evodiamine profile

ID Source	ID
PubMed CID	151289
CHEMBL ID	81925
CHEBI ID	95196
SCHEMBL ID	139349
MeSH ID	M0142130

Synonym
nsc-258314
nsc258314
evodiamine ,
OPREA1_236793
evodiamine, evodia rutaecarpa
NCGC00163553-01
isoevodiamine
5956-87-6
AC1L9C8E ,
FT-0651829
indolo(2',3':3,4)pyrido(2,1-b)quinazolin-5(7h)-one, 8,13,13b,14-tetrahydro-14-methyl-
BCP9000671
PUBCHEM18244 ,
NCGC00163553-02
AKOS015894237
S2382
BRD-A68631409-001-01-3
CCG-208627
SCHEMBL139349
bdbm50016250
chembl81925 ,
AC-24421
surecn682158
8,13,13b,14-tetrahydro-14-methylindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7h)-one
E1012
(+/-)-evodiamine
518-18-3
evodiamine;
mfcd06407824
CHEBI:95196
21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20] henicosa-2(10),4,6,8,15,17,19-heptaen-14-one
SR-05000002159-2
sr-05000002159
NCGC00163553-03
14-methyl-7,8,13b,14-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(13h)-one
lsm-6483
Q5418554
evodiamine (isoevodiamine)
21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15,17,19-heptaen-14-one
AS-15078
indolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7h)-one,8,13,13b,14-tetrahydro-14-methyl-, (13bs)-
T72558
(1s)-21-methyl-3,13,21-triazapentacyclo[11.8.0.0^{2,10.0^{4,9.0^{15,20]henicosa-2(10),4,6,8,15,17,19-heptaen-14-one
XE178590
CS-0173730
HY-N0114A
( inverted exclamation marka)-evodiamine
DTXSID401347170
mfcd00016673
(?)-evodiamine

Research Excerpts

Overview

Evodiamine (EVO) is a natural quinolone alkaloid firstly isolated from the fruit of Evodia rutaecarpa. It is one of the most frequently used traditional Chinese herb for treating a variety of ailments.

Excerpt	Reference	Relevance
"Evodiamine (Evo) is a quinazolinocarboline alkaloid found in "	( Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer. Chen, ZS; Li, D; Qiu, Y; Wu, L; Xu, J; Xu, S; Yang, DH; Yao, H; Zhou, M, 2021)	2.31
"Evodiamine (EVO) is a bioactive alkaloid that exerts antitumor activity in various cancers, including prostate cancer (PCa). "	( Identification of evodiamine as a suppressor of prostate cancer progression by reducing AR transcriptional activity via targeting Src. Cheng, P; Fan, J; Liu, C; Wang, X; Xu, C; Zhang, X; Zhao, X, 2022)	2.5
"Evodiamine (EVO) is a natural quinolone alkaloid firstly isolated from the fruit of Evodia rutaecarpa, which is one of the most frequently used traditional Chinese herb for treating a variety of ailments, including headaches, abdominal pain, vomiting, diarrhea, amenorrhea difficult menstruation, postpartum hemorrhage, and other diseases. "	( Evodiamine: A Privileged Structure with Broad-ranging Biological Activities. Jiang, X; Li, D; Li, Y; Liu, W; Zhao, Q, 2022)	3.61
"Evodiamine (EVO) is an alkaloid extracted from "	( Serum untargeted metabolomics analysis of the mechanisms of evodiamine on type 2 diabetes mellitus model rats. Chen, F; Liao, J; Lu, Q; Niu, C; Wang, H; Wang, S; Yu, Y, 2022)	2.41
"Evodiamine is a major alkaloid component found in the fruit of Evodia rutaecarpa. "	( Evodiamine as an anticancer agent: a comprehensive review on its therapeutic application, pharmacokinetic, toxicity, and metabolism in various cancers. Biswal, BK; Panda, M; Tripathi, SK; Zengin, G, 2023)	3.8
"Evodiamine (EVO) is an alkaloid component in the fruit of Evodia rutaecarpa, which has antioxidant and detoxification functions."	( Mechanism of evodiamine blocking Nrf2/MAPK pathway to inhibit apoptosis of grass carp hepatocytes induced by DEHP. Gao, M; Lei, Y; Lin, H; Zhang, W, 2023)	2
"Evodiamine (Evo) is a natural, biologically active plant alkaloid with wide range of pharmacological activities. "	( Folate Functionalized and Evodiamine-Loaded Pluronic Nanomicelles for Augmented Cervical Cancer Cell Killing. Jadav, M; Jangid, AK; Kulhari, H; Patel, S; Solanki, R, 2023)	2.65
"Evodiamine (EVO) is an indole alkaloid with anti-inflammatory, antitumor, and antioxidant pharmacological activity."	( Evodiamine alleviates DEHP-induced hepatocyte pyroptosis, necroptosis and immunosuppression in grass carp through ROS-regulated TLR4 / MyD88 / NF-κB pathway. Gao, M; Lei, Y; Lin, H; Sun, W; Wang, X; Xu, T, 2023)	3.07
"Evodiamine (Evo) is a quinolone alkaloid extracted from the traditional herbal medicine plant Evodia rutaecarpa."	( BMP9 mediates the anticancer activity of evodiamine through HIF‑1α/p53 in human colon cancer cells. Cui, MZ; Deng, Y; He, BC; Hu, Y; Huang, J; Li, FS; Li, L; Li, PP; Shu, DZ; Zeng, JR, 2020)	1.55
"Evodiamine (EVO) is a natural compound derived from Tetradium ruticarpum (A.Juss.) T.G.Hartley used to treat pain and migraine in traditional Chinese medicine. "	( Evodiamine via targeting nNOS and AMPA receptor GluA1 inhibits nitroglycerin-induced migraine-like response. Chen, J; Li, C; Li, Z; Lin, J; Lu, H; Wu, Z; Yang, X; Zhang, X; Zhang, Y, 2020)	3.44
"Evodiamine (EVO) is an indoloquinazoline alkaloid that exerts its various anti-oncogenic actions by blocking phosphatidylinositol-3-kinase/protein kinase B (PI3K/Akt), mitogen-activated protein kinase (MAPK), c-Met, and nuclear factor kappa B (NF-κB) signaling pathways, thus leading to apoptosis of tumor cells. "	( Evodiamine Mitigates Cellular Growth and Promotes Apoptosis by Targeting the c-Met Pathway in Prostate Cancer Cells. Ahn, KS; Alharbi, SA; Blough, BE; Chinnathambi, A; Hwang, ST; Namjoshi, OA; Narula, AS; Um, JY, 2020)	3.44
"Evodiamine (EVO) is a wildly used multifunctional traditional Chinese medicine extract."	( Evodiamine inhibits high-fat diet-induced colitis-associated cancer in mice through regulating the gut microbiota. Chang, GL; Liu, G; Ye, B; Yu, DD; Yu, XM; Zhang, J; Zhang, L; Zhao, MS; Zhu, LQ, 2021)	2.79
"Evodiamine (EVO) is an active medicinal compound derived from the traditional herbal medicine Evodia rutaecarpa. "	( Evodiamine Prevents Glioma Growth, Induces Glioblastoma Cell Apoptosis and Cell Cycle Arrest through JNK Activation. Chen, YC; Chien, CC; Chiu, WT; Liu, KH; Wu, WS, 2017)	3.34
"Evodiamine is a botanical alkaloid compound extracted from Tetradium plants. "	( Evodiamine promotes differentiation and inhibits proliferation of C2C12 muscle cells. Li, Y; Peng, Y; Xi, F; Yang, G; Yao, X; Yu, T; Zhao, C, 2018)	3.37
"Evodiamine is a natural product extracted from herbal plants such as Tetradium which has shown to have anti-fat uptake and anti-proliferation properties. "	( Proteomic analysis of evodiamine-induced cytotoxicity in thyroid cancer cells. Chan, HL; Chou, HC; Chuang, HH; Lee, YR; Liao, EC; Lin, LH; Lu, CH; Su, YC; Tsai, YT; Wei, YS; Yang, YT; Yu, HI, 2018)	2.24
"Evodiamine is an alkaloid with attractive multitargeting antiproliferative activity."	( Antiproliferative Effects of Alkaloid Evodiamine and Its Derivatives. Chu, C; Hu, X; Hua, H; Jia, Y; Li, D; Li, X; Wang, X; Xu, F, 2018)	1.47
"Evodiamine (EVO) is a plant-derived indolequinazoline alkaloid with potential anticancer activity. "	( Preparation, characterization, and anticancer efficacy of evodiamine-loaded PLGA nanoparticles. Bao, J; Chen, F; Chen, M; He, C; Wang, L; Wang, S; Wang, Y; Zou, L, 2016)	2.12
"Evodiamine is an indole alkaloid found in the traditional Chinese medicinal plant Evodia rutaecarpa."	( Evodiamine activates AMPK and promotes adiponectin multimerization in 3T3-L1 adipocytes. Chen, ZF; Guo, WW; Li, Z; Liu, LH; Wu, GY; Xie, JY; Yi, JY; Zhang, L; Zhang, ZJ, 2014)	2.57
"Evodiamine is a major alkaloid compound extracted from the dry unripened fruit Evodia fructus (Evodia rutaecarpa Benth., Rutaceae), which has a variety of pharmacological activities. "	( Antidepressant-like effect of evodiamine on chronic unpredictable mild stress rats. Gong, GQ; Jiang, ML; Li, YZ; Wang, XH; Yan, W; Zhang, ZX, 2015)	2.15
"Evodiamine (Evo) is an quinolone alkaloid from the traditional herb medicine Evodia rutaecarpa."	( Antiproliferation effect of evodiamine in human colon cancer cells is associated with IGF-1/HIF-1α downregulation. Chen, QZ; Chen, ZH; He, BC; Huang, J; Li, Y; Ren, CM; Shao, Y; Sun, WJ; Wang, DX; Wu, K; Wu, QX; Yu, Y; Yuan, SX; Zeng, YH, 2015)	1.43
"Evodiamine is a chemical extracted from the Evodia rutaecarpa (Juss.) Benth, we showed that evodiamine could induce anti-proliferation and apoptosis in four wild-type EGFR NSCLC cell lines, and combining evodiamine with erlotinib might successfully inhibit cell proliferation and survival in wild-type EGFR NSCLC cells, characterized as erlotinib-resistant."	( Evodiamine induces apoptosis and enhances apoptotic effects of erlotinib in wild-type EGFR NSCLC cells via S6K1-mediated Mcl-1 inhibition. Dong, JY; Li, YL; Lin, NM; Mao, SY; Pan, JP; Pan, YN; Sun, J; Wu, WJ; Zhang, C; Zhang, DY; Zhao, YM, 2016)	2.6
"Evodiamine is an alkaloid with antitumor activity present in E. rutaecarpa and has potential to be developed into a therapeutic antitumor agent."	( Effect of evodiamine on the proliferation and apoptosis of A549 human lung cancer cells. Lin, L; Qi, J; Ren, L; Wang, Y; Wen, L, 2016)	1.56
"Evodiamine is an indole alkaloid extracted from the Chinese medicine, evodia, and has been shown to inhibit tumor cell proliferation and protect the cardiovascular system."	( Evodiamine inhibits PDGF‑BB‑induced proliferation of rat vascular smooth muscle cells through the suppression of cell cycle progression and oxidative stress. Chen, SY; Ge, X; Liang, TM; Liu, C; Liu, M, 2016)	2.6
"Evodiamine (EVO) is a major alkaloid compound extracted from the dry unripened fruit Evodiae fructus (Evodia rutaecarpa Benth., Rutaceae). "	( Evodiamine and Its Role in Chronic Diseases. Tan, Q; Zhang, J, 2016)	3.32
"Evodiamine is an alkaloid extracted from Euodia rutaecarpa (Juss.) Benth. "	( Anti-tumor effect of evodiamine by inducing Akt-mediated apoptosis in hepatocellular carcinoma. Ji, L; Liang, T; Shen, Y; Shi, L; Xu, L; Yang, F; Zhang, G; Zhu, F, 2017)	2.22
"Evodiamine is a chemical extracted from a kind of Chinese herb named Wu-Chu-Yu and has been demonstrated to be effective in preventing the growth of a variety of cancer cells."	( Anti-proliferative effects of evodiamine on human thyroid cancer cell line ARO. Chen, MC; Chi, CW; Ho, LL; Kan, SF; Lee, CH; Lin, LC; Pu, HF; Wang, PS; Wang, SW; Yu, CH, 2010)	1.37
"Evodiamine (Evo) is an indole quinazoline alkaloid isolated from the fruit of Evodia rutaecarpa Bentham. "	( Induction of apoptosis by evodiamine involves both activation of mitotic arrest and mitotic slippage. Bi, W; Du, BY; Li, JF; Liu, XD; Tan, YH; Wu, YY; Zhu, LH, 2011)	2.11
"Evodiamine is a quinazolinocarboline alkaloid isolated from the fruits of traditional Chinese herb Evodiae fructus . "	( New tricks for an old natural product: discovery of highly potent evodiamine derivatives as novel antitumor agents by systemic structure-activity relationship analysis and biological evaluations. Dong, G; Guo, Z; Miao, Z; Sheng, C; Wang, S; Yao, J; Zhang, W; Zhang, Y, 2012)	2.06
"Evodiamine is a previously described biological agent that possesses a cytotoxic activity in multiple cancer cells."	( Evodiamine activates autophagy as a cytoprotective response in murine Lewis lung carcinoma cells. Fan, X; Liang, HP; Tu, YJ; Yang, X; Zhang, C, 2013)	2.55
"Evodiamine is an alkaloidal compound with antiobesity effects that have been thought to be due to uncoupling protein-1 (UCP1) thermogenesis similar to the effects of capsaicin, but the underlying mechanisms are poorly understood. "	( Evodiamine improves diet-induced obesity in a uncoupling protein-1-independent manner: involvement of antiadipogenic mechanism and extracellularly regulated kinase/mitogen-activated protein kinase signaling. Kobayashi, Y; Kontani, Y; Mori, N; Sato, Y; Wang, T; Wang, Y; Yamashita, H, 2008)	3.23
"Evodiamine is a bioactive alkaloid extracted from a Chinese herb named Wu-Chu-Yu, which possesses thermoregulatory, analgesic, and cardiovascular effects. "	( Inhibitory effect of evodiamine on aldosterone release by Zona glomerulosa cells in male rats. Chen, CF; Hung, PH; Lin, LC; Wang, GJ; Wang, PS, 2001)	2.07

Effects

Evodiamine (EVO) has been demonstrated to promote apoptosis of ovarian cancer cells, and upregulate miR-152-3p level in colorectal cancer. The anti-inflammatory property of EVO has been proved in the treatment of infectious disease, Alzheimer's disea.

