2-piperidone profile

2-Piperidone is a cyclic lactam with a wide range of applications. It is used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and polymers. It is also an important intermediate in the production of other cyclic compounds. 2-Piperidone has been studied for its potential therapeutic effects, including its ability to inhibit the growth of cancer cells. It has also been investigated for its potential use in the treatment of epilepsy and Alzheimer's disease. The compound's biological activity is attributed to its ability to interact with various receptors and enzymes in the body. 2-Piperidone is typically synthesized through the cyclization of a linear precursor, such as 5-aminovaleric acid, followed by ring closure. It is often studied for its potential pharmacological activity and its role in various chemical processes.'

2-piperidone: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

piperidin-2-one : A delta-lactam that is piperidine which is substituted by an oxo group at position 2. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	12665
CHEMBL ID	12193
CHEBI ID	77761
MeSH ID	M0127690

Synonym
valerolactam
AC-15619
wln0gqq6ek ,
unii-wln0gqq6ek
piperidone-2
EN300-24025
675-20-7
.delta.-valerolactam
2-piperidone
wln: t6nvtj
pentanoic acid, lactam
piperidon
nsc2305
2-piperidinone
nsc-2305
5-pentanolactam
valerolactim
.alpha.-piperidone
NCI60_001574
d-valerolactam
nsc-18894
nsc18894
piperidone,2-
chembl12193 ,
bdbm10
pentanoic acid, 5-amino-, lactam
piperidon [german]
alpha-piperidone
nsc 2305
einecs 211-622-9
piperidone-2 [french]
ai3-33342
nsc 18894
delta-valerolactam
inchi=1/c5h9no/c7-5-3-1-2-4-6-5/h1-4h2,(h,6,7
piperidin-2-one
delta-valerolactam, 98%
piperidinone
chebi:77761 ,
P0455
2-azacyclohexanone
piperidin-2-one;2-piperidone
A9047
piperidone
AKOS005206867
piperidones
27154-43-4
STL281850
FT-0613368
AM20100626
2-oxopiperidine
piperidine-2-one
piperadine-2-one
2-piperadinone
oxopiperidine
d-valero-lactam
BBL027557
DTXSID1060976
2-oxo-piperidine
W-104710
AC-33837
mfcd00006037
?-valerolactam
F0001-1780
5-amino-lactam-pentanoic acid
5-amino-lactam-pentanoate
piperidon (german)
a-piperidone
SY011119
CS-W022933
Q4596918
BCP00878
v1l ,
ketopiperidine
5-pentanelactam
HY-W042193
F10312
SB41073
25036-00-4
delta -valerolactam
Z168817684

Excerpt	Reference	Relevance
" No compound-related adverse effects were noted in clinical signs, body weights, food consumption, clinical laboratory evaluations, neurobehavioral evaluations, neuropathology, or sperm counts."	( Inhalation toxicity of dimethyl piperidinone. Elliott, GS; Kennedy, GL; Malley, LA; O'Neill, AJ; Ross, PE, 2003)	0.32
" It was, therefore, concluded that DMPD was not selectively toxic to the rat conceptus."	( Developmental toxicity study of dimethylpiperidone. Hurtt, ME; Kennedy, GL; Munley, SM; O'Neill, AJ; Tyler, DL, 2004)	0.32
"The development of smart anticancer drugs that can selectively kill cancer cells while sparing the surrounding healthy tissues/cells is of paramount importance for safe and effective cancer therapy."	( Safe and targeted anticancer efficacy of a novel class of antioxidant-conjugated difluorodiarylidenyl piperidones: differential cytotoxicity in healthy and cancer cells. Ahmed, S; Bratasz, A; Dayton, A; Hideg, K; Kálai, T; Kuppusamy, ML; Kuppusamy, P; Rivera, BK; Selvendiran, K; Tazi, M; Tong, L, 2010)	0.36
" The incidences of adverse events were similar in all study subjects."	( A multicenter, randomized, placebo-controlled, double-blind phase II trial evaluating the optimal dose, efficacy and safety of LC 15-0444 in patients with type 2 diabetes. Bae, HY; Baik, SH; Cha, BS; Kim, DK; Kim, JA; Kim, MJ; Kim, SW; Kim, YK; Lee, HW; Lee, IK; Lee, MK; Lee, WY; Min, KW; Park, JY; Park, KS; Rhee, EJ; Yoo, SJ; Yoon, KH, 2010)	0.36
" The overall incidence rates for adverse events were similar in the gemigliptin and placebo groups."	( A multicentre, multinational, randomized, placebo-controlled, double-blind, phase 3 trial to evaluate the efficacy and safety of gemigliptin (LC15-0444) in patients with type 2 diabetes. Agarwal, PK; Baik, SH; Dharmalingam, M; Gandhi, P; Gupta, SK; Kim, DM; Kim, JA; Kim, PK; Kim, YS; Mahesh, U; Min, KW; Mohan, V; Park, JY; Pitale, SU; Shivane, VK; Sosale, A; Yang, SJ, 2013)	0.39
" The analogs 2a and 2b have submicromolar IC(50) values towards human HCT-116 colon cancer cells but are far less toxic to human non-malignant CRL-1790 colon cells."	( Mitochondrial dysfunction contributes to the cytotoxicity of some 3,5-bis(benzylidene)-4-piperidone derivatives in colon HCT-116 cells. Bandy, B; Das, U; Dimmock, JR; Helal, M; Islam, A; Nazarali, AJ, 2013)	0.39
" There was no increased risk of adverse effects with this dose of gemigliptin compared with sitagliptin 100 mg qd."	( Efficacy and safety of the dipeptidyl peptidase-4 inhibitor gemigliptin compared with sitagliptin added to ongoing metformin therapy in patients with type 2 diabetes inadequately controlled with metformin alone. Chung, CH; Jang, HC; Kim, JA; Kim, SW; Lee, WY; Min, KW; Nam-Goong, IS; Rhee, EJ; Shivane, VK; Sosale, AR, 2013)	0.39
" In vivo testing showed that HO-3867 could block xenograft tumor growth without toxic side effects."	( HO-3867, a safe STAT3 inhibitor, is selectively cytotoxic to ovarian cancer. Bid, HK; Bravo, V; Cohn, DE; Elnaggar, AC; Hideg, K; Houghton, P; Kuppusamy, P; Lata, P; Leone, G; McCann, GA; Naidu, SK; Rath, KS; Rivera, BK; Selvendiran, K; Tierney, BJ, 2014)	0.4
" Piperlonguminine was the more effective amide, showing toxic activity with LD50 of approximately 12 microg/ml against the larvae of Ae."	( Cytotoxicity of piperamides towards Aedes aegypti (Diptera: Culicidae). Ferreira, B; Guimarães, A; Kato, M; Maleck, M; Mallet, J, 2014)	0.4
"This review considers the pharmacokinetic profile, adverse effects and drug interactions of DPP-4 inhibitors."	( The pharmacokinetic considerations and adverse effects of DPP-4 inhibitors [corrected]. Athyros, VG; Elisaf, MS; Filippatos, TD, 2014)	0.4
" However, DPP-4 inhibitors have certain differences in their pharmacokinetic properties that may be associated with different clinical effects and adverse event profiles."	( The pharmacokinetic considerations and adverse effects of DPP-4 inhibitors [corrected]. Athyros, VG; Elisaf, MS; Filippatos, TD, 2014)	0.4
" The overall rates of adverse events were similar between the 2 groups."	( Comparative efficacy and safety of gemigliptin versus linagliptin in type 2 diabetes patients with renal impairment: A 40-week extension of the GUARD randomized study. Cha, DR; Han, BG; Han, SY; Jang, Y; Jeong, KH; Jo, YI; Kang, SW; Kim, B; Kim, NH; Kim, SG; Na, KR; Oh, KH; Park, HC; Park, SH; Shin, S; Yoon, SA, 2018)	0.48
" There were no significant differences in adverse events among the groups."	( Efficacy and safety of fixed-dose combination therapy with gemigliptin (50 mg) and rosuvastatin compared with monotherapy in patients with type 2 diabetes and dyslipidaemia (BALANCE): A multicentre, randomized, double-blind, controlled, phase 3 trial. Bae, JC; Cha, BS; Han, S; Hong, EG; Kim, KA; Kim, YH; Min, KW; Park, CY, 2019)	0.51
"The FDC of gemigliptin and rosuvastatin is safe and is effective in reducing both blood glucose and LDL-C levels; thus, it could be a good therapeutic choice for type 2 diabetic patients with dyslipidaemia."	( Efficacy and safety of fixed-dose combination therapy with gemigliptin (50 mg) and rosuvastatin compared with monotherapy in patients with type 2 diabetes and dyslipidaemia (BALANCE): A multicentre, randomized, double-blind, controlled, phase 3 trial. Bae, JC; Cha, BS; Han, S; Hong, EG; Kim, KA; Kim, YH; Min, KW; Park, CY, 2019)	0.51
" The aggresome pathway has been described as an escape mechanism from proteotoxicity by sequestering toxic cellular aggregates."	( Proteasome inhibitor b-AP15 induces enhanced proteotoxicity by inhibiting cytoprotective aggresome formation. Brnjic, S; D'Arcy, P; Hillert, EK; Linder, S; Mazurkiewicz, M; Mofers, A; Saei, AA; Selvaraju, K; Zhang, X; Zubarev, R, 2019)	0.51
" The incidence of overall adverse events and the number of hypoglycaemic adverse events were similar between the study groups."	( Efficacy and safety of gemigliptin as add-on therapy to insulin, with or without metformin, in patients with type 2 diabetes mellitus (ZEUS II study). Benjachareonwong, S; Chamnan, P; Cho, YM; Choi, S; Deerochanawong, C; Kang, ES; Kim, S; Kosachunhanun, N; Kwon, S; Lee, MK; Lee, WJ; Oh, T; Pratipanawatr, T; Sattanon, S; Seekaew, S; Sirirak, T; Suraamornkul, S; Suwanwalaikorn, S, 2020)	0.56
" Eighty-two patients (85%) experienced ≥1 grade 3/4 treatment-emergent adverse events (AEs), most commonly neutropenia (51%), infections (24%), anemia (12%), and febrile neutropenia (10%)."	( Avadomide monotherapy in relapsed/refractory DLBCL: safety, efficacy, and a predictive gene classifier. Bouabdallah, R; Buchholz, TJ; Carpio, C; Carrancio, S; Cordoba, R; Couto, S; Damian, S; Gandhi, AK; Gharibo, M; Hagner, PR; Hege, K; Lopez-Martin, JA; Martin, A; Panizo, C; Pinto, A; Pourdehnad, M; Rasco, D; Ribrag, V; Risueño, A; Salar, A; Salles, G; Sancho, JM; Santoro, A; Schmitz, F; Trotter, MWB; Van den Neste, E; Verhoef, G; Wang, M; Wang, X; Wei, X; Weng, A; Ysebaert, L, 2020)	0.56
" The results established different antiproliferative efficacy of the L-2663 and HO-4589 compounds, with a targeted action on cancer cells while being less toxic to noncancerous cells."	( Selective Induction of Cellular Toxicity and Anti-tumor Efficacy by N-Methylpiperazinyl Diarylidenylpiperidone and its Pro-nitroxide Conjugate through ROS-mediated Mitochondrial Dysfunction and G2/M Cell-cycle Arrest in Human Pancreatic Cancer. Axelrod, K; Bognár, B; Hinds, JW; Kálai, T; Kmiec, MM; Kuppusamy, ML; Kuppusamy, P; Mast, JM; Tse, D, 2020)	0.56
" The secondary outcomes were alterations in glucose, glycaemic targets, lipids, insulin resistance, and adverse events."	( Efficacy and Safety of the Novel Dipeptidyl Peptidase-4 Inhibitor Gemigliptin in the Management of Type 2 Diabetes: A Meta-Analysis. Agarwal, A; Dutta, D; Khandelwal, D; Maisnam, I; Sharma, M; Singla, R, 2021)	0.62
" Unfortunately, the drugs used in cancer chemotherapy are toxic to both neoplasms and normal tissues, while many available medications have low potencies."	( 1-[4-(2-Dimethylaminoethoxy)phenylcarbonyl]-3,5-Bis(3,4,5-Trimethoxybenzylidene)- 4-Piperidone Hydrochloride and Related Compounds: Potent Cytotoxins Demonstrate Greater Toxicity to Neoplasms than Non- Malignant Cells. Das, U; Dimmock, JR; Okudaira, N; Roayapalley, PK; Sakagami, H; Sharma, RK, 2022)	0.72

Excerpt	Reference	Relevance
" Mean (+/- SD) values for the half-life (9."	( Pharmacokinetics of methyprylon following a single oral dose. Gwilt, PR; Pankaskie, MC; Shoenthal, DR; Thornburg, JE; Zustiak, R, 1985)	0.27
" In this project, we studied the in vivo pharmacokinetic behavior and anti-tumor efficacy of this novel compound."	( A novel hydroxamic acid compound, BMD188, demonstrates anti-prostate cancer effects by inducing apoptosis. II: In vivo efficacy and pharmacokinetic studies. Crissman, JD; Honn, KV; Johnson, CR; Joshi, B; Li, L; Marnett, LJ; Porter, AT; Tang, DG; Zhang, C; Zhu, Z, )	0.13
"The aim of this study was to investigate the pharmacokinetic (PK), pharmacodynamic (PD), and tolerability profiles of a single dose of LC15-0444 in healthy male subjects."	( Pharmacokinetics, pharmacodynamics, and tolerability of the dipeptidyl peptidase IV inhibitor LC15-0444 in healthy Korean men: a dose-block-randomized, double-blind, placebo-controlled, ascending single-dose, Phase I study. Cho, JY; Choi, YJ; Hong, JH; Hwang, DM; Jang, IJ; Kim, JA; Kim, JR; Kim, KP; Kwon, OH; Lim, KS; Shin, HS; Shin, KH; Shin, SG; Yu, KS, 2008)	0.35
" * LC15-0444 possesses pharmacokinetic and pharmacodynamic characteristics that support a once-daily dosing regimen."	( Pharmacokinetics and pharmacodynamics of LC15-0444, a novel dipeptidyl peptidase IV inhibitor, after multiple dosing in healthy volunteers. Cho, JY; Jang, IJ; Kim, BH; Kim, DK; Kim, HS; Kim, JR; Kim, SH; Lee, SH; Lim, KS; Shin, SG; Yim, HJ; Yu, KS, 2009)	0.35
" The aim was to investigate the pharmacokinetic (PK) and pharmacodynamic (PD) profiles after multiple oral ascending doses of LC15-0444 in healthy male subjects."	( Pharmacokinetics and pharmacodynamics of LC15-0444, a novel dipeptidyl peptidase IV inhibitor, after multiple dosing in healthy volunteers. Cho, JY; Jang, IJ; Kim, BH; Kim, DK; Kim, HS; Kim, JR; Kim, SH; Lee, SH; Lim, KS; Shin, SG; Yim, HJ; Yu, KS, 2009)	0.35
" Mean elimination half-life was in a range 16."	( Pharmacokinetics and pharmacodynamics of LC15-0444, a novel dipeptidyl peptidase IV inhibitor, after multiple dosing in healthy volunteers. Cho, JY; Jang, IJ; Kim, BH; Kim, DK; Kim, HS; Kim, JR; Kim, SH; Lee, SH; Lim, KS; Shin, SG; Yim, HJ; Yu, KS, 2009)	0.35
"The effects of multiple oral doses of ketoconazole (a potent CYP3A4 inhibitor) and multiple oral doses of rifampicin (a potent CYP3A4 inducer) on the pharmacokinetic properties of a single oral dose of gemigliptin were evaluated in fasting healthy male Korean volunteers."	( Effects of ketoconazole and rifampicin on the pharmacokinetics of gemigliptin, a dipeptidyl peptidase-IV inhibitor: a crossover drug-drug interaction study in healthy male Korean volunteers. Bae, KS; Choi, HY; Jin, SJ; Kim, MJ; Kim, YH; Lim, HS; Noh, YH; Sung, HR, 2012)	0.38
" Pharmacokinetic parameters were estimated via noncompartmental methods."	( Effects of ketoconazole and rifampicin on the pharmacokinetics of gemigliptin, a dipeptidyl peptidase-IV inhibitor: a crossover drug-drug interaction study in healthy male Korean volunteers. Bae, KS; Choi, HY; Jin, SJ; Kim, MJ; Kim, YH; Lim, HS; Noh, YH; Sung, HR, 2012)	0.38
" This study was conducted to investigate the effects of food on the pharmacokinetic (PK) profile of the FDC tablets."	( Effects of food on the pharmacokinetics of gemigliptin/metformin sustained-release 50/1,000 mg (25/500 mg x 2 tablets) fixeddose combination tablet in healthy male volunteers. Bae, KS; Choi, HY; Kim, B; Kim, JA; Kim, MJ; Kim, YH; Lee, SH; Lim, HS; Noh, YH, 2014)	0.4
" This study evaluated possible pharmacodynamic and pharmacokinetic interactions between gemigliptin and metformin and investigated their tolerability."	( Pharmacokinetic and pharmacodynamic interaction between gemigliptin and metformin in healthy subjects. Ahn, JY; Cho, JY; Cho, YM; Jang, IJ; Kim, JA; Lee, H; Lee, S; Lim, KS; Shin, D; Yu, KS, 2014)	0.4
" Blood samples were drawn over 24 h on the seventh day of each period for pharmacokinetic and pharmacodynamic evaluations, including plasma DPP-4 activity and total/active glucagon-like peptide-1 (GLP-1) levels."	( Pharmacokinetic and pharmacodynamic interaction between gemigliptin and metformin in healthy subjects. Ahn, JY; Cho, JY; Cho, YM; Jang, IJ; Kim, JA; Lee, H; Lee, S; Lim, KS; Shin, D; Yu, KS, 2014)	0.4
"Coadministration of gemigliptin and metformin showed beneficial anti-diabetic effects without pharmacokinetic drug-drug interactions."	( Pharmacokinetic and pharmacodynamic interaction between gemigliptin and metformin in healthy subjects. Ahn, JY; Cho, JY; Cho, YM; Jang, IJ; Kim, JA; Lee, H; Lee, S; Lim, KS; Shin, D; Yu, KS, 2014)	0.4
"21-fold) increase of mean area under the time-plasma concentration curve from 0 to infinity (AUCinf) [maximum plasma concentration (Cmax)] of gemigliptin, respectively."	( Effect of renal impairment and haemodialysis on the pharmacokinetics of gemigliptin (LC15-0444). Kim, EY; Kim, N; Kim, YH; Lee, SH; Oh, MK; Park, SJ; Shin, JG; Shon, JH, 2014)	0.4
"This review considers the pharmacokinetic profile, adverse effects and drug interactions of DPP-4 inhibitors."	( The pharmacokinetic considerations and adverse effects of DPP-4 inhibitors [corrected]. Athyros, VG; Elisaf, MS; Filippatos, TD, 2014)	0.4
" However, DPP-4 inhibitors have certain differences in their pharmacokinetic properties that may be associated with different clinical effects and adverse event profiles."	( The pharmacokinetic considerations and adverse effects of DPP-4 inhibitors [corrected]. Athyros, VG; Elisaf, MS; Filippatos, TD, 2014)	0.4
" The terminal elimination half-life and plasma clearance values were 73."	( Mouse pharmacokinetics and metabolism of the curcumin analog, 4-piperidinone,3,5-bis[(2-fluorophenyl)methylene]-acetate(3E,5E) (EF-24; NSC 716993). Ames, MM; Buhrow, SA; Gilbert, JA; Jia, L; Reid, JM; Shoji, M; Snyder, JP, 2014)	0.4
"Gemigliptin and glimepiride did not alter the pharmacokinetic properties of each other when they were co-administered in healthy volunteers, and were generally tolerated."	( Evaluation of pharmacokinetic drug interactions between gemigliptin (dipeptidylpeptidase-4 inhibitor) and glimepiride (sulfonylurea) in healthy volunteers. Bae, KS; Bang, K; Choi, HY; Han, S; Kim, MJ; Kim, YH; Lee, SH; Lim, HS, 2014)	0.4
"The primary PK parameters - Cmax and AUCτ - were compared to the geometric mean ratios (GMRs) and 90% confidence intervals (90% CIs) that were determined for the combination therapies and monotherapies."	( Evaluation of the pharmacokinetics of the DPP-4 inhibitor gemigliptin when coadministered with rosuvastatin or irbesartan to healthy subjects. Bae, KS; Choi, HY; Jeon, HS; Jung, JH; Kim, HJ; Kim, MJ; Kim, YH; Lee, SH; Lee, YK; Lim, HS, 2015)	0.42
" The objective of the study reported here was to compare the pharmacodynamic (PD), pharmacokinetic (PK), and tolerability profiles of gemigliptin and extended-release metformin (metformin XR) between FDC and separate tablets."	( A fixed-dose combination tablet of gemigliptin and metformin sustained release has comparable pharmacodynamic, pharmacokinetic, and tolerability profiles to separate tablets in healthy subjects. Jang, IJ; Jung, JH; Kim, JA; Lee, H; Lim, KS; Oh, J; Park, SI; Yu, KS, 2015)	0.42
" The objectives of the investigations reported in this article were to characterize the pharmacokinetic and drug metabolism properties of AMG 232 in pre-clinical species in vivo and in vitro, and in humans in vitro, and to predict its pharmacokinetics in humans through integrating PKDM data."	( Pharmacokinetics and metabolism of AMG 232, a novel orally bioavailable inhibitor of the MDM2-p53 interaction, in rats, dogs and monkeys: in vitro-in vivo correlation. Huang, WT; Jiang, M; Jin, L; Ling, Y; Olson, SH; Sun, D; Wong, BK; Xu, G; Yan, X; Ye, Q, 2015)	0.42
"The aim of this study was to assess the pharmacokinetic interactions between a newly developed dipeptidyl peptidase (DPP)-4 inhibitor, gemigliptin, and metformin in healthy Mexican male volunteers, and the differences in the pharmacokinetic profile of gemigliptin between Korean and Mexican healthy volunteers."	( Pharmacokinetic Interactions Between Gemigliptin and Metformin, and Potential Differences in the Pharmacokinetic Profile of Gemigliptin Between the Mexican and Korean Populations: A Randomized, Open-label Study in Healthy Mexican Volunteers. Conde-Carmona, I; García-Medina, S; Jiménez-Vargas, JM; Lee, SH; Martínez-Muñoz, A, 2018)	0.48
" Subjects were randomized to 1 of 3 treatment sequences and received gemigliptin 50mg once a day, metformin1000mg BID, or both drugs during a 7-day treatment period, and underwent sampling for pharmacokinetic analysis and tolerability assessments."	( Pharmacokinetic Interactions Between Gemigliptin and Metformin, and Potential Differences in the Pharmacokinetic Profile of Gemigliptin Between the Mexican and Korean Populations: A Randomized, Open-label Study in Healthy Mexican Volunteers. Conde-Carmona, I; García-Medina, S; Jiménez-Vargas, JM; Lee, SH; Martínez-Muñoz, A, 2018)	0.48
" Considering the flat effect-concentration curve and wide therapeutic range of gemigliptin, the pharmacokinetic profile of gemigliptin observed in healthy Mexican and Korean subjects suggests that gemigliptin use in Mexican patients may be associated with outcomes, in terms of efficacy and tolerability, similar to those observed in the Korean population."	( Pharmacokinetic Interactions Between Gemigliptin and Metformin, and Potential Differences in the Pharmacokinetic Profile of Gemigliptin Between the Mexican and Korean Populations: A Randomized, Open-label Study in Healthy Mexican Volunteers. Conde-Carmona, I; García-Medina, S; Jiménez-Vargas, JM; Lee, SH; Martínez-Muñoz, A, 2018)	0.48
" The aim of this study was to assess the pharmacokinetic equivalence of the high dose of the FDC tablet (gemigliptin/metformin sustained release [SR] 50/1,000 mg) and a corresponding co-administered dose of individual tablets."	( Pharmacokinetic Equivalence of the High Dose Strength Fixed-Dose Combination Tablet of Gemigliptin/Metformin Sustained Release (SR) and Individual Component Gemigliptin and Metformin XR Tablets in Healthy Subjects. Bae, KS; Cho, YS; Lee, SH; Lim, HS, 2018)	0.48
"FDC tablet exhibited pharmacokinetic equivalence and comparable safety and tolerability to co-administration of corresponding doses of gemigliptin and metformin XR as individual tablets."	( Pharmacokinetic Equivalence of the High Dose Strength Fixed-Dose Combination Tablet of Gemigliptin/Metformin Sustained Release (SR) and Individual Component Gemigliptin and Metformin XR Tablets in Healthy Subjects. Bae, KS; Cho, YS; Lee, SH; Lim, HS, 2018)	0.48
" Pharmacokinetic parameters were derived using a noncompartmental method."	( Pharmacokinetic comparison of gemigliptin 50 mg and metformin 500 mg as a fixed-dose combination and loose combination . Chung, JY; Lee, S; Lee, SW; Park, SI; Yu, KS, 2019)	0.51

Excerpt	Reference	Relevance
" These effects were also observed in vivo, where the combination with piplartine but not piperine with 5-FU led to a higher tumor growth inhibition."	( In vitro and in vivo antitumor effect of 5-FU combined with piplartine and piperine. Alves, AP; Bezerra, DP; Costa-Lotufo, LV; de Alencar, NM; de Castro, FO; de Moraes, MO; Elmiro, FJ; Lima, MA; Lima, MW; Mesquita, RO; Pessoa, C; Silveira, ER, 2008)	0.35
