variety of crops.	2.06	1	0	conazole fungicide; monofluorobenzenes; organosilicon compound; triazole fungicide; triazoles	antifungal agrochemical; EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor; environmental contaminant; xenobiotic
citronellal, (r)-isomer (R)-(+)-citronellal : The (3R)-stereoisomer of 3,7-dimethyloct-6-enal (citronellal).	2.01	1	0	citronellal
n-(hydroxymethyl)carbazole N-(hydroxymethyl)carbazole: structure given in first source	2.1	1	0
4'-methoxyflavone 4'-methoxyflavone: from seeds of Psoralea corylifolia (Fabaceae); structure in first source	2.1	1	0	ether; flavonoids
rosiglitazone [no description available]	2.07	1	0	aminopyridine; thiazolidinediones	EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; insulin-sensitizing drug
quinoline-4-carbaldehyde [no description available]	2.21	1	0
2-quinolinecarboxaldehyde 2-quinolinecarboxaldehyde: structure in first source	2.21	1	0
methyl 3-(4-hydroxyphenyl)propionate methyl 3-(4-hydroxyphenyl)propionate: a root-exuded compound responsible for biological nitrification inhibition by sorghum (Sorghum bicolor); structure in first source. methyl 3-(4-hydroxyphenyl)propionate : A methyl ester resulting from the formal condensation of the carboxy group of phloretic acid with methanol. It is a nitrification inhibitor and a plant growth regulator.	2	1	0	methyl ester; phenols	nitrification inhibitor; plant growth regulator
n-hydroxysuccinimide N-hydroxysuccinimide: structure	2.03	1	0
2-bromobenzaldehyde 2-bromobenzaldehyde: structure in first source	2.21	1	0
3,4-dihydroxyphenylethanol 3,4-dihydroxyphenylethanol: serotonin metabolite; structure	2.31	1	0	catechols; primary alcohol	antineoplastic agent; antioxidant; metabolite
platinum oxide [no description available]	2.08	1	0
4-methoxy-1-naphthalaldehyde 4-methoxy-1-naphthalaldehyde: used for fluorometric assays for isozymes of human alcohol dehydrogenase; structure given in first source	2.21	1	0
dimethomorph [no description available]	2.06	1	0	mixture; morpholine fungicide	antifungal agrochemical; environmental contaminant; xenobiotic
fludioxonil fludioxonil: structure in first source. fludioxonil : A member of the class of benzodioxoles that is 2,2-difluoro-1,3-benzodioxole substituted at position 4 by a 3-cyanopyrrol-4-yl group. A fungicide seed treatment for control of a range of diseases including Fusarium, Rhizoctonia and Alternaria.	2.06	1	0	benzodioxoles; nitrile; organofluorine compound; pyrroles	androgen antagonist; antifungal agrochemical; estrogen receptor agonist
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	7.74	10	1	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
sennoside B sennoside B : A member of the class of sennosides that is (9R,9'S)-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylic acid which is substituted by hydroxy groups at positions 4 and 4', by beta-D-glucopyranosyloxy groups at positions 5 and 5', and by oxo groups at positions 10 and 10'.	2.01	1	0	oxo dicarboxylic acid; sennosides
aucubin [no description available]	2.07	1	0	organic molecular entity	metabolite
catalpol [no description available]	2.07	1	0	organic molecular entity	metabolite
hydroxyisohexyl 3-cyclohexene carboxaldehyde hydroxyisohexyl 3-cyclohexene carboxaldehyde: structure in first source	2.42	2	0
fosthiazate fosthiazate: structure in first source	2.13	1	0	organic phosphonate; organothiophosphate insecticide; phosphonic ester	agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; nematicide
totarol totarol: structure given in first source; isolated from the bark of Podocarpus nagi	3.6	2	0	diterpenoid	metabolite
beta-hydroxyphenylpropionic acid beta-hydroxyphenylpropionic acid: benzoic acid metabolite in urine. 3-hydroxy-3-phenylpropionic acid : A 3-hydroxy carboxylic acid that is 3-phenylpropionic acid in which one of the hydrogens beta to the carboxy group is replaced by a hydroxy group.	1.98	1	0	3-hydroxy carboxylic acid; monocarboxylic acid
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	2.52	2	0	D-glucuronic acid	algal metabolite
2-hydroxy-5-methoxybenzaldehyde 2-hydroxy-5-methoxybenzaldehyde: structure in first source. 5-methoxysalicylaldehyde : A member of the class of benzaldehydes carrying hydroxy and methoxy substituents at positions 2 and 5 respectively.	2.55	2	0	benzaldehydes; monomethoxybenzene; phenols
syringaresinol [no description available]	2.17	1	0	aromatic ether; furofuran; lignan; polyether; polyphenol	plant metabolite
karanjin karanjin: structure given in first source	2.1	1	0	extended flavonoid
dicentrine dicentrine: structure given in first source; RN refers to (S)-isomer	2.08	1	0	aporphine alkaloid
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	8.27	6	0	cobalt group element atom; metal allergen	micronutrient
hydrogen sulfite [no description available]	2.25	1	0	sulfur oxoanion	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
imipenem, anhydrous Imipenem: Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with CILASTATIN, a renal dipeptidase inhibitor.. imipenem : A broad-spectrum, intravenous beta-lactam antibiotic of the carbapenem subgroup.	2.25	1	0	beta-lactam antibiotic allergen; carbapenems; zwitterion	antibacterial drug
diacetyldichlorofluorescein diacetyldichlorofluorescein: stable storage form of dichlorofluorescein	2.15	1	0
cyanates Cyanates: Organic salts of cyanic acid containing the -OCN radical.. cyanates : Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N.. isocyanates : Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N).	2.53	2	0
pregnenolone sulfate pregnenolone sulfate: RN given refers to (3 beta)-isomer	2.08	1	0	steroid sulfate	EC 2.7.1.33 (pantothenate kinase) inhibitor; human metabolite
thiamethoxam Thiamethoxam: A nitro-oxazine and thiazole derivative that is used as a broad spectrum neonicotinoid insecticide.. thiamethoxam : An oxadiazane that is tetrahydro-N-nitro-4H-1,3,5-oxadiazin-4-imine bearing (2-chloro-1,3-thiazol-5-yl)methyl and methyl substituents at positions 3 and 5 respectively.	2.13	1	0	1,3-thiazoles; 2-nitroguanidine derivative; organochlorine compound; oxadiazane	antifeedant; carcinogenic agent; environmental contaminant; neonicotinoid insectide; xenobiotic
hypotaurine [no description available]	2.13	1	0	aminosulfinic acid; zwitterion	human metabolite; metabolite; mouse metabolite
geniposide [no description available]	2.6	1	0	terpene glycoside
procyanidin Proanthocyanidins: Dimers and oligomers of flavan-3-ol units (CATECHIN analogs) linked mainly through C4 to C8 bonds to leucoanthocyanidins. They are structurally similar to ANTHOCYANINS but are the result of a different fork in biosynthetic pathways.	9.71	8	0	proanthocyanidin
phosphites Phosphites: Inorganic salts or organic esters of phosphorous acid that contain the (3-)PO3 radical. (From Grant & Hackh's Chemical Dictionary, 5th ed). phosphite(3-) : A trivalent inorganic anion obtained by removal of all three protons from phosphorous acid.	2.05	1	0	phosphite ion; trivalent inorganic anion
daidzin daidzin: a potent, selective, and reversible inhibitor of human mitochondrial aldehyde dehydrogenase. daidzein 7-O-beta-D-glucoside : A glycosyloxyisoflavone that is daidzein attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It is used in the treatment of alcohol dependency (antidipsotropic).	7	1	0	7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; monosaccharide derivative	plant metabolite
triptolide [no description available]	2.02	1	0	diterpenoid; epoxide; gamma-lactam; organic heteroheptacyclic compound	antispermatogenic agent; plant metabolite
proanthocyanidin proanthocyanidin: RN given refers to proanthocyanidin A; Cannabinoid Receptor CB1 antagonist. proanthocyanidin : A flavonoid oligomer obtained by the the condensation of two or more units of hydroxyflavans.	2.72	2	0
parthenolide [no description available]	2.02	1	0	germacranolide
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	2.43	2	0
3-deoxyglucosone 3-deoxyglucosone: RN given refers to (D)-isomer. 3-deoxyglucosone : A deoxyketohexose comprising the open-chain form of D-glucose lacking the -OH group at the 3-position and having the keto group at the 2-position.	1.99	1	0	deoxyglucose; deoxyketohexose
thromboxanes thromboxane : A class of oxygenated oxane derivatives, originally derived from prostaglandin precursors in platelets, that stimulate aggregation of platelets and constriction of blood vessels.	2.05	1	0
benzoyl glucuronide benzoyl glucuronide: RN given refers to (beta-D)-isomer	1.98	1	0	glucosiduronic acid
gallium nitride [no description available]	7.08	1	0
aspidin bb [no description available]	3.25	1	0
carbene carbene: electrically neutral species H2C: and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons; carbene is the name of the parent hydride :CH2 ; hence, the name dichlorocarbene for :CCl2. However, names for acyclic and cyclic hydrocarbons containing one or more divalent carbon atoms are derived from the name of the corresponding all-4-hydrocarbon using the suffix -ylidene; methylene carbene also available. carbene : The electrically neutral species H2C(2.) and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons, which may be spin-paired (singlet state) or spin-non-paired (triplet state).	4.41	6	0	carbene; methanediyl
glabridin [no description available]	2.6	1	0	hydroxyisoflavans	antiplasmodial drug
glycerophosphoinositol 4,5-bisphosphate glycerophosphoinositol 4,5-bisphosphate: do not confuse with phosphatidylinositols which have fatty acids esterified at the C-1 and C-2 hydroxyl groups of glycerol	2.03	1	0
tiglic acid tiglic acid : A 2-methylbut-2-enoic acid having its double bond in trans-configuration.. 2-methylbut-2-enoic acid : A branched-chain fatty acid consisting of 2-butenoic acid having a methyl group at position 2.	1.99	1	0	2-methylbut-2-enoic acid	plant metabolite
methotrexate [no description available]	2.41	1	0	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent
desacetyluvaricin desacetyluvaricin: isolated from Uvaria accuminata; structure given in first source	2.06	1	0
cyanidin cyanidin: RN given refers to parent cpd; structure. cyanidin cation : An anthocyanidin cation that is flavylium substituted at positions 3, 3', 4', 5 and 7 by hydroxy groups.	2.02	1	0	5-hydroxyanthocyanidin	antioxidant; metabolite; neuroprotective agent
isothiobarbamin isothiobarbamin: thiobarbituric acid derivative	2.05	1	0
carbapenems [no description available]	2.6	1	0
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	2	1	0	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
docetaxel anhydrous Docetaxel: A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER.. docetaxel anhydrous : A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.	2.6	1	0	secondary alpha-hydroxy ketone; tetracyclic diterpenoid	antimalarial; antineoplastic agent; photosensitizing agent
vatalanib [no description available]	2.17	1	0	monochlorobenzenes; phthalazines; pyridines; secondary amino compound	angiogenesis inhibitor; antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; vascular endothelial growth factor receptor antagonist
4'-chloroflavone 4'-chloroflavone: structure given in first source	2.1	1	0
farnesylacetic acid farnesylacetic acid: RN given refers to cpd without isomeric designation	2.21	1	0
naproxen Naproxen: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.. naproxen : A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.	1.97	1	0	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	2.13	1	0	oxygen hydride; oxygen radical; reactive oxygen species
camphora camphora: a component of Guanxingao, a kind of traditional Chinese rubber electuary medicine which is able to either cure or guard against coronary heart disease and angina pectoris. (R)-camphor : The (R)- enantiomer of camphor.	4.75	5	0	camphor
rhodioloside [no description available]	2.02	1	0	glycoside
4-toluenesulfonamide-formaldehyde resin 4-toluenesulfonamide-formaldehyde resin: does not contain free formaldehyde	1.96	1	0
threo-pentos-2-ulose threo-pentos-2-ulose: RN given refers to cpd without isomeric designation; structure given in first source. 2-keto-D-xylose : A 2-keto-xylose having D-threo configuration; a degradation product of D-ascorbic acid.	1.99	1	0	2-keto-xylose
fenton's reagent Fenton's reagent: used for oxidizing sugars & alcohols	2.13	1	0
cannabidiolic acid cannabidiolic acid: structure. cannabidiolic acid : A dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a 3-p-mentha-1,8-dien-3-yl (limonene) group.	3.15	1	0	dihydroxybenzoic acid; phytocannabinoid; polyketide; resorcinols
vanillactic acid vanillactic acid: metabolite of catecholamines	2.06	1	0	2-oxo monocarboxylic acid
ag 3-5 icilin: a cooling compound that activates TRPM8	4.9	6	0	C-nitro compound
methylinositol methylinositol: from Ebenus haussknechtii; structure in first source. pinitol : A cyclitol ether formed by etherification of the 3-hydroxy group of chiro-inositol. It is plant metabolite isolated from the leaves of Sutherlandia frutescens.. 1D-4-O-methyl-myo-inositol : A member of the class of methyl myo-inositols that is cyclohexane-1,2,3,4,5-pentol substituted by a methoxy group at position 6 (the 1R,2S,3S,4S,5S,6S-isomer).. D-pinitol : The D-enantiomer of pinitol.	3.25	1	0
tartrazine Tartrazine: An anionic, hydrophilic azo dye with an orange-yellow color used in fabrics, foods and cosmetics, and as a biological stain.. tartrazine : An organic sodium salt which is the trisodium salt of tartrazine acid. A synthetic lemon yellow azo dye used as a food colouring.	2.31	1	0