Excerpt	Reference	Relevance
"Evodiamine has a 6/5/6/6/6 ring system, and the structural modifications are focused on rings A, D, E, C5, N-13, and N-14. "	( The Synthesis, Structural Modification and Mode of Anticancer Action of Evodiamine: A Review. Fan, M; Yao, L, 2022)	2.4
"Evodiamine has a 6/5/6/6/6 ring system, and the structural modifications are focused on rings A, D, E, C5, N-13, and N-14. "	( The Synthesis, Structural Modification and Mode of Anticancer Action of Evodiamine: A Review. Fan, M; Yao, L, 2022)	2.4
"Evodiamine (EVO) has been demonstrated to promote apoptosis of ovarian cancer cells, and upregulate miR-152-3p level in colorectal cancer. "	( Evodiamine inhibits malignant progression of ovarian cancer cells by regulating lncRNA-NEAT1/miR-152-3p/CDK19 axis. Chai, J; Ding, H; Mao, M; Sheng, Y; Zheng, X, 2023)	3.8
"Evodiamine (EVD), which has been reported to cause liver damage, is the main constituent of Evodia rutaecarpa (Juss.) Benth and may be bioactivated into reactive metabolites mediated by cytochrome P450. "	( Elucidation of the relationship between evodiamine-induced liver injury and CYP3A4-mediated metabolic activation by UPLC-MS/MS analysis. Feng, X; Gao, Q; Li, N; Peng, T; Qiu, F; Rao, J; Song, Z; Wang, K; Wang, Y; Zhang, T, 2023)	2.62
"Evodiamine (EV) has anti-inflammatory functions in peripheral tissues."	( Evodiamine Inhibits Lipopolysaccharide (LPS)-Induced Inflammation in BV-2 Cells via Regulating AKT/Nrf2-HO-1/NF-κB Signaling Axis. Du, J; Fu, S; Gao, X; He, D; Hu, G; Huang, B; Liu, D; Meng, T; Su, Y; Zhang, Y; Zhou, A, 2021)	2.79
"Evodiamine (EVO) has been reported to play an important role in regulating gastrointestinal motility, but the evidence is insufficient, and the mechanism remains unknown. "	( Evodiamine inhibits gastrointestinal motility via CCK and CCK1 receptor in water-avoidence stress rat model. Luo, HS; Ren, HX; Tang, QC; Xia, H; Yan, L, 2018)	3.37
"Evodiamine has evolved a superior ability to bind various proteins, so we also argue that it is good starting point for multi-target drugs."	( Pharmacological actions of multi-target-directed evodiamine. Gong, W; Jin, H; Liang, H; Wang, Z; Yu, H, 2013)	1.37
"Evodiamine (Evo) has been proved to elicit a variety of biological effects through its anti-inflammatory property in the treatment of infectious disease, Alzheimer's disease and hypoxia-induced inflammatory response."	( Pretreatment by evodiamine is neuroprotective in cerebral ischemia: up-regulated pAkt, pGSK3β, down-regulated NF-κB expression, and ameliorated BBB permeability. Bai, X; Chen, L; Cui, L; Wang, L; Zhang, J; Zhang, L; Zhang, X; Zhao, T; Zhao, X; Zhao, Y, 2014)	1.47
"Evodiamine has been reported to exhibit anti-inflammatory and anti-nociceptive effects, but the underlying mechanisms remain to be defined. "	( Beneficial effects of evodiamine on P2X(4)-mediated inflammatory injury of human umbilical vein endothelial cells due to high glucose. Gao, Y; Guo, L; Li, G; Liang, S; Liu, S; Lv, Q; Wang, S; Xie, J; Xu, H; Xue, Y; Ying, M; Zhang, X; Zou, L, 2015)	2.17
"Evodiamine has anti-tumor effects on HCCs through inhibiting β-catenin, which interacts with and reduces VEGFa expression, thus inhibiting angiogenesis."	( Evodiamine exerts anti-tumor effects against hepatocellular carcinoma through inhibiting β-catenin-mediated angiogenesis. Liu, Q; Liu, Y; Luo, F; Shi, L; Yang, F; Zhang, F; Zou, M, 2016)	2.6
"Evodiamine has the potential to be a therapeutic medicine for HCCs."	( Anti-tumor effect of evodiamine by inducing Akt-mediated apoptosis in hepatocellular carcinoma. Ji, L; Liang, T; Shen, Y; Shi, L; Xu, L; Yang, F; Zhang, G; Zhu, F, 2017)	1.5
"Evodiamine (evo) has been shown to exert anti-inflammatory, antinociceptive and anticancer effects. "	( Inhibitory effect of evodiamine alone and in combination with rosiglitazone on in vitro adipocyte differentiation and in vivo obesity related to diabetes. Bak, EJ; Cha, JH; Kim, JM; Park, HG; Yoo, YJ, 2010)	2.12
"Evodiamine has therapeutic potential against cancers. "	( Enhanced antitumor efficacy of gemcitabine by evodiamine on pancreatic cancer via regulating PI3K/Akt pathway. Chen, H; Guo, HC; Lin, SZ; Liu, DL; Liu, HB; Ni, ZL; Tong, HF; Wang, ZH; Wei, WT, 2012)	2.08

Actions

Evodiamine can inhibit the growth of ovarian cancer cells by G2/M arrest and intrinsic and extrinsic apoptosis. It was found to inhibit HeLa cell growth in dose- and time-dependent manners.

Excerpt	Reference	Relevance
"Evodiamine was able to suppress BCC proliferation and induce apoptosis of the cells captured in G2/M phase, as previously reported."	( Evodiamine Eliminates Colon Cancer Stem Cells via Suppressing Notch and Wnt Signaling. Choi, S; Kim, H; Kim, WY; Lee, H; Lee, JH; Yu, J; Yu, Y, 2019)	2.68
"Evodiamine can inhibit the growth of ovarian cancer cells by G2/M arrest and intrinsic and extrinsic apoptosis. "	( [Evodiamine induces extrinsic and intrinsic apoptosis of ovarian cancer cells via the mitogen-activated protein kinase/phosphatidylinositol-3-kinase/protein kinase B signaling pathways]. Cao, Z; Jin, X; Li, W; Wei, L, 2016)	2.79
"Evodiamine was found to inhibit HeLa cell growth in dose- and time-dependent manners. "	( [Studies on evodiamine induced HeLa cell apoptosis]. Fei, XF; Ikejima, T; Wang, BX, 2002)	2.14

Treatment

Pretreatment with evodiamine (30 or 60 microg/kg, i.v.) markedly increased the content of CGRP in plasma concomitantly with a significant reduction in infarct size. The effects of evodsamine were completely abolished by capsazepine (5.0 mg/kg), a competitive vanilloid receptor antago.

Excerpt	Reference	Relevance
"Evodiamine treatment reduced IgE and IFN-γ levels as well as the inflammatory cell infiltrate in the lung tissue of asthmatic rats."	( Evodiamine protects against airway remodelling and inflammation in asthmatic rats by modulating the HMGB1/NF-κB/TLR-4 signalling pathway. Cui, Y; Wang, J; Wang, Q; Wu, X, 2021)	2.79
"Evodiamine treatment of cells decreased cell viability, and Bcl2 and phospho-AKT protein levels. "	( Evodiamine Suppresses Survival, Proliferation, Migration and Epithelial-Mesenchymal Transition of Thyroid Carcinoma Cells. Choi, MG; Ihm, SH; Kang, JG; Kim, CS; Kim, SH; Lee, SJ, 2018)	3.37
"Evodiamine treatments also ameliorated the corticosterone hypersecretion induced by CUMS."	( Antidepressant-like effect of evodiamine on chronic unpredictable mild stress rats. Gong, GQ; Jiang, ML; Li, YZ; Wang, XH; Yan, W; Zhang, ZX, 2015)	1.43
"Evodiamine treatment also reduced insulin-stimulated phosphorylation of Akt, a crucial regulator of adipocyte differentiation; and the reduction of phosphorylated-Akt and augmentation of phosphorylated ERK were reversed by blockade of the MAPK kinase/MAPK signaling pathway, restoring adipogenesis in the cultures."	( Evodiamine improves diet-induced obesity in a uncoupling protein-1-independent manner: involvement of antiadipogenic mechanism and extracellularly regulated kinase/mitogen-activated protein kinase signaling. Kobayashi, Y; Kontani, Y; Mori, N; Sato, Y; Wang, T; Wang, Y; Yamashita, H, 2008)	2.51
"(2) Evodiamine pretreatment had a greater inhibitory effect on the phenylephrine-induced tonic contraction (via Ca2+ influx) than on the phasic contraction (via Ca2+ release)."	( The vasorelaxant effect of evodiamine in rat isolated mesenteric arteries: mode of action. Chen, CF; Chiou, WF; Chou, CJ; Shum, AY, 1992)	1.06
"Pretreatment with evodiamine reduced capsaicin-induced currents significantly."	( Evodiamine suppresses capsaicin-induced thermal hyperalgesia through activation and subsequent desensitization of the transient receptor potential V1 channels. Aoki, S; Dai, Y; Iwaoka, E; Kogure, Y; Matsuyoshi, N; Noguchi, K; Wang, S; Yamamoto, S, 2016)	2.2
"Pretreatment with evodiamine (30 or 60 microg/kg, i.v.) markedly increased the content of CGRP in plasma concomitantly with a significant reduction in infarct size, the activity of serum creatine kinase, and TNF-alpha level, and the effects of evodiamine were completely abolished by capsazepine (5.0 mg/kg, s.c.), a competitive vanilloid receptor antagonist."	( Protective effects of evodiamine on myocardial ischemia-reperfusion injury in rats. Deng, HW; Du, YH; Hu, CP; Li, YJ; Peng, J; Rang, WQ; Xu, KP; Ye, F, 2004)	0.96

Toxicity

Excerpt	Reference	Relevance
" EF is a toxic drug and causes hepatotoxicity in humans."	( Toxicity of Evodiae fructus on rat liver mitochondria: the role of oxidative stress and mitochondrial permeability transition. Cai, Q; Li, W; Shi, S; Wang, Q; Wei, J; Wei, R; Zhang, Y; Zhao, W, 2014)	0.4
" Meanwhile, more efforts should be made to develop novel efficient and low toxic derivatives."	( Evodiamine: A review of its pharmacology, toxicity, pharmacokinetics and preparation researches. Li, X; Song, J; Sun, Q; Xie, L, 2020)	2
" In addition, unresolved issues include toxic mechanisms, pharmacokinetics, novel pharmaceutical researches and relationship between residues and intestinal environment, which are still being explored and excavate before achieving integration into clinical practice."	( Evodiamine: A review of its pharmacology, toxicity, pharmacokinetics and preparation researches. Li, X; Song, J; Sun, Q; Xie, L, 2020)	2

Pharmacokinetics

Plasma concentrations of evodiamine were determined by high-performance liquid chromatography (HPLC), and the pharmacokinetic parameters were calculated using DAS 2. The method described in this report has high sensitivity and selectivity.

Excerpt	Reference	Relevance
" The method was applied to a pharmacokinetic study of evodiamine in rats after 2 mg/kg intravenous administration."	( High-performance liquid chromatographic determination of evodiamine in rat plasma: application to pharmacokinetic studies. Chen, CF; Chou, CJ; Jeng, KF; Lin, LC; Lin, YH; Tsai, TH, 1995)	0.78
"To establish a SPE-HPLC method for the determination and pharmacokinetic study of evodiamine and rutacarpine in rat plasma."	( [Determination of evodiamine and rutaecarpine of compound Wuzhuyu cataplasm in plasma by SPE-HPLC: application to its pharmacokinetics]. Kang, C; Li, M; Liu, S; Tong, H; Wang, Y; Yin, W; Zhou, Z, 2009)	0.91
"After transdermal administration to rats, the pharmacokinetic behavior of evodiamine and rutaecarpine belongs to the one-compartment model."	( [Determination of evodiamine and rutaecarpine of compound Wuzhuyu cataplasm in plasma by SPE-HPLC: application to its pharmacokinetics]. Kang, C; Li, M; Liu, S; Tong, H; Wang, Y; Yin, W; Zhou, Z, 2009)	0.92
" It is proved to be suitable for pharmacokinetic study of evodiamine and rutaecarpine."	( [Determination of evodiamine and rutaecarpine of compound Wuzhuyu cataplasm in plasma by SPE-HPLC: application to its pharmacokinetics]. Kang, C; Li, M; Liu, S; Tong, H; Wang, Y; Yin, W; Zhou, Z, 2009)	0.93
"5, 3 and 4h) after administration, the concentrations of Rut and Evo in rat whole blood were determined by HPLC, and main pharmacokinetic parameters were calculated."	( Pharmacokinetic comparisons of rutaecarpine and evodiamine after oral administration of Wu-Chu-Yu extracts with different purities to rats. Chen, F; Ding, J; He, L; Li, Y; Peng, J; Xu, S; Zhang, J, 2012)	0.63
" Furthermore, the newly developed method is successfully used for the determination of evodiamine and rutecarpine in rabbit plasma for pharmacokinetic study."	( Simultaneous determination of evodiamine and rutecarpine in rabbit plasma by LC-ESI-MS and its application to pharmacokinetics. Cai, J; Li, W; Lin, C; Lin, G; Ma, J; Pan, J; Pan, X; Wang, X, 2011)	0.88
"The method described in this report has high sensitivity and selectivity, and was suitable for pharmacokinetic studies of evodiamine and rutaecarpine."	( [Studies on pharmacokinetics of evodiamine and rutaecarpine in rats plasma after oral administration extracts of euodiae fructus]. Bao, T; Dong, Y; Li, Y; Weng, X; Yang, Q; Zhang, Y; Zhu, X, 2011)	0.86
"A simple and sensitive high-performance liquid chromatographic method was developed for the simultaneous determination and pharmacokinetic analysis of seven alkaloids dehydroevodiamine (DHED), 10-hydroxyrutaecarpine (HDR), evodiamine (EDM), rutaecarpine (RCP), 1-methyl-2-n-nonyl-4(1H)quinolone (MNQ), evocarpine (ECP), and dihydroevocarpine (DHE), and two flavonoids isorhamnetin-7-O-rutinoside (RIM) and diosmetin-7-O-β-d-glucopyranoside (GRD) in rat plasma after oral administration of Wuzhuyu decoction."	( Simultaneous determination and pharmacokinetic analysis of seven alkaloids and two flavonoids from rat plasma by HPLC-DAD after oral administration of Wuzhuyu decoction. Hu, CQ; Li, F; Yang, XW, 2012)	0.57
"To compare the pharmacokinetic parameters of evodiamine hydroxypropyl-β-cyclodextrin inclusion complex and free evodiamine suspension in rats, and investigate the pharmacokinetic characteristics of evodiamine inclusion complex."	( [A preliminary study of pharmacokinetics of evodiamine hydroxypropyl-β-cyclodextrin inclusion complex]. Feng, J; Lei, TT; Liu, HM; Zhang, JQ; Zhang, X, 2016)	0.96
" The pharmacokinetic parameters of evodiamine inclusion complex and free evodiamine in rats were as follows: Cmax, 252."	( [A preliminary study of pharmacokinetics of evodiamine hydroxypropyl-β-cyclodextrin inclusion complex]. Feng, J; Lei, TT; Liu, HM; Zhang, JQ; Zhang, X, 2016)	0.97
" The pharmacokinetic and pharmacodynamics-based collaborations of evodiamine are also included."	( Evodiamine as an anticancer agent: a comprehensive review on its therapeutic application, pharmacokinetic, toxicity, and metabolism in various cancers. Biswal, BK; Panda, M; Tripathi, SK; Zengin, G, 2023)	2.59