"In this open-label, 2-part, 3-treatment, 1-sequence, 2-period crossover drug-drug interaction study, 1 group of subjects received a single 50-mg oral dose of gemigliptin on 2 separate occasions-once as monotherapy and again after pretreatment with 400 mg of oral ketoconazole once daily for 7 days."	( Effects of ketoconazole and rifampicin on the pharmacokinetics of gemigliptin, a dipeptidyl peptidase-IV inhibitor: a crossover drug-drug interaction study in healthy male Korean volunteers. Bae, KS; Choi, HY; Jin, SJ; Kim, MJ; Kim, YH; Lim, HS; Noh, YH; Sung, HR, 2012)	0.38
" These findings suggest that gemigliptin may require a dose adjustment when concurrently administered with drugs that alter CYP3A4 activity."	( Effects of ketoconazole and rifampicin on the pharmacokinetics of gemigliptin, a dipeptidyl peptidase-IV inhibitor: a crossover drug-drug interaction study in healthy male Korean volunteers. Bae, KS; Choi, HY; Jin, SJ; Kim, MJ; Kim, YH; Lim, HS; Noh, YH; Sung, HR, 2012)	0.38
" Sulfonylureas are commonly used in combination with other antidiabetic drugs to improve glycemic control."	( Evaluation of pharmacokinetic drug interactions between gemigliptin (dipeptidylpeptidase-4 inhibitor) and glimepiride (sulfonylurea) in healthy volunteers. Bae, KS; Bang, K; Choi, HY; Han, S; Kim, MJ; Kim, YH; Lee, SH; Lim, HS, 2014)	0.4
"The effect of the dipeptidyl peptidase-IV inhibitor gemigliptin alone or in combination with the heat shock protein 90 inhibitor NVP-AUY922 (AUY922) on survival of thyroid carcinoma cells was elucidated."	( The dipeptidyl peptidase-IV inhibitor gemigliptin alone or in combination with NVP-AUY922 has a cytotoxic activity in thyroid carcinoma cells. Choi, MG; Ihm, SH; Kang, JG; Kim, CS; Kim, SH; Lee, SJ; Yoo, HJ, 2017)	0.46
" The efficacy of EF24 alone or combined with mitotane (reference drug for adrenocortical cancer) was evaluated in two adrenocortical tumor cell lines, SW13 and H295R."	( Biological Effects of EF24, a Curcumin Derivative, Alone or Combined with Mitotane in Adrenocortical Tumor Cell Lines. Armanini, D; Barollo, S; Bertazza, L; Faccio, I; Mari, ME; Mian, C; Pezzani, R; Redaelli, M; Rubin, B; Zorzan, M, 2019)	0.51
" Furthermore, Wnt/β-catenin, NF-κB, MAPK, and PI3k/Akt pathways were modulated by Western blot analysis when treating cells with EF24 alone or combined with mitotane."	( Biological Effects of EF24, a Curcumin Derivative, Alone or Combined with Mitotane in Adrenocortical Tumor Cell Lines. Armanini, D; Barollo, S; Bertazza, L; Faccio, I; Mari, ME; Mian, C; Pezzani, R; Redaelli, M; Rubin, B; Zorzan, M, 2019)	0.51
" Consequently, the potential of iberdomide as a victim of drug-drug interactions (DDI) was evaluated in a clinical study with healthy subjects."	( Evaluation of iberdomide and cytochrome p450 drug-drug interaction potential in vitro and in a phase 1 study in healthy subjects. Atsriku, C; Gaudy, A; Liu, L; MacGorman, K; Palmisano, M; Surapaneni, S; Xue, Y; Ye, Y, 2021)	0.62
"6 mg) and when administered with the CYP3A and P-gp inhibitor itraconazole (200 mg twice daily on day 1 and 200 once daily on days 2 through 9)."	( Evaluation of iberdomide and cytochrome p450 drug-drug interaction potential in vitro and in a phase 1 study in healthy subjects. Atsriku, C; Gaudy, A; Liu, L; MacGorman, K; Palmisano, M; Surapaneni, S; Xue, Y; Ye, Y, 2021)	0.62
" Curcumin reduces cell viability of renal cell carcinoma (RCC) cells when combined with TNF-related apoptosis-inducing ligand (TRAIL), a cytokine that specifically targets cancer cells, by helping overcome TRAIL resistance."	( Effects of Curcumin Analogues DMC and EF24 in Combination with the Cytokine TRAIL against Kidney Cancer. Cassidy, H; Ibáñez Gaspar, V; McCaul, J; McMorrow, T; Slattery, C, 2021)	0.62
"This study test was designed to investigate the possible modulatory effect of rapamycin combined with HO-3867 in monocrotaline(MCT)-induced pulmonary arterial hypertension in rats."	( The therapeutic effect and mechanism of Rapamycin combined with HO-3867 on monocrotaline-induced pulmonary hypertension in rats. Chen, W; Chen, Z; Cheng, S; Hu, S; Li, H; Ouyang, M; Peng, H; Xue, J; Yu, S; Zeng, W; Zhang, Y; Zhou, L, 2022)	0.72
" AMG 232 PK exposures were not altered when AMG 232 was combined with T±D."	( Targeting wild-type TP53 using AMG 232 in combination with MAPK inhibition in Metastatic Melanoma; a phase 1 study. Flaherty, KT; Henary, HA; Johnson, DB; Lewis, KD; Long, GV; Moschos, SJ; Puzanov, I; Sandhu, S; Sullivan, RJ; Upreti, VV; Wong, H, 2022)	0.72

Excerpt	Reference	Relevance
" The bioavailability of A10 capsules was determined with tritium-labelled A10 in rabbits."	( Studies of the release rate and bioavailability of antineoplaston A10 capsule. Wang, H; Xu, W; Yuan, Y, 1990)	0.28
" Plasma concentration-time data were fitted to a two-compartment model with either first-order absorption, zero-order absorption, or two consecutive, discontinuous, first-order absorption rate constants."	( Pharmacokinetics of methyprylon following a single oral dose. Gwilt, PR; Pankaskie, MC; Shoenthal, DR; Thornburg, JE; Zustiak, R, 1985)	0.27
" In addition, curcumin's low bioavailability and efficacy profile in vivo further hinders its clinical development."	( EF24, a novel curcumin analog, disrupts the microtubule cytoskeleton and inhibits HIF-1. Giannakakou, P; Hamel, E; Liotta, D; Malik, S; Snyder, JP; Thomas, SL; Zhong, D; Zhou, W, 2008)	0.35
" Systematic optimization of different positions (P', P3, and P1) of the inhibitor resulted in the identification of the lead compound 46, which had an excellent potency (K(i)* = 4 nM, EC(90) = 30 nM) and good pharmacokinetic profile (22% and 35% bioavailability in rats and dogs, respectively)."	( Second-generation highly potent and selective inhibitors of the hepatitis C virus NS3 serine protease. Arasappan, A; Bennett, F; Blackman, ML; Bogen, SL; Chen, KX; Cheng, KC; Nair, L; Njoroge, FG; Padilla, AI; Pan, W; Prongay, A; Shih, NY; Tong, X; Venkatraman, S; Vibulbhan, B; Yang, W, 2009)	0.35
" Finally, (18)F-radiolabeled PAC and curcumin were produced to study their bioavailability and tissue biodistribution in mice."	( PAC, a novel curcumin analogue, has anti-breast cancer properties with higher efficiency on ER-negative cells. Aboussekhra, A; Al-Haza'a, A; Al-Hujaily, EM; Al-Hussein, K; Al-Jammaz, I; Al-Otaibi, B; Al-Sharif, I; Manogaran, PS; Mohamed, AG; Youssef, KM, 2011)	0.37
"The synthetic compound 3,5-bis(2-flurobenzylidene)piperidin-4-one (EF24) is a potent analog of curcumin that exhibits enhanced biological activity and bioavailability without increasing toxicity."	( In vivo and in vitro suppression of hepatocellular carcinoma by EF24, a curcumin analog. Han, T; Liang, Y; Liu, H; Liu, L; Pan, S; Song, R; Tian, L; Wang, L, 2012)	0.38
" This compound is selectively cytotoxic against cancer cells by induction of oxidative stress, induces genotoxicity, as an alternative strategy to killing tumor cells, has excellent oral bioavailability in mice, inhibits tumor growth in mice, and presents only weak systemic toxicity."	( Overview of the therapeutic potential of piplartine (piperlongumine). Bezerra, DP; Costa-Lotufo, LV; de Moraes, MO; Pessoa, C; Saker-Neto, N; Silveira, ER, 2013)	0.39
" Salts (II) and (III) possess increased aqueous solubility compared with the original API and thus enhance the bioavailability of the API."	( Supramolecular synthesis based on piperidone derivatives and pharmaceutically acceptable co-formers. Draguta, S; Khrustalev, VN; Kinnibrugh, TL; Sandhu, B; Timofeeva, TV, 2013)	0.39
" However, since systemic absorption and bioavailability of curcumin from gastrointestinal tract is considerably poor, synthetic curcuminoids are being developed as better alternatives."	( Antibacterial activity of synthetic curcumin derivatives: 3,5-bis(benzylidene)-4-piperidone (EF24) and EF24-dimer linked via diethylenetriaminepentacetic acid (EF2DTPA). Awasthi, S; Awasthi, V; King, C; Lagisetty, P; Vilekar, P, 2014)	0.4
" Pharmacologic analysis revealed greater bioabsorption and bioavailability of the active (cytotoxic) metabolites in cancer cells compared with normal cells."	( HO-3867, a safe STAT3 inhibitor, is selectively cytotoxic to ovarian cancer. Bid, HK; Bravo, V; Cohn, DE; Elnaggar, AC; Hideg, K; Houghton, P; Kuppusamy, P; Lata, P; Leone, G; McCann, GA; Naidu, SK; Rath, KS; Rivera, BK; Selvendiran, K; Tierney, BJ, 2014)	0.4
" The (14)C-labeled gemigliptin was rapidly absorbed after oral administration, and its bioavailability was 95."	( Absorption, distribution, metabolism and excretion of gemigliptin, a novel dipeptidyl peptidase IV inhibitor, in rats. Kim, DH; Kim, IS; Kim, U; Kim, Y; Lee, J; Lee, SH; Yoo, HH, 2014)	0.4
"25 × Qh) and moderate to high oral bioavailability in mice, rats and monkeys (>42%), but high clearance (0."	( Pharmacokinetics and metabolism of AMG 232, a novel orally bioavailable inhibitor of the MDM2-p53 interaction, in rats, dogs and monkeys: in vitro-in vivo correlation. Huang, WT; Jiang, M; Jin, L; Ling, Y; Olson, SH; Sun, D; Wong, BK; Xu, G; Yan, X; Ye, Q, 2015)	0.42
"5-fold increase in oral bioavailability as compared to free PL."	( Nanoemulsion formulations for anti-cancer agent piplartine--Characterization, toxicological, pharmacokinetics and efficacy studies. Fofaria, NM; Liu, X; Qhattal, HS; Srivastava, SK, 2016)	0.43
" 3,5-bis(2-fluorobenzylidene)-4-piperidone (EF24), a novel synthetic curcumin analog, has shown promising in vitro therapeutic efficacy in various human cancer cells, but insufficient water solubility and systemic bioavailability limit its clinical application."	( A liposomal formulation of the synthetic curcumin analog EF24 (Lipo-EF24) inhibits pancreatic cancer progression: towards future combination therapies. Bendas, G; Bisht, S; Brossart, P; Feldmann, G; Holdenrieder, S; Nolting, J; Rupp, A; Schlesinger, M; Schubert, R; Wenzel, J, 2016)	0.43
"We report herein the discovery of exceptionally potent and orally bioavailable PROTAC AR degraders with ARD-2585 being the most promising compound."	( Discovery of ARD-2585 as an Exceptionally Potent and Orally Active PROTAC Degrader of Androgen Receptor for the Treatment of Advanced Prostate Cancer. Han, X; He, M; Kirchhoff, PD; Matvekas, A; McEachern, D; Metwally, H; Miao, B; Qin, C; Sun, D; Wang, L; Wang, S; Wang, Y; Wen, B; Xiang, W; Zhao, L, 2021)	0.62
"Curcumin has demonstrated potential cytotoxicity across various cell lines despite its poor bioavailability and rapid metabolism."	( Curcumin piperidone derivatives induce anti-proliferative and anti-migratory effects in LN-18 human glioblastoma cells. A Jamal, AR; Chan, KM; Kamaluddin, NF; Lam, KW; Rajab, NF; Razali, NSC, 2022)	0.72
" SJ6986 is a potent, selective, orally bioavailable GSPT1/2 degrader that shows broad antileukemic activity and has potential for clinical development."	( The orally bioavailable GSPT1/2 degrader SJ6986 exhibits in vivo efficacy in acute lymphoblastic leukemia. Akahane, K; Chang, Y; Chepyala, D; Fischer, M; Gao, Q; Ghate, PS; Goto, H; High, AA; Iacobucci, I; Keramatnia, F; Mishra, A; Mullighan, CG; Nishiguchi, G; Peng, J; Rankovic, Z; Yang, JJ; Yang, L, 2023)	0.91
" However, its lack of solubility, instability, and poor bioavailability are impediments to its therapeutic use."	( Diarylidene-N-Methyl-4-Piperidones and Spirobibenzopyrans as Antioxidant and Anti-Inflammatory Agents. Choudhury, AR; Farkas, ME; Golakoti, NR; Joshi, BP; Joshi, M; Kar, S; Kumar Rokkam, S; Mas-Rosario, JA, 2023)	0.91

Excerpt	Relevance	Reference
" The volume of distribution (Vd) was evaluated in the rats by intravenous dosage of 150 mg/kg of 3H-A10 dissolved in dimethyl sulfoxide."	( Pharmacokinetic study of radioactive antineoplaston A10 in rats and mice. Wang, H; Xu, W; Yuan, Y, 1990)	0.28
" In order to investigate a possible mechanism for the embryolethality, GD 11 embryos were dissected from females at 4 h after dosing of 1 mg/kg and incubated for 5 h in vitro."	( Embryotoxic effects of L-691,121, a class III antiarrhythmic agent, in rats. Ban, Y; Fujii, T; Kawana, K; Konishi, R; Manson, JM; Nakatsuka, T, 1994)	0.29
" The median duration of treatment was 6 months and the average dosage of antineoplaston A10 was 11."	( Phase II study of antineoplaston A10 and AS2-1 in patients with recurrent diffuse intrinsic brain stem glioma: a preliminary report. Axler, ML; Bestak, M; Burzynski, SR; Janicki, TJ; Jurida, GF; Khan, MI; Lewy, RI; Paszkowiak, JK; Szymkowski, BG; Weaver, RA, 2003)	0.32
" The average dosage of A10 was 10."	( Long-term survival of high-risk pediatric patients with primitive neuroectodermal tumors treated with antineoplastons A10 and AS2-1. Burzynski, SR; Dolgopolov, V; Janicki, T; Jurida, G; Khan, M; Szymkowski, B; Weaver, RA, 2005)	0.33
" In addition, doses >or=200 mg of LC15-0444 inhibited plasma DPP IV activity by >80% over a 24-hour dosing interval, and a 600-mg dose increased active glucagon-like peptide-1 levels after a standardized meal."	( Pharmacokinetics, pharmacodynamics, and tolerability of the dipeptidyl peptidase IV inhibitor LC15-0444 in healthy Korean men: a dose-block-randomized, double-blind, placebo-controlled, ascending single-dose, Phase I study. Cho, JY; Choi, YJ; Hong, JH; Hwang, DM; Jang, IJ; Kim, JA; Kim, JR; Kim, KP; Kwon, OH; Lim, KS; Shin, HS; Shin, KH; Shin, SG; Yu, KS, 2008)	0.35
" * LC15-0444 possesses pharmacokinetic and pharmacodynamic characteristics that support a once-daily dosing regimen."	( Pharmacokinetics and pharmacodynamics of LC15-0444, a novel dipeptidyl peptidase IV inhibitor, after multiple dosing in healthy volunteers. Cho, JY; Jang, IJ; Kim, BH; Kim, DK; Kim, HS; Kim, JR; Kim, SH; Lee, SH; Lim, KS; Shin, SG; Yim, HJ; Yu, KS, 2009)	0.35
" Blood and urine samples were collected up to 24 h after the first dosing and up to 72 h after the last dosing."	( Pharmacokinetics and pharmacodynamics of LC15-0444, a novel dipeptidyl peptidase IV inhibitor, after multiple dosing in healthy volunteers. Cho, JY; Jang, IJ; Kim, BH; Kim, DK; Kim, HS; Kim, JR; Kim, SH; Lee, SH; Lim, KS; Shin, SG; Yim, HJ; Yu, KS, 2009)	0.35
" LC15-0444 possesses PK and PD characteristics that support a once-daily dosing regimen."	( Pharmacokinetics and pharmacodynamics of LC15-0444, a novel dipeptidyl peptidase IV inhibitor, after multiple dosing in healthy volunteers. Cho, JY; Jang, IJ; Kim, BH; Kim, DK; Kim, HS; Kim, JR; Kim, SH; Lee, SH; Lim, KS; Shin, SG; Yim, HJ; Yu, KS, 2009)	0.35
" No dosage of LC15-0444 affected weight or waist circumference."	( A multicenter, randomized, placebo-controlled, double-blind phase II trial evaluating the optimal dose, efficacy and safety of LC 15-0444 in patients with type 2 diabetes. Bae, HY; Baik, SH; Cha, BS; Kim, DK; Kim, JA; Kim, MJ; Kim, SW; Kim, YK; Lee, HW; Lee, IK; Lee, MK; Lee, WY; Min, KW; Park, JY; Park, KS; Rhee, EJ; Yoo, SJ; Yoon, KH, 2010)	0.36
" In a human small-cell lung carcinoma (SCLC) primary xenograft model, ME and CME compounds were found to be highly potent in inhibiting overall metastasis even at the lowest dosage used (degree of inhibition: 96."	( Emergence of potent inhibitors of metastasis in lung cancer via syntheses based on migrastatin. Danishefsky, SJ; Downey, R; Lecomte, N; Moore, MA; Nagorny, P; Njardarson, JT; Ouerfelli, O; Yang, G, 2011)	0.37
" Clinical pharmacokinetic and pharmacodynamic data suggest the efficacy and once daily dosing of gemigliptin."	( Gemigliptin, a novel dipeptidyl peptidase 4 inhibitor: first new anti-diabetic drug in the history of Korean pharmaceutical industry. Kim, SH; Lee, SH; Yim, HJ, 2013)	0.39
" After oral or intraperitoneal dosing of mice, RA190 distributed to plasma and major organs except the brain and inhibited proteasome function in skin and muscle."	( A bis-benzylidine piperidone targeting proteasome ubiquitin receptor RPN13/ADRM1 as a therapy for cancer. Anchoori, RK; Chen, X; Hung, CF; Jiang, R; Karanam, B; Matsui, W; Orlowski, RZ; Peng, S; Roden, RB; Rudek, MA; Tanno, T; Walters, KJ; Wang, JW; Zhao, M, 2013)	0.39
" These results indicate that the FDC tablet can be administered in the same dosing regimen as each component, especially that of metformin sustained-release."	( Effects of food on the pharmacokinetics of gemigliptin/metformin sustained-release 50/1,000 mg (25/500 mg x 2 tablets) fixeddose combination tablet in healthy male volunteers. Bae, KS; Choi, HY; Kim, B; Kim, JA; Kim, MJ; Kim, YH; Lee, SH; Lim, HS; Noh, YH, 2014)	0.4
" Twenty-seven subjects received gemigliptin (50 mg once daily), metformin (1,000 mg twice a day), or both drugs for 7 days per dosing period."	( Pharmacokinetic and pharmacodynamic interaction between gemigliptin and metformin in healthy subjects. Ahn, JY; Cho, JY; Cho, YM; Jang, IJ; Kim, JA; Lee, H; Lee, S; Lim, KS; Shin, D; Yu, KS, 2014)	0.4
" Each subject received the following treatments (A and B) with a 7-day washout period: treatment A consisted of gemigliptin 50 mg once daily administered orally for 6 days, followed by concomitant oral dosing of glimepiride 4 mg and gemigliptin 50 mg on day 7; treatment B consisted of a single dose of glimepiride 4 mg."	( Evaluation of pharmacokinetic drug interactions between gemigliptin (dipeptidylpeptidase-4 inhibitor) and glimepiride (sulfonylurea) in healthy volunteers. Bae, KS; Bang, K; Choi, HY; Han, S; Kim, MJ; Kim, YH; Lee, SH; Lim, HS, 2014)	0.4
" Each drug was administered as part of once daily, 7 day, repeated dosing regimens with a 14 day washout period."	( Evaluation of the pharmacokinetics of the DPP-4 inhibitor gemigliptin when coadministered with rosuvastatin or irbesartan to healthy subjects. Bae, KS; Choi, HY; Jeon, HS; Jung, JH; Kim, HJ; Kim, MJ; Kim, YH; Lee, SH; Lee, YK; Lim, HS, 2015)	0.42
" However, monotherapy with rapamycin at safe dosage fails to induce cell apoptosis and tumor regression which has hampered its clinical application."	( Synergistic antitumor activity of rapamycin and EF24 via increasing ROS for the treatment of gastric cancer. Chen, W; Chen, X; Cui, R; Fan, X; Ji, J; Liang, G; Vinothkumar, R; Wu, F; Zhang, Q; Zhao, Z; Zou, P, 2016)	0.43
"5 mg, 28-day continuous dosing cycles)."	( A First-in-Human Study of Novel Cereblon Modulator Avadomide (CC-122) in Advanced Malignancies. Chopra, R; DiMartino, J; Gandhi, AK; Hagner, PR; Hege, K; Li, Y; Papadopoulos, KP; Pourdehnad, M; Rasco, DW; Shih, K; Wei, X, 2019)	0.51
"Gemigliptin is a potent, selective dipeptidyl peptidase (DPP)-4 inhibitor that does not require any dosage adjustment based on renal function."	( Efficacy and Safety of Gemigliptin in Post-Transplant Patients With Type 2 Diabetes Mellitus. Bae, J; Cha, BS; Cho, Y; Huh, KH; Joo, DJ; Kang, ES; Kim, MS; Kim, Y; Kim, YS; Lee, BW; Lee, JY; Lee, M; Lee, YH, 2019)	0.51
" Safety was evaluated by examining its influence on immunosuppressive treatment, as determined by the blood trough level and dosage of calcineurin inhibitors, as well as changes in parameters related to liver and renal function."	( Efficacy and Safety of Gemigliptin in Post-Transplant Patients With Type 2 Diabetes Mellitus. Bae, J; Cha, BS; Cho, Y; Huh, KH; Joo, DJ; Kang, ES; Kim, MS; Kim, Y; Kim, YS; Lee, BW; Lee, JY; Lee, M; Lee, YH, 2019)	0.51
" The dosage of immunosuppressants was also stable."	( Efficacy and Safety of Gemigliptin in Post-Transplant Patients With Type 2 Diabetes Mellitus. Bae, J; Cha, BS; Cho, Y; Huh, KH; Joo, DJ; Kang, ES; Kim, MS; Kim, Y; Kim, YS; Lee, BW; Lee, JY; Lee, M; Lee, YH, 2019)	0.51
" Serial blood samples were collected up to 72 hrs after dosing to measure plasma concentrations of gemigliptin, its active metabolite LC15-0636, and rosuvastatin for PK assessment, and DPP-4 activity for PD assessment."	( A Fixed-Dose Combination Of Gemigliptin And Rosuvastatin Exhibits Similar Pharmacokinetics, Pharmacodynamics, And Safety Compared To That Of A Loose Combination In Healthy Subjects. Jang, IJ; Kim, E; Lee, S; Park, KR; Yu, KS, 2019)	0.51
" For PK and PD analyses, serial blood samples were collected up to 72 hours after dosing to determine plasma concentrations of gemigliptin, its active metabolite LC15-0636 and rosuvastatin, and plasma dipeptidyl peptidase-4 (DPP-4) activity."	( Pharmacokinetic and Pharmacodynamic Comparison of Two Formulations of a Fixed-Dose Combination of Gemigliptin/Rosuvastatin 50/20 mg: A Randomized, Open-Label, Single-Dose, Two-Way Crossover Study. Jang, IJ; Lee, S; Yang, E; Yoo, H; Yu, KS, 2021)	0.62
" Dose-response relationships existed between the exposure concentrations of target heavy metals and the production of indigoidine."	( Indigoidine biosynthesis triggered by the heavy metal-responsive transcription regulator: a visual whole-cell biosensor. Chen, YT; Guo, Y; Hui, CY; Li, LM; Liu, L; Yi, J; Zhang, NX, 2021)	0.62
" Intermittent dosing schedules supported by preclinical data provide a strategy to reduce frequency and severity of neutropenia; however, the identification of optimal dosing schedules remains a clinical challenge."	( Quantitative Systems Pharmacology Modeling of Avadomide-Induced Neutropenia Enables Virtual Clinical Dose and Schedule Finding Studies. Abbiati, RA; Carrancio, S; Kasibhatla, S; Loos, R; McConnell, M; Pierce, DW; Pourdehnad, M; Ratushny, AV; Santini, CC; Trotter, MWB, 2021)	0.62

Role	Description
EC 1.2.1.88 (L-glutamate gamma-semialdehyde dehydrogenase) inhibitor	An EC 1.2.1.* (oxidoreductase acting on donor aldehyde/oxo group with NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of L-glutamate gamma-semialdehyde dehydrogenase (EC 1.2.1.88).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
piperidones
delta-lactam	A lactam in which the amide bond is contained within a six-membered ring, which includes the amide nitrogen and the carbonyl carbon.