anacardic acid anacardic acid: isolated from Anacardium occidentale; monophenol monooxygenase inhibitor. anacardic acid : A hydroxybenzoic acid that is salicylic acid substituted by a pentadecyl group at position 6. It is a major component of cashew nut shell liquid and exhibits an extensive range of bioactivities.	7.6	1	0	hydroxy monocarboxylic acid; hydroxybenzoic acid	anti-inflammatory agent; antibacterial agent; anticoronaviral agent; apoptosis inducer; EC 2.3.1.48 (histone acetyltransferase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; neuroprotective agent; plant metabolite
palladium(ii) acetate [no description available]	2.05	1	0
10-gingerol [no description available]	3.25	1	0	beta-hydroxy ketone; monomethoxybenzene; phenols
iron (3+) oxalate Sensodyne: a commercial dentifrice; contains 5% potassium nitrate, 0.76% sodium monofluorophosphate in a dicalcium phosphate dihydrate base	2.03	1	0
isophorone diisocyanate [no description available]	2.11	1	0	diisocyanate
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	2.69	3	0
lignin Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.	3.28	6	0
4'-o-methylepigallocatechin 4'-methylepigallocatechin: antispasmodic from Maytenus rigida Mart (Celestraceae); structure in first source	2.02	1	0	catechin	metabolite
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	2.45	2	0	divalent inorganic anion; phosphite ion
dexketoprofen trometamol dexketoprofen trometamol: a water-soluble tromethamine salt of the racemic ketoprofen, rac(+-)-ketoprofen	2.11	1	0
dichamanetin dichamanetin: structure in first source	3.21	1	0	diarylheptanoid	metabolite
psyllium Psyllium: Dried, ripe seeds of PLANTAGO PSYLLIUM; PLANTAGO INDICA; and PLANTAGO OVATA. Plantain seeds swell in water and are used as demulcents and bulk laxatives.	3.23	1	0	very long-chain fatty acid
scutellarin scutellarin: see scutellarein for aglycone. scutellarin : The glycosyloxyflavone which is the 7-O-glucuronide of scutellarein.	2.07	1	0	glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antineoplastic agent; proteasome inhibitor
ergolide ergolide: a potent cytotoxic sesquiterpene lactone from Inula sp.; structure given in first source. ergolide : A sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetyloxy group at position 4. It has been isolated from the aerial parts of Inula hupehensis.	2.02	1	0	acetate ester; cyclic ketone; gamma-lactone; organic heterotricyclic compound; sesquiterpene lactone	anti-inflammatory agent; antineoplastic agent; metabolite; NF-kappaB inhibitor; plant metabolite
propargylglycine propargylglycine: RN given refers to cpd without isomeric designation; structure	2.13	1	0
aflatoxin b1 Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	3.53	7	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
n(alpha)-lauroylarginine ethyl ester N(alpha)-lauroylarginine ethyl ester: an antimicrobial surfactant; RN given refers to (L)-isomer	2.11	1	0
cirsimaritin cirsimaritin: has antagonist or partial agonist activity on benzodiazepine receptors. cirsimaritin : A dimethoxyflavone that is flavone substituted by methoxy groups at positions 6 and 7 and hydroxy groups at positions 5 and 4' respectively.	2.02	1	0	dihydroxyflavone; dimethoxyflavone
n-phenylacrylamide N-phenylacrylamide: structure in first source	2.58	2	0
tenulin tenulin: toxic constituent of Helenium amarum (bitter sneezeweed); structure	2.02	1	0	sesquiterpene lactone
lilial [no description available]	7.51	2	0
lupeol [no description available]	3.25	1	0	pentacyclic triterpenoid; secondary alcohol	anti-inflammatory drug; plant metabolite
hycanthone methanesulfonate hycanthone methanesulfonate: structure. hycanthone mesylate : A methanesulfonate salt resulting from the reaction of equimolar amounts of hycanthone and methanesulfonic acid. It was formerly used as a schistosomicide for individual or mass treatement of infection with Schistosoma haematobium and S. mansoni, but due to its toxicity and concern about possible carcinogenicity, it has been replaced by other drugs such as praziquantel.	1.96	1	0	methanesulfonate salt	alkylating agent; mutagen; schistosomicide drug
wortmannin [no description available]	2.15	1	0	acetate ester; cyclic ketone; delta-lactone; organic heteropentacyclic compound	anticoronaviral agent; antineoplastic agent; autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector; Penicillium metabolite; radiosensitizing agent
2-oxindole 2-oxindole: RN given refers to parent cpd; structure. indolin-2-one : An indolinone carrying an oxo group at position 2.	2.1	1	0	gamma-lactam; indolinone
2-benzyloxybenzaldehyde [no description available]	2.21	1	0
3,4-dihydroxyphenylpropionic acid 3,4-dihydroxyphenylpropionic acid: metabolite of caffeic acid; RN given refers to parent cpd; structure. 3-(3,4-dihydroxyphenyl)propanoic acid : A monocarboxylic acid that is 3-phenylpropionic acid substituted by hydroxy groups at positions 3 and 4. Also known as dihydrocaffeic acid, it is a metabolite of caffeic acid and exhibits antioxidant activity.	2.06	1	0	(dihydroxyphenyl)propanoic acid	antioxidant; human xenobiotic metabolite
4-oxy-6-(4-oxybezoyloxy)dauc-8,9-en 4-oxy-6-(4-oxybezoyloxy)dauc-8,9-en: RN given for (3R-(3alpha,3abeta,4beta,8aalpha))-isomer; a natural benzyl ester of a carotyl type azulene sesquiterpenoid; structure in first source	2.04	1	0
jatrorrhizine chloride [no description available]	2.07	1	0
piperitenone piperitenone: structure given in first source	1.99	1	0	p-menthadien-3-one
pomolic acid pomolic acid: from Rosa woodsii & Hyptis capitata; structure in first source	3.25	1	0	triterpenoid	metabolite
dihydropyridines Dihydropyridines: Pyridine moieties which are partially saturated by the addition of two hydrogen atoms in any position.	7.04	1	0
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	2.99	4	0
sorbose sorbopyranose : The pyranose form of sorbose.. L-sorbopyranose : The L-stereoisomer of sorbopyranose.	2.52	2	0	L-sorbose; sorbopyranose
n-acetylneuraminic acid N-Acetylneuraminic Acid: An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518). N-acetylneuraminic acid : An N-acylneuraminic acid where the N-acyl group is specified as acetyl.	2.11	1	0	N-acetylneuraminic acids	antioxidant; bacterial metabolite; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; human metabolite; mouse metabolite
bradykinin [no description available]	2.44	2	0	oligopeptide	human blood serum metabolite; vasodilator agent
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	4.06	4	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
ouabain Ouabain: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE.. cardiac glycoside : Steroid lactones containing sugar residues that act on the contractile force of the cardiac muscles.. ouabain : A steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+)/K(+)-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus.	2.01	1	0	11alpha-hydroxy steroid; 14beta-hydroxy steroid; 5beta-hydroxy steroid; alpha-L-rhamnoside; cardenolide glycoside; steroid hormone	anti-arrhythmia drug; cardiotonic drug; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; ion transport inhibitor; plant metabolite
taxifolin (+)-taxifolin : A taxifolin that has (2R,3R)-configuration.	3.35	1	0	taxifolin	metabolite
eriodictyol eriodictyol: structure. eriodictyol : A tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' respectively.	3.35	1	0	3'-hydroxyflavanones; tetrahydroxyflavanone
(+)-limonene (4R)-limonene : An optically active form of limonene having (4R)-configuration.	2.01	1	0	limonene	plant metabolite
arbutin hydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.	2.01	1	0	beta-D-glucoside; monosaccharide derivative	Escherichia coli metabolite; plant metabolite
monensin Monensin: An antiprotozoal agent produced by Streptomyces cinnamonensis. It exerts its effect during the development of first-generation trophozoites into first-generation schizonts within the intestinal epithelial cells. It does not interfere with hosts' development of acquired immunity to the majority of coccidial species. Monensin is a sodium and proton selective ionophore and is widely used as such in biochemical studies.. monensin A : A spiroketal, monensin A is the major component of monensin, a mixture of antibiotic substances produced by Streptomyces cinnamonensis. An antiprotozoal, it is used as the sodium salt as a feed additive for the prevention of coccidiosis in poultry and as a growth promoter in cattle.	5.12	5	2	cyclic hemiketal; monocarboxylic acid; polyether antibiotic; spiroketal	antifungal agent; coccidiostat; ionophore
limonene-1,2-epoxide limonene-1,2-epoxide: RN given refers to cpd without isomeric designation. (4R)-limonene 1,2-epoxide : The (R)-enantiomer of limonene 1,2-epoxide.	3.25	1	0	limonene 1,2-epoxide
linezolid [no description available]	2.21	1	0	acetamides; morpholines; organofluorine compound; oxazolidinone	antibacterial drug; protein synthesis inhibitor
carnosol carnosol: isolated from Lepechinia hastata	2.58	2	0	diterpenoid
vernolepin [no description available]	2.15	1	0	delta-lactone
alpha-copaene alpha-copaene: from Olea europaea; structure in first source. alpha-copaene : A sesquiterpene that is tricyclo[4.4.0.0(2,7)]dec-3-ene bearing an isopropyl substituent at position 8 and two methyl substituents at positions 1 and 3 (the 1S,6S,7S,8S-diastereomer).	2.11	1	0
patchouli alcohol patchouli alcohol: major component of the essential oil of patchouli; perfumery raw material. patchouli alcohol : A carbotricyclic compound and sesquiterpenoid tertiary alcohol that is tricyclo[5.3.1.0(3,8)]undecan-3-ol which is substituted at positions 2, 2, 6 and 8 by methyl groups (the 1R,3R,6S,7S,8S-diastereoisomer).	2.6	1	0
ochratoxin a ochratoxin A: structure in first source & in Merck, 9th ed, #6549. ochratoxin A : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin alpha). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.	2.54	2	0	isochromanes; monocarboxylic acid amide; N-acyl-L-phenylalanine; organochlorine compound; phenylalanine derivative	Aspergillus metabolite; calcium channel blocker; carcinogenic agent; mycotoxin; nephrotoxin; Penicillium metabolite; teratogenic agent
gingerol gingerol: an active ingredient in GINGER along with SHOGAOL. a nonvolatile methoxy phenyl decanone. gingerol : A beta-hydroxy ketone that is 5-hydroxydecan-3-one substituted by a 4-hydroxy-3-methoxyphenyl moiety at position 1; believed to inhibit adipogenesis. It is a constituent of fresh ginger.	3.56	2	0	beta-hydroxy ketone; guaiacols	antineoplastic agent; plant metabolite
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	2.59	2	0
sodium arsenite sodium arsenite : An inoganic sodium salt with formula with formula NaAsO2.	2.21	1	0	arsenic molecular entity; inorganic sodium salt	antibacterial agent; antifungal agent; antineoplastic agent; carcinogenic agent; herbicide; insecticide; rodenticide
validamycin a validamycin A : A member of the class of validamycins that is (1R,2S,3S,4S,6R)-4-amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol in which the hydroxy group at position 1 has been converted to its beta-D-glucoside and in which one of the hydrogens attached to the nitrogen is replaced by a (1R,4R,5R,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl group. It is the major validamycin produced by Streptomyces hygroscopicus.	2.06	1	0	antibiotic fungicide; polyol; secondary amino compound; validamycins	antifungal agrochemical; EC 2.4.1.231 [alpha,alpha-trehalose phosphorylase (configuration-retaining)] inhibitor; EC 2.4.1.64 (alpha,alpha-trehalose phosphorylase) inhibitor; EC 3.2.1.28 (alpha,alpha-trehalase) inhibitor
epiafzelechin epiafzelechin: antioxidant; 3'-deoxy form of epicatechin; structure in first source. (-)-epiafzelechin : A catechin derivative having (2R,3R)-configuration.	2.02	1	0	catechin	plant metabolite
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	3.78	8	0	cyclodextrin
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	8.21	55	0	cinnamic acid	plant metabolite
ergosterol [no description available]	3.38	6	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	2.69	3	0	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
fumaric acid fumaric acid: see also record for ferrous fumarate; use FUMARATES for general fumaric acid esters. fumaric acid : A butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.	7.52	2	0	butenedioic acid	food acidity regulator; fundamental metabolite; geroprotector
farnesol Farnesol: A colorless liquid extracted from oils of plants such as citronella, neroli, cyclamen, and tuberose. It is an intermediate step in the biological synthesis of cholesterol from mevalonic acid in vertebrates. It has a delicate odor and is used in perfumery. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). (2-trans,6-trans)-farnesol : The (2-trans,6-trans)-stereoisomer of farnesol.. farnesol : A farnesane sesquiterpenoid that is dodeca-2,6,10-triene substituted by methyl groups at positions 3, 7 and 11 and a hydroxy group at position 1.	7.87	3	0	farnesol	plant metabolite
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	9.79	5	0	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
tacrolimus Tacrolimus: A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.. tacrolimus (anhydrous) : A macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.	2.05	1	0	macrolide lactam	bacterial metabolite; immunosuppressive agent
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	5.17	8	0	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