Compound-Compound Interactions

The impact of evodiamine in combination with histone deacetylase (HDAC) inhibitors on survival of thyroid carcinoma cells was identified. repression of PI3K/Akt signaling synergistically reinforces cytotoxicity.

Excerpt	Reference	Relevance
" In this study, we investigated the effects of evo alone and in combination with rosiglitazone (rosi) on in vitro adipocyte differentiation and in vivo obesity related to diabetes."	( Inhibitory effect of evodiamine alone and in combination with rosiglitazone on in vitro adipocyte differentiation and in vivo obesity related to diabetes. Bak, EJ; Cha, JH; Kim, JM; Park, HG; Yoo, YJ, 2010)	0.68
"The presence of evo or evo combined with rosi during adipogenic induction has been shown to inhibit adipocyte differentiation to a significant degree, particularly at the commitment and early induction stages."	( Inhibitory effect of evodiamine alone and in combination with rosiglitazone on in vitro adipocyte differentiation and in vivo obesity related to diabetes. Bak, EJ; Cha, JH; Kim, JM; Park, HG; Yoo, YJ, 2010)	0.68
" Cell cycle and cell apoptosis were assessed by flow cytometry (FCM) combined with PI staining and annexin V-FITC/PI, respectively."	( [Inhibitory effect of norcantharidin combined with evodiamine on the growth of human hepatic carcinoma cell line HepG2 in vitro]. Liao, H; Liu, Y; You, Z; Zahng, J, 2014)	0.65
"EVO combined with NCTD showed synergetic effect on anti-proliferation and pro-apoptosis in HepG2 cells."	( [Inhibitory effect of norcantharidin combined with evodiamine on the growth of human hepatic carcinoma cell line HepG2 in vitro]. Liao, H; Liu, Y; You, Z; Zahng, J, 2014)	0.65
"The impact of evodiamine in combination with histone deacetylase (HDAC) inhibitors on survival of thyroid carcinoma cells was identified."	( Evodiamine in combination with histone deacetylase inhibitors has synergistic cytotoxicity in thyroid carcinoma cells. Choi, MG; Ihm, SH; Kang, JG; Kim, CS; Kim, SH; Lee, SJ, 2019)	2.32
" Moreover, repression of PI3K/Akt signaling synergistically reinforces cytotoxicity of evodiamine combined with HDAC inhibitors in thyroid carcinoma cells."	( Evodiamine in combination with histone deacetylase inhibitors has synergistic cytotoxicity in thyroid carcinoma cells. Choi, MG; Ihm, SH; Kang, JG; Kim, CS; Kim, SH; Lee, SJ, 2019)	2.18

Bioavailability

The relative bioavailability of evodiamine-phospholipid complex was 256. NEEPN with its favorable in vivo kinetic characteristics clearly enhanced the gastrointestinal absorption and oral bio availability of EDA.

Excerpt	Reference	Relevance
"The bioavailability of Rut and Evo was increased along with the increasing of purity (16%-80%) in Wu-Chu-Yu extracts."	( Pharmacokinetic comparisons of rutaecarpine and evodiamine after oral administration of Wu-Chu-Yu extracts with different purities to rats. Chen, F; Ding, J; He, L; Li, Y; Peng, J; Xu, S; Zhang, J, 2012)	0.63
" However, low bioavailability caused by its poor water solubility limits it anticancer efficacy in clinic."	( Preparation, characterization, and anticancer efficacy of evodiamine-loaded PLGA nanoparticles. Bao, J; Chen, F; Chen, M; He, C; Wang, L; Wang, S; Wang, Y; Zou, L, 2016)	0.68
" The possible explanations for improved absorption and bioavailability were put forward here."	( Supermolecular evodiamine loaded water-in-oil nanoemulsions: enhanced physicochemical and biological characteristics. Fang, C; Hu, J; Sun, L; Tan, Q; Wang, H; Ye, M; Zhang, J; Zhang, L; Zhao, D, 2014)	0.76
"Compared with EDA or conventional nanoemulsions containing EDA instead of evodiamine-phospholipid complex, NEEPN with its favorable in vivo kinetic characteristics clearly enhanced the gastrointestinal absorption and oral bioavailability of EDA; for example, the relative bioavailability of NEEPN to free EDA was calculated to be 630."	( Improved absorption and in vivo kinetic characteristics of nanoemulsions containing evodiamine-phospholipid nanocomplex. Chen, D; Hu, J; Jiang, R; Tan, Q; Zhang, J; Zhu, B, 2014)	0.86
"NEEPN markedly improved the oral bioavailability of EDA, which was probably due to its increased gastrointestinal absorption."	( Improved absorption and in vivo kinetic characteristics of nanoemulsions containing evodiamine-phospholipid nanocomplex. Chen, D; Hu, J; Jiang, R; Tan, Q; Zhang, J; Zhu, B, 2014)	0.63
" The relative bioavailability of evodiamine inclusion complex was 256."	( [A preliminary study of pharmacokinetics of evodiamine hydroxypropyl-β-cyclodextrin inclusion complex]. Feng, J; Lei, TT; Liu, HM; Zhang, JQ; Zhang, X, 2016)	0.98
" These ingredients are expected to have much better absorption and higher bioavailability than synthetic antitumor agents."	( Improved delivery of natural alkaloids into lung cancer through woody oil-based emulsive nanosystems. Hu, X; Li, Y; Liu, S; Yan, S; Yang, L; Zeng, M; Zhang, J; Zhang, Y; Zhao, H; Zhao, J, 2018)	0.48
" Previous findings demonstrate that evodiamine (Evo), an indolequinone alkaloid, is effective in combating CRC; however, its poor aqueous solubility and low oral bioavailability limit its application in the prevention of invasion and metastasis of CRC."	( Development of EGFR-targeted evodiamine nanoparticles for the treatment of colorectal cancer. Cai, G; Cai, J; Gao, R; Ji, Q; Li, C; Li, Q; Song, D; Sui, H; Teng, P; Wang, Y; Zhou, L, 2019)	1.08
"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
" In vivo experimental results indicated that compared to intragastric administration of drug solution, the intranasal administration of hydrogel increased bioavailability of BBR and EVO, approximately 135 and 112 folds, respectively."	( Intranasal co-delivery of berberine and evodiamine by self-assembled thermosensitive in-situ hydrogels for improving depressive disorder. Cui, YL; Qiao, T; Qiu, C; Wang, Y; Xu, D, 2021)	0.89
" Due to its poor bioavailability, synthetic analogs of evodiamine and its nano capsule have been formulated to enhance its bioavailability and reduce toxicity."	( Evodiamine as an anticancer agent: a comprehensive review on its therapeutic application, pharmacokinetic, toxicity, and metabolism in various cancers. Biswal, BK; Panda, M; Tripathi, SK; Zengin, G, 2023)	2.6

Dosage Studied

Excerpt	Relevance	Reference
" Dose-response relationships for evodiamine, rutaecarpine and capsaicin were obtained."	( The positive inotropic and chronotropic effects of evodiamine and rutaecarpine, indoloquinazoline alkaloids isolated from the fruits of Evodia rutaecarpa, on the guinea-pig isolated right atria: possible involvement of vanilloid receptors. Hoshikuma, K; Kamiya, T; Kobayashi, Y; Nakano, Y; Yokoo, Y, 2001)	0.84
" In comparison to capsaicin, coadministration of 1 and capsaicin increased the half-maximal effective concentration (EC50) of capsaicin-activated TRPV1 currents as shown by a right shift in the dose-response curve, whereas coadministration of 1 with protons failed to inhibit the proton-induced current."	( Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa. Dai, Y; Kogure, Y; Noguchi, K; Wang, S; Yamamoto, S; Zhang, W, 2016)	0.68

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Class	Description
beta-carbolines	Any pyridoindole containing a beta-carboline skeleton and their hydrogenated derivatives
[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)
PPM1D protein	Homo sapiens (human)	Potency	10.4353	0.0052	9.4661	32.9993	AID1347411
Smad3	Homo sapiens (human)	Potency	22.3872	0.0052	7.8098	29.0929	AID588855
EWS/FLI fusion protein	Homo sapiens (human)	Potency	25.1747	0.0013	10.1577	42.8575	AID1259252; AID1259253; AID1259256
Interferon beta	Homo sapiens (human)	Potency	10.4353	0.0033	9.1582	39.8107	AID1347411
[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 V member 1	Rattus norvegicus (Norway rat)	IC50 (µMol)	0.4400	0.0004	0.2147	4.0000	AID1317282
Acetylcholinesterase	Electrophorus electricus (electric eel)	IC50 (µMol)	10.0000	0.0000	0.9453	9.9400	AID1143297
cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)	IC50 (µMol)	2.1000	0.0000	1.1843	9.6140	AID1723558
Cholinesterase	Equus caballus (horse)	IC50 (µMol)	4.6200	0.0000	2.2214	9.4000	AID1143296
[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 V member 1	Rattus norvegicus (Norway rat)	EC50 (µMol)	0.7417	0.0005	0.4318	2.3800	AID1317246; AID1317248; AID1317252; AID1317253; AID1317254; AID1317255
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
positive regulation of cardiac muscle hypertrophy	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
regulation of nitric oxide mediated signal transduction	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
T cell proliferation	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
negative regulation of T cell proliferation	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
cGMP catabolic process	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
oocyte development	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
negative regulation of cardiac muscle contraction	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
relaxation of cardiac muscle	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
positive regulation of oocyte development	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
cAMP-mediated signaling	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
cell surface receptor signaling pathway via JAK-STAT	Interferon beta	Homo sapiens (human)
response to exogenous dsRNA	Interferon beta	Homo sapiens (human)
B cell activation involved in immune response	Interferon beta	Homo sapiens (human)
cell surface receptor signaling pathway	Interferon beta	Homo sapiens (human)
cell surface receptor signaling pathway via JAK-STAT	Interferon beta	Homo sapiens (human)
response to virus	Interferon beta	Homo sapiens (human)
positive regulation of autophagy	Interferon beta	Homo sapiens (human)
cytokine-mediated signaling pathway	Interferon beta	Homo sapiens (human)
natural killer cell activation	Interferon beta	Homo sapiens (human)
positive regulation of peptidyl-serine phosphorylation of STAT protein	Interferon beta	Homo sapiens (human)
cellular response to interferon-beta	Interferon beta	Homo sapiens (human)
B cell proliferation	Interferon beta	Homo sapiens (human)
negative regulation of viral genome replication	Interferon beta	Homo sapiens (human)
innate immune response	Interferon beta	Homo sapiens (human)
positive regulation of innate immune response	Interferon beta	Homo sapiens (human)
regulation of MHC class I biosynthetic process	Interferon beta	Homo sapiens (human)
negative regulation of T cell differentiation	Interferon beta	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Interferon beta	Homo sapiens (human)
defense response to virus	Interferon beta	Homo sapiens (human)
type I interferon-mediated signaling pathway	Interferon beta	Homo sapiens (human)
neuron cellular homeostasis	Interferon beta	Homo sapiens (human)
cellular response to exogenous dsRNA	Interferon beta	Homo sapiens (human)
cellular response to virus	Interferon beta	Homo sapiens (human)
negative regulation of Lewy body formation	Interferon beta	Homo sapiens (human)
negative regulation of T-helper 2 cell cytokine production	Interferon beta	Homo sapiens (human)
positive regulation of apoptotic signaling pathway	Interferon beta	Homo sapiens (human)
response to exogenous dsRNA	Interferon beta	Homo sapiens (human)
B cell differentiation	Interferon beta	Homo sapiens (human)
natural killer cell activation involved in immune response	Interferon beta	Homo sapiens (human)
adaptive immune response	Interferon beta	Homo sapiens (human)
T cell activation involved in immune response	Interferon beta	Homo sapiens (human)
humoral immune response	Interferon beta	Homo sapiens (human)
phototransduction, visible light	Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'	Homo sapiens (human)
retinal cone cell development	Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'	Homo sapiens (human)
cAMP-mediated signaling	Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'	Homo sapiens (human)
visual perception	Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
3',5'-cyclic-nucleotide phosphodiesterase activity	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
protein binding	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
cGMP binding	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
metal ion binding	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activity	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activity	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
cytokine activity	Interferon beta	Homo sapiens (human)
cytokine receptor binding	Interferon beta	Homo sapiens (human)
type I interferon receptor binding	Interferon beta	Homo sapiens (human)
protein binding	Interferon beta	Homo sapiens (human)
chloramphenicol O-acetyltransferase activity	Interferon beta	Homo sapiens (human)
cGMP binding	Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'	Homo sapiens (human)
metal ion binding	Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'	Homo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activity	Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'	Homo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activity	Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
cellular_component	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
cytosol	cGMP-specific 3',5'-cyclic phosphodiesterase	Homo sapiens (human)
extracellular space	Interferon beta	Homo sapiens (human)
extracellular region	Interferon beta	Homo sapiens (human)
plasma membrane	Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (153)