[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	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Alcohol dehydrogenase E chain	Equus caballus (horse)	Ki	13,000.0000	0.1412	2.8927	8.7000	AID33720
Alcohol dehydrogenase S chain	Equus caballus (horse)	Ki	13,000.0000	0.1412	2.8927	8.7000	AID33720
[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)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
protein folding	Peptidyl-prolyl cis-trans isomerase FKBP5	Homo sapiens (human)
response to bacterium	Peptidyl-prolyl cis-trans isomerase FKBP5	Homo sapiens (human)
chaperone-mediated protein folding	Peptidyl-prolyl cis-trans isomerase FKBP5	Homo sapiens (human)
protein peptidyl-prolyl isomerization	Peptidyl-prolyl cis-trans isomerase FKBP5	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
peptidyl-prolyl cis-trans isomerase activity	Peptidyl-prolyl cis-trans isomerase FKBP5	Homo sapiens (human)
protein binding	Peptidyl-prolyl cis-trans isomerase FKBP5	Homo sapiens (human)
FK506 binding	Peptidyl-prolyl cis-trans isomerase FKBP5	Homo sapiens (human)
protein-macromolecule adaptor activity	Peptidyl-prolyl cis-trans isomerase FKBP5	Homo sapiens (human)
heat shock protein binding	Peptidyl-prolyl cis-trans isomerase FKBP5	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
cytoplasm	Peptidyl-prolyl cis-trans isomerase FKBP5	Homo sapiens (human)
nucleoplasm	Peptidyl-prolyl cis-trans isomerase FKBP5	Homo sapiens (human)
cytosol	Peptidyl-prolyl cis-trans isomerase FKBP5	Homo sapiens (human)
membrane	Peptidyl-prolyl cis-trans isomerase FKBP5	Homo sapiens (human)
extracellular exosome	Peptidyl-prolyl cis-trans isomerase FKBP5	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID70688	Percentage of benzidine-positive murine erythroleukemia cells on day 6.	1981	Journal of medicinal chemistry, Sep, Volume: 24, Issue:9	Induction of differentiation of leukemia cells in vitro by N-substituted amides, lactams, and 2-pyridones.
AID71833	Ability to displace radioligand [35S]TBPS from Gamma-aminobutyric acid A receptor binding site in rat brain membranes	1997	Journal of medicinal chemistry, Jan-03, Volume: 40, Issue:1	Synthesis and anticonvulsant activities of 3,3-dialkyl- and 3-alkyl-3-benzyl-2-piperidinones (delta-valerolactams) and hexahydro-2H-azepin-2-ones (epsilon-caprolactams).
AID28468	Compound was evaluated for rate of hydrolysis expressed in hours at a pH of 12.	2000	Journal of medicinal chemistry, Nov-02, Volume: 43, Issue:22	Hydrolytic stability versus ring size in lactams: implications for the development of lactam antibiotics and other serine protease inhibitors.
AID113779	Anticonvulsant activity expressed as dose at which 50% of the mice were protected from tonic hindlimb seizures induced by maximal electroshock (MES)	1997	Journal of medicinal chemistry, Jan-03, Volume: 40, Issue:1	Synthesis and anticonvulsant activities of 3,3-dialkyl- and 3-alkyl-3-benzyl-2-piperidinones (delta-valerolactams) and hexahydro-2H-azepin-2-ones (epsilon-caprolactams).
AID1649765	Binding affinity to 15N-labeled FKBP51 (1 to 140 residues) (unknown origin) expressed in Escherichia coli OD2N assessed as induction of chemical shift perturbations at Leu81, Gly82, Gln85, Ile87, Ala89, Trp90, Asp91, Met97, and Glu110 residues by two-dime	2020	Journal of medicinal chemistry, 06-11, Volume: 63, Issue:11	Hybrid Screening Approach for Very Small Fragments: X-ray and Computational Screening on FKBP51.
AID25749	Compound was evaluated for the second order hydrolysis rate constant	2000	Journal of medicinal chemistry, Nov-02, Volume: 43, Issue:22	Hydrolytic stability versus ring size in lactams: implications for the development of lactam antibiotics and other serine protease inhibitors.
AID70689	Cell growth was measured on day 3, after murine erythroleukemia cells were exposed at a cell concentration of 1*10e5 cells/mL.	1981	Journal of medicinal chemistry, Sep, Volume: 24, Issue:9	Induction of differentiation of leukemia cells in vitro by N-substituted amides, lactams, and 2-pyridones.
AID212342	Neurotoxicity was evaluated by a rotarod test	1997	Journal of medicinal chemistry, Jan-03, Volume: 40, Issue:1	Synthesis and anticonvulsant activities of 3,3-dialkyl- and 3-alkyl-3-benzyl-2-piperidinones (delta-valerolactams) and hexahydro-2H-azepin-2-ones (epsilon-caprolactams).
AID70690	Cell growth was measured on day 6 after murine erythroleukemia cells were exposed at a cell concentration of 1*10e5 cells/mL.	1981	Journal of medicinal chemistry, Sep, Volume: 24, Issue:9	Induction of differentiation of leukemia cells in vitro by N-substituted amides, lactams, and 2-pyridones.
AID113777	Anticonvulsant activity expressed as dose at which 50% of the mice were protected from clonic seizures induced by pentylenetetrazole (85 mg/Kg)	1997	Journal of medicinal chemistry, Jan-03, Volume: 40, Issue:1	Synthesis and anticonvulsant activities of 3,3-dialkyl- and 3-alkyl-3-benzyl-2-piperidinones (delta-valerolactams) and hexahydro-2H-azepin-2-ones (epsilon-caprolactams).
AID70691	Concentration producing the maximum percentage of benzidine-positive cells after 6-days of continuous exposure in murine leukemia cells.	1981	Journal of medicinal chemistry, Sep, Volume: 24, Issue:9	Induction of differentiation of leukemia cells in vitro by N-substituted amides, lactams, and 2-pyridones.
AID1649766	Binding affinity to 15N-labeled FKBP51 (1 to 140 residues) (unknown origin) expressed in Escherichia coli OD2N by two-dimensional 1H/15N HSQC NMR spectroscopy	2020	Journal of medicinal chemistry, 06-11, Volume: 63, Issue:11	Hybrid Screening Approach for Very Small Fragments: X-ray and Computational Screening on FKBP51.
AID33720	In vitro inhibition against horse liver alcohol dehydrogenase	1983	Journal of medicinal chemistry, Jun, Volume: 26, Issue:6	Inhibition by carboxamides and sulfoxides of liver alcohol dehydrogenase and ethanol metabolism.
AID15691	Calculated partition coefficient (clogP)	1995	Journal of medicinal chemistry, Jan-06, Volume: 38, Issue:1	X-ray crystal structure, partitioning behavior, and molecular modeling study of piracetam-type nootropics: insights into the pharmacophore.
AID19839	Partition coefficient (logP)	1995	Journal of medicinal chemistry, Jan-06, Volume: 38, Issue:1	X-ray crystal structure, partitioning behavior, and molecular modeling study of piracetam-type nootropics: insights into the pharmacophore.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	292 (23.14)	18.7374
1990's	97 (7.69)	18.2507
2000's	245 (19.41)	29.6817
2010's	499 (39.54)	24.3611
2020's	129 (10.22)	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	65 (4.98%)	5.53%
Reviews	34 (2.61%)	6.00%
Case Studies	16 (1.23%)	4.05%
Observational	3 (0.23%)	0.25%
Other	1,187 (90.96%)	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
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	3.28	6	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
aminolevulinic acid Aminolevulinic Acid: A compound produced from succinyl-CoA and GLYCINE as an intermediate in heme synthesis. It is used as a PHOTOCHEMOTHERAPY for actinic KERATOSIS.. 5-aminolevulinic acid : The simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp.	2.07	1	0	4-oxo monocarboxylic acid; amino acid zwitterion; delta-amino acid	antineoplastic agent; dermatologic drug; Escherichia coli metabolite; human metabolite; mouse metabolite; photosensitizing agent; plant metabolite; prodrug; Saccharomyces cerevisiae metabolite
5-aminovaleric acid 5-aminovaleric acid: from red fox anal secretion; RN given refers to parent cpd. 5-aminopentanoic acid : A delta-amino acid comprising pentanoic acid with an amino substituent at C-5; a methylene homologue of gamma-aminobutyric acid (GABA) that is a weak GABA agonist.	2.71	3	0	amino acid zwitterion; delta-amino acid; omega-amino fatty acid	human metabolite
5-hydroxytryptophan 5-Hydroxytryptophan: The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant.. 5-hydroxytryptophan : A tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5.	2.01	1	0	hydroxytryptophan	human metabolite; neurotransmitter
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.	2.7	3	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetamide acetimidic acid : A carboximidic acid that is acetic acid in which the carbonyl oxygen is replaced by an imino group.	2.21	1	0	acetamides; carboximidic acid; monocarboxylic acid amide; N-acylammonia
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	1.95	1	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
adenine [no description available]	2.15	1	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.	2.4	2	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
benzene [no description available]	2.44	2	0	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	2.66	3	0	halide anion; monoatomic bromine
cadaverine [no description available]	8.81	3	0	alkane-alpha,omega-diamine	Daphnia magna metabolite; Escherichia coli metabolite; mouse metabolite; plant metabolite
carbamates [no description available]	2.88	4	0	amino-acid anion
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	2.02	1	0	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	2.05	1	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
choline [no description available]	2.41	1	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	2.41	1	0	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.41	2	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	1.95	1	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	1.96	1	0	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant metabolite
3,4-dihydroxyphenylacetic acid 3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.	2.02	1	0	catechols; dihydroxyphenylacetic acid	human metabolite
aminocaproic acid Aminocaproic Acid: An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties.. 6-aminohexanoic acid : An epsilon-amino acid comprising hexanoic acid carrying an amino substituent at position C-6. Used to control postoperative bleeding, and to treat overdose effects of the thrombolytic agents streptokinase and tissue plasminogen activator.	3.66	2	0	amino acid zwitterion; epsilon-amino acid; omega-amino fatty acid	antifibrinolytic drug; hematologic agent; metabolite
cytosine [no description available]	2.08	1	0	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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.	2.76	3	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
dihydrouracil hexahydropyrimidine-2,4-dione: structure in first source. 5,6-dihydrouracil : A pyrimidine obtained by formal addition of hydrogen across the 5,6-position of uracil.	1.98	1	0	pyrimidone	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	4.32	6	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	2.67	3	0	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
glycine [no description available]	2.7	3	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	2.48	2	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
histamine [no description available]	1.98	1	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	2.98	4	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroxylamine amino alcohol : An alcohol containing an amino functional group in addition to the alcohol-defining hydroxy group.	2.08	1	0	hydroxylamines	algal metabolite; bacterial xenobiotic metabolite; EC 1.1.3.13 (alcohol oxidase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor; nitric oxide donor; nucleophilic reagent
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	2.44	2	0	imidazole
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	2.03	1	0	diatomic iodine	nutrient
pipecolic acid pipecolic acid: RN given refers to cpd without isomeric designation. pipecolic acid : A piperidinemonocarboxylic acid in which the carboxy group is located at position C-2.. pipecolate : A piperidinecarboxylate that is the conjugate base of pipecolic acid.	3.27	1	0	piperidinemonocarboxylic acid
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.	2.88	4	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
inositol Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.	1.96	1	0	cyclitol; hexol
melatonin [no description available]	2.48	2	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
acetanilide acetanilide: a phenylacetamide; use ACETANILIDES for the plural group meaning of the singular term. N-phenylacetamide : A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a phenyl group.	1.96	1	0	acetamides; anilide	analgesic
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	2.49	2	0	metal allergen; nickel group element atom	epitope; micronutrient
niacinamide nicotinamide : A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.	2.85	3	0	pyridine alkaloid; pyridinecarboxamide; vitamin B3	anti-inflammatory agent; antioxidant; cofactor; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; Escherichia coli metabolite; geroprotector; human urinary metabolite; metabolite; mouse metabolite; neuroprotective agent; Saccharomyces cerevisiae metabolite; Sir2 inhibitor
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.39	2	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitroxyl nitroxyl: hydroxamic acid oxidized to nitroxyl free radical. nitroxyl : A nitrogen oxoacid consisting of an oxygen atom double-bonded to an NH group.	2.4	2	0	nitrogen oxoacid
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	1.95	1	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
hydroxide ion [no description available]	2.52	2	0	oxygen hydride	mouse metabolite
phenylacetic acid phenylacetic acid : A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.	2	1	0	benzenes; monocarboxylic acid; phenylacetic acids	allergen; Aspergillus metabolite; auxin; EC 6.4.1.1 (pyruvate carboxylase) inhibitor; Escherichia coli metabolite; human metabolite; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite; toxin
phosphoric acid phosphoric acid: concise etchant is 37% H3PO4. phosphoric acid : A phosphorus oxoacid that consists of one oxo and three hydroxy groups joined covalently to a central phosphorus atom.	2.15	1	0	phosphoric acids	algal metabolite; fertilizer; human metabolite; NMR chemical shift reference compound; solvent
pyrazole 1H-pyrazole : The 1H-tautomer of pyrazole.	2.08	1	0	pyrazole
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	1.93	1	0	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
pyruvic acid Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.	2.11	1	0	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
taurine [no description available]	2.13	1	0	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
tetramethylene sulfoxide [no description available]	1.96	1	0	tetrahydrothiophenes
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	3.52	2	0	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	4.67	9	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
8-hydroxy-2-(di-n-propylamino)tetralin 8-Hydroxy-2-(di-n-propylamino)tetralin: A serotonin 1A-receptor agonist that is used experimentally to test the effects of serotonin.. 8-OH-DPAT : A tetralin substituted at positions 1 and 7 by hydroxy and dipropylamino groups respectively	3.43	7	0	phenols; tertiary amino compound; tetralins	serotonergic antagonist
4-iodo-2,5-dimethoxyphenylisopropylamine 4-iodo-2,5-dimethoxyphenylisopropylamine: RN given refers to unlabeled parent cpd without isomeric designation; a serotonin agonist. 2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine : An organoiodine compound that is amphetamine bearing two methoxy substituents at positions 2 and 5 as well as an iodo substituent at position 4.	2.17	1	0	amphetamines; dimethoxybenzene; organoiodine compound
1-(3-chlorophenyl)piperazine 1-(3-chlorophenyl)piperazine: supposed metabolite of TRAZODONE; RN given refers to parent cpd; structure. 1-(3-chlorophenyl)piperazine : A N-arylpiperazine that is piperazine carrying a 3-chlorophenyl substituent at position 1. It is a metabolite of the antidepressant drug trazodone.	2.43	2	0	monochlorobenzenes; N-arylpiperazine	drug metabolite; environmental contaminant; serotonergic agonist; xenobiotic
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	2.13	1	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
1h-(1,2,4)oxadiazolo(4,3-a)quinoxalin-1-one 1H-(1,2,4)oxadiazolo(4,3-a)quinoxalin-1-one: structure given in first source; inhibits guanylyl cyclase. 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one : A member of the class of oxadiazoloquinoxalines that is 1H-[1,2,4]oxadiazolo[4,3-a]quinoxaline substituted at position 1 by an oxo group.	2.08	1	0	oxadiazoloquinoxaline	EC 4.6.1.2 (guanylate cyclase) inhibitor
2,2'-dipyridyl 2,2'-Dipyridyl: A reagent used for the determination of iron.. 2,2'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'.	1.94	1	0	bipyridine	chelator; ferroptosis inhibitor
3-hydroxybenzylhydrazine 3-hydroxybenzylhydrazine: decarboxylase inhibitor; RN given refers to parent cpd; structure	2.01	1	0	phenols
homovanillic acid Homovanillic Acid: A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.. homovanillate : A hydroxy monocarboxylic acid anion which is obtained by deprotonation of the carboxy group of homovanillic acid.. homovanillic acid : A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.	2.38	2	0	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
5,5-dimethyl-1-pyrroline-1-oxide 5,5-dimethyl-1-pyrroline-1-oxide: do not confuse with DMPO (4',5'-dihydroxy-7-methoxy-4-phenyl-5,2'-oxidocoumarin). 5,5-dimethyl-1-pyrroline N-oxide : A member of the class of 1-pyrroline nitrones (1-pyrroline N-oxides) resulting from the formal N-oxidation of 5,5-dimethyl-1-pyrroline. Used as a spin trap for the study of radicals formed by enzymatic acetaldehyde oxidation.	2.7	3	0	1-pyrroline nitrones	neuroprotective agent; spin trapping reagent
phenytoin [no description available]	2.64	3	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
5-carboxamidotryptamine 5-carboxamidotryptamine: agonist of 5-HT receptor; structure given in first source	3.11	5	0	tryptamines
hydroxyindoleacetic acid (5-hydroxyindol-3-yl)acetic acid : A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.	2.45	2	0	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
5-methoxytryptamine 5-Methoxytryptamine: Serotonin derivative proposed as potentiator for hypnotics and sedatives.. 5-methoxytryptamine : A member of the class of tryptamines that is the methyl ether derivative of serotonin.	2	1	0	aromatic ether; primary amino compound; tryptamines	5-hydroxytryptamine 2A receptor agonist; 5-hydroxytryptamine 2B receptor agonist; 5-hydroxytryptamine 2C receptor agonist; antioxidant; cardioprotective agent; human metabolite; mouse metabolite; neuroprotective agent; radiation protective agent; serotonergic agonist
6-nitroso-1,2-benzopyrone [no description available]	2.06	1	0
7-nitroindazole 7-nitroindazole: an inhibitor of nitric oxide synthase; exhibits anti-nociceptive activity without increasing blood pressure	2.08	1	0
albuterol Albuterol: A short-acting beta-2 adrenergic agonist that is primarily used as a bronchodilator agent to treat ASTHMA. Albuterol is prepared as a racemic mixture of R(-) and S(+) stereoisomers. The stereospecific preparation of R(-) isomer of albuterol is referred to as levalbuterol.. albuterol : A member of the class of phenylethanolamines that is 4-(2-amino-1-hydroxyethyl)-2-(hydroxymethyl)phenol having a tert-butyl group attached to the nirogen atom. It acts as a beta-adrenergic agonist used in the treatment of asthma and chronic obstructive pulmonary disease (COPD).	1.98	1	0	phenols; phenylethanolamines; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; environmental contaminant; xenobiotic
alpha-methylserotonin alpha-methylserotonin: potent agonist at M & D receptors of serotonin; RN given refers to parent cpd	2.01	1	0	tryptamines	serotonergic agonist
am 251 AM 251: an analog of SR141716A; structure given in first source. AM-251 : A carbohydrazide obtained by formal condensation of the carboxy group of 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid with the amino group of 1-aminopiperidine. An antagonist at the CB1 cannabinoid receptor.	2.17	1	0	amidopiperidine; carbohydrazide; dichlorobenzene; organoiodine compound; pyrazoles	antidepressant; antineoplastic agent; apoptosis inducer; CB1 receptor antagonist
aminoglutethimide Aminoglutethimide: An aromatase inhibitor that is used in the treatment of advanced BREAST CANCER.. aminoglutethimide : A dicarboximide that is a six-membered cyclic compound having ethyl and 4-aminophenyl substituents at the 3-position.	2.67	3	0	dicarboximide; piperidones; substituted aniline	adrenergic agent; anticonvulsant; antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
pimagedine pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.	2.1	1	0	guanidines; one-carbon compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 1.4.3.4 (monoamine oxidase) inhibitor
amobarbital Amobarbital: A barbiturate with hypnotic and sedative properties (but not antianxiety). Adverse effects are mainly a consequence of dose-related CNS depression and the risk of dependence with continued use is high. (From Martindale, The Extra Pharmacopoeia, 30th ed, p565). amobarbital : A member of the class of barbiturates that is pyrimidine-2,4,6(1H,3H,5H)-trione substituted by a 3-methylbutyl and an ethyl group at position 5. Amobarbital has been shown to exhibit sedative and hypnotic properties.	2.64	3	0	barbiturates
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	2.67	3	0	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
azasetron azasetron: a selective 5-HT3 receptor antagonist; structure given in first source;	2.03	1	0	benzoxazine
barbital 5,5-diethylbarbituric acid : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by two ethyl groups. Formerly used as a hypnotic (sleeping aid).	1.98	1	0	barbiturates	drug allergen
bemegride Bemegride: A CNS stimulant that is used to induce convulsions in experimental animals. It has also been used as a respiratory stimulant and in the treatment of barbiturate overdose.	4.08	16	0	piperidones
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	1.97	1	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
bepridil Bepridil: A long-acting calcium-blocking agent with significant anti-anginal activity. The drug produces significant coronary vasodilation and modest peripheral effects. It has antihypertensive and selective anti-arrhythmia activities and acts as a calmodulin antagonist.. bepridil : A tertiary amine in which the substituents on nitrogen are benzyl, phenyl and 3-(2-methylpropoxy)-2-(pyrrolidin-1-yl)propyl.	2	1	0	pyrrolidines; tertiary amine	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent
bromisovalum Bromisovalum: A sedative and mild hypnotic with potentially toxic effects.. bromisoval : A racemate comprising equimolar amounts of (R)- and (S)-bromisoval. It was previously used for its hypnotic and sedative properties but the use of bromides is now deprecated due to the possibility of the toxic accumulation of bromine in the body.. 2-bromo-N-carbamoyl-3-methylbutanamide : An N-acylurea that is urea in which one of the hydrogens is replaced by a 2-bromo-3-methybutanoyl group.	3.05	1	0	N-acylurea; organobromine compound
buspirone Buspirone: An anxiolytic agent and serotonin receptor agonist belonging to the azaspirodecanedione class of compounds. Its structure is unrelated to those of the BENZODIAZAPINES, but it has an efficacy comparable to DIAZEPAM.. buspirone : An azaspiro compound that is 8-azaspiro[4.5]decane-7,9-dione substituted at the nitrogen atom by a 4-(piperazin-1-yl)butyl group which in turn is substituted by a pyrimidin-2-yl group at the N(4) position.	2.92	4	0	azaspiro compound; N-alkylpiperazine; N-arylpiperazine; organic heteropolycyclic compound; piperidones; pyrimidines	anxiolytic drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; sedative; serotonergic agonist
caffeine [no description available]	2.67	3	0	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	2	1	0	aromatic ether; nitrile; polyether; tertiary amino compound
carbamazepine Carbamazepine: A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties.. carbamazepine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant.	1.95	1	0	dibenzoazepine; ureas	analgesic; anticonvulsant; antimanic drug; drug allergen; EC 3.5.1.98 (histone deacetylase) inhibitor; environmental contaminant; glutamate transporter activator; mitogen; non-narcotic analgesic; sodium channel blocker; xenobiotic
carisoprodol Carisoprodol: A centrally acting skeletal muscle relaxant whose mechanism of action is not completely understood but may be related to its sedative actions. It is used as an adjunct in the symptomatic treatment of musculoskeletal conditions associated with painful muscle spasm. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1202). carisoprodol : A carbamate ester that is the mono-N-isopropyl derivative of meprobamate (which is a significant metabolite). Carisoprodol interrupts neuronal communication within the reticular formation and spinal cord, resulting in sedation and alteration in pain perception. It is used as a muscle relaxant in the symptomatic treatment of musculoskeletal conditions associated with painful muscle spasm.	1.94	1	0	carbamate ester	muscle relaxant
celecoxib [no description available]	2.15	1	0	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug
cetylpyridinium Cetylpyridinium: Cationic bactericidal surfactant used as a topical antiseptic for skin, wounds, mucous membranes, instruments, etc.; and also as a component in mouthwash and lozenges.	1.97	1	0	pyridinium ion
chloral hydrate [no description available]	4.43	7	0	aldehyde hydrate; ethanediol; organochlorine compound	general anaesthetic; mouse metabolite; sedative; xenobiotic
chlordiazepoxide Chlordiazepoxide: An anxiolytic benzodiazepine derivative with anticonvulsant, sedative, and amnesic properties. It has also been used in the symptomatic treatment of alcohol withdrawal.. chlordiazepoxide : A benzodiazepine that is 3H-1,4-benzodiazepine 4-oxide substituted by a chloro group at position 7, a phenyl group at position 5 and a methylamino group at position 2.	2.86	4	0	benzodiazepine
chlorpromazine Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.	2.64	3	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
ciclopirox [no description available]	2.03	1	0	cyclic hydroxamic acid; hydroxypyridone antifungal drug; pyridone	antibacterial agent; antiseborrheic
citalopram Citalopram: A furancarbonitrile that is one of the serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from TARDIVE DYSKINESIA in preference to tricyclic antidepressants, which aggravate dyskinesia.. citalopram : A racemate comprising equimolar amounts of (R)-citalopram and its enantiomer, escitalopram. It is used as an antidepressant, although only escitalopram is active.. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile : A nitrile that is 1,3-dihydro-2-benzofuran-5-carbonitrile in which one of the hydrogens at position 1 is replaced by a p-fluorophenyl group, while the other is replaced by a 3-(dimethylamino)propyl group.	2.74	3	0	2-benzofurans; cyclic ether; nitrile; organofluorine compound; tertiary amino compound
conduritol epoxide conduritol epoxide: conduritol C epoxide refers to the (epi & neo)-isomers; structure. conduritol epoxide : An epoxide resulting from the epoxidation of the double bond of a conduritol.	1.96	1	0	cyclitol; epoxide; tetrol