pectins Pectins: High molecular weight polysaccharides present in the cell walls of all plants. Pectins cement cell walls together. They are used as emulsifiers and stabilizers in the food industry. They have been tried for a variety of therapeutic uses including as antidiarrheals, where they are now generally considered ineffective, and in the treatment of hypercholesterolemia.. alpha-D-galacturonic acid : The alpha-anomer of D-galacturonic acid.	2.46	2	0	D-galactopyranuronic acid
clindamycin Clindamycin: An antibacterial agent that is a semisynthetic analog of LINCOMYCIN.. clindamycin : A carbohydrate-containing antibiotic that is the semisynthetic derivative of lincomycin, a natural antibiotic.	7.03	1	0
fosfomycin Fosfomycin: An antibiotic produced by Streptomyces fradiae.. fosfomycin : A phosphonic acid having an (R,S)-1,2-epoxypropyl group attached to phosphorus.	2.06	1	0	epoxide; phosphonic acids	antimicrobial agent; EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor
2-butenal crotonaldehyde : An enal consisting of propene having a formyl group at the 1-position.	4.87	6	0	enal
prostaglandin d2 Prostaglandin D2: The principal cyclooxygenase metabolite of arachidonic acid. It is released upon activation of mast cells and is also synthesized by alveolar macrophages. Among its many biological actions, the most important are its bronchoconstrictor, platelet-activating-factor-inhibitory, and cytotoxic effects.. prostaglandin D2 : A member of the class of prostaglandins D that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9 and 15 and an oxo group at position 11 (the 5Z,9alpha,13E,15S- stereoisomer).	2	1	0	prostaglandins D	human metabolite; mouse metabolite
diethylstilbestrol Diethylstilbestrol: A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed). diethylstilbestrol : An olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.	2.08	1	0	olefinic compound; polyphenol	antifungal agent; antineoplastic agent; autophagy inducer; calcium channel blocker; carcinogenic agent; EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; endocrine disruptor; xenoestrogen
6-bromoindirubin-3'-oxime 6-bromoindirubin-3'-oxime: structure in first source. 6-bromoindirubin-3'-oxime : A member of the class of biindoles that is indirubin substituted at position 6 by a bromo group and in which the keto group at position 3' has undergone condensation with hydroxylamine to form the corresponding oxime.	3.31	1	0
apogossypol apogossypol: structure in first source	3.35	1	0
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	2.31	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
kazinol b kazinol B: a natural isoprenylated flavan	2.02	1	0
8-isopentenylnaringenin 8-isopentenylnaringenin: a non-steroidal phytoestrogen from Anaxagorea luzonensis; structure in first source	2.04	1	0	flavanones
sodium bicarbonate Sodium Bicarbonate: A white, crystalline powder that is commonly used as a pH buffering agent, an electrolyte replenisher, systemic alkalizer and in topical cleansing solutions.	2.08	1	0	one-carbon compound; organic sodium salt	antacid; food anticaking agent
seychellene seychellene: from the essential oil of Indian valerian (Valeriana jatamansi); structure in first source	2.6	1	0
alpha-asarone asarone: structure in Merck Index, 9th ed, #847. asarone : A phenylpropanoid that is benzene substituted by methoxy groups at positions 1, 2 and 4 and a propen-1-yl group at position 5. It has been isolated from Acorus.. alpha-asarone : The trans-isomer of asarone.	2.06	1	0	asarone	anticonvulsant; GABA modulator
crotonic acid crotonic acid: a stereospecific unsaturated carboxylic acid found in CROTON OIL. butenoic acid : Any C4, straight-chain fatty acid containing one double bond.. crotonic acid : A but-2-enoic acid with a trans- double bond at C-2. It has been isolated from Daucus carota.	2.06	1	0	2-butenoic acid	plant metabolite
methyl cinnamate methyl cinnamate: RN given refers to cpd without isomeric designation. methyl cinnamate : A methyl ester resulting from the formal condensation of methyl cinnamic acid with methanol. It is found naturally in the essential oils of Alpinia and Basil leaf oil, and widely used in the flavor and perfume industries.. methyl trans-cinnamate : The E (trans) isomer of methyl cinnamate.	2.94	4	0	methyl cinnamate	antibacterial agent; fungal metabolite; nematicide; plant metabolite
2-hydroxycinnamic acid trans-2-coumaric acid : The trans-isomer of 2-coumaric acid.. 2-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring.	2.75	3	0	2-coumaric acid; phenols	antioxidant; metabolite
3-coumaric acid 3-coumaric acid: RN given refers to cpd without isomeric designation in Chemline. trans-3-coumaric acid : A 3-coumaric acid that is phenol substituted with trans-2-propenoic acid at position C-3.. 3-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-3 of the phenyl ring.	2.06	1	0	3-coumaric acid
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	4.54	7	0	4-coumaric acid	food component; mouse metabolite; plant metabolite
anethole anethole: an isomer of estragole; structurally similar to CAPSAICIN; has some neurological and insecticidal and skin absorption effects; RN given refers to unspecified stereoisomer. anethole : A monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4.. trans-anethole : The trans-stereoisomer of anethole.	4.7	8	0	anethole	flavouring agent
2,4-hexadienal 2,4-hexadienal: RN given refers to compound with no isomeric designation. hexadienal : An enal that is hexadiene carrying an oxo group at position 1.. (E,E)-2,4-hexadienal : A hexadienal that is hexanal with trans double bonds at positions 2 and 4. It is found in tomatoes, kiwi fruit, mangoes, potato chips, herbs and spices.	2.01	1	0	hexadienal; polyunsaturated fatty aldehyde; volatile organic compound	flavouring agent; plant metabolite
geraniol [no description available]	8.81	11	0	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
dimethyl fumarate [no description available]	2.21	1	0	diester; enoate ester; methyl ester	antipsoriatic; immunomodulator
glycosides [no description available]	2.25	1	0
ethyl cinnamate ethyl cinnamate: a pine weevil antifeedant; structure in first source	2.17	1	0	alkyl cinnamate; ethyl ester
benzylideneacetone benzylideneacetone: RN given refers to cpd without isomeric; structure in Merck Index, 9th ed, #1153. trans-benzylideneacetone : The trans-isomer of benzylideneacetone. It acts as an inhibitor of the enzyme phospholipase A2 (EC 3.1.1.4) of insects like diamond back moth.. benzylideneacetone : An enone in which a phenyl ring is attached to the beta-carbon atom of but-3-en-2-one. Although both cis- and trans-isomers are possible for the alpha,beta-unsaturated ketone, only the trans-isomer is observed.	2.71	3	0	benzylideneacetone	bacterial metabolite; EC 3.1.1.4 (phospholipase A2) inhibitor; flavouring agent; fragrance
chalcone trans-chalcone : The trans-isomer of chalcone.	3	4	0	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
crotonyl alcohol crotonyl alcohol: RN given refers to cpd without isomeric designation. crotyl alcohol : A primary alcohol in which the hydroxy function is bonded to a CH3CH=CHCH2- (crotyl) group.	2.03	1	0	primary alcohol
citral citral: Xref geranial: geraniol is also available; Xref neral: nerol is also available; vitamin A antagonist; oxygenated monoterpene; inhibits cytosolic dehydrogenases; structure. citral : An enal that consists of octa-2,6-dienal bearing methyl substituents at positions 3 and 7. A mixture of the two geometric isomers geranial and neral, it is the major constituent (75-85%) of oil of lemon grass, the volatile oil of Cymbopogon citratus, or of C. flexuosus. It also occurs in oils of verbena, lemon, and orange.	6.18	29	0	enal; monoterpenoid; polyprenal	plant metabolite; volatile oil component
beta-ionone beta-ionone: stimulator of carotenogenesis; carotenoid inhibitor; intermediate in synthesis of Vit A; RN given refers to cpd without isomeric designation; structure. beta-ionone : An ionone that is but-3-en-2-one substituted by a 2,6,6-trimethylcyclohex-1-en-1-yl group at position 4.	2.72	3	0	ionone	antioxidant; fragrance
piperine piperine : A N-acylpiperidine that is piperidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum.	11.73	9	0	benzodioxoles; N-acylpiperidine; piperidine alkaloid; tertiary carboxamide	food component; human blood serum metabolite; NF-kappaB inhibitor; plant metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.48	2	0	stilbene
diethyl fumarate diethyl fumarate : A dieter obtained by the formal condensation of fumaric acid with ethanol.	2.37	2	0	diester	metabolite
2'-hydroxychalcone 2'-hydroxychalcone : A member of the class of chalcones that is trans-chalcone substituted by a hydroxy group at position 2'.	2.1	1	0	chalcones; phenols	anti-inflammatory agent
dibenzylidene acetone dibenzylidene acetone: structure in first source	2.15	1	0
4-methoxycinnamaldehyde [no description available]	2.6	1	0	cinnamaldehydes
2-methoxycinnamaldehyde 2-methoxycinnamaldehyde: inhibits growth & mycotoxin production in fungi; structure	4.95	13	0	cinnamaldehydes
p-hydroxycinnamaldehyde p-hydroxycinnamaldehyde: an antibacterial substance from the saw fly, Acantholyda parki S.; structure in first source. 4-hydroxycinnamaldehyde : A cinnamaldehyde that is (E)-cinnamaldehyde substituted at position 4 on the phenyl ring by a hydroxy group.	2.75	3	0	cinnamaldehydes	apoptosis inducer; EC 1.14.13.39 (nitric oxide synthase) inhibitor; plant metabolite
sorbic acid Sorbic Acid: Mold and yeast inhibitor. Used as a fungistatic agent for foods, especially cheeses.. (2E,4E)-hexa-2,4-dienoic acid : A sorbic acid having trans-double bonds at positions 2 and 4; a food preservative that can induce cutaneous vasodilation and stinging upon topical application to humans. It is the most thermodynamically stable of the four possible geometric isomers possible, as well as the one with the highest antimicrobial activity.. sorbic acid : A hexadienoic acid with double bonds at C-2 and C-4; it has four geometrical isomers, of which the trans,trans-form is naturally occurring.	3.1	5	0	alpha,beta-unsaturated monocarboxylic acid; sorbic acid
cannabidiol Cannabidiol: Compound isolated from Cannabis sativa extract.. cannabidiol : An cannabinoid that is cyclohexene which is substituted by a methyl group at position 1, a 2,6-dihydroxy-4-pentylphenyl group at position 3, and a prop-1-en-2-yl group at position 4.	8.64	2	0	olefinic compound; phytocannabinoid; resorcinols	antimicrobial agent; plant metabolite
sesquiterpenes [no description available]	3.66	9	0
sb 366791 N-(3-methoxyphenyl)-4-chlorocinnamanilide: a TRPV1 antagonist; structure in first source	3.03	4	0
(e)-3-(4-t-butylphenyl)-n-(2,3-dihydrobenzo(b)(1,4)dioxin-6-yl)acrylamide 3-(4-t-butylphenyl)-N-(2,3-dihydrobenzo(b)(1,4)dioxin-6-yl)acrylamide: a vanilloid receptor 1 antagonist and antihyperalgesic agent; structure in first source	2.08	1	0
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	5.29	9	0	caffeic acid	geroprotector; mouse metabolite
methyl caffeate methyl caffeate: from plant Gaillardia pulchella. methyl caffeate : An alkyl caffeate ester formed by the formal condensation of caffeic acid with methyl alcohol.	2.06	1	0	alkyl caffeate ester; methyl ester
captax captax: RN given refers to parent cpd. 1,3-benzothiazole-2-thiol : 1,3-Benzothiazole substituted at the 2-position with a sulfanyl group.	1.98	1	0	aryl thiol; benzothiazoles	carcinogenic agent; metabolite
3-(3,4-dimethoxyphenyl)propenoic acid 3-(3,4-dimethoxyphenyl)propenoic acid: structure given in first source; RN given refers to parent cpd. 3,4-dimethoxycinnamic acid : A methoxycinnamic acid that is trans-cinnamic acid substituted by methoxy groups at positions 3' and 4' respectively.	3.84	3	0	methoxycinnamic acid
isoferulic acid isoferulic acid: isomer of ferulic acid; structure. isoferulic acid : A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 4 and 3 respectively on the phenyl ring.	2.07	1	0	ferulic acids	antioxidant; biomarker; metabolite
isoeugenol trans-isoeugenol : The trans-stereoisomer of isoeugenol.	5.82	17	0	isoeugenol	plant metabolite
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	7.84	21	0	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
hc 030031 2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)-N-(4-isopropylphenyl)acetamide: a TRPA1 channel blocker	5.78	15	0
urb 597 cyclohexyl carbamic acid 3'-carbamoylbiphenyl-3-yl ester: a fatty acid amide hydrolase inhibitor; structure in first source	3.61	2	0	biphenyls
zucapsaicin [no description available]	2.25	1	0	methoxybenzenes; phenols
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	11.7	53	5	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
coniferyl alcohol coniferyl alcohol: structure. coniferol : A phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring.	2	1	0	guaiacols; phenylpropanoid	animal metabolite; monolignol; mouse metabolite; pheromone; plant metabolite; volatile oil component
beta-styrylacrylic acid beta-styrylacrylic acid: RN given refers to parent cpd; structure	2.06	1	0
hexyl cinnamic aldehyde [no description available]	1.99	1	0	cinnamaldehydes
2-pentylcinnamaldehyde 2-pentylcinnamaldehyde: jasmine-like odor, widely used synthetic fragrance & suspected allergen; structure given in first source	2.69	3	0	cinnamaldehydes
oxazolone Oxazolone: Immunologic adjuvant and sensitizing agent.	2.44	2	0
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	5.14	5	0	cinnamate ester; tannin	food component; plant metabolite
thioguanine anhydrous Thioguanine: An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia.. tioguanine : A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia.	1.97	1	0	2-aminopurines	anticoronaviral agent; antimetabolite; antineoplastic agent