Assay ID	Title	Year	Journal	Article
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.
AID1347159	Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
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.
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.
AID1347160	Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347411	qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Mechanism Interrogation Plate v5.0 (MIPE) Libary	2020	ACS chemical biology, 07-17, Volume: 15, Issue:7	High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1911720	Induction of apoptosis in human Huh-7 cells assessed as cell shrinkage at 60 nM incubated for 24 hrs by Giemsa staining based microscopy
AID1911752	Induction of apoptosis in human SK-Hep1 cells assessed as late apoptotic cells at 80 nM incubated for 24 hrs by annexin V-FITC/PI staining flow cytometry (Rvb = 1.13 %)
AID1465329	Antiproliferative activity against human PC3 cells treated for 24 hrs measured after 72 hrs by MTT assay	2017	Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22	Design and synthesis of novel nitrogen mustard-evodiamine hybrids with selective antiproliferative activity.
AID1317285	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin current density at 0.1 uM pretreated for 180 sec followed by capsaicin addition at -60 mV holding potential in presence of extracellular calcium by whole-ce	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911739	Induction of apoptosis in human Huh-7 cells assessed as early apoptotic cells at 80 nM incubated for 24 hrs by annexin V-FITC/PI staining flow cytometry (Rvb = 0.33 %)
AID1317273	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 1 uM by whole-cell patch clamp method (Rvb = -151.2 +/- 33 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911765	Antiproliferative activity against TGF-beta-1-stimulated rat HSC-T6 cells assessed as suppression of cell proliferation at 0.70 to 60 uM preincubated with TGFbeta-1 for 1 day followed by compound addition and measured after 48 hrs
AID1911681	Antiproliferative activity against human SK-HEP1 cells treated for 72 hrs by MTT assay
AID1143300	Inhibition of equine serum BChE at 10 uM by Ellman's method	2014	European journal of medicinal chemistry, Jun-23, Volume: 81	Identification of a neuroprotective and selective butyrylcholinesterase inhibitor derived from the natural alkaloid evodiamine.
AID1911793	Toxicity in BALB/c mouse xenografted with human Huh-7 cells assessed as reduction in WBC levels at 10 mg/kg, ip qd for 11 days and measured on day 11
AID1317264	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 0.6 uM by whole-cell patch clamp method (Rvb = -431 +/- 43.1 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1723559	Inhibition of human PDE6C (2-854 residues) expressed in Sf9 cells incubated for 15 mins using [3H]-cGMP as substrate by liquid scintillation counting method
AID1317249	Desensitization of rat TRPV1 expressed in HEK293 cells at 10 uM for 30 sec at -60 mV holding potential in presence of extracellular calcium by whole-cell patch clamp method	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911753	Induction of apoptosis in human SK-Hep1 cells assessed as necrotic cells at 80 nM incubated for 24 hrs by annexin V-FITC/PI staining flow cytometry (Rvb = 0.73 %)
AID1317277	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 10 uM by whole-cell patch clamp method (Rvb = -480.7 +/- 96.9 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1808033	Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition rate at 10 uM incubated for 72 hrs by MTT assay	2021	Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23	Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer.
AID1808038	Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition rate incubated for 72 hrs by MTT assay	2021	Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23	Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer.
AID1911721	Induction of apoptosis in human Huh-7 cells assessed as chromatin agglutination at 60 nM incubated for 24 hrs by Giemsa staining based microscopy
AID1317248	Agonist activity at rat TRPV1 expressed in CHO cells assessed as induction of 45Ca2+ uptake measured after 5 mins by scintillation counting method	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317262	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 0.6 uM by whole-cell patch clamp method (Rvb = -497 +/- 89.6 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317261	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 0.1 uM by whole-cell patch clamp method (Rvb = -7 +/- 2.6 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911699	Induction of cell cycle arrest in human Huh-7 cells assessed as accumulation at G1 phase at 80 nM treated for 24 hrs by PI staining based flow cytometry (Rvb = 60.77 %)
AID1808032	Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition rate at 100 uM incubated for 72 hrs by MTT assay	2021	Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23	Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer.
AID1911685	Inhibition of Top1 (unknown origin) assessed as inhibition of relaxation of supercoiled pBR322 plasmid DNA at 12.5 uM incubated for 25 mins by ethidium bromide staining based agarose gel electrophoresis analysis relative to control
AID1911729	Induction of apoptosis in human SK-Hep1 cells assessed as cytoskeleton disintegration at 60 nM incubated for 24 hrs by Giemsa staining based microscopy
AID1723558	Inhibition of human PDE5A1 (535-860 residues) expressed in Escherichia coli BL21 incubated for 15 mins using [3H]-cGMP as substrate by liquid scintillation counting method
AID1808082	Antiproliferative activity against HEK293 cells assessed as inhibition rate incubated for 72 hrs by MTT assay	2021	Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23	Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer.
AID1911700	Induction of cell cycle arrest in human Huh-7 cells assessed as accumulation at G2 phase at 80 nM treated for 24 hrs by PI staining based flow cytometry (Rvb = 15.90 %)
AID1143301	Inhibition of electric eel AChE at 10 uM by Ellman's method	2014	European journal of medicinal chemistry, Jun-23, Volume: 81	Identification of a neuroprotective and selective butyrylcholinesterase inhibitor derived from the natural alkaloid evodiamine.
AID1317278	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 10 uM by whole-cell patch clamp method (Rvb = -431 +/- 43.1 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317276	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 10 uM by whole-cell patch clamp method (Rvb = -497 +/- 89.6 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317266	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 0.6 uM by whole-cell patch clamp method (Rvb = -151.2 +/- 33 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911773	Induction of apoptosis in rat HSC-T6 cells assessed as viable cells at 80 nM pretreated with TGFbeta-1 for 1 day followed by compound addition and measured after 24 hrs by flow cytometry (Rvb = 97.5 %)
AID1317279	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 10 uM by whole-cell patch clamp method (Rvb = -327.4 +/- 52.3 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317275	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 10 uM by whole-cell patch clamp method	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911698	Induction of cell cycle arrest in human SK-Hep1 cells assessed as accumulation at S phase at 80 nM treated for 24 hrs by PI staining based flow cytometry (Rvb = 24.98 %)
AID1317234	Induction of channel current in human HEK293 cells at 10 uM at -60 mV holding potential by voltage-clamp method	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911741	Induction of apoptosis in human Huh-7 cells assessed as necrotic cells at 80 nM incubated for 24 hrs by annexin V-FITC/PI staining flow cytometry (Rvb = 1.08 %)
AID1317245	Agonist activity at rat TRPV1 channel expressed in HEK293 cells assessed as induction of channel current at -60 mV holding potential in presence of capsazepine by whole-cell patch-clamp method	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911701	Induction of cell cycle arrest in human Huh-7 cells assessed as accumulation at S phase at 80 nM treated for 24 hrs by PI staining based flow cytometry (Rvb = 23.33 %)
AID1808083	Antiproliferative activity against human MCF-10A cells assessed as inhibition rate incubated for 72 hrs by MTT assay	2021	Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23	Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer.
AID1303758	Antiproliferative activity against human Bel7402 cells after 72 hrs by MTT assay	2016	Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13	Antiproliferative activity and apoptosis inducing effects of nitric oxide donating derivatives of evodiamine.
AID1357857	Antiproliferative activity against human SGC7901 cells after 72 hrs by MTT assay
AID1808035	Antiproliferative activity against human MDA-MB-435 cells assessed as inhibition rate incubated for 72 hrs by MTT assay	2021	Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23	Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer.
AID1317282	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as inhibition of capsaicin-induced inward current at -60 mV holding potential pretreated for 180 secs prior to capsaicin addition in presence of extracellular calcium by whole-cel	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911686	Inhibition of human Top2-alpha expressed in baculovirus assessed as inhibition of relaxation of supercoiled pBR322 plasmid DNA at 100 uM incubated for 30 mins in presence of ATP by ethidium bromide staining based agarose gel electrophoresis analysis relat
AID1317295	Desensitization of rat TRPV1 expressed in HEK293 cells at 10 uM for 20 sec at -60 mV holding potential in absence of extracellular calcium by whole-cell patch clamp method	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317267	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 0.6 uM by whole-cell patch clamp method (Rvb = -7 +/- 2.6 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317265	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 0.6 uM by whole-cell patch clamp method (Rvb = -327.4 +/- 52.3 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1357859	Antiproliferative activity against human HL60 cells after 72 hrs by MTT assay
AID1317240	Agonist activity at rat TRPV1 channel expressed in HEK293 cells assessed as outward rectifying current at 10 uM and -60 mV holding potential by whole-cell patch-clamp method	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1808034	Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition rate at 1 uM incubated for 72 hrs by MTT assay	2021	Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23	Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer.
AID1357860	Antiproliferative activity against human PBMC cells after 72 hrs by MTT assay
AID1317242	Agonist activity at rat TRPV1 channel expressed in HEK293 cells assessed as reversal potential at 10 uM and -60 mV holding potential by whole-cell patch-clamp method	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1465330	Antiproliferative activity against human HepG2 cells treated for 24 hrs measured after 72 hrs by MTT assay	2017	Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22	Design and synthesis of novel nitrogen mustard-evodiamine hybrids with selective antiproliferative activity.
AID1317252	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as capsaicin EC50 for induction of channel current at 0.1 uM at -60 mV holding potential by whole-cell patch clamp method (Rvb = 0.06 uM)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317286	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin current density at 0.5 uM pretreated for 180 sec followed by capsaicin addition at -60 mV holding potential in presence of extracellular calcium by whole-ce	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317236	Agonist activity at human TRPA1 channel expressed in HEK293 cells assessed as induction of channel current at 10 uM and -60 mV holding potential by voltage-clamp method	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317269	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 1 uM by whole-cell patch clamp method (Rvb = -497 +/- 89.6 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317283	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as desensitization of capsaicin-induced inward current at 10 uM and -60 mV holding potential pretreated for 60 secs prior to capsaicin-challenge in absence of calcium by whole-cel	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317259	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 0.1 uM by whole-cell patch clamp method (Rvb = -327.4 +/- 52.3 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1357858	Antiproliferative activity against human Caco2 cells after 72 hrs by MTT assay
AID1911680	Antiproliferative activity against human Huh-7 cells treated for 72 hrs by MTT assay
AID1911727	Induction of apoptosis in human SK-Hep1 cells assessed as cell shrinkage at 60 nM incubated for 24 hrs by Giemsa staining based microscopy
AID1808084	Selectivity index, ratio of IC50 for human MCF-10A cells to IC50 for human MDA-MB-231 cells	2021	Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23	Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer.
AID1317280	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 10 uM by whole-cell patch clamp method (Rvb = -151.2 +/- 33 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317253	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as capsaicin EC50 for induction of channel current at 0.6 uM at -60 mV holding potential by whole-cell patch clamp method (Rvb = 0.06 uM)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911684	Inhibition of Top1 (unknown origin) assessed as inhibition of relaxation of supercoiled pBR322 plasmid DNA at 50 uM incubated for 25 mins by ethidium bromide staining based agarose gel electrophoresis analysis relative to control
AID1317239	Agonist activity at rat TRPV1 channel expressed in HEK293 cells assessed as induction of inward current at 10 uM and -60 mV holding potential by whole-cell patch-clamp method	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1808036	Antiproliferative activity against human HCT-116 cells assessed as inhibition rate incubated for 72 hrs by MTT assay	2021	Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23	Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer.
AID1317270	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 1 uM by whole-cell patch clamp method (Rvb = -480.7 +/- 96.9 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317287	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin current density at 1 uM pretreated for 180 sec followed by capsaicin addition at -60 mV holding potential in presence of extracellular calcium by whole-cell	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317271	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 1 uM by whole-cell patch clamp method (Rvb = -431 +/- 43.1 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317263	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 0.6 uM by whole-cell patch clamp method (Rvb = -480.7 +/- 96.9 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911750	Induction of apoptosis in human SK-Hep1 cells assessed as viable cells at 80 nM incubated for 24 hrs by annexin V-FITC/PI staining flow cytometry (Rvb = 97.8 %)