cyproheptadine Cyproheptadine: A serotonin antagonist and a histamine H1 blocker used as antipruritic, appetite stimulant, antiallergic, and for the post-gastrectomy dumping syndrome, etc.. cyproheptadine : The product resulting from the formal oxidative coupling of position 5 of 5H-dibenzo[a,d]cycloheptene with position 4 of 1-methylpiperidine resulting in the formation of a double bond between the two fragments. It is a sedating antihistamine with antimuscarinic and calcium-channel blocking actions. It is used (particularly as the hydrochloride sesquihydrate) for the relief of allergic conditions including rhinitis, conjunctivitis due to inhalant allergens and foods, urticaria and angioedema, and in pruritic skin disorders. Unlike other antihistamines, it is also a seratonin receptor antagonist, making it useful in conditions such as vascular headache and anorexia.	2.17	1	0	piperidines; tertiary amine	anti-allergic agent; antipruritic drug; gastrointestinal drug; H1-receptor antagonist; serotonergic antagonist
dapi DAPI: RN given refers to parent cpd.	2.03	1	0	indoles	fluorochrome
decanoic acid decanoate : A fatty acid anion 10:0 that is the conjugate base of decanoic acid.. decanoic acid : A C10, straight-chain saturated fatty acid.	2.04	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; anti-inflammatory agent; antibacterial agent; human metabolite; plant metabolite; volatile oil component
deferoxamine Deferoxamine: Natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form.. desferrioxamine B : An acyclic desferrioxamine that is butanedioic acid in which one of the carboxy groups undergoes formal condensation with the primary amino group of N-(5-aminopentyl)-N-hydroxyacetamide and the second carboxy group undergoes formal condensation with the hydroxyamino group of N(1)-(5-aminopentyl)-N(1)-hydroxy-N(4)-[5-(hydroxyamino)pentyl]butanediamide. It is a siderophore native to Streptomyces pilosus biosynthesised by the DesABCD enzyme cluster as a high affinity Fe(III) chelator.	2.69	3	0	acyclic desferrioxamine	bacterial metabolite; ferroptosis inhibitor; iron chelator; siderophore
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	3.21	6	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
pentetic acid Pentetic Acid: An iron chelating agent with properties like EDETIC ACID. DTPA has also been used as a chelator for other metals, such as plutonium.	2.1	1	0	pentacarboxylic acid	copper chelator
diphenhydramine Diphenhydramine: A histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects.. diphenhydramine : An ether that is the benzhydryl ether of 2-(dimethylamino)ethanol. It is a H1-receptor antagonist used as a antipruritic and antitussive drug.. antitussive : An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.	1.95	1	0	ether; tertiary amino compound	anti-allergic agent; antidyskinesia agent; antiemetic; antiparkinson drug; antipruritic drug; antitussive; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; oneirogen; sedative
stallimycin [no description available]	2.01	1	0
valproic acid Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.	1.99	1	0	branched-chain fatty acid; branched-chain saturated fatty acid	anticonvulsant; antimanic drug; EC 3.5.1.98 (histone deacetylase) inhibitor; GABA agent; neuroprotective agent; psychotropic drug; teratogenic agent
ethinamate ethinamate: short duration hypnotic with fast onset & relatively low toxicity; may cause dependence; minor descriptor (76-85); on-line & Index Medicus search CARBAMATES (76-85). ethinamate : A carbamate ester that is the 1-vinylcyclohexyl ester of carbamic acid. A short-acting sedative-hypnotic, it was formerly used to treat insomnia.	1.93	1	0	carbamate ester; terminal acetylenic compound	sedative
ethosuximide Ethosuximide: An anticonvulsant especially useful in the treatment of absence seizures unaccompanied by other types of seizures.. ethosuximide : A dicarboximide that is pyrrolidine-2,5-dione in which the hydrogens at position 3 are substituted by one methyl and one ethyl group. An antiepileptic, it is used in the treatment of absence seizures and may be used for myoclonic seizures, but is ineffective against tonic-clonic seizures.	2.65	3	0	dicarboximide; pyrrolidinone	anticonvulsant; geroprotector; T-type calcium channel blocker
fenbendazole Fenbendazole: Antinematodal benzimidazole used in veterinary medicine.. fenbendazole : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted at positons 2 and 5 by (methoxycarbonyl)amino and phenylsulfanediyl groups, respectively. A broad-spectrum anthelmintic, it is used, particularly in veterinary medicine, for the treatment of nematodal infections.	2.25	1	0	aryl sulfide; benzimidazoles; carbamate ester	antinematodal drug
fenfluramine Fenfluramine: A centrally active drug that apparently both blocks serotonin uptake and provokes transport-mediated serotonin release.. fenfluramine : A secondary amino compound that is 1-phenyl-propan-2-amine in which one of the meta-hydrogens is substituted by trifluoromethyl, and one of the hydrogens attached to the nitrogen is substituted by an ethyl group. It binds to the serotonin reuptake pump, causing inhbition of serotonin uptake and release of serotonin. The resulting increased levels of serotonin lead to greater serotonin receptor activation which in turn lead to enhancement of serotoninergic transmission in the centres of feeding behavior located in the hypothalamus. This suppresses the appetite for carbohydrates. Fenfluramine was used as the hydrochloride for treatment of diabetes and obesity. It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertension.	2.02	1	0	(trifluoromethyl)benzenes; secondary amino compound	appetite depressant; serotonergic agonist; serotonin uptake inhibitor
fentanyl Fentanyl: A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078). fentanyl : A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of N-phenyl-1-(2-phenylethyl)piperidin-4-amine with propanoic acid.	2.44	2	0	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
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.	4.67	6	1	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
fluoxetine Fluoxetine: The first highly specific serotonin uptake inhibitor. It is used as an antidepressant and often has a more acceptable side-effects profile than traditional antidepressants.. fluoxetine : A racemate comprising equimolar amounts of (R)- and (S)-fluoxetine. A selective serotonin reuptake inhibitor (SSRI), it is used (generally as the hydrochloride salt) for the treatment of depression (and the depressive phase of bipolar disorder), bullimia nervosa, and obsessive-compulsive disorder.. N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine : An aromatic ether consisting of 4-trifluoromethylphenol in which the hydrogen of the phenolic hydroxy group is replaced by a 3-(methylamino)-1-phenylpropyl group.	3.27	6	0	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
flurazepam Flurazepam: A benzodiazepine derivative used mainly as a hypnotic.. flurazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a 2-(diethylamino)ethyl group, 2-fluorophenyl group and chloro group at positions 1, 5 and 7, respectively. It is a partial agonist of GABAA receptors and used for the treatment of insomnia.	1.95	1	0	1,4-benzodiazepinone; monofluorobenzenes; organochlorine compound; tertiary amino compound	anticonvulsant; anxiolytic drug; GABAA receptor agonist; sedative
glimepiride glimepiride: structure given in first source	5.17	3	3	sulfonamide
glutethimide Glutethimide: A hypnotic and sedative. Its use has been largely superseded by other drugs.	5.93	26	1	piperidines
glyburide Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.	2.42	2	0	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent
go 6976 [no description available]	2.02	1	0	indolocarbazole; organic heterohexacyclic compound	EC 2.7.11.13 (protein kinase C) inhibitor
guaifenesin Guaifenesin: An expectorant that also has some muscle relaxing action. It is used in many cough preparations.	2.08	1	0	methoxybenzenes
guvacine guvacine: RN given refers to parent cpd. guvacine : A alpha,beta-unsaturated monocarboxylic acid that is nicotinic acid which has been hydrogenated at the 1-2 and 5-6 positions of the pyridine ring.	1.92	1	0	alpha,beta-unsaturated monocarboxylic acid; beta-amino acid; pyridine alkaloid; secondary amino compound; tetrahydropyridine	GABA reuptake inhibitor; plant metabolite
haloperidol Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.	4.03	3	1	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
hexamethonium Hexamethonium: A nicotinic cholinergic antagonist often referred to as the prototypical ganglionic blocker. It is poorly absorbed from the gastrointestinal tract and does not cross the blood-brain barrier. It has been used for a variety of therapeutic purposes including hypertension but, like the other ganglionic blockers, it has been replaced by more specific drugs for most purposes, although it is widely used a research tool.	2.05	1	0	quaternary ammonium salt
hexamethylene bisacetamide N,N'-diacetyl-1,6-diaminohexane: chemical name obtained from Acta Biol Hung 1990;41(1-3):199-208	3.06	1	0	acetamides
hydroxyurea [no description available]	2.39	2	0	one-carbon compound; ureas	antimetabolite; antimitotic; antineoplastic agent; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; genotoxin; immunomodulator; radical scavenger; teratogenic agent
hypericin [no description available]	1.98	1	0
imipramine Imipramine: The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.. imipramine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom.	2.74	3	0	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	2.37	2	0	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
avapro Irbesartan: A spiro compound, biphenyl and tetrazole derivative that acts as an angiotensin II type 1 receptor antagonist. It is used in the management of HYPERTENSION, and in the treatment of kidney disease.. irbesartan : A biphenylyltetrazole that is an angiotensin II receptor antagonist used mainly for the treatment of hypertension.	5.85	2	2	azaspiro compound; biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
2-propanol 2-Propanol: An isomer of 1-PROPANOL. It is a colorless liquid having disinfectant properties. It is used in the manufacture of acetone and its derivatives and as a solvent. Topically, it is used as an antiseptic.. propan-2-ol : A secondary alcohol that is propane in which one of the hydrogens attached to the central carbon is substituted by a hydroxy group.	1.96	1	0	secondary alcohol; secondary fatty alcohol	protic solvent
nsc 664704 kenpaullone: inhibits CDK1/cyclin B; structure in first source. kenpaullone : An indolobenzazepine that is paullone in which the hydrogen at position 9 is replaced by a bromo substituent. It is an ATP-competitive inhibitor of cyclin-dependent kinases (CDKs) and glycogen synthase kinase 3beta (GSK3beta).	2.05	1	0	indolobenzazepine; lactam; organobromine compound	cardioprotective agent; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor; EC 2.7.11.26 (tau-protein kinase) inhibitor; geroprotector
ketanserin Ketanserin: A selective serotonin receptor antagonist with weak adrenergic receptor blocking properties. The drug is effective in lowering blood pressure in essential hypertension. It also inhibits platelet aggregation. It is well tolerated and is particularly effective in older patients.. ketanserin : A member of the class of quinazolines that is quinazoline-2,4(1H,3H)-dione which is substituted at position 3 by a 2-[4-(p-fluorobenzoyl)piperidin-1-yl]ethyl group.	2.41	2	0	aromatic ketone; organofluorine compound; piperidines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; cardiovascular drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist
ketoconazole 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.	4.37	1	1	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine
mimosine Mimosine: 3-Hydroxy-4-oxo-1(4H)-pyridinealanine. An antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca.	2.03	1	0	alpha-amino acid
meprobamate Meprobamate: A carbamate with hypnotic, sedative, and some muscle relaxant properties, although in therapeutic doses reduction of anxiety rather than a direct effect may be responsible for muscle relaxation. Meprobamate has been reported to have anticonvulsant actions against petit mal seizures, but not against grand mal seizures (which may be exacerbated). It is used in the treatment of ANXIETY DISORDERS, and also for the short-term management of INSOMNIA but has largely been superseded by the BENZODIAZEPINES. (From Martindale, The Extra Pharmacopoeia, 30th ed, p603)	3.33	7	0	organic molecular entity
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	11.52	19	15	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
methiothepin Methiothepin: A serotonin receptor antagonist in the CENTRAL NERVOUS SYSTEM used as an antipsychotic.. methiothepin : A dibenzothiepine that is 10,11-dihydrodibenzo[b,f]thiepine bearing additional methylthio and 4-methylpiperazin-1-yl substituents at positions 8 and 10 respectively. Potent 5-HT2 antagonist, also active as 5-HT1 antagonist. Differentiates 5-HT1D sub-types. Also displays affinity for rodent 5-HT5B, 5-HT5A, 5-HT7 and 5-HT6 receptors (pK1 values are 6.6, 7.0, 8.4 and 8.7 respectively).	2.72	3	0	aryl sulfide; dibenzothiepine; N-alkylpiperazine; tertiary amino compound	antipsychotic agent; dopaminergic antagonist; geroprotector; serotonergic antagonist
methyprylon methyprylon: was heading 1973-94 (see under HYPNOTICS AND SEDATIVES 1963-72); use PIPERIDONES to search METHYPRYLON 1973-94	4.98	41	0	organic molecular entity
metoclopramide Metoclopramide: A dopamine D2 antagonist that is used as an antiemetic.. metoclopramide : A member of the class of benzamides resulting from the formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with the primary amino group of N,N-diethylethane-1,2-diamine.	2.01	1	0	benzamides; monochlorobenzenes; substituted aniline; tertiary amino compound	antiemetic; dopaminergic antagonist; environmental contaminant; gastrointestinal drug; xenobiotic
mianserin Mianserin: A tetracyclic compound with antidepressant effects. It may cause drowsiness and hematological problems. Its mechanism of therapeutic action is not well understood, although it apparently blocks alpha-adrenergic, histamine H1, and some types of serotonin receptors.. mianserin : A dibenzoazepine (specifically 1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine) methyl-substituted on N-2. Closely related to (and now mostly superseded by) the tetracyclic antidepressant mirtazapinean, it is an atypical antidepressant used in the treatment of depression throughout Europe and elsewhere.	2.02	1	0	dibenzoazepine	adrenergic uptake inhibitor; alpha-adrenergic antagonist; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; H1-receptor antagonist; histamine agonist; sedative; serotonergic antagonist
mitotane Mitotane: A derivative of the insecticide DICHLORODIPHENYLDICHLOROETHANE that specifically inhibits cells of the adrenal cortex and their production of hormones. It is used to treat adrenocortical tumors and causes CNS damage, but no bone marrow depression.	2.21	1	0	diarylmethane
muscimol Muscimol: A neurotoxic isoxazole isolated from species of AMANITA. It is obtained by decarboxylation of IBOTENIC ACID. Muscimol is a potent agonist of GABA-A RECEPTORS and is used mainly as an experimental tool in animal and tissue studies.. muscimol : A member of the class of isoxazoles that is 1,2-oxazol-3(2H)-one substituted by an aminomethyl group at position 5. It has been isolated from mushrooms of the genus Amanita.	2.05	1	0	alkaloid; isoxazoles; primary amino compound	fungal metabolite; GABA agonist; oneirogen; psychotropic drug
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	1.95	1	0	maleimides	anticoronaviral agent; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.1.1 (hexokinase) inhibitor
nan 190 1-(2-methoxyphenyl)-4-(4-(2-phthalimido)butyl)piperazine: RN from Toxlit. NAN 190 : An N-alkylpiperazine that consists of (2-methoxyphenyl)piperazine in which the amine hydrogen is substituted by a 4-(2-phthalimido)butyl group.	2.06	1	0	N-alkylpiperazine; N-arylpiperazine; phthalimides	serotonergic antagonist
nicardipine Nicardipine: A potent calcium channel blockader with marked vasodilator action. It has antihypertensive properties and is effective in the treatment of angina and coronary spasms without showing cardiodepressant effects. It has also been used in the treatment of asthma and enhances the action of specific antineoplastic agents.. nicardipine : A racemate comprising equimolar amounts of (R)- and (S)-nicardipine. It is a calcium channel blocker which is used to treat hypertension.. 2-[benzyl(methyl)amino]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate : A dihydropyridine that is 1,4-dihydropyridine substituted by a methyl, {2-[benzyl(methyl)amino]ethoxy}carbonyl, 3-nitrophenyl, methoxycarbonyl and methyl groups at positions 2, 3, 4, 5 and 6, respectively.	2.38	2	0	benzenes; C-nitro compound; diester; dihydropyridine; methyl ester; tertiary amino compound
nitrazepam Nitrazepam: A benzodiazepine derivative used as an anticonvulsant and hypnotic.. nitrazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one which is substituted at positions 5 and 7 by phenyl and nitro groups, respectively. It is used as a hypnotic for the short-term management of insomnia and for the treatment of epileptic spasms in infants (West's syndrome).	2.35	2	0	1,4-benzodiazepinone; C-nitro compound	anticonvulsant; antispasmodic drug; drug metabolite; GABA modulator; sedative
orphenadrine Orphenadrine: A muscarinic antagonist used to treat drug-induced parkinsonism and to relieve pain from muscle spasm.. orphenadrine : A tertiary amino compound which is the phenyl-o-tolylmethyl ether of 2-(dimethylamino)ethanol.	1.94	1	0	ether; tertiary amino compound	antidyskinesia agent; antiparkinson drug; H1-receptor antagonist; muscarinic antagonist; muscle relaxant; NMDA receptor antagonist; parasympatholytic
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	2.41	2	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
fenclonine Fenclonine: A selective and irreversible inhibitor of tryptophan hydroxylase, a rate-limiting enzyme in the biosynthesis of serotonin (5-HYDROXYTRYPTAMINE). Fenclonine acts pharmacologically to deplete endogenous levels of serotonin.	2.08	1	0	phenylalanine derivative
pargyline Pargyline: A monoamine oxidase inhibitor with antihypertensive properties.	2.03	1	0	aromatic amine
pemoline Pemoline: A central nervous system stimulant used in fatigue and depressive states and to treat hyperkinetic disorders in children.. pemoline : A member of the class of 1,3-oxazoles that is 1,3-oxazol-4(5H)-one which is substituted by an amino group at position 2 and by a phenyl group at position 5. A central nervous system stimulant, it was used to treat hyperactivity disorders in children, but withdrawn from use following reports of serious hepatotoxicity.	1.95	1	0	1,3-oxazoles	central nervous system stimulant
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.	2.64	3	0	barbiturates	GABAA receptor agonist
phenazopyridine Phenazopyridine: A local anesthetic that has been used in urinary tract disorders. Its use is limited by problems with toxicity (primarily blood disorders) and potential carcinogenicity.. phenazopyridine : A diaminopyridine that is 2,6-diaminopyridine substituted at position 3 by a phenylazo group. A local anesthetic that has topical analgesic effect on mucosa lining of the urinary tract. Its use is limited by problems with toxicity (primarily blood disorders) and potential carcinogenicity.	2.17	1	0	diaminopyridine; monoazo compound	anticoronaviral agent; carcinogenic agent; local anaesthetic; non-narcotic analgesic
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	5.28	13	1	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
phenylbutazone Phenylbutazone: A butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. It has been used in ANKYLOSING SPONDYLITIS; RHEUMATOID ARTHRITIS; and REACTIVE ARTHRITIS.. phenylbutazone : A member of the class of pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position.	3.47	2	0	pyrazolidines	antirheumatic drug; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
pindolol Pindolol: A moderately lipophilic beta blocker (ADRENERGIC BETA-ANTAGONISTS). It is non-cardioselective and has intrinsic sympathomimetic actions, but little membrane-stabilizing activity. (From Martindale, The Extra Pharmocopoeia, 30th ed, p638). pindolol : A member of the class of indols which is the 2-hydroxy-3-(isopropylamino)propyl ether derivative of 1H-indol-4-ol.	2.44	2	0	indoles; secondary amine	antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist; serotonergic antagonist; vasodilator agent
pioglitazone Pioglitazone: A thiazolidinedione and PPAR GAMMA agonist that is used in the treatment of TYPE 2 DIABETES MELLITUS.. pioglitazone : A member of the class of thiazolidenediones that is 1,3-thiazolidine-2,4-dione substituted by a benzyl group at position 5 which in turn is substituted by a 2-(5-ethylpyridin-2-yl)ethoxy group at position 4 of the phenyl ring. It exhibits hypoglycemic activity.	4.37	1	1	aromatic ether; pyridines; thiazolidinediones	antidepressant; cardioprotective agent; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; geroprotector; hypoglycemic agent; insulin-sensitizing drug; PPARgamma agonist; xenobiotic
piracetam Piracetam: A compound suggested to be both a nootropic and a neuroprotective agent.	1.98	1	0	organonitrogen compound; organooxygen compound
potassium chloride Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.	2.38	2	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
praziquantel azinox: Russian drug	2.51	2	0	isoquinolines
prazosin Prazosin: A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.. prazosin : A member of the class of piperazines that is piperazine substituted by a furan-2-ylcarbonyl group and a 4-amino-6,7-dimethoxyquinazolin-2-yl group at positions 1 and 4 respectively.	2.42	2	0	aromatic ether; furans; monocarboxylic acid amide; piperazines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
primidone Primidone: A barbiturate derivative that acts as a GABA modulator and anti-epileptic agent. It is partly metabolized to PHENOBARBITAL in the body and owes some of its actions to this metabolite.. primidone : A pyrimidone that is dihydropyrimidine-4,6(1H,5H)-dione substituted by an ethyl and a phenyl group at position 5. It is used as an anticonvulsant for treatment of various types of seizures.	2.35	2	0	pyrimidone	anticonvulsant; environmental contaminant; xenobiotic
procyclidine Procyclidine: A muscarinic antagonist that crosses the blood-brain barrier and is used in the treatment of drug-induced extrapyramidal disorders and in parkinsonism.. procyclidine : A tertiary alcohol that consists of propan-1-ol substituted by a cyclohexyl and a phenyl group at position 1 and a pyrrolidin-1-yl group at position 3.	3.34	1	1	pyrrolidines; tertiary alcohol	antidyskinesia agent; antiparkinson drug; muscarinic antagonist
promazine Promazine: A phenothiazine with actions similar to CHLORPROMAZINE but with less antipsychotic activity. It is primarily used in short-term treatment of disturbed behavior and as an antiemetic.. promazine : A phenothiazine deriative in which the phenothiazine tricycle has a 3-(dimethylaminopropyl) group at the N-10 position.	1.95	1	0	phenothiazines; tertiary amine	antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; muscarinic antagonist; phenothiazine antipsychotic drug; serotonergic antagonist
promethazine Promethazine: A phenothiazine derivative with histamine H1-blocking, antimuscarinic, and sedative properties. It is used as an antiallergic, in pruritus, for motion sickness and sedation, and also in animals.. promethazine : A tertiary amine that is a substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropan-2-amine moiety.	4.03	3	1	phenothiazines; tertiary amine	anti-allergic agent; anticoronaviral agent; antiemetic; antipruritic drug; H1-receptor antagonist; local anaesthetic; sedative
propantheline Propantheline: A muscarinic antagonist used as an antispasmodic, in rhinitis, in urinary incontinence, and in the treatment of ulcers. At high doses it has nicotinic effects resulting in neuromuscular blocking.	1.97	1	0	xanthenes
ritanserin Ritanserin: A selective and potent serotonin-2 antagonist that is effective in the treatment of a variety of syndromes related to anxiety and depression. The drug also improves the subjective quality of sleep and decreases portal pressure.. ritanserin : A thiazolopyrimidine that is 5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one which is substituted at position 7 by a methyl group and at position 6 by a 2-{4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl}ethyl group. A potent and long-acting seratonin (5-hydroxytryptamine, 5-HT) antagonist of the subtype 5-HT2 (Ki = 0.39 nM), it is used in the treatment of a variety of disorders including anxiety, depression and schizophrenia. It has little sedative action.	2.42	2	0	organofluorine compound; piperidines; thiazolopyrimidine	antidepressant; antipsychotic agent; anxiolytic drug; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist
rolipram [no description available]	2.1	1	0	pyrrolidin-2-ones	antidepressant; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
sarpogrelate sarpogrelate: structure given in first source	2.06	1	0	hemisuccinate; stilbenoid
sb 206553 SB 206553: a high-affinity 5-HT(2C/2B) antagonist; structure given in first source	2.03	1	0	pyrroloindole
secobarbital Secobarbital: A barbiturate that is used as a sedative. Secobarbital is reported to have no anti-anxiety activity.. secobarbital : A member of the class of barbiturates that is barbituric acid in which the hydrogens at position 5 are substituted by prop-2-en-1-yl and pentan-2-yl groups.	4.72	7	1	barbiturates	anaesthesia adjuvant; GABA modulator; sedative
spiperone Spiperone: A spiro butyrophenone analog similar to HALOPERIDOL and other related compounds. It has been recommended in the treatment of SCHIZOPHRENIA.. spiperone : An azaspiro compound that is 1,3,8-triazaspiro[4.5]decane which is substituted at positions 1, 4, and 8 by phenyl, oxo, and 4-(p-fluorophenyl)-4-oxobutyl groups, respectively.	2.02	1	0	aromatic ketone; azaspiro compound; organofluorine compound; piperidines; tertiary amino compound	alpha-adrenergic antagonist; antipsychotic agent; dopaminergic antagonist; psychotropic drug; serotonergic antagonist
sumatriptan Sumatriptan: A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of MIGRAINE DISORDERS.. sumatriptan : A sulfonamide that consists of N,N-dimethyltryptamine bearing an additional (N-methylsulfamoyl)methyl substituent at position 5. Selective agonist for a vascular 5-HT1 receptor subtype (probably a member of the 5-HT1D family). Used (in the form of its succinate salt) for the acute treatment of migraine with or without aura in adults.	3.81	11	0	sulfonamide; tryptamines	serotonergic agonist; vasoconstrictor agent