thiosemicarbazide thiosemicarbazide: glutamate decarboxylase antagonist; structure given in first source. hydrazinecarbothioamide : A member of the class of thioureas that is thiourea in which a hydrogen of one of the amino groups is replaced by an amino group.	2.41	1	0	hydrazines; thiocarboxamide; thioureas
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	2.05	1	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
potassium oxonate potassium oxonate: used to induce hyperuricemia in mice	2.04	1	0	organic molecular entity
tempo TEMPO: structure. TEMPO : A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.	2.31	1	0	aminoxyls; piperidines	catalyst; ferroptosis inhibitor; radical scavenger
capsazepine capsazepine: modified capsaicin molecule; a capsaicin receptor antagonist. capsazepine : A benzazepine that is 2,3,4,5-tetrahydro-1H-2-benzazepine which is substituted by hydroxy groups at positions 7 and 8 and on the nitrogen atom by a 2-(p-chlorophenyl)ethylaminothiocarbonyl group. A synthetic analogue of capsaicin, it was the first reported capsaicin receptor antagonist.	3.45	7	0	benzazepine; catechols; monochlorobenzenes; thioureas	capsaicin receptor antagonist
nadp [no description available]	2.74	3	0
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.55	2	0
laccase Laccase: A copper-containing oxidoreductase enzyme that catalyzes the oxidation of 4-benzenediol to 4-benzosemiquinone. It also has activity towards a variety of O-quinols and P-quinols. It primarily found in FUNGI and is involved in LIGNIN degradation, pigment biosynthesis and detoxification of lignin-derived products.	2	1	0
3,7,11,15-tetramethyl-1,2,3-hexadecanetriol 3,7,11,15-tetramethyl-1,2,3-hexadecanetriol: structure in first source. phytantriol : A triol that consists of 3,7,11,15-tetramethylhexadecane bearing three hydroxy substituents at positions 1, 2 and 3.	2.59	2	0	triol
cobaltous chloride cobaltous chloride: RN given refers to unlabeled cpd; RN in Chemline for cobalt trichloride: 10241-04-0; RN for 60-labeled cpd: 14543-09-0; RN for 57-labeled cpd: 164113-89-1; RN for 58-labeled cpd: 29377-09-1; structure. cobalt dichloride : A cobalt salt in which the cobalt metal is in the +2 oxidation state and the counter-anion is chloride. It is used as an indicator for water in desiccants.	2.69	3	0	cobalt salt; inorganic chloride	allergen; calcium channel blocker; sensitiser; two-colour indicator
beta-proline beta-proline: RN given refers to cpd without isomeric designation; structure given in first source	2.21	1	0
cystine [no description available]	2.1	1	0
atractylon atractylon: from Atractylodes rhizomes; has antihepatotoxic activity; structure given in first source	2.03	1	0	sesquiterpenoid
2,3,4-tri-o-acetylarabinopyranosyl isothiocyanate 2,3,4-tri-O-acetylarabinopyranosyl isothiocyanate: RN given refers to (alpha-D)-isomer	2.5	2	0
2-chloro-4-nitrophenylmaltotrioside [no description available]	2.1	1	0
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.31	1	0
salinomycin salinomycin: from Streptomyces albus; RN given refers to parent cpd; structure	2.25	1	0	polyketide; spiroketal	animal growth promotant; potassium ionophore
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	2.52	2	0
sodium dodecyl sulfate Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.	3.28	6	0	organic sodium salt	detergent; protein denaturant
mtt formazan MTT formazan: a blue MEM-insoluble mitochondrial byproduct; used to determine viability of cells with active mitochondrial dehydrogenase enzymes	2.05	1	0
flavan-3-ol flavan-3-ol: structure in first source	3.16	1	0	hydroxyflavonoid
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	2.5	2	0
sodium borohydride sodium borohydride: RN given refers to parent cpd	1.96	1	0	inorganic sodium salt; metal tetrahydridoborate
3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol 3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol: (-)-CP-55,940 and (+)-CP-56,667 are enantiomers; RN refers to CP-55,940	2.05	1	0	alkylbenzene; ring assembly
fraxetin fraxetin : A hydroxycoumarin that is 6-methoxycoumarin in which the hydrogens at positions 7 and 8 have been replaced by hydroxy groups.	2.41	2	0	aromatic ether; hydroxycoumarin	anti-inflammatory agent; antibacterial agent; antimicrobial agent; antioxidant; apoptosis inducer; apoptosis inhibitor; Arabidopsis thaliana metabolite; hepatoprotective agent; hypoglycemic agent
quercetin [no description available]	5.58	12	0	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	4.76	11	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	2.08	1	0	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
coniferin coniferin : A monosaccharide derivative that is coniferol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage.	2.02	1	0	aromatic ether; cinnamyl alcohol beta-D-glucoside; monosaccharide derivative	plant metabolite
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	2.44	2	0	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	2.42	2	0	3'-hydroxyflavonoid; tetrahydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; c-Jun N-terminal kinase inhibitor; EC 2.3.1.85 (fatty acid synthase) inhibitor; immunomodulator; nephroprotective agent; plant metabolite; radical scavenger; vascular endothelial growth factor receptor antagonist
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	2.76	3	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
scopoletin [no description available]	3.88	3	0	hydroxycoumarin	plant growth regulator; plant metabolite
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	2.41	1	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
leukotriene c4 Leukotriene C4: The conjugation product of LEUKOTRIENE A4 and glutathione. It is the major arachidonic acid metabolite in macrophages and human mast cells as well as in antigen-sensitized lung tissue. It stimulates mucus secretion in the lung, and produces contractions of nonvascular and some VASCULAR SMOOTH MUSCLE. (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene C4 : A leukotriene that is (5S,7E,9E,11Z,14Z)-5-hydroxyicosa-7,9,11,14-tetraenoic acid in which a glutathionyl group is attached at position 6 via a sulfide linkage.	2.11	1	0	leukotriene	bronchoconstrictor agent; human metabolite; mouse metabolite
coniferaldehyde coniferaldehyde: from aqueous extract of Senra incana. coniferyl aldehyde : A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3.	3.15	5	0	cinnamaldehydes; guaiacols; phenylpropanoid	antifungal agent; plant metabolite
daphnetin [no description available]	3.56	2	0	hydroxycoumarin
farnesal [no description available]	2.13	1	0	farnesal; polyprenal
rosin rosin: Resin from plant. Do not confuse with the specific compound: 3-phenyl-2-propenyl-(E)-beta-D-glucopyranoside, also know as rosin.	3.5	2	0
furylfuramide Furylfuramide: Used formerly as antimicrobial food additive. It causes mutations in many cell cultures and may be carcinogenic.. (Z)-2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide : A member of the class of acrylamides that is acrylamide which is substituted at positions 2 and 3 by 2-furyl and 5-nitro-2-furyl groups, respectively (the trans isomer). Formerly used as a food preservative, it was withdrawn from the market following suspicions of carcenogenicity.	1.96	1	0	acrylamides; C-nitro compound; nitrofuran antibiotic; primary carboxamide
sinapaldehyde sinapyl aldehyde: structure in first source. (E)-sinapaldehyde : A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.	2.08	1	0	cinnamaldehydes; dimethoxybenzene; phenols	antifungal agent; plant metabolite
quercetin 3-o-glucopyranoside quercetin 3-O-glucopyranoside: structure in first source. quercetin 3-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells	2.02	1	0	beta-D-glucoside; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antineoplastic agent; antioxidant; antipruritic drug; bone density conservation agent; geroprotector; histamine antagonist; osteogenesis regulator; plant metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	2.44	2	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
kaempferol [no description available]	4.1	4	0	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
prostaglandin a2 prostaglandin A2: RN given refers to (5Z,13E,15S)-isomer	3.15	1	0	prostaglandins A	human metabolite
gamma-linolenic acid gamma-Linolenic Acid: An omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted to dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1. (From Merck Index, 11th ed). gamma-linolenic acid : A C18, omega-6 acid fatty acid comprising a linolenic acid having cis- double bonds at positions 6, 9 and 12.	2.41	1	0	linolenic acid; omega-6 fatty acid	human metabolite; mouse metabolite; plant metabolite
alpha-linolenic acid linolenic acid : A two-membered subclass of octadecatrienoic acid comprising the (9Z,12Z,15Z)- and (6Z,9Z,12Z)-isomers. Linolenic acids are nutrients essential to the formation of prostaglandins and are also used in making paints and synthetic resins.. linolenate : A polyunsaturated fatty acid anion obtained by deprotonation of the carboxy group of either alpha- or gamma-linolenic acid.	2.11	1	0	linolenic acid; omega-3 fatty acid	micronutrient; mouse metabolite; nutraceutical
genistein [no description available]	3.57	2	0	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
amphotericin b Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.	2.45	2	0	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
2-hexenal, z-isomer 2-hexenal: product of lipid peroxidation in the rat liver; a green odor chemical; do not confuse with the hexabarbital synonym, hexenal; RN given refers to cpd without isomeric designation. 2-hexenal : A hexenal having the double bond at the 2-position.. (2E)-hexenal : A 2-hexenal in which the olefinic double bond has E configuration. It occurs naturally in a wide range of fruits, vegetables, and spices.	2.69	3	0	2-hexenal	antibacterial agent; flavouring agent; plant metabolite
astaxanthine astaxanthine: a keto form of carotene; pigment in flesh of Scottish salmon (Salmo salar) crustacoa-lobster (Homarus gammarus, flamingo feathers; structure; a carotenoid without vitamin A activity, has shown anti-oxidant and anti-inflammatory activities. astaxanthin : A carotenone that consists of beta,beta-carotene-4,4'-dione bearing two hydroxy substituents at positions 3 and 3' (the 3S,3'S diastereomer). A carotenoid pigment found mainly in animals (crustaceans, echinoderms) but also occurring in plants. It can occur free (as a red pigment), as an ester, or as a blue, brown or green chromoprotein.	2.41	1	0	carotenol; carotenone	animal metabolite; anticoagulant; antioxidant; food colouring; plant metabolite
esculetin esculetin: used in filters for absorption of ultraviolet light; structure. esculetin : A hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light.	2.02	1	0	hydroxycoumarin	antioxidant; plant metabolite; ultraviolet filter
esculin [no description available]	2.01	1	0	beta-D-glucoside; hydroxycoumarin	antioxidant; metabolite
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	3.81	3	0	hydroxycoumarin	fluorescent probe; food component; plant metabolite
costunolide [no description available]	2.45	2	0	germacranolide; heterobicyclic compound	anthelminthic drug; antiinfective agent; antineoplastic agent; antiparasitic agent; antiviral drug; metabolite
zearalenone Zearalenone: (S-(E))-3,4,5,6,8,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione. One of a group of compounds known under the general designation of resorcylic acid lactones. Cis, trans, dextro and levo forms have been isolated from the fungus Gibberella zeae (formerly Fusarium graminearum). They have estrogenic activity, cause toxicity in livestock as feed contaminant, and have been used as anabolic or estrogen substitutes.. zearalenone : A macrolide comprising a fourteen-membered lactone fused to 1,3-dihydroxybenzene; a potent estrogenic metabolite produced by some Giberella species.	7.6	1	0	macrolide; resorcinols	fungal metabolite; mycoestrogen
baicalein [no description available]	3.05	4	0	trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 4.1.1.17 (ornithine decarboxylase) inhibitor; ferroptosis inhibitor; geroprotector; hormone antagonist; plant metabolite; prostaglandin antagonist; radical scavenger
chrysin chrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.	3.55	2	0	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant metabolite
galangin 5,7-dihydroxyflavonol: antimicrobial from the twigs of Populus nigra x Populus deltoides; structure in first source. galangin : A 7-hydroxyflavonol with additional hydroxy groups at positions 3 and 5 respectively; a growth inhibitor of breast tumor cells.	2.46	2	0	7-hydroxyflavonol; trihydroxyflavone	antimicrobial agent; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; plant metabolite
mangiferin shamimin: isolated from the leaves of Bombax ceiba; structure in first source	7.44	2	0	C-glycosyl compound; xanthones	anti-inflammatory agent; antioxidant; hypoglycemic agent; plant metabolite
morusin morusin: from Morus root bark; structure given in first source. morusin : An extended flavonoid that is flavone substituted by hydroxy groups at positions 5, 2' and 4', a prenyl group at position 3 and a 2,2-dimethyl pyran group across positions 7 and 8.	2.02	1	0	extended flavonoid; trihydroxyflavone	antineoplastic agent; plant metabolite
myricetin [no description available]	2.45	2	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