AID1317255	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as capsaicin EC50 for induction of channel current at 10 uM at -60 mV holding potential by whole-cell patch clamp method (Rvb = 0.06 uM)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911679	Antiproliferative activity against human HepG2 cells treated for 72 hrs by MTT assay
AID1911774	Induction of apoptosis in rat HSC-T6 cells assessed as early apoptotic cells at 80 nM pretreated with TGFbeta-1 for 1 day followed by compound addition and measured after 24 hrs by flow cytometry (Rvb = 0.17 %)
AID1317274	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 1 uM by whole-cell patch clamp method (Rvb = -7 +/- 2.6 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317272	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 1 uM by whole-cell patch clamp method (Rvb = -327.4 +/- 52.3 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1143297	Inhibition of electric eel AChE by Ellman's method	2014	European journal of medicinal chemistry, Jun-23, Volume: 81	Identification of a neuroprotective and selective butyrylcholinesterase inhibitor derived from the natural alkaloid evodiamine.
AID1317260	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 0.1 uM by whole-cell patch clamp method (Rvb = -151.2 +/- 33 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911682	Antiproliferative activity against human HCCLM9 cells treated for 72 hrs by MTT assay
AID1911722	Induction of apoptosis in human Huh-7 cells assessed as cytoskeleton disintegration at 60 nM incubated for 24 hrs by Giemsa staining based microscopy
AID1911784	Antitumor activity against human Huh-7 cells xenografted in BALB/c mouse assessed as tumor growth inhibition at 10 mg/kg, ip qd for 11 days and measured every 2 days
AID1143298	Selectivity ratio of IC50 for Electrophorus electricus acetylcholinesterase to IC50 for equine serum butyrylcholinesterase	2014	European journal of medicinal chemistry, Jun-23, Volume: 81	Identification of a neuroprotective and selective butyrylcholinesterase inhibitor derived from the natural alkaloid evodiamine.
AID1317246	Agonist activity at rat TRPV1 channel expressed in HEK293 cells assessed as induction of channel current at -60 mV holding potential by whole-cell patch-clamp method	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1859455	Inhibition of Top1 in [3H]-Thymidine-labeled human MCF7 cells assessed as Top1-DNA complex formation at 30 uM incubated for 60 mins followed by addition of salmon sperm DNA and subsequent addition of KCl relative to control	2022	European journal of medicinal chemistry, Jun-05, Volume: 236	Topoisomerase I inhibitors: Challenges, progress and the road ahead.
AID1317284	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin current density at 10 uM at -60 mV holding potential in absence of extracellular calcium by whole-cell patch-clamp method (Rvb = -2407.7 +/- 850.6 pA)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317290	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as inhibition of proton-induced channel current at 1 or 50 uM and -60 mV holding potential pretreated for 60 secs prior to proton-challenge by whole-cell patch clamp method (Rvb =	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911709	Induction of cell cycle arrest in human SK-Hep1 cells assessed as accumulation at G2 phase at 80 nM treated for 24 hrs by PI staining based flow cytometry (Rvb = 16.55 %)
AID1303756	Antiproliferative activity against human BGC823 cells after 72 hrs by MTT assay	2016	Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13	Antiproliferative activity and apoptosis inducing effects of nitric oxide donating derivatives of evodiamine.
AID1317268	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 1 uM by whole-cell patch clamp method	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1465331	Antiproliferative activity against human THP1 cells treated for 24 hrs measured after 72 hrs by MTT assay	2017	Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22	Design and synthesis of novel nitrogen mustard-evodiamine hybrids with selective antiproliferative activity.
AID1911802	Antiproliferative activity against human SMMC-7721 cells treated for 72 hrs by MTT assay
AID1808037	Antiproliferative activity against human A549 cells assessed as inhibition rate incubated for 72 hrs by MTT assay	2021	Journal of medicinal chemistry, 12-09, Volume: 64, Issue:23	Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer.
AID1317291	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on proton-induced channel current at 1 uM and -60 mV holding potential co-treated with proton by whole-cell patch clamp method	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911775	Induction of apoptosis in rat HSC-T6 cells assessed as late apoptotic cells at 80 nM pretreated with TGFbeta-1 for 1 day followed by compound addition and measured after 24 hrs by flow cytometry (Rvb = 1.76 %)
AID1911683	Antiproliferative activity against human L02 cells treated for 72 hrs by MTT assay
AID1911738	Induction of apoptosis in human Huh-7 cells assessed as viable cells at 80 nM incubated for 24 hrs by annexin V-FITC/PI staining flow cytometry (Rvb = 97.3 %)
AID1317281	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 10 uM by whole-cell patch clamp method (Rvb = -7 +/- 2.6 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911776	Induction of apoptosis in rat HSC-T6 cells assessed as necrotic cells at 80 nM pretreated with TGFbeta-1 for 1 day followed by compound addition and measured after 24 hrs by flow cytometry (Rvb = 0.56 %)
AID1317254	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as capsaicin EC50 for induction of channel current at 1 uM at -60 mV holding potential by whole-cell patch clamp method (Rvb = 0.06 uM)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1303757	Antiproliferative activity against human A549 cells after 72 hrs by MTT assay	2016	Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13	Antiproliferative activity and apoptosis inducing effects of nitric oxide donating derivatives of evodiamine.
AID1317257	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 0.1 uM by whole-cell patch clamp method (Rvb = -480.7 +/- 96.9 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1303759	Antiproliferative activity against human L02 cells after 72 hrs by MTT assay	2016	Bioorganic & medicinal chemistry, 07-01, Volume: 24, Issue:13	Antiproliferative activity and apoptosis inducing effects of nitric oxide donating derivatives of evodiamine.
AID1911708	Induction of cell cycle arrest in human SK-Hep1 cells assessed as accumulation at G1 phase at 80 nM treated for 24 hrs by PI staining based flow cytometry (Rvb = 58.47 %)
AID1911728	Induction of apoptosis in human SK-Hep1 cells assessed as chromatin agglutination at 60 nM incubated for 24 hrs by Giemsa staining based microscopy
AID1911740	Induction of apoptosis in human Huh-7 cells assessed as late apoptotic cells at 80 nM incubated for 24 hrs by annexin V-FITC/PI staining flow cytometry (Rvb = 1.33 %)
AID1357856	Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay
AID1143296	Inhibition of equine serum BChE by Ellman's method	2014	European journal of medicinal chemistry, Jun-23, Volume: 81	Identification of a neuroprotective and selective butyrylcholinesterase inhibitor derived from the natural alkaloid evodiamine.
AID1317258	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 0.1 uM by whole-cell patch clamp method (Rvb = -431 +/- 43.1 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1465332	Antiproliferative activity against human HL60 cells treated for 24 hrs measured after 72 hrs by MTT assay	2017	Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22	Design and synthesis of novel nitrogen mustard-evodiamine hybrids with selective antiproliferative activity.
AID1317247	Agonist activity at rat TRPV1 channel expressed in HEK293 cells assessed as induction of maximum channel current at 10 uM at -60 mV holding potential by whole-cell patch-clamp method	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1911751	Induction of apoptosis in human SK-Hep1 cells assessed as early apoptotic cells at 80 nM incubated for 24 hrs by annexin V-FITC/PI staining flow cytometry (Rvb = 0.30 %)
AID1357855	Antiproliferative activity against human Bel7402 cells after 72 hrs by MTT assay
AID1465333	Antiproliferative activity against human PBMC treated for 24 hrs measured after 72 hrs by MTT assay	2017	Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22	Design and synthesis of novel nitrogen mustard-evodiamine hybrids with selective antiproliferative activity.
AID1317288	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin current density at 10 uM pretreated for 180 sec followed by capsaicin addition at -60 mV holding potential in presence of extracellular calcium by whole-cel	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1317256	Partial antagonist activity at rat TRPV1 expressed in HEK293 cells assessed as effect on capsaicin-induced inward current at 0.1 uM by whole-cell patch clamp method (Rvb = -497 +/- 89.6 pA/pF)	2016	Journal of natural products, 05-27, Volume: 79, Issue:5	Partial Activation and Inhibition of TRPV1 Channels by Evodiamine and Rutaecarpine, Two Major Components of the Fruits of Evodia rutaecarpa.
AID1347090	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347091	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347097	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347094	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
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.
AID1347107	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347102	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347104	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347108	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347096	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
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.
AID1347106	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347089	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347103	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1508630	Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay	2021	Cell reports, 04-27, Volume: 35, Issue:4	A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347105	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347095	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347092	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
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.
AID1347101	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347098	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID1347100	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347154	Primary screen GU AMC qHTS for Zika virus inhibitors	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347099	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347093	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1794808	Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).	2014	Journal of biomolecular screening, Jul, Volume: 19, Issue:6	A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808	Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	3 (0.91)	18.7374
1990's	12 (3.63)	18.2507
2000's	60 (18.13)	29.6817
2010's	173 (52.27)	24.3611
2020's	83 (25.08)	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	1 (0.30%)	5.53%
Reviews	15 (4.46%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	320 (95.24%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
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.	2.01	1	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
adenine [no description available]	2.8	3	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	2.21	1	0	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
cadaverine [no description available]	2.04	1	0	alkane-alpha,omega-diamine	Daphnia magna metabolite; Escherichia coli metabolite; mouse metabolite; plant metabolite
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.	2.13	1	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
histamine [no description available]	2.01	1	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
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.	2.72	3	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
phenethylamine phenethylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7016. 2-phenylethylamine : A phenylethylamine having the phenyl substituent at the 2-position.	2.03	1	0	alkaloid; aralkylamine; phenylethylamine	Escherichia coli metabolite; human metabolite; mouse metabolite
pyridoxal phosphate Pyridoxal Phosphate: This is the active form of VITAMIN B 6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (PYRIDOXAMINE).. pyridoxal 5'-phosphate : The monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal.	2	1	0	methylpyridines; monohydroxypyridine; pyridinecarbaldehyde; vitamin B6 phosphate	coenzyme; cofactor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
huperzine a huperzine A: RN given refers to 5R-(5alpha,9beta,11E)-isomer; structure given in first source. huperzine A : A sesquiterpene alkaloid isolated from a club moss Huperzia serrata that has been shown to exhibit neuroprotective activity. It is also an effective inhibitor of acetylcholinesterase and has attracted interest as a therapeutic candidate for Alzheimer's disease.	3.23	1	0	quinolone
theophylline [no description available]	2.46	2	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
berberine [no description available]	4.26	16	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
chlorambucil Chlorambucil: A nitrogen mustard alkylating agent used as antineoplastic for chronic lymphocytic leukemia, Hodgkin's disease, and others. Although it is less toxic than most other nitrogen mustards, it has been listed as a known carcinogen in the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (Merck Index, 11th ed). chlorambucil : A monocarboxylic acid that is butanoic acid substituted at position 4 by a 4-[bis(2-chloroethyl)amino]phenyl group. A chemotherapy drug that can be used in combination with the antibody obinutuzumab for the treatment of chronic lymphocytic leukemia.	2.15	1	0	aromatic amine; monocarboxylic acid; nitrogen mustard; organochlorine compound; tertiary amino compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
ethoxyresorufin ethoxyresorufin: structure	2.01	1	0	phenoxazine
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.	3.19	5	0	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
furafylline [no description available]	2.01	1	0	oxopurine
2-(4-morpholinyl)-8-phenyl-4h-1-benzopyran-4-one 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one: specific inhibitor of phosphatidylinositol 3-kinase; structure in first source	2.5	2	0	chromones; morpholines; organochlorine compound	autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector
mechlorethamine nitrogen mustard : Compounds having two beta-haloalkyl groups bound to a nitrogen atom, as in (X-CH2-CH2)2NR.	2.15	1	0	nitrogen mustard; organochlorine compound	alkylating agent
nocodazole [no description available]	2.11	1	0	aromatic ketone; benzimidazoles; carbamate ester; thiophenes	antimitotic; antineoplastic agent; microtubule-destabilising agent; tubulin modulator
metoprolol Metoprolol: A selective adrenergic beta-1 blocking agent that is commonly used to treat ANGINA PECTORIS; HYPERTENSION; and CARDIAC ARRHYTHMIAS.. metoprolol : A propanolamine that is 1-(propan-2-ylamino)propan-2-ol substituted by a 4-(2-methoxyethyl)phenoxy group at position 1.	2.13	1	0	aromatic ether; propanolamine; secondary alcohol; secondary amino compound	antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; geroprotector; xenobiotic