thalidomide Thalidomide: A piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects. It has been reintroduced and used for a number of immunological and inflammatory disorders. Thalidomide displays immunosuppressive and anti-angiogenic activity. It inhibits release of TUMOR NECROSIS FACTOR-ALPHA from monocytes, and modulates other cytokine action.. thalidomide : A racemate comprising equimolar amounts of R- and S-thalidomide.. 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione : A dicarboximide that is isoindole-1,3(2H)-dione in which the hydrogen attached to the nitrogen is substituted by a 2,6-dioxopiperidin-3-yl group.	6.83	15	1	phthalimides; piperidones
2,4-thiazolidinedione thiazolidine-2,4-dione: structure in first source. 1,3-thiazolidine-2,4-dione : A thiazolidenedione carrying oxo substituents at positions 2 and 4.	1.93	1	0	thiazolidenedione
8-(n,n-diethylamino)octyl-3,4,5-trimethoxybenzoate 8-(N,N-diethylamino)octyl-3,4,5-trimethoxybenzoate: intracellular calcium antagonist; RN given refers to parent cpd	1.96	1	0	trihydroxybenzoic acid
nikethamide Nikethamide: A central nervous system stimulant. It was formerly used in the treatment of barbiturate overdose but is now considered to be of no value for such purposes and may be dangerous. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1229)	1.94	1	0	pyridinecarboxamide
tremorine [no description available]	1.94	1	0	N-alkylpyrrolidine
triazolam Triazolam: A short-acting benzodiazepine used in the treatment of insomnia. Some countries temporarily withdrew triazolam from the market because of concerns about adverse reactions, mostly psychological, associated with higher dose ranges. Its use at lower doses with appropriate care and labeling has been reaffirmed by the FDA and most other countries.	3.34	1	1	triazolobenzodiazepine	sedative
trifluoperazine [no description available]	1.94	1	0	N-alkylpiperazine; N-methylpiperazine; organofluorine compound; phenothiazines	antiemetic; calmodulin antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor; phenothiazine antipsychotic drug
trimethadione Trimethadione: An anticonvulsant effective in absence seizures, but generally reserved for refractory cases because of its toxicity. (From AMA Drug Evaluations Annual, 1994, p378). trimethadione : An oxazolidinone that is 1,3-oxazolidine-2,4-dione substituted by methyl groups at positions 3, 5 and 5. It is an antiepileptic agent.	1.95	1	0	oxazolidinone	anticonvulsant; geroprotector
trimethoprim Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.	2.11	1	0	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
urethane [no description available]	2.65	3	0	carbamate ester	fungal metabolite; mutagen
corticosterone [no description available]	2.67	3	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	2.07	1	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
thymidine [no description available]	2.65	3	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
benzimidazole 1H-benzimidazole : The 1H-tautomer of benzimidazole.	2.11	1	0	benzimidazole; polycyclic heteroarene
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.	2.03	1	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
dextroamphetamine Dextroamphetamine: The d-form of AMPHETAMINE. It is a central nervous system stimulant and a sympathomimetic. It has also been used in the treatment of narcolepsy and of attention deficit disorders and hyperactivity in children. Dextroamphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulating release of monamines, and inhibiting monoamine oxidase. It is also a drug of abuse and a psychotomimetic.. (S)-amphetamine : A 1-phenylpropan-2-amine that has S configuration.	1.94	1	0	1-phenylpropan-2-amine	adrenergic agent; adrenergic uptake inhibitor; dopamine uptake inhibitor; dopaminergic agent; neurotoxin; sympathomimetic agent
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	2.38	2	0	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
spironolactone Spironolactone: A potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p827). spironolactone : A steroid lactone that is 17alpha-pregn-4-ene-21,17-carbolactone substituted by an oxo group at position 3 and an alpha-acetylsulfanyl group at position 7.	1.95	1	0	3-oxo-Delta(4) steroid; oxaspiro compound; steroid lactone; thioester	aldosterone antagonist; antihypertensive agent; diuretic; environmental contaminant; xenobiotic
aldosterone [no description available]	1.98	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
pilocarpine Pilocarpine: A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma.. (+)-pilocarpine : The (+)-enantiomer of pilocarpine.	1.94	1	0	pilocarpine	antiglaucoma drug
pentylenetetrazole Pentylenetetrazole: A pharmaceutical agent that displays activity as a central nervous system and respiratory stimulant. It is considered a non-competitive GAMMA-AMINOBUTYRIC ACID antagonist. Pentylenetetrazole has been used experimentally to study seizure phenomenon and to identify pharmaceuticals that may control seizure susceptibility.. pentetrazol : An organic heterobicyclic compound that is 1H-tetrazole in which the hydrogens at positions 1 and 5 are replaced by a pentane-1,5-diyl group. A central and respiratory stimulant, it was formerly used for the treatment of cough and other respiratory tract disorders, cardiovascular disorders including hypotension, and pruritis.	3.07	5	0	organic heterobicyclic compound; organonitrogen heterocyclic compound
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	2	1	0	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.44	2	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
benz(a)anthracene benz(a)anthracene: 4 fused rings of which one is angular in contrast to the linear NAPHTHACENES. tetraphene : An angular ortho-fused polycyclic arene consisting of four fused benzene rings.	1.93	1	0	ortho-fused polycyclic arene; tetraphenes
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	3.45	2	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	2.96	4	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
glutamine Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.	11.83	34	13	amino acid zwitterion; glutamine family amino acid; glutamine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	4.53	6	0	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
cyanides Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.	2.38	2	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	1.95	1	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
tubocurarine Tubocurarine: A neuromuscular blocker and active ingredient in CURARE; plant based alkaloid of Menispermaceae.. tubocurarine : A benzylisoquinoline alkaloid muscle relaxant which constitutes the active component of curare.. isoquinoline alkaloid : Any alkaloid that has a structure based on an isoquinoline nucleus. They are derived from the amino acids like tyrosine and phenylalanine.	1.95	1	0	bisbenzylisoquinoline alkaloid	drug allergen; muscle relaxant; nicotinic antagonist
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	2.4	2	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
aminopyrine Aminopyrine: A pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of AGRANULOCYTOSIS. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of CYTOCHROME P-450 metabolic activity in LIVER FUNCTION TESTS.. aminophenazone : A pyrazolone that is 1,2-dihydro-3H-pyrazol-3-one substituted by a dimethylamino group at position 4, methyl groups at positions 1 and 5 and a phenyl group at position 2. It exhibits analgesic, anti-inflammatory, and antipyretic properties.	4.43	5	1	pyrazolone; tertiary amino compound	antipyretic; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2.48	2	0	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
uridine [no description available]	1.95	1	0	uridines	drug metabolite; fundamental metabolite; human metabolite
methoxamine Methoxamine: An alpha-1 adrenergic agonist that causes prolonged peripheral VASOCONSTRICTION.. methoxamine : An amphetamine in which the parent 1-phenylpropan-2-amine skeleton is substituted at position 1 with an hydroxy group and the phenyl ring is 2- and 5-substituted with methoxy groups. It is an antihypotensive agent (pressor), an agonist acting directly at alpha-adrenoceptors with selectivity for the alpha-1 adrenoceptor subtype similar to phenylephrine .	2.05	1	0	amphetamines	alpha-adrenergic agonist; antihypotensive agent
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	2.05	1	0	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
methacholine chloride Methacholine Chloride: A quaternary ammonium parasympathomimetic agent with the muscarinic actions of ACETYLCHOLINE. It is hydrolyzed by ACETYLCHOLINESTERASE at a considerably slower rate than ACETYLCHOLINE and is more resistant to hydrolysis by nonspecific CHOLINESTERASES so that its actions are more prolonged. It is used as a parasympathomimetic bronchoconstrictor agent and as a diagnostic aid for bronchial asthma. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1116)	1.98	1	0	quaternary ammonium salt
aniline [no description available]	2	1	0	anilines; primary arylamine
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	7.41	2	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
desoxycorticosterone Desoxycorticosterone: A steroid metabolite that is the 11-deoxy derivative of CORTICOSTERONE and the 21-hydroxy derivative of PROGESTERONE	1.95	1	0	20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; mineralocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
cytidine [no description available]	1.95	1	0	cytidines	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
cycloheximide Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.	4.22	18	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
egtazic acid Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.	2	1	0	diether; tertiary amino compound; tetracarboxylic acid	chelator
barbituric acid barbituric acid: RN given refers to parent cpd; structure from Merck Index, 9th ed, #966. barbituric acid : A barbiturate, the structure of which is that of perhydropyrimidine substituted at C-2, -4 and -6 by oxo groups. Barbituric acid is the parent compound of barbiturate drugs, although it is not itself pharmacologically active.	3.44	8	0	barbiturates	allergen; xenobiotic
chloroform Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.	1.95	1	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
dimethylformamide Dimethylformamide: A formamide in which the amino hydrogens are replaced by methyl groups.. N,N-dimethylformamide : A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.	1.95	1	0	formamides; volatile organic compound	geroprotector; hepatotoxic agent; polar aprotic solvent
mannitol [no description available]	2	1	0	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
cytarabine [no description available]	1.95	1	0	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
ornithine Ornithine: An amino acid produced in the urea cycle by the splitting off of urea from arginine.. ornithine : An alpha-amino acid that is pentanoic acid bearing two amino substituents at positions 2 and 5.	8.05	5	0	non-proteinogenic L-alpha-amino acid; ornithine	algal metabolite; hepatoprotective agent; mouse metabolite
diethyl sulfoxide [no description available]	1.96	1	0
dinitrofluorobenzene Dinitrofluorobenzene: Irritants and reagents for labeling terminal amino acid groups.. 1-fluoro-2,4-dinitrobenzene : The organofluorine compound that is benzene with a fluoro substituent at the 1-position and two nitro substituents in the 2- and 4-positions.	1.99	1	0	C-nitro compound; organofluorine compound	agrochemical; allergen; chromatographic reagent; EC 2.7.3.2 (creatine kinase) inhibitor; protein-sequencing agent; spectrophotometric reagent
asparagine Asparagine: A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed). asparagine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.	2.08	1	0	amino acid zwitterion; asparagine; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
threonine Threonine: An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins.. threonine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 1-hydroxyethyl group.	2.15	1	0	amino acid zwitterion; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid; threonine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
methaqualone Methaqualone: A quinazoline derivative with hypnotic and sedative properties. It has been withdrawn from the market in many countries because of problems with abuse. (From Martindale, The Extra Pharmacopoeia, 30th ed, p604). methaqualone : A member of the class of quinazolines that is quinazolin-4-one substituted at positions 2 and 3 by methyl and o-tolyl groups respectively. A depressant that increases the activity of the GABA receptors in the brain and nervous system, it is used as a sedative and hypnotic medication. It became popular as a recreational drug and club drug in the late 1960s and 1970s.	5.24	17	0	quinazolines	GABA agonist; sedative
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.	6.18	10	1	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.	2.01	1	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
vinyl chloride Vinyl Chloride: A gas that has been used as an aerosol propellant and is the starting material for polyvinyl resins. Toxicity studies have shown various adverse effects, particularly the occurrence of liver neoplasms.. chloroethene : A monohaloethene that is ethene in which one of the hydrogens has been replaced by a chloro group.	2.25	1	0	chloroethenes; gas molecular entity; monohaloethene	carcinogenic agent
methylene chloride Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.	2.08	1	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
trifluoroethanol Trifluoroethanol: A non-aqueous co-solvent that serves as tool to study protein folding. It is also used in various pharmaceutical, chemical and engineering applications.	1.98	1	0	fluoroalcohol
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	2	1	0	alkyl hydroperoxide	antibacterial agent; oxidising agent
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	2.03	1	0
n-methylacetamide N-methylacetamide: RN given refers to parent cpd. N-methylacetamide : A monocarboxylic acid amide that is the N-methyl derivative of acetamide.	2.38	2	0	acetamides; monocarboxylic acid amide	metabolite
dichloroacetic acid [no description available]	2.25	1	0	monocarboxylic acid; organochlorine compound	astringent; marine metabolite
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.	2.1	1	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	2.79	3	0	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
quinoline [no description available]	1.93	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinolines
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	3.05	4	0	butan-4-olide	metabolite; neurotoxin
furaldehyde Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.	2.1	1	0	aldehyde; furans	Maillard reaction product; metabolite
caprolactam Caprolactam: Cyclic amide of caproic acid used in manufacture of synthetic fibers of the polyamide type. Can cause local irritation.. epsilon-caprolactam : A member of the class of caprolactams that is azepane substituted by an oxo group at position 2.	4.65	8	0	caprolactams	human blood serum metabolite
acrolein [no description available]	2	1	0	enal	herbicide; human xenobiotic metabolite; toxin
allylamine Allylamine: Possesses an unusual and selective cytotoxicity for VASCULAR SMOOTH MUSCLE cells in dogs and rats. Useful for experiments dealing with arterial injury, myocardial fibrosis or cardiac decompensation.	2.07	1	0	alkylamine
glyoxal [no description available]	1.95	1	0	dialdehyde	agrochemical; allergen; pesticide; plant growth regulator
cyclohexanone [no description available]	2.69	3	0	cyclohexanones	human xenobiotic metabolite
3-hydroxypyridine 3-hydroxypyridine: RN given refeirs to parent cpd. 3-pyridinol : A monohydroxypyridine that is pyridine in which the hydrogen at position 3 has been replaced by a hydroxy group. It has been detected as a thermal degradation product from the smoke of the burning leaves of Salvia divinorum, a Mexican psychoactive plant.	2.11	1	0	monohydroxypyridine
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	4.82	31	0	pyrrole; secondary amine
furan furan : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing four carbons and one oxygen, with formula C4H4O. It is a toxic, flammable, low-boiling (31degreeC) colourless liquid.	2.55	2	0	furans; mancude organic heteromonocyclic parent; monocyclic heteroarene	carcinogenic agent; hepatotoxic agent; Maillard reaction product
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.91	4	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
piperidine [no description available]	3.32	7	0	azacycloalkane; piperidines; saturated organic heteromonocyclic parent; secondary amine	base; catalyst; human metabolite; non-polar solvent; plant metabolite; protic solvent; reagent
triethylene glycol triethylene glycol : A poly(ethylene glycol) that is octane-1,8-diol in which the carbon atoms at positions 3 and 6 have been replaced by oxygen atoms.	3.06	1	0	diol; poly(ethylene glycol); primary alcohol	plasticiser
ergotamine Ergotamine: A vasoconstrictor found in ergot of Central Europe. It is a serotonin agonist that has been used as an oxytocic agent and in the treatment of MIGRAINE DISORDERS.. ergotamine : A peptide ergot alkaloid that is dihydroergotamine in which a double bond replaces the single bond between positions 9 and 10.	2.46	2	0	peptide ergot alkaloid	alpha-adrenergic agonist; mycotoxin; non-narcotic analgesic; oxytocic; serotonergic agonist; vasoconstrictor agent
framycetin Framycetin: A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). framycetin : A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.	2.36	2	0	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
2-hydroxypyridine hydroxypyridine : Any member of the class of pyridines with at least one hydroxy substituent.. pyridin-2-ol : A monohydroxypyridine that is pyridine substituted by a hydroxy group at position 2.	2.7	3	0	monohydroxypyridine	plant metabolite
yohimbine Yohimbine: A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of ERECTILE DYSFUNCTION.. yohimbine : An indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina.	2.02	1	0	methyl 17-hydroxy-20xi-yohimban-16-carboxylate	alpha-adrenergic antagonist; dopamine receptor D2 antagonist; serotonergic antagonist
methohexital Methohexital: An intravenous anesthetic with a short duration of action that may be used for induction of anesthesia.. methohexital : A barbiturate, the structure of which is that of barbituric acid substituted at N-1 by a methyl group and at C-5 by allyl and 1-methylpent-2-ynyl groups.	1.95	1	0	acetylenic compound; barbiturates	drug allergen; intravenous anaesthetic
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	2.47	2	0	catechin	antioxidant; plant metabolite
perylene Perylene: A 20-carbon dibenz(de,kl)anthracene that can be viewed as a naphthalene fused to a phenalene or as dinaphthalene. It is used as fluorescent lipid probe in the cytochemistry of membranes and is a polycyclic hydrocarbon pollutant in soil and water. Derivatives may be carcinogenic.. perylene : An ortho- and peri-fused polycyclic arene comprising of five benzene rings that is anthracene in which the d,e and k,l sides are fused to benzene rings.	2.92	4	0	ortho- and peri-fused polycyclic arene; perylenes
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.	3.87	3	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	2.08	1	0	indazole
triethylenediamine triethylenediamine: RN given refers to parent cpd. triethylenediamine : An organic heterobicylic compound that is piperazine with an ethane-1,2-diyl group forming a bridge between N1 and N4. It is typically used as a catalyst in polymerization reactions.	2	1	0	bridged compound; diamine; saturated organic heterobicyclic parent; tertiary amino compound	antioxidant; catalyst; reagent
adamantane Adamantane: A tricyclo bridged hydrocarbon.	4.15	2	0	adamantanes; polycyclic alkane
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	2.68	3	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	2.52	2	0	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	3.46	7	0	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	4.6	8	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.	6.17	9	1	diazine; pyrazines	Daphnia magna metabolite
calcium gluconate [no description available]	2.04	1	0	calcium salt	nutraceutical
hydrazine diamine : Any polyamine that contains two amino groups.	3.23	6	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
monocrotaline Monocrotaline: A pyrrolizidine alkaloid and a toxic plant constituent that poisons livestock and humans through the ingestion of contaminated grains and other foods. The alkaloid causes pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature. Significant attenuation of the cardiopulmonary changes are noted after oral magnesium treatment.	2.41	1	0	pyrrolizidine alkaloid
methysergide Methysergide: An ergot derivative that is a congener of LYSERGIC ACID DIETHYLAMIDE. It antagonizes the effects of serotonin in blood vessels and gastrointestinal smooth muscle, but has few of the properties of other ergot alkaloids. Methysergide is used prophylactically in migraine and other vascular headaches and to antagonize serotonin in the carcinoid syndrome.. methysergide : A synthetic ergot alkaloid, structurally related to the oxytocic agent methylergonovine and to the potent hallucinogen LSD and used prophylactically to reduce the frequency and intensity of severe vascular headaches.	2.08	1	0	ergoline alkaloid
citrulline citrulline : The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position.	1.95	1	0	amino acid zwitterion; citrulline	Daphnia magna metabolite; EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; protective agent; Saccharomyces cerevisiae metabolite
prenylamine Prenylamine: A drug formerly used in the treatment of angina pectoris but superseded by less hazardous drugs. Prenylamine depletes myocardial catecholamine stores and has some calcium channel blocking activity. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1406)	1.95	1	0	diarylmethane
hydantoins Hydantoins: Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS.. imidazolidine-2,4-dione : An imidazolidinone with oxo groups at position 2 and 4.	2.66	3	0	imidazolidine-2,4-dione
fluorobenzenes Fluorobenzenes: Derivatives of BENZENE that contain FLUORINE.. monofluorobenzene : The simplest member of the class of monofluorobenzenes that is benzene carrying a single fluoro substituent.. fluorobenzenes : Any fluoroarene that is a benzene or a substituted benzene carrying at least one fluoro group.	5.85	2	2	monofluorobenzenes	NMR chemical shift reference compound
dextropropoxyphene Dextropropoxyphene: A narcotic analgesic structurally related to METHADONE. Only the dextro-isomer has an analgesic effect; the levo-isomer appears to exert an antitussive effect.. propoxyphene : A racemate of the (1R,2R)- and (1S,2R)- diastereoisomers.. dextropropoxyphene : The (1S,2R)-(+)-diastereoisomer of propoxyphene.	1.93	1	0	1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propanoate	mu-opioid receptor agonist; opioid analgesic
fusarium Fusarium: A mitosporic Hypocreales fungal genus, various species of which are important parasitic pathogens of plants and a variety of vertebrates. Teleomorphs include GIBBERELLA.	2.06	1	0
indirubin [no description available]	2.04	1	0
phthalimidine phthalimidine: structure given in first source. isoindolin-1-one : A member of the class of isoindoles that is 2,3-dihydro-1H-isoindole in which the hydrogens at positon 1 are replaced by an oxo group.	2.57	2	0	gamma-lactam; isoindoles
emetine Emetine: The principal alkaloid of ipecac, from the ground roots of Uragoga (or Cephaelis) ipecacuanha or U. acuminata, of the Rubiaceae. It is used as an amebicide in many different preparations and may cause serious cardiac, hepatic, or renal damage and violent diarrhea and vomiting. Emetine inhibits protein synthesis in EUKARYOTIC CELLS but not PROKARYOTIC CELLS.. emetine : A pyridoisoquinoline comprising emetam having methoxy substituents at the 6'-, 7'-, 10- and 11-positions. It is an antiprotozoal agent and emetic. It inhibits SARS-CoV2, Zika and Ebola virus replication and displays antimalarial, antineoplastic and antiamoebic properties.	2.36	2	0	isoquinoline alkaloid; pyridoisoquinoline	antiamoebic agent; anticoronaviral agent; antiinfective agent; antimalarial; antineoplastic agent; antiprotozoal drug; antiviral agent; autophagy inhibitor; emetic; expectorant; plant metabolite; protein synthesis inhibitor
kainic acid Kainic Acid: (2S-(2 alpha,3 beta,4 beta))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid. Ascaricide obtained from the red alga Digenea simplex. It is a potent excitatory amino acid agonist at some types of excitatory amino acid receptors and has been used to discriminate among receptor types. Like many excitatory amino acid agonists it can cause neurotoxicity and has been used experimentally for that purpose.	2.1	1	0	dicarboxylic acid; L-proline derivative; non-proteinogenic L-alpha-amino acid; pyrrolidinecarboxylic acid	antinematodal drug; excitatory amino acid agonist
butenolide butenolide: inhibits experimental allergic encephalomyelitis in rats. butenolide : A gamma-lactone that consists of a 2-furanone skeleton and its substituted derivatives.	7.41	1	0	butenolide
cycloheptanone cycloheptanone: structure	2.02	1	0
alpha-aminopyridine alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.	2.45	2	0
thiazolidines Thiazolidines: Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES.	3.19	1	0	thiazolidine
dihydroergotamine Dihydroergotamine: A 9,10alpha-dihydro derivative of ERGOTAMINE. It is used as a vasoconstrictor, specifically for the therapy of MIGRAINE DISORDERS.. dihydroergotamine : Ergotamine in which a single bond replaces the double bond between positions 9 and 10. A semisynthetic ergot alkaloid with weaker oxytocic and vasoconstrictor properties than ergotamine, it is used (as the methanesulfonic or tartaric acid salts) for the treatment of migraine and orthostatic hypotension.	2.08	1	0	ergot alkaloid; semisynthetic derivative	dopamine agonist; non-narcotic analgesic; serotonergic agonist; sympatholytic agent; vasoconstrictor agent
chlormethiazole Chlormethiazole: A sedative and anticonvulsant often used in the treatment of alcohol withdrawal. Chlormethiazole has also been proposed as a neuroprotective agent. The mechanism of its therapeutic activity is not entirely clear, but it does potentiate GAMMA-AMINOBUTYRIC ACID receptors response and it may also affect glycine receptors.	1.96	1	0	thiazoles
tropolone Tropolone: A seven-membered aromatic ring compound. It is structurally related to a number of naturally occurring antifungal compounds (ANTIFUNGAL AGENTS).. tropolone : A cyclic ketone that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2. It is a toxin produced by the agricultural pathogen Burkholderia plantarii.	3.19	1	0	alpha-hydroxy ketone; cyclic ketone; enol	bacterial metabolite; fungicide; toxin
isovaleramide isovaleramide: inhibits liver alcohol dehydrogenases	1.96	1	0
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.31	1	0	dialdehyde	biomarker