myricitrin myricitrin: isolated from root bark of Myrica cerifera L.; structure. myricitrin : A glycosyloxyflavone that consists of myricetin attached to a alpha-L-rhamnopyranosyl residue at position 3 via a glycosidic linkage. Isolated from Myrica cerifera, it exhibits anti-allergic activity.	2.06	1	0	alpha-L-rhamnoside; glycosyloxyflavone; monosaccharide derivative; pentahydroxyflavone	anti-allergic agent; EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; plant metabolite
wogonin wogonin: structure in first source. wogonin : A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-8.	2.45	2	0	dihydroxyflavone; monomethoxyflavone	angiogenesis inhibitor; antineoplastic agent; cyclooxygenase 2 inhibitor; plant metabolite
gingerenone a gingerenone A: has antineoplastic activity; isolated from Zingiber officinale; structure in first source	3.25	1	0	diarylheptanoid
caffeic acid phenethyl ester phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.	2.02	1	0	alkyl caffeate ester	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiviral agent; immunomodulator; metabolite; neuroprotective agent
rosmarinic acid rosmarinic acid: RN given refers to parent cpd; promote OT project. (R)-rosmarinic acid : A stereoisomer of rosmarinic acid having (R)-configuration.. rosmarinic acid : The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid.	2.44	2	0	rosmarinic acid	geroprotector; plant metabolite
shogaol shogaol: from ginger, ZINGIBER OFFICINALE; less mutagenic than GINGEROL; structure given in first source	3.25	1	0	enone; monomethoxybenzene; phenols
ellagic acid [no description available]	3.9	3	0	catechols; cyclic ketone; lactone; organic heterotetracyclic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor; EC 2.4.1.1 (glycogen phosphorylase) inhibitor; EC 2.5.1.18 (glutathione transferase) inhibitor; EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor; EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor; EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; food additive; fungal metabolite; geroprotector; plant metabolite; skin lightening agent
prostaglandin a1 [no description available]	3.15	1	0	prostaglandins A
anandamide anandamide : An N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.	5.22	3	1	endocannabinoid; N-acylethanolamine 20:4	human blood serum metabolite; neurotransmitter; vasodilator agent
alpha-ionone alpha-ionone: RN given refers to cpd without isomeric designation; structure	2.1	1	0	enone; ionone; methyl ketone
cinnamyl acetate cinnamyl acetate: structure in first source. cinnamyl acetate : An acetate ester resulting from the formal condensation of cinnamyl alcohol with acetic acid. Found in cinnamon leaf oil.	2.47	2	0	acetate ester	plant metabolite
rhoifolin rhoifolin: from many plants. apigenin 7-O-neohesperidoside : An apigenin derivative having an alpha-(1->2)-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety attached to the 7-hydroxy group.	2.02	1	0	dihydroxyflavone; glycosyloxyflavone; neohesperidoside	metabolite
tranilast tranilast: antiallergic drug; potent inhibitor of homologous passive cutaneous anaphylaxis. tranilast : An amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 3,4-dimethoxycinnamoyl group.	2.21	1	0	amidobenzoic acid; cinnamamides; dimethoxybenzene; secondary carboxamide	anti-allergic agent; anti-asthmatic drug; antineoplastic agent; aryl hydrocarbon receptor agonist; calcium channel blocker; hepatoprotective agent; nephroprotective agent
2-octenal 2-octenal: RN given refers to cpd without isomeric designation. (E)-oct-2-enal : The (E)-isomer of oct-2-enal.. oct-2-enal : An enal consisting of oct-2-ene having an oxo group at the 1-position.	2.15	1	0	oct-2-enal	antifungal agent; volatile oil component
4-hydroxy-2-nonenal 4-hydroxy-2-nonenal: cytotoxic product from peroxidation of liver microsomal lipids; RN given refers to cpd without isomeric designation. 4-hydroxynon-2-enal : An enal consisting of non-2-ene having an oxo group at the 1-position and a hydroxy group at the 4-position.. 4-hydroxynonenal : A monounsaturated fatty aldehyde that is nonanal that has undergone dehydrogenation to introduce a double bond at any position in the aliphatic chain and in which a hydrogen at position 4 has been replaced by a hydroxy group.	4.89	6	0	4-hydroxynon-2-enal; 4-hydroxynonenal
1-monooleoyl-rac-glycerol Peceol: lipid excipient containing readily dispersible mixture of mono- & diglycerides of oleic acid. 1-oleoylglycerol : A 1-monoglyceride where the acyl group is oleoyl.. monooleoylglycerol : A monoglyceride in which the acyl group is oleoyl with the position of acylation unspecified.	2.31	1	0	1-acylglycerol 18:1; monooleoylglycerol	plant metabolite
beta-nitrostyrene beta-nitrostyrene: RN given refers to cpd without isomeric designation	2.21	1	0
3-amino-1,4-dimethyl-5h-pyrido(4,3-b)indole 3-amino-1,4-dimethyl-5H-pyrido(4,3-b)indole: structure	1.99	1	0	pyridoindole
4-dimethylaminocinnamaldehyde [no description available]	2.04	1	0	cinnamaldehydes
granisetron Granisetron: A serotonin receptor (5HT-3 selective) antagonist that has been used as an antiemetic for cancer chemotherapy patients.. granisetron : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 1-methyl-1H-indazole-3-carboxylic acid with the primary amino group of (3-endo)-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine. A selective 5-HT3 receptor antagonist, it is used (generally as the monohydrochloride salt) to manage nausea and vomiting caused by cancer chemotherapy and radiotherapy, and to prevent and treat postoperative nausea and vomiting.	2.05	1	0	aromatic amide; indazoles
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	8.09	4	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	7.63	2	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
demycarosylturimycin h [no description available]	3.35	1	0
olvanil [no description available]	5.22	3	1	methoxybenzenes; phenols
15-deoxy-delta(12,14)-prostaglandin j2 15-deoxy-delta(12,14)-prostaglandin J2: 15-deoxy-PGJ2 is also available; check for double bonds (indicated by delta) at 12 and 14 positions. 15-deoxy-Delta(12,14)-prostaglandin J2 : A prostaglandin J derivative comprising prostaglandin J2 lacking the 15-hydroxy group and having C=C double bonds at the 12- and 14-positions.	3.59	2	0	prostaglandins J	electrophilic reagent; insulin-sensitizing drug; metabolite
sulprostone sulprostone: structure	2.01	1	0	prostanoid
cannabigerol cannabigerol: RN given refers to (E)-isomer; structure given in first source. cannabigerol : A member of the class of resorcinols that is resorcinol which is substituted by a (2E)-3,7-dimethylocta-2,6-dien-1-yl group at position 2 and by a pentyl group at position 5. It is a natural product found in Cannabis sativa and Helichrysum species.	3.15	1	0	phytocannabinoid; resorcinols	anti-inflammatory agent; antibacterial agent; antioxidant; appetite enhancer; cannabinoid receptor agonist; neuroprotective agent; plant metabolite
cinnamyl alcohol cinnamyl alcohol: RN given refers to parent cpd without isomeric designation. (E)-cinnamyl alcohol : The E (trans) stereoisomer of cinnamyl alcohol.. cinnamyl alcohol : A primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified).	7.32	56	0	cinnamyl alcohol	plant metabolite
syringin syringin: a phenylpropanoid glycoside; see also eleutherosides & lyoniside for eleutheroside A: 474-58-8. syringin : A monosaccharide derivative that is trans-sinapyl alcohol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage.	2.02	1	0	beta-D-glucoside; dimethoxybenzene; monosaccharide derivative; primary alcohol	hepatoprotective agent; plant metabolite
(E)-3-(2-Hydroxyphenyl)-2-propenal [no description available]	2.76	3	0	cinnamaldehydes
icaritin icaritin: structure in first source	2.04	1	0
icariin [no description available]	2.04	1	0	flavonols; glycosyloxyflavone	antioxidant; bone density conservation agent; EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; phytoestrogen
methyl-p-coumarate methyl-p-coumarate: structure in first source. 4-coumaric acid methyl ester : A cinnamate ester that is the methyl ester of 4-coumaric acid.	2	1	0	4-coumaric acid methyl ester
osthenol osthenol: structure in first source. osthenol : A hydroxycoumarin that is umbelliferone in which the hydrogen at position 8 has been replaced by a prenyl group.	2.02	1	0	hydroxycoumarin	antifungal agent; plant metabolite
angiotensin amide psilostachyin A: has antineoplastic, anti-inflammatory, leishmanicidal, and molluscicidal activities; isolated from Ambrosia psilostachya; structure in first source	2.02	1	0
caryophyllene caryophyllene: RN given refers to cpd without isomeric designation; structure given in first source	8.76	2	0
2'-hydroxy-4-methoxychalcone [no description available]	2.1	1	0
4-amylcinnamoylanthranilic acid 4-amylcinnamoylanthranilic acid: phospholipase A2 inhibitor. N-(p-amylcinnamoyl)anthranilic acid : An amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 4-pentylcinnamoyl group. It is a transient receptor potential (TRP) channel blocker and phospholipase A2 (PLA2) inhibitor.	2.21	1	0	amidobenzoic acid; cinnamamides; secondary carboxamide	EC 3.1.1.4 (phospholipase A2) inhibitor; TRP channel blocker
farnesylthioacetic acid farnesylthioacetic acid: a competitive inhibitor of isoprenylated protein methyltransferase; structure in first source	3.15	1	0
methyl-3-methoxy-4-hydroxystyryl ketone methyl-3-methoxy-4-hydroxystyryl ketone: structure given in first source; RN given refers to cpd without isomeric designation	1.99	1	0	hydroxycinnamic acid
cinnamyl isobutyrate cinnamyl isobutyrate: structure	7.21	1	0	styrenes
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	7.25	1	0	boron group element atom; elemental aluminium; metal atom
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	2.78	3	0	metalloid atom; pnictogen	micronutrient
gallium Gallium: A rare, metallic element designated by the symbol, Ga, atomic number 31, and atomic weight 69.72.. gallium atom : A metallic element predicted as eka-aluminium by Mendeleev in 1870 and discovered by Paul-Emile Lecoq de Boisbaudran in 1875. Named in honour of France (Latin Gallia) and perhaps also from the Latin gallus cock, a translation of Lecoq.	7.08	1	0	boron group element atom
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	1.95	1	0	chalcogen; nonmetal atom	macronutrient
2-pentenal 2-pentenal: RN given refers to cpd without isomeric designation. 2-pentenal : An enal consisting of pent-2-ene having an oxo group at the 1-position. (E)-2-pentenal : A 2-pentenal in which the double bond has (E)-configuration. It is found in cigarette smoke, virgin olive oil, and milk.	3.86	3	0	2-pentenal	plant metabolite
alpha-bromocinnamaldehyde alpha-bromocinnamaldehyde: anti-mildew agent; structure given in first source on page 29	2.07	1	0
puerarin [no description available]	7	1	0	C-glycosyl compound; isoflavonoid
ajoene ajoene: major antiplatelet compound in methanol extract of garlic; also inhibits trypanothione reductase.	2.02	1	0	sulfoxide
sinomenine sinomenine: isolated from root of Sinomenium acutum; antirheumatic, antineuralgic	8.36	5	0	morphinane alkaloid
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	2.68	3	0	butenedioate; C4-dicarboxylate	human metabolite; metabolite; Saccharomyces cerevisiae metabolite
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	8.33	6	0	cysteinium	fundamental metabolite
gamma-mangostin gamma-mangostin : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3, 6 and 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antitumour activity.	2.02	1	0	phenols; xanthones	antineoplastic agent; plant metabolite; protein kinase inhibitor
lavandulol lavandulol: defensive pheromone of the red-lined carrion beetle and additive in perfumes; structure in first source. lavandulol : A monoterpenoid alcohol that is hepta-1-5-diene which is substituted at positions 2 and 6 by methyl groups and at position 3 by a hydroxymethyl group. It is commonly found in lavender oil.	2.08	1	0	lavandulol
s-trans,trans-farnesylthiosalicylic acid farnesylthiosalicylic acid: structure in first source	3.61	2	0	sesquiterpenoid
phytochlorin phytochlorin: RN given refers to (2S-trans)-isomer; structure given in the first source	2.21	1	0
cefuroxime [no description available]	2.08	1	0	3-(carbamoyloxymethyl)cephalosporin; furans; oxime O-ether	drug allergen
narcissin flavonol narcissin flavonol: flavanol glycoside from Strumpfia maritima; do not confuse with other narcissin in Chemline, an alkaloid (lycorine (NM))	2.07	1	0	disaccharide derivative; glycosyloxyflavone; monomethoxyflavone; trihydroxyflavone
pachymic acid pachymic acid: inhibits phospholipase A2; isolated from Poria cocos; structure in first source	2.31	1	0	triterpenoid
myricetin 3-o-glucuronide myricetin 3-O-glucuronide: from Epilobium angustifolium. myricetin 3-O-glucuronide : A myricetin O-glucuronide that is myricetin with a beta-D-glucosiduronic acid residue attached at the 3-position.	2.02	1	0	monosaccharide derivative; myricetin O-glucuronide; pentahydroxyflavone	metabolite
arglabin arglabin: a sesquiterpene lactone from the Chinese herb Artemisia myriantha; structure given in first source. arglabin : An organic heterotetracyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-dimethyl-1,3a,4,5,6,7-hexahydroazulen-5-yl group in which the double bond in the 7-membered ring has been epoxidised and in which the hydroxy group and the carboxy group have undergone formal condensation to give the corresponding gamma-lactone. It is found in Artemisia glabella. Arglabin-DMA HCl, the hydrochloride salt of the adduct resulting from the conjugate addition of dimethylamine to the ene-lactone moiety, has been successfully used in Khazakhstan for the treatment of breast, colon, ovarian and lung cancers.	2.15	1	0	epoxide; gamma-lactone; organic heterotetracyclic compound; sesquiterpene lactone	antineoplastic agent; metabolite