midazolam Midazolam: A short-acting hypnotic-sedative drug with anxiolytic and amnestic properties. It is used in dentistry, cardiac surgery, endoscopic procedures, as preanesthetic medication, and as an adjunct to local anesthesia. The short duration and cardiorespiratory stability makes it useful in poor-risk, elderly, and cardiac patients. It is water-soluble at pH less than 4 and lipid-soluble at physiological pH.. midazolam : An imidazobenzodiazepine that is 4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted by a methyl, 2-fluorophenyl and chloro groups at positions 1, 6 and 8, respectively.	2.13	1	0	imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative
monodansylcadaverine monodansylcadaverine: inhibits cross linkage of fibrin. monodansylcadaverine : A sulfonamide obtained by formal condensation of the sulfo group of 5-(dimethylamino)naphthalene-1-sulfonic acid with one of the amino groups of cadaverine.	2.04	1	0	aminonaphthalene; primary amino compound; sulfonamide; tertiary amino compound	EC 2.3.2.13 (protein-glutamine gamma-glutamyltransferase) inhibitor; fluorochrome; protective agent
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	2.11	1	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
nitroglycerin Nitroglycerin: A volatile vasodilator which relieves ANGINA PECTORIS by stimulating GUANYLATE CYCLASE and lowering cytosolic calcium. It is also sometimes used for TOCOLYSIS and explosives.. nitroglycerol : A nitrate ester that is glycerol in which nitro group(s) replace the hydrogen(s) attached to one or more of the hydroxy groups.. nitroglycerin : A nitroglycerol that is glycerol in which the hydrogen atoms of all three hydroxy groups are replaced by nitro groups. It acts as a prodrug, releasing nitric oxide to open blood vessels and so alleviate heart pain.	7.25	1	0	nitroglycerol	explosive; muscle relaxant; nitric oxide donor; prodrug; tocolytic agent; vasodilator agent; xenobiotic
omeprazole Omeprazole: A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.. omeprazole : A racemate comprising equimolar amounts of (R)- and (S)-omeprazole.. 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5.	2.13	1	0	aromatic ether; benzimidazoles; pyridines; sulfoxide
pd 98059 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one: inhibits MAP kinase kinase (MEK) activity, p42 MAPK and p44 MAPK; structure in first source. 2-(2-amino-3-methoxyphenyl)chromen-4-one : A member of the class of monomethoxyflavones that is 3'-methoxyflavone bearing an additional amino substituent at position 2'.	2.46	2	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
pentobarbital Pentobarbital: A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236). pentobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	1.97	1	0	barbiturates	GABAA receptor agonist
phenacetin Saridon: contains phenacetin, caffeine, propyphenazone & pyrithyldione	2.13	1	0	acetamides; aromatic ether	cyclooxygenase 3 inhibitor; non-narcotic analgesic; peripheral nervous system drug
pyridoxal phosphate-6-azophenyl-2',4'-disulfonic acid pyridoxal phosphate-6-azophenyl-2',4'-disulfonic acid: a novel antagonist that selectively blocks P2 purinoceptor receptors; a useful tool to study co-transmission in tissues when ATP and coexisting neurotransmitters act in concert. 5'-phosphopyridoxal-6-azobenzene-2,4-disulfonic acid : An arenesulfonic acid that is pyridoxal 5'-phosphate carrying an additional 2,4-disulfophenylazo substituent at position 6.	2	1	0	arenesulfonic acid; azobenzenes; methylpyridines; monohydroxypyridine; organic phosphate; pyridinecarbaldehyde	purinergic receptor P2X antagonist
vorinostat Vorinostat: A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME.. vorinostat : A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL).	7.17	1	0	dicarboxylic acid diamide; hydroxamic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
tolbutamide Tolbutamide: A sulphonylurea hypoglycemic agent with actions and uses similar to those of CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). tolbutamide : An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.	2.13	1	0	N-sulfonylurea	human metabolite; hypoglycemic agent; insulin secretagogue; potassium channel blocker
troglitazone Troglitazone: A chroman and thiazolidinedione derivative that acts as a PEROXISOME PROLIFERATOR-ACTIVATED RECEPTORS (PPAR) agonist. It was formerly used in the treatment of TYPE 2 DIABETES MELLITUS, but has been withdrawn due to hepatotoxicity.	2.11	1	0	chromanes; thiazolidinone	anticoagulant; anticonvulsant; antineoplastic agent; antioxidant; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; hypoglycemic agent; platelet aggregation inhibitor; vasodilator agent
urethane [no description available]	2.25	1	0	carbamate ester	fungal metabolite; mutagen
corticosterone [no description available]	7.48	2	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
hydroxyproline Hydroxyproline: A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.. hydroxyproline : A proline derivative that is proline substituted by at least one hydroxy group.	2.21	1	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
aldosterone [no description available]	7	1	0	11beta-hydroxy steroid; 18-oxo steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; mineralocorticoid; primary alpha-hydroxy ketone; steroid aldehyde	human metabolite; mouse 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.	7.08	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
physostigmine Physostigmine: A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity.	2.1	1	0	carbamate ester; indole alkaloid	antidote to curare poisoning; EC 3.1.1.8 (cholinesterase) inhibitor; miotic
carbostyril Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.	3.83	3	0	monohydroxyquinoline; quinolone	bacterial xenobiotic 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.	1.98	1	0	phenols; phenylethanolamines; secondary amino compound	alpha-adrenergic agonist; cardiotonic drug; mydriatic agent; nasal decongestant; protective agent; sympathomimetic agent; vasoconstrictor agent
methicillin Methicillin: One of the PENICILLINS which is resistant to PENICILLINASE but susceptible to a penicillin-binding protein. It is inactivated by gastric acid so administered by injection.. methicillin : A penicillin that is 6-aminopenicillanic acid in which one of the amino hydrogens is replaced by a 2,6-dimethoxybenzoyl group.	7.17	1	0	penicillin allergen; penicillin	antibacterial drug
desoxycorticosterone Desoxycorticosterone: A steroid metabolite that is the 11-deoxy derivative of CORTICOSTERONE and the 21-hydroxy derivative of PROGESTERONE	2.05	1	0	20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; mineralocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
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.	1.99	1	0	psoralens	plant metabolite
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	2.41	1	0	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae 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.	2.45	2	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
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.	2.21	1	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
rhodamine b rhodamine B: RN & N1 from 9th CI Form Index; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7973; TETRAETHYLRHODAMINE was see RHODAMINES 1975-93; use RHODAMINES to search TETRAETHYLRHODAMINE 1975-93. rhodamine B : An organic chloride salt having N-[9-(2-carboxyphenyl)-6-(diethylamino)-3H-xanthen-3-ylidene]-N-ethylethanaminium as the counterion. An amphoteric dye commonly used as a fluorochrome.	2.07	1	0	organic chloride salt; xanthene dye	fluorescent probe; fluorochrome; histological dye
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	2.41	1	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
skimmianine skimmianine: furanoquinoline alkaloid from Teclea (RUTACEAE)	2.05	1	0	alkaloid antibiotic; organic heterotricyclic compound; organonitrogen heterocyclic compound; oxacycle
gramine gramine : An aminoalkylindole that is indole carrying a dimethylaminomethyl substituent at postion 3.	2.13	1	0	aminoalkylindole; indole alkaloid; tertiary amino compound	antibacterial agent; antiviral agent; plant metabolite; serotonergic antagonist
synephrine [no description available]	2.72	3	0	ethanolamines; phenethylamine alkaloid; phenols	alpha-adrenergic agonist; plant metabolite
diethylhexyl phthalate Diethylhexyl Phthalate: An ester of phthalic acid. It appears as a light-colored, odorless liquid and is used as a plasticizer for many resins and elastomers.. bis(2-ethylhexyl) phthalate : A phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	3.01	2	0	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
pyrazolanthrone pyrazolanthrone: JNK (c-Jun N-terminal kinase) inhibitor; structure in first source. anthra[1,9-cd]pyrazol-6(2H)-one : A member of the class of anthrapyrazoles that is anthra[1,9-cd]pyrazole substituted at position 6 by an oxo group. An inhibitor of c-Jun N-terminal kinase.	2.79	3	0	anthrapyrazole; aromatic ketone; cyclic ketone	antineoplastic agent; c-Jun N-terminal kinase inhibitor; geroprotector
pregnenolone [no description available]	2.05	1	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
potassium cyanide [no description available]	1.97	1	0	cyanide salt; one-carbon compound; potassium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; neurotoxin
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	11.79	303	1	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
thiazoles [no description available]	2.44	2	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
pyrazines Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.	2.07	1	0	diazine; pyrazines	Daphnia magna metabolite
hydrazine diamine : Any polyamine that contains two amino groups.	2.03	1	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
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.	2.8	3	0	dialdehyde	biomarker
ethylene glycol diethyl ether [no description available]	2.6	1	0
deoxycytidine [no description available]	2.07	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
tetramethylpyrazine tetramethylpyrazine: found in Ligusticum chuanxiong. tetramethylpyrazine : A member of the class of pyrazines that is pyrazine in which all four hydrogens have been replaced by methyl groups. An alkaloid extracted from Chuanxiong (Ligusticum wallichii).	2.07	1	0	alkaloid; pyrazines	antineoplastic agent; apoptosis inhibitor; bacterial metabolite; neuroprotective agent; platelet aggregation inhibitor; vasodilator agent
4-n-bis(2-chloroethyl)aminobenzoic acid 4-N-bis(2-chloroethyl)aminobenzoic acid: structure given in first source	2.15	1	0
glycyrrhizic acid glycyrrhizinic acid : A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.	7.25	1	0	enone; glucosiduronic acid; pentacyclic triterpenoid; tricarboxylic acid; triterpenoid saponin	EC 3.4.21.5 (thrombin) inhibitor; plant metabolite
fluorescein-5-isothiocyanate Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.	2.15	1	0	fluorescein isothiocyanate
palmatine burasaine: structure in first source	2.05	1	0	berberine alkaloid; organic heterotetracyclic compound	plant metabolite
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.	2.08	1	0	elemental platinum; nickel group element atom; platinum group metal 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.	2.17	1	0	iron group element atom; platinum group metal atom
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	9.59	7	0	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
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.	2.74	3	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
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.	2.25	1	0	benzenes; phenyl acetates
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.	2.05	1	0	3',5'-cyclic purine nucleotide; adenyl ribonucleotide; organobromine compound	antidepressant; protein kinase agonist
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	3.01	4	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising 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.	2.71	3	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
staurosporine [no description available]	2.31	1	0	indolocarbazole alkaloid; organic heterooctacyclic compound	apoptosis inducer; bacterial metabolite; EC 2.7.11.13 (protein kinase C) inhibitor; geroprotector
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.	2.43	2	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
gemcitabine gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.	7.07	1	0	organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; environmental contaminant; immunosuppressive agent; photosensitizing agent; prodrug; radiosensitizing agent; xenobiotic
irinotecan [no description available]	3.95	3	0	carbamate ester; delta-lactone; N-acylpiperidine; pyranoindolizinoquinoline; ring assembly; tertiary alcohol; tertiary amino compound	antineoplastic agent; apoptosis inducer; EC 5.99.1.2 (DNA topoisomerase) inhibitor; prodrug
acridine orange Acridine Orange: A cationic cytochemical stain specific for cell nuclei, especially DNA. It is used as a supravital stain and in fluorescence cytochemistry. It may cause mutations in microorganisms.. acridine orange : Fluorescent dye useful for cell cycle determination. It is cell-permeable, and interacts with DNA and RNA by intercalation or electrostatic attractions respectively.. acridine orange free base : A member of the class of aminoacridines that is acridine carrying two dimethylamino substituents at positions 3 and 6. The hydrochloride salt is the fluorescent dye 'acridine orange', used for cell cycle determination.	2.44	2	0	aminoacridines; aromatic amine; tertiary amino compound	fluorochrome; histological dye
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.	2.15	1	0	D-glucopyranose	epitope; mouse 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.	2.44	2	0	organic bromide salt	colorimetric reagent; dye
baicalin [no description available]	3.23	1	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
25-hydroxycholesterol [no description available]	2.05	1	0	25-hydroxy steroid; oxysterol	human metabolite
pyrrolidine dithiocarbamate pyrrolidine dithiocarbamic acid: spelled pyrolidine in J Nutr 1979 reference; RN given refers to parent cpd. pyrrolidine dithiocarbamate : A member of the class of dithiocarbamic acids that is the N-dithiocarboxy derivative of pyrrolidine.	2.45	2	0	dithiocarbamic acids; pyrrolidines	anticonvulsant; antineoplastic agent; geroprotector; neuroprotective agent; NF-kappaB inhibitor; radical scavenger
rutecarpine rutacarpine: from Evodia rutaecarpa; an ingredient in zhuyu hewei zhitong capsules	7.09	60	0	beta-carbolines
2-hydroxy-4-methoxybenzaldehyde 2-hydroxy-4-methoxybenzaldehyde: from African medicinal plants: Mondia whitei (Apocynaceae), Rhus vulagaris (Anacardiaceae), Sclerocarya caffra (Anacardiaceae)	2.13	1	0	methoxybenzenes; phenols
dapoxetine [no description available]	7.13	1	0	naphthalenes
jatrorrhizine jatrorrhizine: isolated from bark of Enantia chlorantha (Annonaceae); structure given in first source	2.15	1	0	alkaloid
berberrubine berberrubine: RN refers to chloride salt; a protoberberine alkaloid antitumor agent which exhibits topoisomerase II poison activity as well as catalytic inhibition activity; structure in first source	2.25	1	0
rosiglitazone [no description available]	7.05	1	0	aminopyridine; thiazolidinediones	EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; insulin-sensitizing drug