trinitrobenzenesulfonic acid Trinitrobenzenesulfonic Acid: A reagent that is used to neutralize peptide terminal amino groups.. 2,4,6-trinitrobenzenesulfonic acid : The arenesulfonic acid that is benzenesulfonic acid with three nitro substituents in the 2-, 4- and 6-positions.	2.53	2	0	arenesulfonic acid; C-nitro compound	epitope; explosive; reagent
eosine yellowish-(ys) Eosine Yellowish-(YS): A versatile red dye used in cosmetics, pharmaceuticals, textiles, etc., and as tissue stain, vital stain, and counterstain with HEMATOXYLIN. It is also used in special culture media.. eosin YS dye : An organic sodium salt that is 2',4',5',7'-tetrabromofluorescein in which the carboxy group and the phenolic hydroxy group have been deprotonated and the resulting charge is neutralised by two sodium ions.	1.97	1	0	organic sodium salt; organobromine compound	fluorochrome; histological dye
violacein [no description available]	3.19	1	0
lucanthone hydrochloride Schistosomicides: Agents that act systemically to kill adult schistosomes.	2.53	2	0
hematoporphyrin Hematoporphyrins: Iron-free derivatives of heme with 4 methyl groups, 2 hydroxyethyl groups and 2 propionic acid groups attached to the pyrrole rings. Some of these PHOTOSENSITIZING AGENTS are used in the PHOTOTHERAPY of malignant NEOPLASMS.. hematoporphyrin : A dicarboxylic acid that is protoporphyrin in which the vinyl groups at positions 7 and 12 are replaced by 1-hydroxyethyl groups.	2.38	2	0
succinimide succinimide: RN given refers to parent cpd. succinimide : A dicarboximide that is pyrrolidine which is substituted by oxo groups at positions 2 and 5.	2.37	2	0	dicarboximide; pyrrolidinone
n-methylbenzamide N-methylbenzamide: RN given refers to parent cpd	1.96	1	0
2-pyrrolidone 2-pyrrolidone: RN given refers to parent cpd. pyrrolidin-2-one : The simplest member of the class of pyrrolidin-2-ones, consisting of pyrrolidine in which the hydrogens at position 2 are replaced by an oxo group. The lactam arising by the formal intramolecular condensation of the amino and carboxy groups of gamma-aminobutyric acid (GABA).	2.67	3	0	pyrrolidin-2-ones	metabolite; polar solvent
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.15	1	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
erythromycin Erythromycin: A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.. erythromycin : Any of several wide-spectrum macrolide antibiotics obtained from actinomycete Saccharopolyspora erythraea (formerly known as Streptomyces erythraeus).. erythromycin A : An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively.	1.97	1	0	cyclic ketone; erythromycin
n-methyl-2-pyridone N-methyl-2-pyridone: structure in first source	1.96	1	0	pyridone
4-methylimidazole 4-methylimidazole: RN given refers to parent cpd. 4-methylimidazole : Imidazole substituted at position 4 by a methyl group.	2.25	1	0	imidazoles	carcinogenic agent; reaction intermediate
tempidon 2,2,6,6-tetramethyl-4-piperidinone: structure in first source	4.78	32	0	piperidones
n-methylpyrrolidone 1-methylpyrrolidin-2-one: structure in first source. N-methylpyrrolidin-2-one : A member of the class of pyrrolidine-2-ones that is pyrrolidin-2-one in which the hydrogen attached to the nitrogen is replaced by a methyl group.	1.96	1	0	lactam; N-alkylpyrrolidine; pyrrolidin-2-ones	polar aprotic solvent
cyclopentenone 2-cyclopenten-1-one : An enone that is cyclopentanone having a C=C double bond at position 2.	2.04	1	0	alicyclic ketone; enone	Hsp70 inducer
2-phenoxypropanoic acid 2-phenoxypropanoic acid: structure in first source	2.03	1	0	aromatic ether; carboxylic acid
deoxycytidine [no description available]	2.7	3	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
cyclohexamethylene carbamide cyclohexamethylene carbamide: structure	1.96	1	0
methyl phenyl sulfoxide (methylsulfinyl)benzene : A sulfoxide resulting from the formal oxidation of the sulfur atom of thioanisole.	1.96	1	0	benzenes; sulfoxide
2,2'-dipyridylamine dipyridin-2-ylamine: structure in first source	2.05	1	0
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	2.05	1	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
pregnenolone carbonitrile Pregnenolone Carbonitrile: A catatoxic steroid and microsomal enzyme inducer having significant effects on the induction of cytochrome P450. It has also demonstrated the potential for protective capability against acetaminophen-induced liver damage.	1.95	1	0	aliphatic nitrile
n-ethyl-2-pyrrolidone N-ethyl-2-pyrrolidone: structure in first source	1.96	1	0	N-alkylpyrrolidine
2,2-bis(bromomethyl)-1,3-propanediol 2,2-bis(bromomethyl)-1,3-propanediol: structure given in first source	1.96	1	0	primary alcohol
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.	2.04	1	0	fluorescein isothiocyanate
1-benzyl-4-piperidone 1-benzyl-4-piperidone: structure in first source	2.03	1	0
tranylcypromine Tranylcypromine: A propylamine formed from the cyclization of the side chain of amphetamine. This monoamine oxidase inhibitor is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in panic and phobic disorders. (From AMA Drug Evaluations Annual, 1994, p311). tranylcypromine : A racemate comprising equal amounts of (1R,2S)- and (1S,2R)-2-phenylcyclopropan-1-amine. An irreversible monoamine oxidase inhibitor that is used as an antidepressant (INN tranylcypromine).. (1R,2S)-tranylcypromine : A 2-phenylcyclopropan-1-amine that is the (1R,2S)-enantiomer of tranylcypromine.	1.94	1	0	2-phenylcyclopropan-1-amine
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	2.11	1	0	cobalt group element atom; platinum group metal atom
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	2.05	1	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
niobium Niobium: A metal element atomic number 41, atomic weight 92.906, symbol Nb.	2.04	1	0	vanadium group element atom
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	8.19	5	0	metal allergen; nickel group element atom; platinum group metal atom
rhodium Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.	3.13	5	0	cobalt group element atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	2.05	1	0	iron group element atom; platinum group metal atom
technetium Technetium: The first artificially produced element and a radioactive fission product of URANIUM. Technetium has the atomic symbol Tc, and atomic number 43. All technetium isotopes are radioactive. Technetium 99m (m=metastable) which is the decay product of Molybdenum 99, has a half-life of about 6 hours and is used diagnostically as a radioactive imaging agent. Technetium 99 which is a decay product of technetium 99m, has a half-life of 210,000 years.	2.52	2	0	manganese group element atom
titanium Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.	2.95	4	0	titanium group element atom
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	2.66	2	0	cadmium molecular entity; zinc group element atom
chromium Chromium: A trace element that plays a role in glucose metabolism. It has the atomic symbol Cr, atomic number 24, and atomic weight 52. According to the Fourth Annual Report on Carcinogens (NTP85-002,1985), chromium and some of its compounds have been listed as known carcinogens.. chromium ion : An chromium atom having a net electric charge.. chromium atom : A chromium group element atom that has atomic number 24.	2.39	2	0	chromium group element atom; metal allergen	micronutrient
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	3.8	3	0	copper group element atom; elemental gold
hypochlorous acid Hypochlorous Acid: An oxyacid of chlorine (HClO) containing monovalent chlorine that acts as an oxidizing or reducing agent.. hypochlorous acid : A chlorine oxoacid with formula HOCl; a weak, unstable acid, it is the active form of chlorine in water.	2.06	1	0	chlorine oxoacid; reactive oxygen species	EC 2.5.1.18 (glutathione transferase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; human metabolite
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	2.15	1	0	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
ferric chloride ferric chloride: RN given refers to cpd with MF of Fe-Cl3; used to induce experimental arterial thrombosis to evaluate antithrombotic agents	2.11	1	0	iron coordination entity	astringent; Lewis acid
potassium nitrate potassium nitrate: RN given refers to cpd with MF of K-HNO3; when combined with charcoal and sulfur it can form EXPLOSIVE AGENTS. potassium nitrate : The inorganic nitrate salt of potassium.	2.11	1	0	inorganic nitrate salt; potassium salt	fertilizer
tricalcium phosphate tricalcium phosphate: a form of tricalcium phosphate used as bioceramic bone replacement material; see also records for alpha-tricalcium phosphate, beta-tricalcium phosphate, calcium phosphate; apatitic tricalcium phosphate Ca9(HPO4)(PO4)5(OH) is the calcium orthophosphate leading to beta tricalcium phosphate Ca3(PO4)2 (b-TCP). calcium phosphate : A calcium salt composed of calcium and phosphate/diphosphate ions; present in milk and used for the mineralisation of calcified tissues.	2.1	1	0	calcium phosphate
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2.89	4	0	dihydrogen
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	1.94	1	0	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	2.03	1	0	diatomic chlorine; gas molecular entity	bleaching agent
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	2.21	1	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
ammonium chloride Ammonium Chloride: An acidifying agent that has expectorant and diuretic effects. Also used in etching and batteries and as a flux in electroplating.. ammonium chloride : An inorganic chloride having ammonium as the counterion.	2.11	1	0	ammonium salt; inorganic chloride	ferroptosis inhibitor
titanium dioxide titanium dioxide: used medically as protectant against externally caused irritation & sunlight; high concentrations of dust may cause irritation to respiratory tract; RN given refers to titanium oxide (TiO2); structure. titanium dioxide : A titanium oxide with the formula TiO2. A naturally occurring oxide sourced from ilmenite, rutile and anatase, it has a wide range of applications.	2.41	2	0	titanium oxides	food colouring
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	4.9	11	0
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2.05	1	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
fluorides [no description available]	2	1	0	halide anion; monoatomic fluorine
1-deoxynojirimycin 1-deoxy-nojirimycin: structure in first source. duvoglustat : An optically active form of 2-(hydroxymethyl)piperidine-3,4,5-triol having 2R,3R,4R,5S-configuration.	1.96	1	0	2-(hydroxymethyl)piperidine-3,4,5-triol; piperidine alkaloid	anti-HIV agent; anti-obesity agent; bacterial metabolite; EC 3.2.1.20 (alpha-glucosidase) inhibitor; hepatoprotective agent; hypoglycemic agent; plant metabolite
taurolidine [no description available]	2.13	1	0	thiadiazinane
iodine [no description available]	1.95	1	0	halide anion; monoatomic iodine	human metabolite
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.	8.69	18	3	benzenes; phenyl acetates
n-phenylethanolamine [no description available]	2.44	2	0	aralkylamine
paraldehyde Paraldehyde: A hypnotic and sedative with anticonvulsant effects. However, because of the hazards associated with its administration, its tendency to react with plastic, and the risks associated with its deterioration, it has largely been superseded by other agents. It is still occasionally used to control status epilepticus resistant to conventional treatment. (From Martindale, The Extra Pharmacopoeia, 30th ed, p608-9). paraldehyde : A trioxane that is 1,3,5-trioxane substituted by methyl groups at positions 2, 4 and 6.	2.65	3	0	trioxane	sedative
pyrrolidine [no description available]	2.51	2	0	azacycloalkane; pyrrolidines; saturated organic heteromonocyclic parent
1,4-dioxane 1,4-dioxane: dehydrating agent; polar solvent miscible both with water & most organic solvents. dioxane : Any member of the class of dioxanes that is a cyclohexane in which two carbon atoms are replaced by oxygen atoms.. 1,4-dioxane : A dioxane with oxygen atoms at positions 1 and 4.	2	1	0	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
triamcinolone Triamcinolone: A glucocorticoid given, as the free alcohol or in esterified form, orally, intramuscularly, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. (From Martindale, The Extra Pharmacopoeia, 30th ed, p739). triamcinolone : A C21-steroid hormone that is 1,4-pregnadiene-3,20-dione carrying four hydroxy substituents at positions 11beta, 16alpha, 17alpha and 21 as well as a fluoro substituent at position 9. Used in the form of its 16,17-acetonide to treat various skin infections.	1.95	1	0	11beta-hydroxy steroid; 16alpha-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	anti-allergic agent; anti-inflammatory drug
dimethylacetamide hallucinogen : Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.. N,N-dimethylacetamide : A member of the class of acetamides that is acetamide in which the hydrogens attached to the N atom have been replaced by two methyl groups respectively. Metabolite observed in cancer metabolism.	1.96	1	0	acetamides; monocarboxylic acid amide	human metabolite
fludrocortisone Fludrocortisone: A synthetic mineralocorticoid with anti-inflammatory activity.	1.95	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; fluorinated steroid; mineralocorticoid	adrenergic agent; anti-inflammatory drug
n-chlorosuccinimide N-chlorosuccinimide : A five-membered cyclic dicarboximide compound having a chloro substituent on the nitrogen atom.	2.06	1	0	dicarboximide; pyrrolidinone
4-methoxyamphetamine 4-methoxyamphetamine: para-methoxy derivative to amphetamine with hallucinogenic properties; minor descriptor (75-86); on line & INDEX MEDICUS search AMPHETAMINES (75-86); RN given refers to parent compound without isomeric designation	1.93	1	0
alkenes [no description available]	3.46	7	0
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	3.74	10	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
torpedo Torpedo: A genus of the Torpedinidae family consisting of several species. Members of this family have powerful electric organs and are commonly called electric rays.	2.08	1	0
sodium azide Sodium Azide: A cytochrome oxidase inhibitor which is a nitridizing agent and an inhibitor of terminal oxidation. (From Merck Index, 12th ed). sodium azide : The sodium salt of hydrogen azide (hydrazoic acid).	2.69	3	0	inorganic sodium salt	antibacterial agent; explosive; mitochondrial respiratory-chain inhibitor; mutagen
7-ethoxycoumarin 7-ethoxycoumarin : A member of the class of coumarins that is umbelliferone in which the hydroxy group at position 7 is replaced by an ethoxy group.	2	1	0	aromatic ether; coumarins
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).	2.44	2	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
etoposide [no description available]	2.84	3	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	2.5	2	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	2.45	2	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
epirubicin Epirubicin: An anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA.	2.08	1	0	aminoglycoside; anthracycline antibiotic; anthracycline; deoxy hexoside; monosaccharide derivative; p-quinones; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	antimicrobial agent; antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
propiconazole Orbit: Bony cavity that holds the eyeball and its associated tissues and appendages.	2.31	1	0	conazole fungicide; cyclic ketal; dichlorobenzene; triazole fungicide; triazoles	antifungal agrochemical; EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor; environmental contaminant; xenobiotic
paroxetine Paroxetine: A serotonin uptake inhibitor that is effective in the treatment of depression.. paroxetine : A benzodioxole that consists of piperidine bearing 1,3-benzodioxol-5-yloxy)methyl and 4-fluorophenyl substituents at positions 3 and 4 respectively; the (3S,4R)-diastereomer. Highly potent and selective 5-HT uptake inhibitor that binds with high affinity to the serotonin transporter (Ki = 0.05 nM). Ki values are 1.1, 350 and 1100 nM for inhibition of [3H]-5-HT, [3H]-l-NA and [3H]-DA uptake respectively. Displays minimal affinity for alpha1-, alpha2- or beta-adrenoceptors, 5-HT2A, 5-HT1A, D2 or H1 receptors at concentrations below 1000 nM, however displays weak affinity for muscarinic ACh receptors (Ki = 42 nM). Antidepressant and anxiolytic in vivo.	2.41	2	0	aromatic ether; benzodioxoles; organofluorine compound; piperidines	antidepressant; anxiolytic drug; hepatotoxic agent; P450 inhibitor; serotonin uptake inhibitor
captopril Captopril: A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin.. captopril : A L-proline derivative in which L-proline is substituted on nitrogen with a (2S)-2-methyl-3-sulfanylpropanoyl group. It is used as an anti-hypertensive ACE inhibitor drug.	1.96	1	0	alkanethiol; L-proline derivative; N-acylpyrrolidine; pyrrolidinemonocarboxylic acid	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
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.	2.47	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
fomesafen fomesafen: a protoporphyrinogen oxidase-inhibiting herbicide. fomesafen : An N-sulfonylcarboxamide that is N-(methylsulfonyl)benzamide in which the phenyl ring is substituted by a nitro group at position 2 and a 2-chloro-4-(trifluoromethyl)phenoxy group at position 5. A protoporphyrinogen oxidase inhibitor, it was specially developed for use (generally as the corresponding sodium salt, fomesafen-sodium) for post-emergence control of broad-leaf weeds in soya.	1.95	1	0	aromatic ether; C-nitro compound; monochlorobenzenes; N-sulfonylcarboxamide; organofluorine compound; phenols	agrochemical; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide
swainsonine Swainsonine: An indolizidine alkaloid from the plant Swainsona canescens that is a potent alpha-mannosidase inhibitor. Swainsonine also exhibits antimetastatic, antiproliferative, and immunomodulatory activity.. swainsonine : An indolizidine alkaloid isolated from the plant Swainsona canescens with three hydroxy substituents at positions 1, 2 and 8.	2.11	1	0	indolizidine alkaloid	antineoplastic agent; EC 3.2.1.114 (mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase) inhibitor; immunological adjuvant; plant metabolite
gepirone gepirone: RN given refers to parent cpd; structure given in first source	2.01	1	0	N-arylpiperazine
itraconazole Itraconazole: A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis.. itraconazole : An N-arylpiperazine that is cis-ketoconazole in which the imidazol-1-yl group is replaced by a 1,2,4-triazol-1-yl group and in which the actyl group attached to the piperazine moiety is replaced by a p-[(+-)1-sec-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]phenyl group. A potent P-glycoprotein and CYP3A4 inhibitor, it is used as an antifungal drug for the treatment of various fungal infections, including aspergillosis, blastomycosis, candidiasis, chromoblastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, and sporotrichosis.	4.62	1	1	aromatic ether; conazole antifungal drug; cyclic ketal; dichlorobenzene; dioxolane; N-arylpiperazine; triazole antifungal drug; triazoles	EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; Hedgehog signaling pathway inhibitor; P450 inhibitor
antineoplaston a10 antineoplaston A10: peptide analogue isolated from human urine	13.79	86	13
sparfloxacin [no description available]	2	1	0	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone
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.	2.54	2	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]	2.15	1	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
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	1.95	1	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
trifluoromethanesulfonic acid trifluoromethanesulfonic acid: deblocking reagent for peptide synthesis; RN given refers to parent cpd. triflic acid : A one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines.	2.05	1	0	one-carbon compound; perfluoroalkanesulfonic acid
potassium phosphate potassium phosphate: used in dental materials and to treat hypophosphatemia; RN given refers to cpd with unspecified MF. tripotassium phosphate : An inorganic potassium salt that is the tripotassium salt of phosphoric acid.	2.04	1	0	inorganic phosphate salt; inorganic potassium salt
lonetil m3 lonetil M3: Russian Drug; structure	1.96	1	0
febrifugine febrifugine: antimalarials; structure	2.04	1	0	quinazolines
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.	4.34	4	1	D-glucopyranose	epitope; mouse metabolite
n-methylnicotinamide N-methylnicotinamide: structure. N-methylnicotinamide : A pyridinecarboxamide that is nicotinamide in which one of the amide hydrogens is substituted by a methyl group.	1.96	1	0	pyridinecarboxamide	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.	2.05	1	0	organic bromide salt	colorimetric reagent; dye
nojirimycin nojirimycin: from Streptomyces ficellus; RN given refers to parent cpd without isomeric designation	1.96	1	0	amino monosaccharide; hydroxypiperidine
cephalosporin c cephalosporin C: RN given refers to parent cpd; structure in Merck, 9th ed, #1937. cephalosporin C : A cephalosporin antibiotic carrying a 3-acetoxymethyl substituent and a 6-oxo-N(6)-L-lysino group at position 7.	2.31	1	0	cephalosporin	fungal metabolite
anpirtoline anpirtoline: structure given in first source	2.48	2	0	aryl sulfide
goralatide goralatide: from fetal calf bone marrow; exerts a high inhibitory activity on the proliferation of hematopoietic pluripotent stem cells. goralatide : A tetrapeptide that is Ser-Asp-Lys-Pro in which the N-terminal amino group carries an acetyl group. It is selective inhibitor of primitive haematopoietic cell proliferation and exhibits anti-inflammatory, anti-fibrotic, and pro-angiogenic properties.	2.02	1	0	oligopeptide; tetrapeptide	anti-inflammatory agent; pro-angiogenic agent
alniditan alniditan: structure given in first source	2.41	2	0
dioxadrol dioxadrol: See also records for d- and l-forms which are referred to as dexoxadrol and levoxadrol, respectfully	2.05	1	0	diarylmethane
bromosuccinimide Bromosuccinimide: A brominating agent that replaces hydrogen atoms in benzylic or allylic positions. It is used in the oxidation of secondary alcohols to ketones and in controlled low-energy brominations. (From Miall's Dictionary of Chemistry, 5th ed; Hawley's Condensed Chemical Dictionary, 12th ed,).	2.06	1	0	dicarboximide; organobromine compound; pyrrolidinone	reagent
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	5.83	6	1	1,2,3-triazole
1-piperideine 1-piperideine: RN given refers to parent cpd; structure given in first source	6.96	1	0	piperideine
isobutyramide [no description available]	1.96	1	0	carboximidic acid
fluorodeoxyglucose f18 Fluorodeoxyglucose F18: The compound is given by intravenous injection to do POSITRON-EMISSION TOMOGRAPHY for the assessment of cerebral and myocardial glucose metabolism in various physiological or pathological states including stroke and myocardial ischemia. It is also employed for the detection of malignant tumors including those of the brain, liver, and thyroid gland. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1162)	2.08	1	0	2-deoxy-2-((18)F)fluoro-D-glucose; 2-deoxy-2-fluoro-aldehydo-D-glucose
mesulergine mesulergine: RN given refers to parent cpd; CU 32-085 is synonymous to mono-HCl; metabolized into dopaminergic agonists; structure given in first source. mesulergine : A member of the class of ergot alkaloids that is known to act on serotonin and dopamine receptors.	2.41	2	0	ergot alkaloid; sulfamides	antiparkinson drug; dopamine agonist; serotonergic antagonist
glutarimide [no description available]	7.1	112	0	dicarboximide; piperidones
n-methylscopolamine N-Methylscopolamine: A muscarinic antagonist used to study binding characteristics of muscarinic cholinergic receptors.	2.03	1	0
cromakalim Cromakalim: A potassium-channel opening vasodilator that has been investigated in the management of hypertension. It has also been tried in patients with asthma. (Martindale, The Extra Pharmacopoeia, 30th ed, p352)	3.08	5	0
teleocidin b-4 teleocidins: structure; RN given refers to teleocidin	3.06	1	0
oxazolidin-2-one Oxazolidinones: Derivatives of oxazolidin-2-one. They represent an important class of synthetic antibiotic agents.. oxazolidin-2-one : An oxazolidinone that is 1,3-oxazolidine with an oxo substituent at position 2.. oxazolidinone : An oxazolidine containing one or more oxo groups.	2.03	1	0	carbamate ester; oxazolidinone	metabolite
3-tropinone 3-tropinone: structure; RN given refers to parent cpd	2.37	2	0
3-methylpiperidine 3-methylpiperidine: structure in first source	1.93	1	0
3-chloropropionamide 3-chloropropionamide: structure in first source	1.96	1	0
cyclopropanecarboxamide cyclopropylcarboxamide : Carboxamides RC(=O)NR'R'' where R is a cyclopropyl group.	1.96	1	0	cyclopropylcarboxamide
hypobromous acid [no description available]	2.06	1	0	bromine oxoacid
bromates Bromates: Negative ions or salts derived from bromic acid, HBrO3.	2.06	1	0	bromine oxoanion; monovalent inorganic anion
tetramethylene glutaric acid [no description available]	2.04	1	0
kampirone 1-(2-pyrimidinyl)piperazine: metabolite of buspirone; structure given in first source	2.01	1	0	N-arylpiperazine
n-(3,5-dichlorophenyl)succinimide N-(3,5-dichlorophenyl)succinimide: nephrotoxic; post-treatment enhanced induction of renal cell tumors in rats by dimethylnitrosamine, pre-treatment inhibited induction of tumors, & alone caused interstitial nephritis but no tumors	1.98	1	0	pyrrolidines
fibrinogen Fibrinogen: Plasma glycoprotein clotted by thrombin, composed of a dimer of three non-identical pairs of polypeptide chains (alpha, beta, gamma) held together by disulfide bonds. Fibrinogen clotting is a sol-gel change involving complex molecular arrangements: whereas fibrinogen is cleaved by thrombin to form polypeptides A and B, the proteolytic action of other enzymes yields different fibrinogen degradation products.. D-iditol : The D-enantiomer of iditol.	2.41	1	0	iditol	fungal metabolite
streptovitacin a streptovitacin A: structure	2.39	2	0
iodosobenzene iodosobenzene: oxygen donor	2.05	1	0
phenylacetylglutamine N(2)-phenylacetyl-L-glutamine : An a N(2)-phenylacetylglutamine having L-configuration.	2	1	0	N(2)-phenylacetylglutamine	human metabolite
quebrachamine quebrachamine: an indole alkaloid; isolated from Aspidosperma tree; structure given in first source	2.03	1	0	alkaloid
phenglutarimide phenglutarimide: RN given refers to parent cpd; structure	2.34	2	0	piperidines
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	1.93	1	0	cobalt group element atom; metal allergen	micronutrient
tert-butylbicyclophosphorothionate tert-butylbicyclophosphorothionate: binds to GABA & ion recognition sites; structure given in first source	1.99	1	0	organic thiophosphate
arginyl-glycyl-aspartic acid arginyl-glycyl-aspartic acid: amino acid sequence of basic unit of widespread cellular recognition system	2.04	1	0	oligopeptide
cyanates Cyanates: Organic salts of cyanic acid containing the -OCN radical.. cyanates : Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N.. isocyanates : Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N).	2.04	1	0