resiniferatoxin resiniferatoxin: phorbol related diterpene ester; potent agonist of vanilloid TRPV1 receptors. resiniferatoxin : A heteropentacyclic compound found in Euphorbia poissonii with molecular formula C37H40O9. It is an agonist of the transient receptor potential cation channel subfamily V member 1 (TrpV1).	2.75	3	0	carboxylic ester; diterpenoid; enone; monomethoxybenzene; organic heteropentacyclic compound; ortho ester; phenols; tertiary alpha-hydroxy ketone	analgesic; neurotoxin; plant metabolite; TRPV1 agonist
carbocyanines Carbocyanines: Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials.	2.13	1	0	cyanine dye; organic iodide salt	fluorochrome
cefotaxime Cefotaxime: Semisynthetic broad-spectrum cephalosporin.. cefotaxime : A cephalosporin compound having acetoxymethyl and [2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side groups.	2.25	1	0	1,3-thiazoles; cephalosporin; oxime O-ether	antibacterial drug; drug allergen
cinnamylamine [no description available]	1.98	1	0
bisabolol bisabolol: monocyclic sesquiterpene alcohol with strong bacteriocidal effects, especilly against M. Tuberc.; isolated from seed plant Populus tacamacaha; RN given refers to cpd without isomeric desigation	7.61	2	0
monorden monorden: inhibits HSP90 Heat-Shock Proteins, DNA topoisomerase VI and human Topoisomerase II	2.02	1	0	cyclic ketone; enone; epoxide; macrolide antibiotic; monochlorobenzenes; phenols	antifungal agent; metabolite; tyrosine kinase inhibitor
tetrodotoxin Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.	2.25	1	0	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
germanium Germanium: A rare metal element with a blue-gray appearance and atomic symbol Ge, atomic number 32, and atomic weight 72.63.	1.96	1	0	carbon group element atom; metalloid atom; nonmetal atom
quaternium-15 quaternium-15 : A quaternary ammonium salt derived from hexamethylenetetramine; used as a preservative in many cosmetics and industrial substances. Also acts as a disinfectant and allergenic agent.	2.04	1	0
columbianadin columbianadin: furanocoumarin isolated from Peucedanum palustre; RN given refers to columbianadin, (S-(Z))-isomer. columbianadin : An alpha,beta-unsaturated carboxylic ester obtained by formal condensation of the carboxy group of angelic acid with the hydroxy group of 2-[(8S)-2-oxo-8,9-dihydro-2H-furo[2,3-h][1]benzopyran-8-yl]propan-2-ol.	2.07	1	0	alpha,beta-unsaturated carboxylic ester; furanocoumarin	anti-inflammatory agent; antineoplastic agent; apoptosis inducer; hepatoprotective agent; plant metabolite; rat metabolite
9-oxo-15-hydroxy-delta 7,10,13-prostatrienoic acid methyl ester [no description available]	2.15	1	0
plicatin b acrylate plicatin B acrylate: isolated from the medicinal plants Psoralea juncaea and P. plicata; structure given in first source	2	1	0
drupanin Drupanin: anti-oxidant and anti-cancer; structure in first source	2	1	0
sanshool sanshool: isolated from the stem bark of Zanthoxylum liebmannianum; RN given for (E,E,Z,E)-isomer; structure in first source	2.78	3	0	fatty amide
(10)-shogaol (10)-shogaol: isolated from ginger; structure in first source	3.25	1	0	enone; monomethoxybenzene; phenols
hydroxysafflor yellow a hydroxysafflor yellow A: from Carthamus tinctorius; structure given in first source. hydroxysafflor yellow A : A C-glycosyl compound that is 3,4,5-trihydroxycyclohexa-2,5-dien-1-one which is substituted by beta-D-glucosyl groups at positions 2 and 4, and by a p-hydroxycinnamoyl group at position 6. It is the main bioactive compound of a traditional Chinese medicine obtained from safflower (Carthamus tinctorius).	2.06	1	0
4-oxo-2-nonenal 4-oxo-2-nonenal: reacts with 2'-deoxyguanosine; a product of lipid peroxidation; structure in first source. (E)-4-oxonon-2-enal : The enal that is (E)-non-2-enal substituted with an oxo group at C-4.	3.15	1	0	enal; enone	human metabolite
3,3'-dioctadecyloxacarbocyanine 3,3'-dioctadecyloxacarbocyanine: lipophilic axon tracer; RN given for iodide salt	2.13	1	0
alpha-cyperone alpha-cyperone: isolated from the rhizomes of Cyperus rotundus; structure in first source	2.07	1	0
beta-escin [no description available]	3.15	5	0
emetine hydrochloride [no description available]	2.01	1	0
bay-k-8644, (-)-isomer (S)-Bay-K-8644 : A methyl 2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylate in which the 4-position has (S)-configuration.	3.15	1	0	(trifluoromethyl)benzenes; methyl 2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylate
l-165041 4-(3-(2-propyl-3-hydroxy-4-acetyl)phenoxy)propyloxyphenoxy acetic acid: a PPAR-delta agonist has regulatory effects on a variety of adipokines, and these effects might explain some of their metabolic function.	2.11	1	0	aromatic ketone
s-nitroso-n-acetylpenicillamine S-Nitroso-N-Acetylpenicillamine: A sulfur-containing alkyl thionitrite that is one of the NITRIC OXIDE DONORS.	2.11	1	0	nitroso compound; nitrosothio compound	nitric oxide donor; vasodilator agent
nitrofurantoin Nitrofurantoin: A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression.. nitrofurantoin : An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.	2.06	1	0	imidazolidine-2,4-dione; nitrofuran antibiotic; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic	antibacterial drug; antiinfective agent; hepatotoxic agent
bay-k-8644 (R)-Bay-K-8644 : A methyl 2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylate in which the 4-position has (R)-configuration.	3.15	1	0	(trifluoromethyl)benzenes; methyl 2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylate
morphinans Morphinans: Compounds based on a partially saturated iminoethanophenanthrene, which can be described as ethylimino-bridged benzo-decahydronaphthalenes. They include some of the OPIOIDS found in PAPAVER that are used as ANALGESICS.	3.36	5	0	isoquinoline alkaloid fundamental parent; morphinane alkaloid
ci 940 leptomycin : A complex, very long chain, polyunsaturated fatty acid whose core structure comprises 8-oxononadeca-2,10,12,16,18-pentaenoic acid having methyl substituents at positions 3, 5, 7, 9, 11 and 15 and a 3,6-dihydropyran-6-one-2-yl group at position 19.	2.15	1	0	hydroxy polyunsaturated fatty acid; leptomycin	antifungal agent; bacterial metabolite
isoborneol isoborneol: RN given refers to cpd without isomeric designation; structure	2.72	3	0	borneol
cinnamaldehyde thiosemicarbazone cinnamaldehyde thiosemicarbazone: has antimicrobial activity; structure in first source	2.41	1	0
chlorhexidine Chlorhexidine: A disinfectant and topical anti-infective agent used also as mouthwash to prevent oral plaque.. chlorhexidine : A bisbiguanide compound with a structure consisting of two (p-chlorophenyl)guanide units linked by a hexamethylene bridge.	7.72	2	0	biguanides; monochlorobenzenes	antibacterial agent; antiinfective agent
formazans Formazans: Colored azo compounds formed by the reduction of tetrazolium salts. Employing this reaction, oxidoreductase activity can be determined quantitatively in tissue sections by allowing the enzymes to act on their specific substrates in the presence of tetrazolium salts.	2.44	2	0
4-(4-chlorophenyl)-3-methylbut-3-en-2-oxime 4-(4-chlorophenyl)-3-methylbut-3-en-2-oxime: a TRPA1 antagonist	3.87	3	0
capsiate [no description available]	2.11	1	0	carboxylic ester; monomethoxybenzene; phenols	angiogenesis inhibitor; anti-allergic agent; anti-inflammatory agent; antioxidant; capsaicin receptor agonist; hypoglycemic agent; plant metabolite
fr 148083 5Z-7-oxozeaenol : A macrolide that is the 7-oxo derivative of zeaenol (the 5Z stereoisomer). Isolated from Fungi, it exhibits cytotoxic, antibacterial and inhibitory activity against NF-kappaB.	2.15	1	0	aromatic ether; macrolide; phenols; secondary alcohol; secondary alpha-hydroxy ketone	antibacterial agent; antineoplastic agent; metabolite; NF-kappaB inhibitor
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	3.17	5	0	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
hirsutanonol hirsutanonol: a diarylheptanoid from the bark of Alnus hirsuta var. sibirica; inhibits cyclooxygenase-2 expression; structure in first source	2.02	1	0
n-(4-tert-butylphenyl)-4-(3-chloropyridin-2-yl)tetrahydropyrazine-1(2h)-carboxamide N-(4-tert-butylphenyl)-4-(3-chloropyridin-2-yl)tetrahydropyrazine-1(2H)-carboxamide: a vanilloid receptor 1 antagonist and analgesic; structure in first source	2.1	1	0	piperazines; pyridines
zeolites [no description available]	7.9	2	0
aluminum oxide Aluminum Oxide: An oxide of aluminum, occurring in nature as various minerals such as bauxite, corundum, etc. It is used as an adsorbent, desiccating agent, and catalyst, and in the manufacture of dental cements and refractories.	2.46	2	0
licoflavone c licoflavone C: Antimutagenic Agent; a naturally occurring prenyl-flavone extracted from Genista ephedroides; structure in first source	2.04	1	0
2'-benzoyloxycinnamaldehyde 2'-benzoyloxycinnamaldehyde: induces apoptosis in cancer cells; possible antineoplastic agent	9.25	5	0
ly 341495 LY 341495: structure in first source	2.03	1	0
pyrrocidine a pyrrocidine A: an antifungal antibiotic isolated from Acremonium zeae; structure in first souce	2.15	1	0
nystatin a1 Nystatin: Macrolide antifungal antibiotic complex produced by Streptomyces noursei, S. aureus, and other Streptomyces species. The biologically active components of the complex are nystatin A1, A2, and A3.. nystatin : A heterogeneous mixture of polyene compounds produced by cultures of Streptomyces noursei. It mainly consists of three biologically active components designated nystatin A1, nystatin A2, and nystatin A3. It is used to treat oral and dermal fungal infections.. nystatin A1 : A polyene macrolide antibiotic; part of the nystatin complex produced by several Streptomyces species. It is an antifungal antibiotic used for the treatment of topical fungal infections caused by a broad spectrum of fungal pathogens comprising yeast-like and filamentous species.	2.07	1	0	nystatins
calcimycin Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.	2.05	1	0	benzoxazole
oregonin oregonin: a diarylheptanoid from the bark of Alnus hirsuta var. sibirica; inhibits cyclooxygenase-2 expression; structure in first source	2.02	1	0	diarylheptanoid
jujubogenin jujubogenin: dammarane type triterpene	2.05	1	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2.91	4	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	3.21	5	0
cholecystokinin Cholecystokinin: A peptide, of about 33 amino acids, secreted by the upper INTESTINAL MUCOSA and also found in the central nervous system. It causes gallbladder contraction, release of pancreatic exocrine (or digestive) enzymes, and affects other gastrointestinal functions. Cholecystokinin may be the mediator of satiety.	2.08	1	0
dynorphins Dynorphins: A class of opioid peptides including dynorphin A, dynorphin B, and smaller fragments of these peptides. Dynorphins prefer kappa-opioid receptors (RECEPTORS, OPIOID, KAPPA) and have been shown to play a role as central nervous system transmitters.	2.08	1	0
tannins gallotannin : A class of hydrolysable tannins obtained by condensation of the carboxy group of gallic acid (and its polymeric derivatives) with the hydroxy groups of a monosaccharide (most commonly glucose).	3.35	1	0	tannin
neuropeptide y Neuropeptide Y: A 36-amino acid peptide present in many organs and in many sympathetic noradrenergic neurons. It has vasoconstrictor and natriuretic activity and regulates local blood flow, glandular secretion, and smooth muscle activity. The peptide also stimulates feeding and drinking behavior and influences secretion of pituitary hormones.	2.13	1	0
tannins Tannins: Polyphenolic compounds with molecular weights of around 500-3000 daltons and containing enough hydroxyl groups (1-2 per 100 MW) for effective cross linking of other compounds (ASTRINGENTS). The two main types are HYDROLYZABLE TANNINS and CONDENSED TANNINS. Historically, the term has applied to many compounds and plant extracts able to render skin COLLAGEN impervious to degradation. The word tannin derives from the Celtic word for OAK TREE which was used for leather processing.	4.32	5	0
oligonucleotides [no description available]	2.03	1	0
glucagon-like peptide 1 Glucagon-Like Peptide 1: A peptide of 36 or 37 amino acids that is derived from PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. GLP-1(1-37 or 1-36) is further N-terminally truncated resulting in GLP-1(7-37) or GLP-1-(7-36) which can be amidated. These GLP-1 peptides are known to enhance glucose-dependent INSULIN release, suppress GLUCAGON release and gastric emptying, lower BLOOD GLUCOSE, and reduce food intake.	2.08	1	0
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	3.16	5	0	glycoside
quercetin [no description available]	2.11	1	0
endothelin-1 Endothelin-1: A 21-amino acid peptide produced in a variety of tissues including endothelial and vascular smooth-muscle cells, neurons and astrocytes in the central nervous system, and endometrial cells. It acts as a modulator of vasomotor tone, cell proliferation, and hormone production. (N Eng J Med 1995;333(6):356-63)	2.05	1	0
amikacin [no description available]	2.6	1	0
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	2.41	1	0	chlorophyll; methyl ester	cofactor
thimerosal Thimerosal: An ethylmercury-sulfidobenzoate that has been used as a preservative in VACCINES; ANTIVENINS; and OINTMENTS. It was formerly used as a topical antiseptic. It degrades to ethylmercury and thiosalicylate.. thimerosal : An alkylmercury compound (approximately 49% mercury by weight) used as an antiseptic and antifungal agent.	1.95	1	0	alkylmercury compound	antifungal drug; antiseptic drug; disinfectant; drug allergen