norcantharidin norcantharidin: structure given in first source; RN given refers to cpds without isomeric designation	7.1	1	0	furofuran
diosgenin [no description available]	2.08	1	0	3beta-sterol; hexacyclic triterpenoid; sapogenin; spiroketal	antineoplastic agent; antiviral agent; apoptosis inducer; metabolite
phorbolol myristate acetate [no description available]	2.03	1	0
fangchinoline fangchinoline: RN given refers to parent cpd; limacine is the (1'beta)-isomer; 7-O-demethyltetrandrine is the (1S,1'S)-isomer. fangchinoline : A bisbenzylisoquinoline alkaloid that is (1beta)- berbaman which has been substituted by methyl groups at the 2 and 2' positions, by methoxy groups at the 6, 6', and 12 positions, and by a hydroxy group at position 7. Isolated from Stephania tetrandra, it has been found to possess neuroprotective and anti-tumour activity.	2.07	1	0
p-methoxy-n-methylphenethylamine p-Methoxy-N-methylphenethylamine: A potent mast cell degranulator. It is involved in histamine release.. N,O-dimethyltyramine : A secondary amino compound that is tyramine in which the hydrogen of the phenolic hydroxy group has been replaced by a methyl group.	2.03	1	0	aromatic ether; secondary amino compound	metabolite
fulvestrant Fulvestrant: An estradiol derivative and estrogen receptor antagonist that is used for the treatment of estrogen receptor-positive, locally advanced or metastatic breast cancer.. fulvestrant : A 3-hydroxy steroid that is 17beta-estradiol in which the 7alpha hydrogen has been replaced by a nonyl group in which one of the hydrogens of the terminal methyl has been replaced by a (4,4,5,5,5-pentafluoropentyl)sulfinyl group. An estrogen receptor antagonist, it is used in the treatment of breast cancer.	2.08	1	0	17beta-hydroxy steroid; 3-hydroxy steroid; organofluorine compound; sulfoxide	antineoplastic agent; estrogen antagonist; estrogen receptor antagonist
tanshinone tanshinone: from root of Salvia miltiorrhiza Bunge; RN given refers to tanshinone I; cardioprotective agent and neuroprotective agent	3.23	1	0	abietane diterpenoid	anticoronaviral agent
stachydrine stachydrine: RN given refers to hydroxide inner salt (S)-isomer; structure. L-proline betaine : An amino acid betaine that is L-proline zwitterion in which both of the hydrogens attached to the nitrogen are replaced by methyl groups.	2.07	1	0	alkaloid; amino-acid betaine; N-methyl-L-alpha-amino acid	food component; human blood serum metabolite; plant metabolite
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.	2.55	2	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
ungeremine ungeremine: RN given refers to parent cpd; structure	2.21	1	0
cyc 202 seliciclib : 2,6-Diaminopurine carrying benzylamino, (2R)-1-hydroxybutan-2-yl and isopropyl substituents at C-6, C-2-N and N-9 respectively. It is an experimental drug candidate in the family of pharmacological cyclin-dependent kinase (CDK) inhibitors.	2.03	1	0	2,6-diaminopurines	antiviral drug; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	2	1	0	amino acid zwitterion; angiotensin II	human metabolite
sb 203580 [no description available]	2.46	2	0	imidazoles; monofluorobenzenes; pyridines; sulfoxide	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector; Hsp90 inhibitor; neuroprotective agent
erlotinib hydrochloride [no description available]	2.13	1	0	hydrochloride; terminal acetylenic compound	antineoplastic agent; protein kinase inhibitor
limonin [no description available]	2.97	4	0	epoxide; furans; hexacyclic triterpenoid; lactone; limonoid; organic heterohexacyclic compound	inhibitor; metabolite; volatile oil component
wortmannin [no description available]	2.47	2	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
evodine evodine: structure in first source	7.97	4	0
leupeptins Leupeptins: A group of acylated oligopeptides produced by Actinomycetes that function as protease inhibitors. They have been known to inhibit to varying degrees trypsin, plasmin, KALLIKREINS, papain and the cathepsins.	2.11	1	0
rutaevin rutaevin: from root bark of Dictamnus daycarpus Turcz.	2.1	1	0	steroid lactone
ginsenoside rg1 [no description available]	3.63	2	0	12beta-hydroxy steroid; 3beta-hydroxy-4,4-dimethylsteroid; beta-D-glucoside; ginsenoside; tetracyclic triterpenoid	neuroprotective agent; pro-angiogenic agent
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)	1.99	1	0
n-formylmethionine leucyl-phenylalanine N-Formylmethionine Leucyl-Phenylalanine: A formylated tripeptide originally isolated from bacterial filtrates that is positively chemotactic to polymorphonuclear leucocytes, and causes them to release lysosomal enzymes and become metabolically activated.. N-formyl-L-methionyl-L-leucyl-L-phenylalanine : A tripeptide composed of L-Met, L-Leu and L-Phe in a linear sequence with a formyl group at the amino terminus. It acts as a potent inducer of leucocyte chemotaxis and macrophage activator as well as a ligand for the FPR receptor.	2.03	1	0	tripeptide
devazepide Devazepide: A derivative of benzodiazepine that acts on the cholecystokinin A (CCKA) receptor to antagonize CCK-8's (SINCALIDE) physiological and behavioral effects, such as pancreatic stimulation and inhibition of feeding.. devazepide : An indolecarboxamide obtained by formal condensation of the carboxy group of indole-2-carboxylic acid with the exocyclic amino group of (3S)-3-amino-1-methyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one. A cholecystokinin antagonist used for treatment of gastrointestinal disorders.	2.01	1	0	1,4-benzodiazepinone; indolecarboxamide	antineoplastic agent; apoptosis inducer; cholecystokinin antagonist; gastrointestinal drug
vinpocetine vinpocetine: whole issue of Arzneim Forsch (23 articles) discuss this drug; Arzneim Forsch 26(10a);1976; RN given refers to parent cpd with unspecified isomeric designation	1.97	1	0	alkaloid	geroprotector
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.13	1	0	cyclodextrin
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	2.07	1	0	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
dactinomycin Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)	2.01	1	0	actinomycin	mutagen
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	2.15	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
benzyloxycarbonylleucyl-leucyl-leucine aldehyde benzyloxycarbonylleucyl-leucyl-leucine aldehyde: proteasome inhibitor. N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal : A tripeptide that is L-leucyl-L-leucyl-L-leucine in which the C-terminal carboxy group has been reduced to the corresponding aldehyde and the N-terminal amino group is protected as its benzyloxycarbonyl derivative.	2.11	1	0	amino aldehyde; carbamate ester; tripeptide	proteasome inhibitor
schizandrin schizandrin: a dibenzocyclooctadiene lignan; schizandra is the plant name	1.99	1	0
isoliquiritigenin [no description available]	2.25	1	0	chalcones	antineoplastic agent; biological pigment; EC 1.14.18.1 (tyrosinase) inhibitor; GABA modulator; geroprotector; metabolite; NMDA receptor antagonist
gw9662 2-chloro-5-nitrobenzanilide: pretreatment of peroxisome proliferator activated receptors with GW9662 results in the irreversible loss of ligand binding	2.13	1	0	benzamides
sesquiterpenes [no description available]	3.6	2	0
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.	3.63	2	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
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.	5.03	9	1	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
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.	2.96	4	0	benzazepine; catechols; monochlorobenzenes; thioureas	capsaicin receptor antagonist
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)	2.03	1	0
rtki cpd RTKI cpd: preferentially inhibits human glioma cells expressing truncated rather than wild-type epidermal growth factor receptors	2.05	1	0
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.15	1	0
ginsenosides ginsenoside : Triterpenoid saponins with a dammarane-like skeleton originally isolated from ginseng (Panax) species. Use of the term has been extended to include semi-synthetic derivatives.	3.63	2	0
quercetin [no description available]	2.1	1	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.	2.99	4	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
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.	2.03	1	0	leukotriene	bronchoconstrictor agent; human metabolite; mouse metabolite
herbacetin herbacetin: from Ramose Scouring Rush Herb; structure in first source. herbacetin : A pentahydroxyflavone that is kaempferol substituted by a hydroxy group at position 8. It is a natural flavonoid from flaxseed which exerts antioxidant, anti-inflammatory and anticancer activities.	2.25	1	0	7-hydroxyflavonol; pentahydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antilipemic drug; antineoplastic agent; apoptosis inducer; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 4.1.1.17 (ornithine decarboxylase) inhibitor; plant metabolite
kaempferol [no description available]	2.21	1	0	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
genistein [no description available]	2.05	1	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
thromboxane b2 Thromboxane B2: A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin).. thromboxane B2 : A member of the class of thromboxanes B that is (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.	2.07	1	0	thromboxanes B	human metabolite; mouse metabolite
l 365260 L 365260: a CCK-B antagonist; structure given in first source; potent & selective CCK-B & gastrin receptor ligand; L 365260 and L 365346 are (R)- and (S)-stereoisomers, respectively	2.01	1	0	benzodiazepine
evocarpine evocarpine: structure given in first source; RN given refers to (Z)-isomer	1.97	1	0	quinolines
icariin [no description available]	3.23	1	0	flavonols; glycosyloxyflavone	antioxidant; bone density conservation agent; EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; phytoestrogen
nerolidol nerolidol: sesquiterpene; RN given refers to cpd without isomeric designation; nerol is also available. nerolidol : A farnesane sesquiterpenoid that is dodeca-1,6,10-triene which carries methyl groups at positions 3, 7 and 11 and a hydroxy group at position 3. It is a natural product that is present in various flowers and plants with a floral odor. Chemically, it exists in two geometric isomers, trans and cis forms. It is widely used in cosmetics (e.g. shampoos and perfumes), in non-cosmetic products (e.g. detergents and cleansers) and also as a food flavoring agent.. (6Z)-nerolidol : A nerolidol in which the double bond at position 6 adopts a cis-configuration.	2.07	1	0	nerolidol
malealdehyde malealdehyde: RN given refers to cpd without isomeric designation; fumaraldehyde refers to (E)-isomer	2.15	1	0	but-2-enedial
ag-490 [no description available]	2.08	1	0	catechols; enamide; monocarboxylic acid amide; nitrile; secondary carboxamide	anti-inflammatory agent; antioxidant; apoptosis inducer; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; geroprotector; STAT3 inhibitor
ethyl oleate [no description available]	2.17	1	0	long-chain fatty acid ethyl ester	acaricide; plant metabolite
sinomenine sinomenine: isolated from root of Sinomenium acutum; antirheumatic, antineuralgic	2.07	1	0	morphinane alkaloid
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.	2.41	1	0	cysteinium	fundamental 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).	2.02	1	0	carboxylic ester; diterpenoid; enone; monomethoxybenzene; organic heteropentacyclic compound; ortho ester; phenols; tertiary alpha-hydroxy ketone	analgesic; neurotoxin; plant metabolite; TRPV1 agonist
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.	2.11	1	0	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
dihydroergotoxine Dihydroergotoxine: A mixture of three different hydrogenated derivatives of ERGOTAMINE: DIHYDROERGOCORNINE; DIHYDROERGOCRISTINE; and DIHYDROERGOCRYPTINE. Dihydroergotoxine has been proposed to be a neuroprotective agent and a nootropic agent. The mechanism of its therapeutic actions is not clear, but it can act as an alpha-adrenergic antagonist and a dopamine agonist. The methanesulfonate salts of this mixture of alkaloids are called ERGOLOID MESYLATES.	1.97	1	0
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.	2.07	1	0	isoquinoline alkaloid fundamental parent; morphinane alkaloid
staurosporine staurosporinium : Conjugate acid of staurosporine.	2.43	2	0	ammonium ion derivative
dehydroevodiamine dehydroevodiamine: RN given refers to hydroxide, inner salt; structure in first source.	9.92	11	0
sincalide Sincalide: An octapeptide hormone present in the intestine and brain. When secreted from the gastric mucosa, it stimulates the release of bile from the gallbladder and digestive enzymes from the pancreas.	2.17	1	0	oligopeptide
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).	2.11	1	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
lamellarin d lamellarin D: a benzo-isoquinoline-coumarin	3.51	1	0
ginsenoside rb1 [no description available]	2.13	1	0	ginsenoside; glycoside; tetracyclic triterpenoid	anti-inflammatory drug; anti-obesity agent; apoptosis inhibitor; neuroprotective agent; plant metabolite; radical scavenger
luotonin a luotonin A: structure in first source	3.51	1	0	quinazolines
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.	2.03	1	0	benzoxazole
acid phosphatase Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.	2.21	1	0
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.	2.52	2	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.	2.01	1	0
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.	2.05	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)	2.07	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.	2.13	1	0	chlorophyll; methyl ester	cofactor
gdc 0449 HhAntag691: inhibits the hedgehog pathway and ABC transporters; has antineoplastic activity	2.11	1	0	benzamides; monochlorobenzenes; pyridines; sulfone	antineoplastic agent; Hedgehog signaling pathway inhibitor; SMO receptor antagonist; teratogenic agent
oxymatrine oxymatrine: structure in first source; has anti-apoptosis effects	2.07	1	0
glycolipids [no description available]	2.06	1	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.	2.84	3	0
7-methyl-5-(1-((3-(trifluoromethyl)phenyl)acetyl)-2,3-dihydro-1h-indol-5-yl)-7h-pyrrolo(2,3-d)pyrimidin-4-amine 7-methyl-5-(1-((3-(trifluoromethyl)phenyl)acetyl)-2,3-dihydro-1H-indol-5-yl)-7H-pyrrolo(2,3-d)pyrimidin-4-amine: inhibits protein kinase R (PKR)-like endoplasmic reticulum kinase (PERK); structure in first source	2.53	2	0
piroxicam [no description available]	2.06	1	0	benzothiazine; monocarboxylic acid amide; pyridines	analgesic; antirheumatic drug; cyclooxygenase 1 inhibitor; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	2.21	1	0
okadaic acid Okadaic Acid: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING.. okadaic acid : A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.	7.31	1	0	ketal
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.	2.8	3	0
benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone: an interleukin-1beta converting enzyme (ICE)-like protease inhibitor	2.01	1	0
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	2.6	1	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
3-methyladenine N3-methyladenine: structure in first source	2.08	1	0
chir-124 [no description available]	3.51	1	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.	2.05	1	0
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2.25	1	0