gr 127935 GR 127935: a 5-HT 1D receptor antagonist. GR 127935 : A member of the class of benzamides obtained by formal condensation of the carboxy group of 2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxylic acid and the anilino group of 4-methoxy-3-(4-methylpiperazin-1-yl)aniline. Potent and selective 5-HT1B/1D receptor antagonist (pKi values are 8.5 for both guinea pig 5-HT1D and rat 5-HT1B receptors). Displays > 100-fold selectivity over 5HT1A, 5-HT2A, 5-HT2C receptors and other receptor types. Centrally active following oral administration.	3.88	12	0	1,2,4-oxadiazole; benzamides; N-alkylpiperazine; N-arylpiperazine
procyanidin Proanthocyanidins: Dimers and oligomers of flavan-3-ol units (CATECHIN analogs) linked mainly through C4 to C8 bonds to leucoanthocyanidins. They are structurally similar to ANTHOCYANINS but are the result of a different fork in biosynthetic pathways.	2.05	1	0	proanthocyanidin
6-chloro-2-(1-piperazinyl)pyrazine [no description available]	2.03	1	0	N-arylpiperazine
5-methoxy 3-(1,2,3,6-tetrahydro-4-pyridinyl)1h indole [no description available]	2.41	2	0	indoles
ribonolactone ribonolactone: structure given in first source; RN given refers to cpd without isomeric designation. D-ribono-1,4-lactone : A five-membered form of ribonolactone having D-configuration.	2.05	1	0	butan-4-olide; ribonolactone	metabolite
leucinol leucinol: RN given for (L)-isomer	2.05	1	0
way 100135 WAY 100135: a selective antagonist at presynaptic & postsynaptic 5-HT(1A) receptors; structure given in first source	2	1	0	piperazines
brl 44408 BRL 44408: has selectivity for adrenergic alpha-2A receptors; BRL 48962 is the R-enantiomer; BRL 48553 is the R-enantiomer	2.02	1	0
carbene carbene: electrically neutral species H2C: and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons; carbene is the name of the parent hydride :CH2 ; hence, the name dichlorocarbene for :CCl2. However, names for acyclic and cyclic hydrocarbons containing one or more divalent carbon atoms are derived from the name of the corresponding all-4-hydrocarbon using the suffix -ylidene; methylene carbene also available. carbene : The electrically neutral species H2C(2.) and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons, which may be spin-paired (singlet state) or spin-non-paired (triplet state).	2.05	1	0	carbene; methanediyl
peroxynitrous acid Peroxynitrous Acid: A potent oxidant synthesized by the cell during its normal metabolism. Peroxynitrite is formed from the reaction of two free radicals, NITRIC OXIDE and the superoxide anion (SUPEROXIDES).	2.08	1	0	nitrogen oxoacid
gefitinib [no description available]	2.15	1	0	aromatic ether; monochlorobenzenes; monofluorobenzenes; morpholines; quinazolines; secondary amino compound; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist
cp 93129 3-(1,2,5,6-tetrahydropyrid-4-yl)pyrrolo(3,2-b)pyrid-5-one: serotonin agonist; structure given in first source	3.64	9	0	pyrrolopyridine
ferric bleomycin iron bleomycin: iron-bleomycin complexes	1.98	1	0
cyclohexylaminoglutethimide cyclohexylaminoglutethimide: structure given in first source	2.38	2	0
rwj 26629 RWJ 26629: structure given in first source; RN refers to (cis-(+-))-isomer	2.67	3	0
3-(3-(dimethylamino)propyl)-4-hydroxy-n-(4-(4-pyridinyl)phenyl)benzamide 3-(3-(dimethylamino)propyl)-4-hydroxy-N-(4-(4-pyridinyl)phenyl)benzamide: a 5-HT(1D) receptor antagonist; RN given refers to HCl salt	2.46	2	0
im 2 autoregulator IM 2 autoregulator: controls blue pigment and nucleoside antibiotic production in Streptomyces; RN given for (3R-(3alpha(R*),4beta))-isomer	2.54	2	0
brl 55834 BRL 55834: potassium channel activator	3.09	5	0
serotonin-o-carboxymethyl-gly-tyr serotonin-O-carboxymethyl-Gly-Tyr: structure given in first source; ligand for serotonin receptor subtypes	2.02	1	0
3-(mercaptomethyl)-2-oxo-1-piperidineacetic acid [no description available]	2.39	2	0
imiloxan [no description available]	2.02	1	0	benzodioxine
dimethylselenoxide [no description available]	2.25	1	0
pomalidomide 3-aminophthalimidoglutarimide: structure in first source	5.65	3	1	aromatic amine; dicarboximide; isoindoles; piperidones	angiogenesis inhibitor; antineoplastic agent; immunomodulator
beta-lactams 2-azetidinone: structure in first source. azetidin-2-one : An unsubstituted beta-lactam compound.. beta-lactam : A lactam in which the amide bond is contained within a four-membered ring, which includes the amide nitrogen and the carbonyl carbon.	2	1	0	beta-lactam antibiotic allergen; beta-lactam
3,3-tetramethyleneglutarimide 3,3-tetramethyleneglutarimide: structure in first source	2.04	1	0
phorbols Phorbols: The parent alcohol of the tumor promoting compounds from CROTON OIL (Croton tiglium).	2.08	1	0	diterpene; terpenoid fundamental parent
cyanopindolol [no description available]	2.44	2	0	indoles
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	3.1	5	0	oxygen hydride; oxygen radical; reactive oxygen species
gizzerosine gizzerosine: found in overheated fish meal; causes gizzard erosion in chicks; RN refers to (L)-isomer; structure in first source	3.13	1	0
singlet oxygen Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.	3.63	9	0	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
silver phosphate silver phosphate: for chloride analysis in cystic fibrosis patch test	2.04	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.	2.05	1	0	2,6-diaminopurines	antiviral drug; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
adepren adepren: Bulgarian preperation	3.34	1	1
atx 70 ATX 70: structure given in first source; a gallium-porphyrin complex	1.98	1	0
l 691121 L 691121: structure given in first source	3.08	5	0
isoindigotin isoindigotin: used in treatment of chronic granulocytic leukemia; structure given in first source	2.04	1	0
dihydrocorynantheol dihydrocorynantheol: alkaloid from Mitragyna species; isomer of corynantheidol;	2.05	1	0
ferric thiocyanate [no description available]	2.11	1	0
paromomycin Paromomycin: An aminoglycoside antibacterial and antiprotozoal agent produced by species of STREPTOMYCES.. paromomycin : An amino cyclitol glycoside that is the 1-O-(2-amino-2-deoxy-alpha-D-glucopyranoside) and the 3-O-(2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl)-beta-D-ribofuranoside of 4,6-diamino-2,3-dihydroxycyclohexane (the 1R,2R,3S,4R,6S diastereoisomer). It is obtained from various Streptomyces species. A broad-spectrum antibiotic, it is used (generally as the sulfate salt) for the treatment of acute and chronic intestinal protozoal infections, but is not effective for extraintestinal protozoal infections. It is also used as a therapeutic against visceral leishmaniasis.	2.08	1	0	amino cyclitol glycoside; aminoglycoside antibiotic	anthelminthic drug; antibacterial drug; antiparasitic agent; antiprotozoal drug
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	2.64	3	0
sb 203580 [no description available]	2.51	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
sb 216763 [no description available]	2.05	1	0	indoles; maleimides
agn 2979 AGN 2979: RN given refers to parent cpd; structure given in first source	4.98	9	1
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	2.05	1	0	divalent inorganic anion; phosphite ion
bms 181101 BMS 181101: structure given in first source	2.01	1	0
mk 912 L 657743: structure given in first source	2.02	1	0
indigoidine indigoidine: structure in first source. indigoidine : A member of the class of pyridone that is a dimeric blue pigment biosynthesised from L-glutamine.	6.19	39	0
nothapodytine b nothapodytine B: isolated from Nothapodytes foetida; structure in first source	2.01	1	0
pipermethystine pipermethystine: structure in first source	7.15	1	0	dihydropyridine
3-(hydroxyacetyl)indole 3-(hydroxyacetyl)indole: structure in first source	2.1	1	0	indoles
sorafenib [no description available]	2.08	1	0	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; phenylureas; pyridinecarboxamide	angiogenesis inhibitor; anticoronaviral agent; antineoplastic agent; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; ferroptosis inducer; tyrosine kinase inhibitor
lenalidomide [no description available]	6.96	6	1	aromatic amine; dicarboximide; isoindoles; piperidones	angiogenesis inhibitor; antineoplastic agent; immunomodulator
propargylamine propargylamine: RN given refers to parent cpd; structure	2.03	1	0
3-octanone 3-octanone : A dialkyl ketone that is octane in which the two methylene protons at position 3 have been replaced by an oxo group.	2.05	1	0	dialkyl ketone	antifeedant; biomarker; fungal metabolite; human urinary metabolite; insect attractant; plant metabolite; toxin
anisomycin Anisomycin: An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.. (-)-anisomycin : An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.	1.96	1	0	monohydroxypyrrolidine; organonitrogen heterocyclic antibiotic	anticoronaviral agent; antimicrobial agent; antineoplastic agent; antiparasitic agent; bacterial metabolite; DNA synthesis inhibitor; protein synthesis inhibitor
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	2.02	1	0
Harringtonine harringtonin: alkaloid C from Caphalotaxus fortunei	2.31	1	0	alkaloid
2-oxindole 2-oxindole: RN given refers to parent cpd; structure. indolin-2-one : An indolinone carrying an oxo group at position 2.	2.08	1	0	gamma-lactam; indolinone
3,5-bis(benzylidene)-4-piperidone 3,5-bis(benzylidene)-4-piperidone: structure in first source	3.96	12	0
bortezomib [no description available]	3.73	9	0	amino acid amide; L-phenylalanine derivative; pyrazines	antineoplastic agent; antiprotozoal drug; protease inhibitor; proteasome inhibitor
glucosamine D-glucosamine : An amino sugar whose structure comprises D-glucose having an amino substituent at position 2.. 2-amino-2-deoxy-D-glucopyranose : A D-glucosamine whose structure comprises D-glucopyranose having an amino substituent at position 2.	1.96	1	0	D-glucosamine	Escherichia coli metabolite; geroprotector; mouse metabolite
carnosine polaprezinc: stimulates bone growth	2	1	0	amino acid zwitterion; dipeptide	anticonvulsant; antineoplastic agent; antioxidant; Daphnia magna metabolite; geroprotector; human metabolite; mouse metabolite; neuroprotective agent
diaminopimelic acid Diaminopimelic Acid: A diamino derivative of heptanedioic acid with amino groups at C-2 and C-6 and the general formula (COOH)CH(NH2)CH2CH2CH2CH(NH2)(COOH).. LL-2,6-diaminopimelic acid : A 2,6-diaminopimelic acid in which both chiral centres have S configuration. It is a component of bacterial cell wall.	1.97	1	0	2,6-diaminopimelic acid; amino acid zwitterion	Escherichia coli metabolite
puromycin [no description available]	2.67	3	0	puromycins	antiinfective agent; antimicrobial agent; antineoplastic agent; EC 3.4.11.14 (cytosol alanyl aminopeptidase) inhibitor; EC 3.4.14.2 (dipeptidyl-peptidase II) inhibitor; nucleoside antibiotic; protein synthesis inhibitor
alpha-aminobutyric acid alpha-aminobutyric acid: RN given refers to cpd without isomeric designation. alpha-aminobutyric acid : An alpha-amino acid that is butyric acid bearing a single amino substituent located at position 2.. D-alpha-aminobutyric acid : An optically active form of alpha-aminobutyric acid having D-configuration.	2.15	1	0	alpha-aminobutyric acid; D-alpha-amino acid
strychnine Strychnine: An alkaloid found in the seeds of STRYCHNOS NUX-VOMICA. It is a competitive antagonist at glycine receptors and thus a convulsant. It has been used as an analeptic, in the treatment of nonketotic hyperglycinemia and sleep apnea, and as a rat poison.. strychnine : A monoterpenoid indole alkaloid that is strychnidine bearing a keto substituent at the 10-position.	2.38	2	0	monoterpenoid indole alkaloid; organic heteroheptacyclic compound	avicide; cholinergic antagonist; glycine receptor antagonist; neurotransmitter agent; rodenticide
griseofulvin Griseofulvin: An antifungal agent used in the treatment of TINEA infections.. griseofulvin : An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.	1.94	1	0	1-benzofurans; antibiotic antifungal drug; benzofuran antifungal drug; organochlorine compound; oxaspiro compound	antibacterial agent; Penicillium metabolite
actinorhodin actinorhodin: structure. actinorhodin : A member of the class of benzoisochromanequinone that is produced by Streptomyces coelicolor A3(2) and exhibits antibiotic activity.	2.59	2	0
phorbol phorbol: RN given refers to (1aR-(1a alpha,1b beta,4a beta,7a alpha,7b alpha,8 alpha,9 beta,9b beta))-isomer; synonym isophorbol refers to (4a alpha)-isomer; structure in Merck Index, 9th ed, #7143. phorbol : A diterpenoid with the structure of tigliane hydroxylated at C-4, -9, -12(beta), -13 and -20, with an oxo group at C-3 and unsaturation at the 1- and 6-positions.	2.08	1	0	cyclic ketone; enone; tertiary alcohol; tertiary alpha-hydroxy ketone; tetracyclic diterpenoid
gingerol gingerol: an active ingredient in GINGER along with SHOGAOL. a nonvolatile methoxy phenyl decanone. gingerol : A beta-hydroxy ketone that is 5-hydroxydecan-3-one substituted by a 4-hydroxy-3-methoxyphenyl moiety at position 1; believed to inhibit adipogenesis. It is a constituent of fresh ginger.	2.17	1	0	beta-hydroxy ketone; guaiacols	antineoplastic agent; plant metabolite
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.17	1	0	cyclodextrin
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	3.06	1	0	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	2.05	1	0	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
retinol Vitamin A: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.. vitamin A : Any member of a group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids that exhibit biological activity against vitamin A deficiency. Vitamin A is involved in immune function, vision, reproduction, and cellular communication.. all-trans-retinol : A retinol in which all four exocyclic double bonds have E- (trans-) geometry.. retinol : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).	2.03	1	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
tacrolimus Tacrolimus: A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.. tacrolimus (anhydrous) : A macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.	2.08	1	0	macrolide lactam	bacterial metabolite; immunosuppressive agent
cocaine Cocaine: An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.. cocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.	2.76	3	0	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic
epothilone a Epothilones: A group of 16-member MACROLIDES which stabilize MICROTUBULES in a manner similar to PACLITAXEL. They were originally found in the myxobacterium Sorangium cellulosum, now renamed to Polyangium (MYXOCOCCALES).	3.55	2	0	epothilone; epoxide	antineoplastic agent; metabolite; microtubule-stabilising agent; tubulin modulator
6-bromoindirubin-3'-oxime 6-bromoindirubin-3'-oxime: structure in first source. 6-bromoindirubin-3'-oxime : A member of the class of biindoles that is indirubin substituted at position 6 by a bromo group and in which the keto group at position 3' has undergone condensation with hydroxylamine to form the corresponding oxime.	2.05	1	0
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)	2.35	2	0	actinomycin	mutagen
melphalan Melphalan: An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.. melphalan : A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.	2.13	1	0	L-phenylalanine derivative; nitrogen mustard; non-proteinogenic L-alpha-amino acid; organochlorine compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
riboflavin vitamin B2 : Any member of a group of vitamers that belong to the chemical structural class called flavins that exhibit biological activity against vitamin B2 deficiency. Symptoms associated with vitamin B2 deficiency include glossitis, seborrhea, angular stomaitis, cheilosis and photophobia. The vitamers include riboflavin and its phosphate derivatives (and includes their salt, ionised and hydrate forms).	3.53	2	0	flavin; vitamin B2	anti-inflammatory agent; antioxidant; cofactor; Escherichia coli metabolite; food colouring; fundamental metabolite; human urinary metabolite; mouse metabolite; photosensitizing agent; plant metabolite
ammonium acetate ammonium acetate : An ammonium salt obtained by reaction of ammonia with acetic acid. A deliquescent white crystalline solid, it has a relatively low melting point (114degreeC) for a salt. Used as a food acidity regulator, although no longer approved for this purpose in the EU.	2.25	1	0	acetate salt; ammonium salt	buffer; food acidity regulator
triacetoneamine-n-oxyl Triacetoneamine-N-Oxyl: Cyclic N-oxide radical functioning as a spin label and radiation-sensitizing agent.. 4-oxo-TEMPO : A member of the class of aminoxyls that is TEMPO carrying an oxo group at position 4.	4.72	30	0	aminoxyls; piperidones	radical scavenger
dipyrone Dipyrone: A drug that has analgesic, anti-inflammatory, and antipyretic properties. It is the sodium sulfonate of AMINOPYRINE.. metamizole sodium : An organic sodium salt of antipyrine substituted at C-4 by a methyl(sulfonatomethyl)amino group, commonly used as a powerful analgesic and antipyretic.	4.03	3	1	organic sodium salt	anti-inflammatory agent; antipyretic; antirheumatic drug; cyclooxygenase 3 inhibitor; non-narcotic analgesic; peripheral nervous system drug; prodrug
camalexin camalexin : An indole phytoalexin that is indole substituted at position 3 by a 1,3-thiazol-2-yl group.	2.03	1	0	1,3-thiazoles; indole phytoalexin	metabolite
chalcone trans-chalcone : The trans-isomer of chalcone.	2.07	1	0	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
isomethyleugenol Methylation: Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed)	2.92	4	0	isomethyleugenol
piplartine piplartine: Antineoplastic Agent, Phytogenic; alkaloid from Piper; structure in first source	6.81	43	0	cinnamamides; dicarboximide
piperine piperine : A N-acylpiperidine that is piperidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum.	2.73	3	0	benzodioxoles; N-acylpiperidine; piperidine alkaloid; tertiary carboxamide	food component; human blood serum metabolite; NF-kappaB inhibitor; plant metabolite
phenyl-n-tert-butylnitrone phenyl-N-tert-butylnitrone: a spin-trapping agent	2	1	0
xanthohumol xanthohumol: from hop plant, Humulus lupulus. xanthohumol : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells.	2.21	1	0	aromatic ether; chalcones; polyphenol	anti-HIV-1 agent; antineoplastic agent; antiviral agent; apoptosis inducer; EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor; metabolite
nsc 4347 NSC 4347: structure in first source	6.08	21	0
alpha-methyltryptophan, (l)-isomer [no description available]	2.44	2	0
dieldrin Dieldrin: An organochlorine insecticide whose use has been cancelled or suspended in the United States. It has been used to control locusts, tropical disease vectors, in termite control by direct soil injection, and non-food seed and plant treatment. (From HSDB). dieldrin : An organochlorine compound resulting from the epoxidation of the double bond of aldrin. It is the active metabolite of the proinsecticde aldrin.	1.93	1	0	epoxide; organochlorine compound; organochlorine insecticide	carcinogenic agent; xenobiotic
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.	5.27	46	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
benztropine Benztropine: A centrally active muscarinic antagonist that has been used in the symptomatic treatment of PARKINSON DISEASE. Benztropine also inhibits the uptake of dopamine.. benzatropine : Tropane in which a hydrogen at position 3 is substituted by a diphenylmethoxy group (endo-isomer). An acetylcholine receptor antagonist, it is used (particularly as its methanesulphonate salt) in the treatment of Parkinson's disease, and to reduce parkinsonism and akathisia side effects of antipsychotic treatments.	3.33	1	1	diarylmethane
thiohydantoins Thiohydantoins: Sulfur analogs of hydantoins with one or both carbonyl groups replaced by thiocarbonyl groups.	2.05	1	0
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.	2.05	1	0	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
oxazolone Oxazolone: Immunologic adjuvant and sensitizing agent.	2.08	1	0
thiosemicarbazide thiosemicarbazide: glutamate decarboxylase antagonist; structure given in first source. hydrazinecarbothioamide : A member of the class of thioureas that is thiourea in which a hydrogen of one of the amino groups is replaced by an amino group.	1.96	1	0	hydrazines; thiocarboxamide; thioureas
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	1.96	1	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
indigo carmine Indigo Carmine: Indolesulfonic acid used as a dye in renal function testing for the detection of nitrates and chlorates, and in the testing of milk.. indigo carmine : An organic sodium salt resulting from the formal condensation of indigo carmine (acid form) with two equivalents of sodium hydroxide. It is an indicator at pH 11.5-14, changing from blue to yellow.	2.04	1	0
tempo TEMPO: structure. TEMPO : A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.	2.4	2	0	aminoxyls; piperidines	catalyst; ferroptosis inhibitor; radical scavenger
tamoxifen [no description available]	1.97	1	0	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator
1-butyl-3-methylimidazolium chloride 1-butyl-3-methylimidazolium chloride: structure in first source	2.17	1	0
nadp [no description available]	2.7	3	0
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	3.3	6	0
stattic [no description available]	2.07	1	0	1-benzothiophenes; C-nitro compound; sulfone	antineoplastic agent; radiosensitizing agent; STAT3 inhibitor
fusidic acid Fusidic Acid: An antibiotic isolated from the fermentation broth of Fusidium coccineum. (From Merck Index, 11th ed). It acts by inhibiting translocation during protein synthesis.. fusidic acid : A steroid antibiotic that is isolated from the fermentation broth of Fusidium coccineum.	2.08	1	0	11alpha-hydroxy steroid; 3alpha-hydroxy steroid; alpha,beta-unsaturated monocarboxylic acid; steroid acid; steroid antibiotic; sterol ester	EC 2.7.1.33 (pantothenate kinase) inhibitor; Escherichia coli metabolite; protein synthesis inhibitor
thiopental Thiopental: A barbiturate that is administered intravenously for the induction of general anesthesia or for the production of complete anesthesia of short duration.. thiopental : A barbiturate, the structure of which is that of 2-thiobarbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	2.35	2	0	barbiturates	anticonvulsant; drug allergen; environmental contaminant; intravenous anaesthetic; sedative; xenobiotic
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	2.44	2	0	alkali metal atom
hydroxylysine Hydroxylysine: A hydroxylated derivative of the amino acid LYSINE that is present in certain collagens.. hydroxylysine : A hydroxy-amino acid in which the amino acid specified is lysine. A "closed" class.. erythro-5-hydroxy-L-lysine : A 5-hydroxylysine consisting of L-lysine having an (R)-hydroxy group at the 5-position.. 5-hydroxylysine : A hydroxylysine that is lysine substituted by a hydroxy group at position 5.	2.01	1	0	5-hydroxylysine; hydroxy-L-lysine	human metabolite
2,2-dimethyl-5-hydroxy-1-pyrrolidinyloxy 2,2-dimethyl-5-hydroxy-1-pyrrolidinyloxy: structure given in first source	2	1	0
hirsutine [no description available]	2.05	1	0
silicon nitride [no description available]	2.04	1	0
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	2.72	3	0
sodium dodecyl sulfate Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.	2.6	1	0	organic sodium salt	detergent; protein denaturant
sb 242084 6-chloro-5-methyl-1-((2-(2-methylpyrid-3-yloxy)pyrid-5-yl)carbamoyl)indoline: 5-HT(2C) receptor inverse agonist (antagonist); structure in first source	2.01	1	0
homoserine lactone homoserine lactone: a putative signal for starvation in E. coli; structure in first source. homoserinium lactone : The conjugate acid of homoserine lactone; major species at pH 7.3.. homoserine lactone : A butan-4-olide having an amino substituent at the 2-position.	2.11	1	0	ammonium ion derivative; organic cation
cp 94253 [no description available]	2.95	4	0	pyrrolopyridine
alpha-chymotrypsin Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.	2.52	2	0
17-ketosteroids 17-Ketosteroids: Steroids that contain a ketone group at position 17.. 17-oxo steroid : Any oxo steroid carrying the oxo group at position 17.	1.94	1	0
diethyl maleate diethyl maleate : A maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with ethanol. A colourless liquid at room temperature (m.p. -10degreeC) with boiling point 220degreeC at 1 atm., it is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis.	1.97	1	0	ethyl ester; maleate ester	glutathione depleting agent
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.	2.15	1	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	2.1	1	0	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	2.05	1	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
calcitriol dihydroxy-vitamin D3: as a major in vitro metabolite of 1alpha,25-dihydroxyvitamin D3, produced in primary cultures of neonatal human keratinocytes	3.06	1	0	D3 vitamins; hydroxycalciol; triol	antineoplastic agent; antipsoriatic; bone density conservation agent; calcium channel agonist; calcium channel modulator; hormone; human metabolite; immunomodulator; metabolite; mouse metabolite; nutraceutical
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	2	1	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
pulmicort Budesonide: A glucocorticoid used in the management of ASTHMA, the treatment of various skin disorders, and allergic RHINITIS.. budesonide : A glucocorticoid steroid having a highly oxygenated pregna-1,4-diene structure. It is used mainly in the treatment of asthma and non-infectious rhinitis and for treatment and prevention of nasal polyposis.	2.21	1	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; cyclic acetal; glucocorticoid; primary alpha-hydroxy ketone	anti-inflammatory drug; bronchodilator agent; drug allergen
ethchlorvynol Ethchlorvynol: A sedative and hypnotic that has been used in the short-term management of INSOMNIA. Its use has been superseded by other drugs.. ethchlorvynol : Propargyl alcohol in which the methylene hydrogens are substituted by ethyl and 2-chlorovinyl groups. A hypnotic and sedative, it is used for treatment of insomnia in some cases where an intolerance or allergy to more commonly used drugs exists.	2.64	3	0
8-epi-prostaglandin f2alpha 8-epi-prostaglandin F2alpha: a potent preglomerular vasoconstrictor acting principally through thromboxane A2 receptor activation. 8-epi-prostaglandin F2alpha : An isoprostane that is prostaglandin F2alpha having inverted stereochemistry at the 8-position.	2.1	1	0	F2-isoprostane	biomarker; bronchoconstrictor agent; vasoconstrictor agent
methyl linoleate [no description available]	2.03	1	0	fatty acid methyl ester	plant metabolite
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	2.08	1	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
sirolimus Sirolimus: A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.. sirolimus : A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent.	2.87	3	0	antibiotic antifungal drug; cyclic acetal; cyclic ketone; ether; macrolide lactam; organic heterotricyclic compound; secondary alcohol	antibacterial drug; anticoronaviral agent; antineoplastic agent; bacterial metabolite; geroprotector; immunosuppressive agent; mTOR inhibitor