pinoresinol pinoresinol: in plants; a furo[3,4-c]furan created from dimer of coniferyl alcohol. pinoresinol : A lignan that is tetrahydro-1H,3H-furo[3,4-c]furan substituted at positions 1 and 4 by 4-hydroxy-3-methoxyphenyl groups.	2.21	1	0
alcaftadine alcaftadine : An imidazobenzazepine that is 6,11-dihydro-5H-imidazo[2,1-b][3]benzazepine substituted at position 3 by a formyl group and at position 11 by a 1-methylpiperidin-4-ylidene group. An antihistamine used for treatment of allergic conjunctivitis.	3.35	1	0	aldehyde; imidazobenzazepine; piperidines; tertiary amino compound	anti-allergic agent; H1-receptor antagonist
aflatrem aflatrem: tremorgenic toxin isolated from Aspergillus flavus; structure	2.21	1	0	organic heterotricyclic compound; organooxygen compound
chitosan [no description available]	4.97	30	0
enzacamene enzacamene: structure in first source; 4-MBC for short;	2.11	1	0
sodium hypochlorite Sodium Hypochlorite: It is used as an oxidizing and bleaching agent and as a disinfectant. (From Grant & Hackh's Chemical Dictionary, 5th ed). sodium hypochlorite : An inorganic sodium salt in which hypochlorite is the counterion. It is used as a bleaching and disinfecting agent and is commonly found in household bleach.	4.37	3	1	inorganic sodium salt	bleaching agent; disinfectant
ro13-9904 Ceftriaxone: A broad-spectrum cephalosporin antibiotic and cefotaxime derivative with a very long half-life and high penetrability to meninges, eyes and inner ears.. ceftriaxone : A third-generation cephalosporin compound having 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetylamino and [(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl side-groups.	2.6	1	0
pc190723 PC190723: Antibacterial; an inhibitor of FtsZ with potent and selective anti-staphylococcal activity including methicillin- and multi-drug-resistant Staphylococcus aureus; structure in first source	4.97	4	0
8-iso-prostaglandin a2 8-isoprostaglandin A2: a cyclopentenone isoprostane	3.15	1	0	prostanoid
a 967079 A 967079: a TRPA1 channel antagonist; structure in first source	3.91	3	0
piperidines Piperidines: A family of hexahydropyridines.	5.11	9	0
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	3.71	9	0
kuraridin kuraridin: isolated from Sophora flavescens; structure in first source	2.02	1	0
gnaphalin gnaphalin: a lipophilic flavonol from Helichrysum sp.; structure in first source	2.02	1	0
phillyrin [no description available]	2.02	1	0
colistin Colistin: Cyclic polypeptide antibiotic from Bacillus colistinus. It is composed of Polymyxins E1 and E2 (or Colistins A, B, and C) which act as detergents on cell membranes. Colistin is less toxic than Polymyxin B, but otherwise similar; the methanesulfonate is used orally.. colistin : A multi-component mixture comprising mostly of colistin A (R = Me) and B (R = H), with small amounts of colistin C and other polymyxins, produced by certain strains of Bacillus polymyxa var. colistinus. An antibiotic, it is used as its sulfate salt (for oral or topical use) or as the sodium salt of the N-methylsulfonic acid derivative (the injectable form) in the treatment of severe Gram-negative infections, partiularly those due to Pseudomonas aeruginosa.	2.25	1	0
chrysophaentin a chrysophaentin A: structure in first source	4.76	3	0
peoniflorin [no description available]	2.07	1	0
miogadial miogadial: responsible for hot taste of myoga, Zingiber mioga; structure in first source	3.15	1	0
methylcellulose Methylcellulose: Methylester of cellulose. Methylcellulose is used as an emulsifying and suspending agent in cosmetics, pharmaceutics and the chemical industry. It is used therapeutically as a bulk laxative.	8.58	2	0
jujuboside a [no description available]	2.05	1	0	triterpenoid
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	3.49	7	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
tetracycline Tetracycline: A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.. tetracycline : A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.	2.54	2	0
minocycline Minocycline: A TETRACYCLINE analog, having a 7-dimethylamino and lacking the 5 methyl and hydroxyl groups, which is effective against tetracycline-resistant STAPHYLOCOCCUS infections.. minocycline : A tetracycline analogue having a dimethylamino group at position 7 and lacking the methyl and hydroxy groups at position 5.	2.08	1	0
salicylates Salicylates: The salts or esters of salicylic acids, or salicylate esters of an organic acid. Some of these have analgesic, antipyretic, and anti-inflammatory activities by inhibiting prostaglandin synthesis.. hydroxybenzoate : Any benzoate derivative carrying a single carboxylate group and at least one hydroxy substituent.. salicylates : Any salt or ester arising from reaction of the carboxy group of salicylic acid, or any ester resulting from the condensation of the phenolic hydroxy group of salicylic acid with an organic acid.. salicylate : A monohydroxybenzoate that is the conjugate base of salicylic acid.	3.38	7	0	monohydroxybenzoate	plant metabolite
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	6.51	22	0	benzenes; hydroxycoumarin; methyl ketone
tenuazonic acid Tenuazonic Acid: 3-Acetyl-5-sec-butyl-4-hydroxy-3-pyrrolin-2-one. A metabolite found in a strain of the fungus Alternaria tenuis Auct. which functions as an antibiotic with antiviral and antineoplastic properties, and may also act as a mycotoxin.. tenuazonic acid : A member of the class of pyrrolidin-2-ones that is 5-(butan-2-yl)pyrrolidine-2,4-dione carrying an additional acetyl group at position 3. A mycotoxin produced by various plant pathogenic fungi.	7.31	1	0
4-hydroxycoumarin 2-hydroxychromone: structure	1.99	1	0	hydroxycoumarin
eravacycline eravacycline: has antibacterial activity	7.6	1	0	tetracyclines
clay Clay: A naturally-occurring rock or soil constituent characterized by particles with a diameter of less than 0.005 mm. It is composed primarily of hydrous aluminum silicates, trace amounts of metal OXIDES, and organic matter.	7.9	2	0
saxitoxin Saxitoxin: A compound that contains a reduced purine ring system but is not biosynthetically related to the purine alkaloids. It is a poison found in certain edible mollusks at certain times; elaborated by GONYAULAX and consumed by mollusks, fishes, etc. without ill effects. It is neurotoxic and causes RESPIRATORY PARALYSIS and other effects in MAMMALS, known as paralytic SHELLFISH poisoning.. saxitoxin : An alkaloid isolated from the marine dinoflagellates and cyanobacteria that causes paralytic shellfish poisoning.	2	1	0	alkaloid; carbamate ester; guanidines; ketone hydrate; paralytic shellfish toxin; pyrrolopurine	cyanotoxin; marine metabolite; neurotoxin; sodium channel blocker; toxin
rociletinib rociletinib: inhibits epidermal growth factor receptor tyrosine kinase activity; structure in first source	2.15	1	0
pyrethrins [no description available]	2.21	1	0
osimertinib osimertinib: an EGFR tyrosine kinase inhibitor. osimertinib : A member of the class of aminopyrimidines that is 4-(1-methylindol-3-yl)pyrimidin-2-amine in which one of the amino hydrogens is replaced by a 2-methoxy-4-[2-(dimethylamino)ethyl](methyl)amino-5-acrylamidophenyl group. Used (as the mesylate salt) for treatment of EGFR T790M mutation positive non-small cell lung cancer.	2.15	1	0	acrylamides; aminopyrimidine; biaryl; indoles; monomethoxybenzene; secondary amino compound; secondary carboxamide; substituted aniline; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist
agar Agar: A complex sulfated polymer of galactose units, extracted from Gelidium cartilagineum, Gracilaria confervoides, and related red algae. It is used as a gel in the preparation of solid culture media for microorganisms, as a bulk laxative, in making emulsions, and as a supporting medium for immunodiffusion and immunoelectrophoresis.. agar : A complex mixture of polysaccharides extracted from species of red algae. Its two main components are agarose and agaropectin. Agarose is the component responsible for the high-strength gelling properties of agar, while agaropectin provides the viscous properties.	2.41	1	0
hirudin Hirudin: A 65-residue polypeptide from LEECHES.	2.59	2	0
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	2.49	2	0
caseins Caseins: A mixture of related phosphoproteins occurring in milk and cheese. The group is characterized as one of the most nutritive milk proteins, containing all of the common amino acids and rich in the essential ones.	2.61	2	0
ellagitannin ellagitannin: structure; precoxin A/ praecoxin A is a purified ellagitannin. ellagitannin : A form of hydrolysable tannin produced from ellagic acid. Ellagitannins are glucosides which are readily hydrolysed by water to regenerate ellagic acid when the plants are eaten.	3.27	1	0
benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone: an interleukin-1beta converting enzyme (ICE)-like protease inhibitor	2.08	1	0
hyaluronoglucosaminidase Hyaluronoglucosaminidase: An enzyme that catalyzes the random hydrolysis of 1,4-linkages between N-acetyl-beta-D-glucosamine and D-glucuronate residues in hyaluronate. (From Enzyme Nomenclature, 1992) There has been use as ANTINEOPLASTIC AGENTS to limit NEOPLASM METASTASIS.	2.25	1	0
peoniflorin peoniflorin: from Radix and of Paeonia suffruticosa	2.7	3	0
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	2.08	1	0
peptide yy Peptide YY: A 36-amino acid peptide produced by the L cells of the distal small intestine and colon. Peptide YY inhibits gastric and pancreatic secretion.. peptide YY : A 36-membered human gut polypeptide consisting of Tyr, Pro, Ile, Lys, Pro, Glu, Ala, Pro, Gly, Glu, Asp, Ala, Ser, Pro, Glu, Glu, Leu, Asn, Arg, Tyr, Tyr, Ala, Ser, Leu, Arg, His, Tyr, Leu, Asn, Leu, Val, Thr, Arg, Gln, Arg and Tyr-NH2 residues joined in sequence.	2.08	1	0
lactoferrin Lactoferrin: An iron-binding protein that was originally characterized as a milk protein. It is widely distributed in secretory fluids and is found in the neutrophilic granules of LEUKOCYTES. The N-terminal part of lactoferrin possesses a serine protease which functions to inactivate the TYPE III SECRETION SYSTEM used by bacteria to export virulence proteins for host cell invasion.	2.17	1	0
orabase Orabase: used in therapy of oral mucosal ulcers	9.39	3	1
muramidase Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.	3.18	4	0
cyclic gmp Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.	2.42	2	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
guanosine monophosphate Guanosine Monophosphate: A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature.. guanosine 5'-monophosphate : A purine ribonucleoside 5'-monophosphate having guanine as the nucleobase.	2.52	2	0	guanosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	biomarker; Escherichia coli metabolite; metabolite; mouse metabolite
guanosine triphosphate Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.	2.03	1	0	guanosine 5'-phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
inosinic acid Inosine Monophosphate: Inosine 5'-Monophosphate. A purine nucleotide which has hypoxanthine as the base and one phosphate group esterified to the sugar moiety.	2.52	2	0	inosine phosphate; purine ribonucleoside 5'-monophosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
dacarbazine (E)-dacarbazine : A dacarbazine in which the N=N double bond adopts a trans-configuration.	2.6	1	0	dacarbazine
sildenafil sildenafil : A pyrazolo[4,3-d]pyrimidin-7-one having a methyl substituent at the 1-position, a propyl substituent at the 3-position and a 2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl group at the 5-position.	2.04	1	0	piperazines; pyrazolopyrimidine; sulfonamide	EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; vasodilator agent
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	8.01	4	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
cyadox cyadox: structure	7.15	1	0
methylnitronitrosoguanidine Methylnitronitrosoguanidine: A nitrosoguanidine derivative with potent mutagenic and carcinogenic properties.. N-methyl-N'-nitro-N-nitrosoguanidine : An N-nitroguanidine compound having nitroso and methyl substituents at the N'-position	1.97	1	0	nitroso compound	alkylating agent
molybdopterin cytosine dinucleotide molybdopterin cytosine dinucleotide: pterin of carbon monoxide dehydrogenase from Pseudomonas carboxydoflava; structure has been determined	2.05	1	0	molybdopterin dinucleotide; molybdopterins; thiol
molybdenum cofactor molybdenum cofactor: also see records for molybdopterin cytosine dinucleotide and molybdopterin guanine dinucleotide. MoO2-molybdopterin cofactor(2-) : An organophosphate oxoanion obtained by deprotonation of the phosphate OH groups of MoO2-molybdopterin cofactor.. MoO2-molybdopterin cofactor : An Mo-molybdopterin cofactor in which the coordinated molybdenum species is MoO2.	2.05	1	0	Mo-molybdopterin cofactor; organophosphate oxoanion
maltodextrin maltodextrin : A dextrin in which the D-glucose units are linked by alpha-(1->4) glycosidic bonds.	2.86	3	0
dinitrobenzenes Dinitrobenzenes: Benzene derivatives which are substituted with two nitro groups in the ortho, meta or para positions.	3.06	1	0
formocresol formocresol: preferred agent for performing pulpotomies in primary teeth	2.44	2	0
leptin Leptin: A 16-kDa peptide hormone secreted from WHITE ADIPOCYTES. Leptin serves as a feedback signal from fat cells to the CENTRAL NERVOUS SYSTEM in regulation of food intake, energy balance, and fat storage.	2.55	2	0
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2.74	3	0