Condition	Relationship Strength	Studies
Plasmodium falciparum Malaria [description not available]	2.1	1
Malaria, Falciparum Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.	2.1	1
Congenital Zika Syndrome [description not available]	2.25	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	5.06	14
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	2.25	1
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	2.31	1
Triple Negative Breast Neoplasms Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.	2.31	1
Carcinoma, Epidermoid [description not available]	2.89	3
Cancer of Mouth [description not available]	2.58	2
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	2.89	3
Mouth Neoplasms Tumors or cancer of the MOUTH.	2.58	2
Cancer of Prostate [description not available]	3.21	5
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	3.21	5
Dermatophytoses [description not available]	2.31	1
Hand Dermatosis [description not available]	2.31	1
Hand Dermatoses Skin diseases involving the HANDS.	2.31	1
Tinea Fungal infection of keratinized tissues such as hair, skin and nails. The main causative fungi include MICROSPORUM; TRICHOPHYTON; and EPIDERMOPHYTON.	2.31	1
Experimental Neoplasms [description not available]	2.98	3
Cancer of Stomach [description not available]	3.82	10
Stomach Neoplasms Tumors or cancer of the STOMACH.	3.82	10
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.99	4
Bile Duct Obstruction [description not available]	2.31	1
Cholestasis Impairment of bile flow due to obstruction in small bile ducts (INTRAHEPATIC CHOLESTASIS) or obstruction in large bile ducts (EXTRAHEPATIC CHOLESTASIS).	2.31	1
Hepatocellular Carcinoma [description not available]	4.16	14
Cancer of Liver [description not available]	4.16	14
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	4.16	14
Liver Neoplasms Tumors or cancer of the LIVER.	4.16	14
Fatty Liver, Nonalcoholic [description not available]	2.41	1
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	7.41	1
Alloxan Diabetes [description not available]	2.57	2
Diabetes Mellitus, Adult-Onset [description not available]	2.41	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	2.41	1
Benign Neoplasms [description not available]	5.52	7
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	5.52	7
Degenerative Disc Disease [description not available]	2.41	1
Intervertebral Disc Degeneration Degenerative changes in the INTERVERTEBRAL DISC due to aging or structural damage, especially to the vertebral end-plates.	7.41	1
Carcinoma, Non-Small Cell Lung [description not available]	3.61	7
Cancer of Lung [description not available]	4.1	13
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	3.61	7
Lung Neoplasms Tumors or cancer of the LUNG.	4.1	13
Acute Liver Injury, Drug-Induced [description not available]	2.41	1
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	2.41	1
Blood Clot [description not available]	2.41	1
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	7.41	1
Encephalopathy, Traumatic [description not available]	2.41	1
Brain Injuries, Traumatic A form of acquired brain injury which occurs when a sudden trauma causes damage to the brain.	2.41	1
Esophageal Squamous Cell Carcinoma A carcinoma that originates usually from cells on the surface of the middle and lower third of the ESOPHAGUS. Tumor cells exhibit typical squamous morphology and form large polypoid lesions. Mutations in RNF6, LZTS1, TGFBR2, DEC1, and WWOX1 genes are associated with this cancer.	2.6	1
Cancer of Esophagus [description not available]	2.63	2
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	2.63	2
Cancer of Ovary [description not available]	3.08	4
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	3.08	4
Bladder Cancer [description not available]	2.87	3
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.87	3
Atherogenesis [description not available]	2.55	2
Atheroma [description not available]	2.6	1
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	7.55	2
Cancer of Cervix [description not available]	2.49	2
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	2.49	2
Ebola Hemorrhagic Fever [description not available]	2.6	1
Chemical and Drug Induced Liver Injury, Chronic Liver disease lasting six months or more, caused by an adverse effect of a drug or chemical. The adverse effect may be caused by drugs, drug metabolites, chemicals from the environment, or an idiosyncratic response.	2.6	1
Hemorrhagic Fever, Ebola A highly fatal, acute hemorrhagic fever caused by EBOLAVIRUS.	2.6	1
Cancer of Colon [description not available]	3.57	8
Colonic Neoplasms Tumors or cancer of the COLON.	3.57	8
Cancer of Pancreas [description not available]	2.53	2
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	2.53	2
Adjuvant Arthritis [description not available]	2.25	1
Plica Syndrome [description not available]	2.25	1
Synovitis Inflammation of the SYNOVIAL MEMBRANE.	2.25	1
Liver Dysfunction [description not available]	3.17	1
Liver Diseases Pathological processes of the LIVER.	8.17	1
Cardiac Toxicity [description not available]	2.25	1
Colorectal Cancer [description not available]	3.51	7
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	3.51	7
Cardiotoxicity Damage to the HEART or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.	2.25	1
Allodynia [description not available]	2.58	2
Abdominal Migraine [description not available]	2.58	2
Ache [description not available]	3	4
Migraine Disorders A class of disabling primary headache disorders, characterized by recurrent unilateral pulsatile headaches. The two major subtypes are common migraine (without aura) and classic migraine (with aura or neurological symptoms). (International Classification of Headache Disorders, 2nd ed. Cephalalgia 2004: suppl 1)	2.58	2
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	8	4
B16 Melanoma [description not available]	2.96	4
Innate Inflammatory Response [description not available]	4.77	10
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	4.77	10
Colitis Gravis [description not available]	2.25	1
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	2.25	1
Cirrhosis, Liver [description not available]	2.25	1
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	2.25	1
Glial Cell Tumors [description not available]	2.59	2
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	2.59	2
Colitis-Associated Cancer [description not available]	7.31	1
Angiogenesis, Pathologic [description not available]	3.92	4
Airway Remodeling The structural changes in the number, mass, size and/or composition of the airway tissues.	2.31	1
Asthma, Bronchial [description not available]	2.31	1
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	7.31	1
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	2.95	4
Cirrhosis [description not available]	2.31	1
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	2.63	2
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	7.31	1
Pneumonia Infection of the lung often accompanied by inflammation.	7.63	2
Infections, Helicobacter [description not available]	2.31	1
Helicobacter Infections Infections with organisms of the genus HELICOBACTER, particularly, in humans, HELICOBACTER PYLORI. The clinical manifestations are focused in the stomach, usually the gastric mucosa and antrum, and the upper duodenum. This infection plays a major role in the pathogenesis of type B gastritis and peptic ulcer disease.	2.31	1
Depression, Endogenous [description not available]	2.31	1
Depressive Disorder An affective disorder manifested by either a dysphoric mood or loss of interest or pleasure in usual activities. The mood disturbance is prominent and relatively persistent.	7.31	1
Degenerative Diseases, Central Nervous System [description not available]	2.31	1
Tauopathies Neurodegenerative disorders involving deposition of abnormal tau protein isoforms (TAU PROTEINS) in neurons and glial cells in the brain. Pathological aggregations of tau proteins are associated with mutation of the tau gene on chromosome 17 in patients with ALZHEIMER DISEASE; DEMENTIA; PARKINSONIAN DISORDERS; progressive supranuclear palsy (SUPRANUCLEAR PALSY, PROGRESSIVE); and corticobasal degeneration.	2.31	1
Acute Confusional Senile Dementia [description not available]	3.97	4
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	2.31	1
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	3.97	4
Neurodegenerative Diseases Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.	2.31	1
Carcinoma, Small Cell Lung [description not available]	2.57	2
Small Cell Lung Carcinoma A form of highly malignant lung cancer that is composed of small ovoid cells (SMALL CELL CARCINOMA).	2.57	2
Experimental Hepatoma [description not available]	2.31	1
Mastitis INFLAMMATION of the BREAST, or MAMMARY GLAND.	7.41	1
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	2.15	1
Carcinoma, Anaplastic [description not available]	3.19	5
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	3.19	5
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	3.01	4
Astrocytoma, Grade IV [description not available]	2.8	3
Glioblastoma A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.	2.8	3
Adenocarcinoma Of Kidney [description not available]	2.54	2
Carcinoma, Renal Cell A heterogeneous group of sporadic or hereditary carcinoma derived from cells of the KIDNEYS. There are several subtypes including the clear cells, the papillary, the chromophobe, the collecting duct, the spindle cells (sarcomatoid), or mixed cell-type carcinoma.	2.54	2
Hyperlipemia [description not available]	2.52	2
Hyperlipidemias Conditions with excess LIPIDS in the blood.	2.52	2
Anoxemia [description not available]	2.42	2
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	7.42	2
Bone Cancer [description not available]	2.17	1
Osteogenic Sarcoma [description not available]	2.54	2
Invasiveness, Neoplasm [description not available]	3.47	7
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	2.17	1
Osteosarcoma A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)	2.54	2
Cytomegalovirus A genus of the family HERPESVIRIDAE, subfamily BETAHERPESVIRINAE, infecting the salivary glands, liver, spleen, lungs, eyes, and other organs, in which they produce characteristically enlarged cells with intranuclear inclusions. Infection with Cytomegalovirus is also seen as an opportunistic infection in AIDS.	7.17	1
Cancer of the Thyroid [description not available]	2.81	3
Thyroid Neoplasms Tumors or cancer of the THYROID GLAND.	2.81	3
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	7.21	1
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	3.12	1
Cholangiocellular Carcinoma [description not available]	2.21	1
Bile Duct Cancer [description not available]	2.21	1
Bile Duct Neoplasms Tumors or cancer of the BILE DUCTS.	2.21	1
Cholangiocarcinoma A malignant tumor arising from the epithelium of the BILE DUCTS.	7.21	1
Nerve Pain [description not available]	2.21	1
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.21	1
Age-Related Osteoporosis [description not available]	2.21	1
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	7.21	1
Cancer of the Tongue [description not available]	2.21	1
Tongue Neoplasms Tumors or cancer of the TONGUE.	2.21	1
Acute Kidney Failure [description not available]	2.21	1
Injury, Ischemia-Reperfusion [description not available]	2.21	1
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	7.21	1
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	2.21	1
Electrolytes Substances that dissociate into two or more ions, to some extent, in water. Solutions of electrolytes thus conduct an electric current and can be decomposed by it (ELECTROLYSIS). (Grant & Hackh's Chemical Dictionary, 5th ed)	2.21	1
Breast Cancer [description not available]	3.57	8
Metastase [description not available]	2.72	3
Breast Neoplasms Tumors or cancer of the human BREAST.	3.57	8
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.72	3
Insulin Sensitivity [description not available]	2.49	2
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	2.49	2
Weight Gain Increase in BODY WEIGHT over existing weight.	2.48	2
Cerebral Ischemia [description not available]	7.1	1
Brain Ischemia Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.	2.1	1
Hepatoblastoma A malignant neoplasm occurring in young children, primarily in the liver, composed of tissue resembling embryonal or fetal hepatic epithelium, or mixed epithelial and mesenchymal tissues. (Stedman, 25th ed)	2.1	1
Chronic Illness [description not available]	3.44	2
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	8.44	2
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.45	2
Skin Aging The process of aging due to changes in the structure and elasticity of the skin over time. It may be a part of physiological aging or it may be due to the effects of ultraviolet radiation, usually through exposure to sunlight.	2.11	1
Gastric Ulcer [description not available]	7.11	1
Stomach Ulcer Ulceration of the GASTRIC MUCOSA due to contact with GASTRIC JUICE. It is often associated with HELICOBACTER PYLORI infection or consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	2.11	1
Autoimmune Disease [description not available]	3.03	1
Central Nervous System Disease [description not available]	3.03	1
Diseases, Metabolic [description not available]	3.03	1
Autoimmune Diseases Disorders that are characterized by the production of antibodies that react with host tissues or immune effector cells that are autoreactive to endogenous peptides.	3.03	1
Central Nervous System Diseases Diseases of any component of the brain (including the cerebral hemispheres, diencephalon, brain stem, and cerebellum) or the spinal cord.	3.03	1
Metabolic Diseases Generic term for diseases caused by an abnormal metabolic process. It can be congenital due to inherited enzyme abnormality (METABOLISM, INBORN ERRORS) or acquired due to disease of an endocrine organ or failure of a metabolically important organ such as the liver. (Stedman, 26th ed)	3.03	1
Injury, Myocardial Reperfusion [description not available]	2.46	2
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	2.96	4
Nasopharyngeal Carcinoma A carcinoma that originates in the EPITHELIUM of the NASOPHARYNX and includes four subtypes: keratinizing squamous cell, non-keratinizing, basaloid squamous cell, and PAPILLARY ADENOCARCINOMA. It is most prevalent in Southeast Asian populations and is associated with EPSTEIN-BARR VIRUS INFECTIONS. Somatic mutations associated with this cancer have been identified in NPCR, BAP1, UBAP1, ERBB2, ERBB3, MLL2, PIK3CA, KRAS, NRAS, and ARID1A genes.	7.11	1
Cancer of Nasopharynx [description not available]	2.11	1
Nasopharyngeal Neoplasms Tumors or cancer of the NASOPHARYNX.	2.11	1
Epithelial Ovarian Cancer [description not available]	2.11	1
Epithelial Neoplasms [description not available]	2.11	1
Carcinoma, Ovarian Epithelial A malignant neoplasm that originates in cells on the surface EPITHELIUM of the ovary and is the most common form of ovarian cancer. There are five histologic subtypes: papillary serous, endometrioid, mucinous, clear cell, and transitional cell. Mutations in BRCA1, OPCML, PRKN, PIK3CA, AKT1, CTNNB1, RRAS2, and CDH1 genes are associated with this cancer.	2.11	1
Leucocythaemia [description not available]	2.5	2
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	7.5	2
Cancer of Kidney [description not available]	2.47	2
Kidney Neoplasms Tumors or cancers of the KIDNEY.	2.47	2
Vascular Diseases Pathological processes involving any of the BLOOD VESSELS in the cardiac or peripheral circulation. They include diseases of ARTERIES; VEINS; and rest of the vasculature system in the body.	2.13	1
Adenocarcinoma, Basal Cell [description not available]	2.72	3
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	7.72	3
Arteriosclerosis, Coronary [description not available]	2.08	1
Liver Steatosis [description not available]	2.08	1
Coronary Artery Disease Pathological processes of CORONARY ARTERIES that may derive from a congenital abnormality, atherosclerotic, or non-atherosclerotic cause.	2.08	1
Fatty Liver Lipid infiltration of the hepatic parenchymal cells resulting in a yellow-colored liver. The abnormal lipid accumulation is usually in the form of TRIGLYCERIDES, either as a single large droplet or multiple small droplets. Fatty liver is caused by an imbalance in the metabolism of FATTY ACIDS.	2.08	1
Carcinoma, Lewis Lung A carcinoma discovered by Dr. Margaret R. Lewis of the Wistar Institute in 1951. This tumor originated spontaneously as a carcinoma of the lung of a C57BL mouse. The tumor does not appear to be grossly hemorrhagic and the majority of the tumor tissue is a semifirm homogeneous mass. (From Cancer Chemother Rep 2 1972 Nov;(3)1:325) It is also called 3LL and LLC and is used as a transplantable malignancy.	2.72	3
Anaphylactic Reaction [description not available]	2.01	1
Anaphylaxis An acute hypersensitivity reaction due to exposure to a previously encountered ANTIGEN. The reaction may include rapidly progressing URTICARIA, respiratory distress, vascular collapse, systemic SHOCK, and death.	7.01	1
Leukemia, Acute Monocytic [description not available]	2.42	2
Malignant Melanoma [description not available]	3.63	9
Sarcoma 180 An experimental sarcoma of mice.	2.01	1
Fibrosarcoma A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)	2.42	2
Leukemia, Monocytic, Acute An acute myeloid leukemia in which 80% or more of the leukemic cells are of monocytic lineage including monoblasts, promonocytes, and MONOCYTES.	2.42	2
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	3.63	9
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	7.43	2
ATLL [description not available]	2.02	1
Leukemia-Lymphoma, Adult T-Cell Aggressive T-Cell malignancy with adult onset, caused by HUMAN T-LYMPHOTROPIC VIRUS 1. It is endemic in Japan, the Caribbean basin, Southeastern United States, Hawaii, and parts of Central and South America and sub-Saharan Africa.	2.02	1
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	2.69	3
Itching [description not available]	2.03	1
Pruritus An intense itching sensation that produces the urge to rub or scratch the skin to obtain relief.	2.03	1
Pyrexia [description not available]	1.98	1
Fever An abnormal elevation of body temperature, usually as a result of a pathologic process.	1.98	1

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Research Demand Index: 41.73

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evodiamine

Cross-References

Synonyms (50)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Drug Classes (1)

Protein Targets (9)

Potency Measurements

Inhibition Measurements

Activation Measurements

Biological Processes (43)

Molecular Functions (10)

Ceullar Components (5)

Bioassays (153)

Research

Studies (331)

Market Indicators

Research Demand Index: 41.73

Study Types

Related Drugs (180)

Related Conditions (207)