cinnamaldehyde

Description

Cross-References

Synonyms (163)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Roles (7)

Drug Classes (2)

Protein Targets (36)

Potency Measurements

Inhibition Measurements

Activation Measurements

Other Measurements

Biological Processes (239)

Molecular Functions (55)

Ceullar Components (37)

Bioassays (135)

Research

Studies (1,310)

Market Indicators

Research Demand Index: 69.25

Study Types

Clinical Trials (6)

Trial Overview

Trial Outcomes

Absolute Values of Whole Lung MCC for Each Group

CA-induced Changes in Whole Lung MCC

Percent Polymorphonuclear Leukocytes (PMN) in Induced Sputum

CA-induced Changes in Regional Lung MCC

cinnamaldehyde

Description

Cross-References

Synonyms (163)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Roles (7)

Drug Classes (2)

Protein Targets (36)

Potency Measurements

Inhibition Measurements

Activation Measurements

Other Measurements

Biological Processes (239)

Molecular Functions (55)

Ceullar Components (37)

Bioassays (135)

Research

Studies (1,310)

Market Indicators

Research Demand Index: 69.25

Study Types

Clinical Trials (6)

Trial Overview

Trial Outcomes

Absolute Values of Whole Lung MCC for Each Group

CA-induced Changes in Whole Lung MCC

Percent Polymorphonuclear Leukocytes (PMN) in Induced Sputum

CA-induced Changes in Regional Lung MCC

Related Drugs (966)

Related Conditions (437)