anhydrovitamin a anhydrovitamin A: RN given refers to (all-E)-isomer; structure given in first source	2.03	1	0	sesquiterpenoid
alvocidib alvocidib: structure given in first source. alvocidib : A synthetic dihydroxyflavone that is 5,7-dihydroxyflavone which is substituted by a 3-hydroxy-1-methylpiperidin-4-yl group at position 8 and by a chlorine at the 2' position (the (-)-3S,4R stereoisomer). A cyclin-dependent kinase 9 (CDK9) inhibitor, it has been studied for the treatment of acute myeloid leukaemia, arthritis and atherosclerotic plaque formation.	2.21	1	0	dihydroxyflavone; hydroxypiperidine; monochlorobenzenes; tertiary amino compound	antineoplastic agent; antirheumatic drug; apoptosis inducer; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
arachidonyl-2-chloroethylamide arachidonyl-2-chloroethylamide: a potent and selective agonist of the neuronal cannabinoid receptor; structure in first source. arachidonyl-2'-chloroethylamide : A fatty amide obtained by the formal condensation of arachidonic acid with 2-chloroethanamine. It is a potent agonist of the CB1 receptor (Ki = 1.4 nM) and also has a low affinity for the CB2 receptor (Ki = 3100 nM).	2.17	1	0	fatty amide; organochlorine compound; secondary carboxamide; synthetic cannabinoid	CB1 receptor agonist; CB2 receptor agonist; neuroprotective agent
cp 99994 3-(2-methoxybenzylamino)-2-phenylpiperidine: selective NK(1) receptor antagonist; CP-100263 is the inactive enantiomer	2.1	1	0
mdl 100907 Serotonin 5-HT2 Receptor Antagonists: Drugs that bind to but do not activate SEROTONIN 5-HT2 RECEPTORS, thereby blocking the actions of SEROTONIN or SEROTONIN 5-HT2 RECEPTOR AGONISTS. Included under this heading are antagonists for one or more specific 5-HT2 receptor subtypes.	2.25	1	0
fluvoxamine Fluvoxamine: A selective serotonin reuptake inhibitor that is used in the treatment of DEPRESSION and a variety of ANXIETY DISORDERS.. fluvoxamine : An oxime O-ether that is benzene substituted by a (1E)-N-(2-aminoethoxy)-5-methoxypentanimidoyl group at position 1 and a trifluoromethyl group at position 4. It is a selective serotonin reuptake inhibitor that is used for the treatment of obsessive-compulsive disorder.	2.43	2	0	(trifluoromethyl)benzenes; 5-methoxyvalerophenone O-(2-aminoethyl)oxime	antidepressant; anxiolytic drug; serotonin uptake inhibitor
ag-490 [no description available]	2.1	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
palbociclib [no description available]	2.21	1	0	aminopyridine; aromatic ketone; cyclopentanes; piperidines; pyridopyrimidine; secondary amino compound; tertiary amino compound	antineoplastic agent; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
streptimidone streptimidone: structure	3.21	6	0	tetrahydropyridine
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	2.6	1	0	carbon group element atom; elemental lead; metal atom	neurotoxin
8-oxo-7,8-dihydrodeoxyguanine 8-oxo-7,8-dihydrodeoxyguanine: structure given in first source	2.11	1	0
strontium Strontium: An element of the alkaline earth family of metals. It has the atomic symbol Sr, atomic number 38, and atomic weight 87.62.	1.93	1	0	alkaline earth metal atom
enalapril Enalapril: An angiotensin-converting enzyme inhibitor that is used to treat HYPERTENSION and HEART FAILURE.. enalapril : A dicarboxylic acid monoester that is ethyl 4-phenylbutanoate in which a hydrogen alpha to the carboxy group is substituted by the amino group of L-alanyl-L-proline (S-configuration).	1.96	1	0	dicarboxylic acid monoester; dipeptide	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; geroprotector; prodrug
deoxyribose [no description available]	1.95	1	0	deoxypentose	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	2.72	3	0	cysteinium	fundamental metabolite
silicon Silicon: A trace element that constitutes about 27.6% of the earth's crust in the form of SILICON DIOXIDE. It does not occur free in nature. Silicon has the atomic symbol Si, atomic number 14, and atomic weight [28.084; 28.086].	2.04	1	0	carbon group element atom; metalloid atom; nonmetal atom
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid: chromogen in glucose oxidase-peroxidase method for determining serum glucose; used in free radical scavenging assays; structure in first source	2.96	4	0
demethoxycurcumin demethoxycurcumin: corresponds to curcumin with one methoxy group replaced by hydrogen; isolated from rhizomes of Curcuma longa. demethoxycurcumin : A beta-diketone that is curcumin in which one of the methoxy groups is replaced by hydrogen. It is found in Curcuma zedoaria and Etlingera elatior.	2.31	1	0	beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antineoplastic agent; metabolite
strontium radioisotopes Strontium Radioisotopes: Unstable isotopes of strontium that decay or disintegrate spontaneously emitting radiation. Sr 80-83, 85, and 89-95 are radioactive strontium isotopes.	1.93	1	0
cp 135807 CP 135807: a 5-HT(1D) agonist; RN given for (R)-isomer	2.02	1	0
2-tert-butyl-9-fluoro-3,6-dihydro-7h-benz(h)imidazo(4,5-f)isoquinoline-7-one 2-tert-butyl-9-fluoro-3,6-dihydro-7H-benz(h)imidazo(4,5-f)isoquinoline-7-one: a janus-activated kinase inhibitor. 2-tert-butyl-9-fluoro-1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one : An organic heterotetracyclic compound that is 1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one bearing additional tert-butyl and fluoro substituents at positions 2 and 9 respectively.	1.93	1	0	organic heterotetracyclic compound; organofluorine compound	EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
carbocyanines Carbocyanines: Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials.	2.01	1	0	cyanine dye; organic iodide salt	fluorochrome
ammonium sulfate Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.	2.11	1	0	ammonium salt; inorganic sulfate salt	fertilizer
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	1	0	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
radium Radium: A radioactive element of the alkaline earth series of metals. It has the atomic symbol Ra and atomic number 88. Radium is the product of the disintegration of URANIUM and is present in pitchblende and all ores containing uranium. It is used clinically as a source of beta and gamma-rays in radiotherapy, particularly BRACHYTHERAPY.	1.94	1	0	alkaline earth metal atom
oxalates Oxalates: Derivatives of OXALIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that are derived from the ethanedioic acid structure.	1.95	1	0
hygromycin a hygromycin A: a cinnamide derivative produced by Streptomyces hygroscopicus; structure differs from HYGROMYCIN B	2.21	1	0	hydroxycinnamic acid	metabolite
pericalline pericalline: alkaloid isolated from Catharanthus trichophyllus roots; active against experimental neoplasm; RN in Chemline for (-)-isomer: 2122-36-3	2.1	1	0
epiderstatin epiderstatin: structure given in first source; isolated from Streptomyces pulveraceus subsp. epiderstagenes; inhibits mitogenic activity of epidermal growth factor	3.36	7	0
goniothalamin goniothalamin: has antineoplastic activity; structure given in first source	2.31	1	0
skf 99101h SKF 99101H: RN given for (E)-2-butenedioate(2:1) salt; 5-HT(1B/D) receptor agonist	2.69	3	0
sb 269970 SB 269970: a 5-HT(7) antagonist; structure in first source	2	1	0	sulfonamide
ergoline Ergolines: A series of structurally-related alkaloids that contain the ergoline backbone structure.. ergoline : An indole alkaloid whose structural skeleton is found in many naturally occurring and synthetic ergolines which are known to bind to neurotransmitter receptors, such as dopamine, noradrenaline and serotonin receptors and function as unselective agonists or antagonists at these receptors.	2.41	2	0	diamine; ergoline alkaloid; indole alkaloid fundamental parent; indole alkaloid; organic heterotetracyclic compound
platensimycin platensimycin: has antidiabetic and antisteatotic activities; a pentacyclic ketolide (structurally similar to adamantane) connected by an amide bond to 3-amino-2,4-dihydroxybenzoic acid; inhibits cellular lipid biosynthesis; discovered while screening compounds from Streptomyces platensis bacteria in a South African soil sample with S. aureus bacteria deficient in FabF protein; structure in first source. platensimycin : A monocarboxylic acid amide obtained by the formal condensation of the amino group of 3-amino-2,4-dihydroxybenzoic acid with the carboxy group of the oxatetracyclic cage component. It is an antibiotic isolated from Streptomyces platensis and exhibits inhibitory activity against fatty acid synthase.	3.31	1	0	aromatic amide; cyclic ether; cyclic ketone; dihydroxybenzoic acid; monocarboxylic acid amide; polycyclic cage	antibacterial agent; antimicrobial agent; bacterial metabolite; EC 2.3.1.85 (fatty acid synthase) inhibitor
vilazodone hydrochloride [no description available]	2.02	1	0	hydrochloride	antidepressant; serotonergic agonist; serotonin uptake inhibitor
vildagliptin [no description available]	3.19	1	0	amino acid amide
belinostat [no description available]	2.17	1	0	hydroxamic acid; olefinic compound; sulfonamide	antineoplastic agent; EC 3.5.1.98 (histone deacetylase) inhibitor
tryptophanol tryptophanol: RN given refers to cpd without isomeric designation	2.78	3	0
5-ht-moduline 5-HT-moduline: isolated from rat brain; interacts specifically with HT 1B/1D receptors	2	1	0
staurosporine staurosporinium : Conjugate acid of staurosporine.	2	1	0	ammonium ion derivative
chloralose Chloralose: A derivative of CHLORAL HYDRATE that was used as a sedative but has been replaced by safer and more effective drugs. Its most common use is as a general anesthetic in animal experiments.	1.95	1	0
phosphocreatine Phosphocreatine: An endogenous substance found mainly in skeletal muscle of vertebrates. It has been tried in the treatment of cardiac disorders and has been added to cardioplegic solutions. (Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Englewood, CO, 1996). phosphagen : Any of a group of guanidine or amidine phosphates that function as storage depots for high-energy phosphate in muscle with the purpose of regenerating ATP from ADP during muscular contraction.. N-phosphocreatine : A phosphoamino acid consisting of creatine having a phospho group attached at the primary nitrogen of the guanidino group.	2.11	1	0	phosphagen; phosphoamino acid	human metabolite; mouse metabolite
mannich bases Mannich Bases: Ketonic amines prepared from the condensation of a ketone with formaldehyde and ammonia or a primary or secondary amine. A Mannich base can act as the equivalent of an alpha,beta unsaturated ketone in synthesis or can be reduced to form physiologically active amino alcohols.	2.4	2	0
3,3-diethyl-2-pyrrolidinone 3,3-diethyl-2-pyrrolidinone: structure in first source. 3,3-diethyl-2-pyrrolidinone : A pyrrolidin-2-one substituted by two ethyl groups at position 3.	1.99	1	0	pyrrolidin-2-ones	anticonvulsant; geroprotector
sulphostin sulphostin: isolated from Streptomyces; structure in first source	4.39	6	0
avibactam avibactam : A member of the class of azabicycloalkanes that is (2S,5R)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide in which the amino hydrogen at position 6 is replaced by a sulfooxy group. Used (in the form of its sodium salt) in combination with ceftazidime pentahydrate for the treatment of complicated urinary tract infections including pyelonephritis.	2.31	1	0	azabicycloalkane; hydroxylamine O-sulfonic acid; monocarboxylic acid amide; ureas	antibacterial drug; antimicrobial agent; EC 3.5.2.6 (beta-lactamase) inhibitor
l 772405 L 772405: an h5-HT(1D) receptor agonist; structure in first source	2.02	1	0
dc 107 leinamycin: a thiazole containing macrolide characterized by an unusual 1,3-dioxo-1,2-dithiolane moiety that is spiro fused to an 18 member macrolactam ring; isolated from Streptomyces; MF C22-H26-N2-O6-S3; possible DNA alkylator; the leinamycin biosynthetic gene cluster from Streptomyces atroolivaceus S-140 consists of two polyketide synthases genes	3.31	1	0	dithiolanes
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).	2.52	2	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
dehydroxymethylepoxyquinomicin dehydroxymethylepoxyquinomicin: an NF-kappaB inhibitor; structure in first source	4.29	5	0
3,5-bis(2-fluorobenzylidene)piperidin-4-one 3,5-bis(2-fluorobenzylidene)piperidin-4-one: an antineoplastic agent; structure in first source	5.28	47	0
dapagliflozin [no description available]	3.98	2	1	aromatic ether; C-glycosyl compound; monochlorobenzenes	hypoglycemic agent; sodium-glucose transport protein subtype 2 inhibitor
pnu 142633f PNU 142633F: structure in first source	2.43	2	0
linagliptin Linagliptin: A purine and quinazoline derivative that functions as an INCRETIN and DIPEPTIDYL-PEPTIDASE IV INHIBTOR. It is used as a HYPOGLYCEMIC AGENT in the treatment of TYPE II DIABETES MELLITUS.. linagliptin : A xanthine that is 7H-xanthine bearing (4-methylquinazolin-2-yl)methyl, methyl, but-2-yn-1-yl and 3-aminopiperidin-1-yl substituents at positions 1, 3, 7 and 8 respectively (the R-enantiomer). Used for treatment of type II diabetes.	5.31	3	1	aminopiperidine; quinazolines	EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; hypoglycemic agent
oxadiazoles Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.	4.03	14	0
ribose ribopyranose : The pyranose form of ribose.	2.05	1	0	D-ribose; ribopyranose
migrastatin migrastatin: inhibits tumor cell migration; isolated from Streptomyces; structure in first source. migrastatin : A 14-membered macrolide which is isolated from Streptomyces sp.MK929-43F1 and inhibits cell migration of human esophageal cancer EC17 cells and mouse melanona B16 cells.	6.73	30	0	ether; macrolide antibiotic; piperidones; secondary alcohol	antineoplastic agent; metabolite
epiquinamide epiquinamide: quinolizidine alkaloid and nicotinic agonist from an Ecuadoran poison frog, Epipedobates tricolor; structure in first source	2.46	2	0
nutlin-3a nutlin 3: an MDM2 antagonist; structure in first source	2.17	1	0	stilbenoid
alogliptin alogliptin: structure in first source. alogliptin : A piperidine that is 3-methyl-2,4-dioxo-3,4-dihydropyrimidine carrying additional 2-cyanobenzyl and 3-aminopiperidin-1-yl groups at positions 1 and 2 respectively (the R-enantiomer). Used in the form of its benzoate salt for treatment of type 2 diabetes.	3.19	1	0	nitrile; piperidines; primary amino compound; pyrimidines	EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; hypoglycemic agent
sitagliptin phosphate Sitagliptin Phosphate: A pyrazine-derived DIPEPTIDYL-PEPTIDASE IV INHIBITOR and HYPOGLYCEMIC AGENT that increases the levels of the INCRETIN hormones GLUCAGON-LIKE PEPTIDE-1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP). It is used in the treatment of TYPE 2 DIABETES.	6.61	5	3
zstk474 ZSTK-474 : A triamino-1,3,5-triazine that is 1,3,5-triazine in which two of the hydrogens have been replaced by morpholin-4-yl groups while the third hydrogen has been replaced by a 2-(difluoromethyl)benzimidazol-1-yl group. It is an inhibitor of phosphatidylinositol 3-kinase.	2.17	1	0	benzimidazoles; morpholines; organofluorine compound; triamino-1,3,5-triazine	antineoplastic agent; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor
lactimidomycin lactimidomycin: a glutarimide antibiotic isolated from Streptomyces amphibiosporus	4.42	20	0	macrolide
trametinib [no description available]	4.51	1	1	acetamides; aromatic amine; cyclopropanes; organofluorine compound; organoiodine compound; pyridopyrimidine; ring assembly	anticoronaviral agent; antineoplastic agent; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
pha 767491 PHA 767491: a Cdc7 inhibitor; structure in first source	4.25	16	0	pyrrolopyridine
empagliflozin [no description available]	2.41	1	0	aromatic ether; C-glycosyl compound; monochlorobenzenes; tetrahydrofuryl ether	hypoglycemic agent; sodium-glucose transport protein subtype 2 inhibitor
lc15-0444 LC15-0444: Dipeptidyl Peptidase IV Inhibitors; orally active small molecule for the treatment of type II diabetes	15.48	66	35	organonitrogen compound; organooxygen compound
brl 15572 BRL 15572: specific for h5-HT(1D) receptors; structure in first source. 3-[4-(3-chlorophenyl)piperazin-1-yl]-1,1-diphenylpropan-2-ol hydrochloride : A hydrochloride that is the monohydrochloride salt of 3-[4-(3-chlorophenyl)piperazin-1-yl]-1,1-diphenylpropan-2-ol. A selective h5-HT1D antagonist, displaying 60-fold selectivity over h5-HT1B, and exhibiting little or no affinity for a range of other receptor types.	4.28	18	0	hydrochloride	prodrug; serotonergic antagonist
n-methylpyridine-2-carboxamide N-methylpyridine-2-carboxamide: structure in first source	1.96	1	0
rifamycins [no description available]	1.95	1	0
ants Ants: Insects of the family Formicidae, very common and widespread, probably the most successful of all the insect groups. All ants are social insects, and most colonies contain three castes, queens, males, and workers. Their habits are often very elaborate and a great many studies have been made of ant behavior. Ants produce a number of secretions that function in offense, defense, and communication. (From Borror, et al., An Introduction to the Study of Insects, 4th ed, p676)	2.13	1	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2.11	1	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
isomigrastatin isomigrastatin: isolated from Streptomyces platensis; structure in first source	5.23	15	0	macrolide
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	3.91	3	0
3,5-bis(2-pyridinylmethylidene)-4-piperidone 3,5-bis(2-pyridinylmethylidene)-4-piperidone: structure in first source	3.48	7	0
dermaseptin s dermaseptin: 34 amino acid residues given in first source; antimicrobial peptide of amphibian skin	2.08	1	0
gramicidin a Gramicidin: A group of peptide antibiotics from BACILLUS brevis. Gramicidin C or S is a cyclic, ten-amino acid polypeptide and gramicidins A, B, D are linear. Gramicidin is one of the two principal components of TYROTHRICIN.	1.96	1	0
glucagon Glucagon: A 29-amino acid pancreatic peptide derived from proglucagon which is also the precursor of intestinal GLUCAGON-LIKE PEPTIDES. Glucagon is secreted by PANCREATIC ALPHA CELLS and plays an important role in regulation of BLOOD GLUCOSE concentration, ketone metabolism, and several other biochemical and physiological processes. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1511). glucagon : A 29-amino acid peptide hormone consisting of His, Ser, Gln, Gly, Thr, Phe, Thr, Ser, Asp, Tyr, Ser, Lys, Tyr, Leu, Asp, Ser, Arg, Arg, Ala, Gln, Asp, Phe, Val, Gln, Trp, Leu, Met, Asn and Thr residues joined in sequence.	6.49	3	3	peptide hormone
glucagon-like peptide 1 Glucagon-Like Peptide 1: A peptide of 36 or 37 amino acids that is derived from PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. GLP-1(1-37 or 1-36) is further N-terminally truncated resulting in GLP-1(7-37) or GLP-1-(7-36) which can be amidated. These GLP-1 peptides are known to enhance glucose-dependent INSULIN release, suppress GLUCAGON release and gastric emptying, lower BLOOD GLUCOSE, and reduce food intake.	8.32	8	5
c-peptide C-Peptide: The middle segment of proinsulin that is between the N-terminal B-chain and the C-terminal A-chain. It is a pancreatic peptide of about 31 residues, depending on the species. Upon proteolytic cleavage of proinsulin, equimolar INSULIN and C-peptide are released. C-peptide immunoassay has been used to assess pancreatic beta cell function in diabetic patients with circulating insulin antibodies or exogenous insulin. Half-life of C-peptide is 30 min, almost 8 times that of insulin.	3.53	1	1
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	1.95	1	0	glycoside
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.39	2	0	1,2-diacyl-sn-glycero-3-phosphocholine
9-methylstreptimidone 9-methylstreptimidone: structure	4.82	10	0
platencin platencin: inhibits both FabF and FabH; structure in first source. platencin : A monocarboxylic acid amide obtained by the formal condensation of the amino group of 3-amino-2,4-dihydroxybenzoic acid with the carboxy group of the polycyclic cage component. It is an antibiotic isolated from Streptomyces platensis and exhibits inhibitory activity against fatty acid synthase.	3.31	1	0	aromatic amide; cyclic ketone; dihydroxybenzoic acid; monocarboxylic acid amide; polycyclic cage	antibacterial agent; antimicrobial agent; bacterial metabolite; EC 2.3.1.85 (fatty acid synthase) inhibitor
chitosan [no description available]	2.96	3	0
lyngbyastatin 7 lyngbyastatin 7: potent elastase inhibitor from Floridian marine cyanobacteria, Lyngbya spp.; structure in first source	2.58	2	0
penicillin g potassium benzylpenicillin potassium : Organic potassium salt of benzylpenicillin.	2	1	0	organic potassium salt
chiniofon Hydroxyquinolines: The 8-hydroxy derivatives inhibit various enzymes and their halogenated derivatives, though neurotoxic, are used as topical anti-infective agents, among other uses.	3.49	2	0
hygromycin b [no description available]	2.21	1	0
papuamide a papuamide A: from marine sponge of genus Theonella; structure in first source	2.13	1	0
goniomitine goniomitine: from root bark of Gonioma malagasy; structure in first source	2.47	2	0	monoterpenoid indole alkaloid
picrotoxin Picrotoxin: A noncompetitive antagonist at GABA-A receptors and thus a convulsant. Picrotoxin blocks the GAMMA-AMINOBUTYRIC ACID-activated chloride ionophore. Although it is most often used as a research tool, it has been used as a CNS stimulant and an antidote in poisoning by CNS depressants, especially the barbiturates.. picrotoxin : A mixture consisting of equimolar amounts of picrotoxinin and picrotin found in the climbing plant Anamirta cocculus.	1.93	1	0
mk 2206 MK 2206: a protein kinase inhibitor and antineoplastic agent	2.15	1	0	organic heterotricyclic compound	EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor
cc-122 3-(5-amino-2-methyl-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione: a pleiotropic pathway modifier with antineoplastic activity; structure in first source	8.65	13	5
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	1.93	1	0
cabozantinib cabozantinib: a multikinase inhibitor. cabozantinib : A dicarboxylic acid diamide that is N-phenyl-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide in which the hydrogen at position 4 on the phenyl ring is substituted by a (6,7-dimethoxyquinolin-4-yl)oxy group. A multi-tyrosine kinase inhibitor, used (as its malate salt) for the treatment of progressive, metastatic, medullary thyroid cancer.	2.17	1	0	aromatic ether; dicarboxylic acid diamide; organofluorine compound; quinolines	antineoplastic agent; tyrosine kinase inhibitor
n,n-dimethyl-2-(2-amino-4-cyanophenylthio)benzylamine N,N-dimethyl-2-(2-amino-4-cyanophenylthio)benzylamine: structure in first source	2.02	1	0
glycolipids [no description available]	1.94	1	0
piperidines Piperidines: A family of hexahydropyridines.	10.19	149	3
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.	2.04	1	0
anagliptin anagliptin: anagliptin hydrochloride salt is the active compound	3.19	1	0	amino acid amide
dorrigocin b dorrigocin B: isolated from the fermentation broth & mycelium of Streptomyces platensis; structure given in first source	2.91	4	0
dorrigocin a dorrigocin A: isolated from the fermentation broth & mycelium of Streptomyces platensis; structure given in first source	3.51	8	0
sordarin sordarin: antifungal mold metabolite of Sordaria araneosa; sordarins A and B are stereoisomers. sordarin : An antifungal metabolite of Sordaria araneosa that inhibits protein synthesis. It has a tetracyclic diterpene glycoside structure.	2.08	1	0
tropodithietic acid tropodithietic acid: structure in first source. tropodithietic acid : A monocarboxylic acid that is 8,9-dithiabicyclo[5.2.0]nona-1,3,6-triene substituted by a carboxy group at position 2 and an oxo group at position 3. It is a broad spectrum antibiotic produced by the marine bacterium Phaeobacter inhibens that also acts as a signalling molecule at lower concentrations.	3.19	1	0	cyclic ketone; monocarboxylic acid; organic disulfide; organic heterobicyclic compound; organosulfur heterocyclic compound	antibacterial agent; bacterial metabolite; marine metabolite; signalling molecule; toxin
exenatide Exenatide: A synthetic form of exendin-4, a 39-amino acid peptide isolated from the venom of the Gila monster lizard (Heloderma suspectum). Exenatide increases CYCLIC AMP levels in pancreatic acinar cells and acts as a GLUCAGON-LIKE PEPTIDE-1 RECEPTOR (GLP-1) agonist and incretin mimetic, enhancing insulin secretion in response to increased glucose levels; it also suppresses inappropriate glucagon secretion and slows gastric emptying. It is used an anti-diabetic and anti-obesity agent.	2.13	1	0
dinaciclib [no description available]	2.21	1	0	pyrazolopyrimidine
heme Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.	2.38	2	0
sar405838 SAR405838: an inhibitor of the interaction of MDM2 and p53; has antineoplastic activity; structure in first source	2.17	1	0
3-amino-6-hydroxy-2-piperidone 3-amino-6-hydroxy-2-piperidone: structure in first source	8.36	6	0
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.66	3	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2.43	2	0	benzenes; hydroxycoumarin; methyl ketone
3-deazauridine 3-Deazauridine: 4-Hydroxy-1-(beta-D-ribofuranosyl)-2-pyridinone. Analog of uridine lacking a ring-nitrogen in the 3-position. Functions as an antineoplastic agent.	3.06	1	0	N-glycosyl compound
epidermal growth factor Epidermal Growth Factor: A 6-kDa polypeptide growth factor initially discovered in mouse submaxillary glands. Human epidermal growth factor was originally isolated from urine based on its ability to inhibit gastric secretion and called urogastrone. Epidermal growth factor exerts a wide variety of biological effects including the promotion of proliferation and differentiation of mesenchymal and EPITHELIAL CELLS. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form.	3.23	6	0
kaolinite Kaolin: The most common mineral of a group of hydrated aluminum silicates, approximately H2Al2Si2O8-H2O. It is prepared for pharmaceutical and medicinal purposes by levigating with water to remove sand, etc. (From Merck Index, 11th ed) The name is derived from Kao-ling (Chinese: high ridge), the original site. (From Grant & Hackh's Chemical Dictionary, 5th ed). kaolin : An aluminosilicate soft white mineral named after the hill in China (Kao-ling) from which it was mined for centuries. In its natural state kaolin is a white, soft powder consisting principally of the mineral kaolinite, and varying amounts of other minerals such as muscovite, quartz, feldspar, and anatase. It is used in the manufacture of china and porcelain and also widely used in the production of paper, rubber, paint, drying agents, and many other products.	2.41	1	0	aluminosilicate mineral; mixture	antidiarrhoeal drug; excipient
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
cgs 12066b CGS 12066B: RN given for ((Z)-2-butenedioate (1:2))-salt (CGS 12066B); CGS 12066A is the (ethanedioate (1:2))-salt; structure given in first source. 4-(4-methylpiperazin-1-yl)-7-(trifluoromethyl)pyrrolo[1,2-a]quinoxaline dimaleate : A maleate salt that is the dimaleate salt of 4-(4-methylpiperazin-1-yl)-7-(trifluoromethyl)pyrrolo[1,2-a]quinoxaline. A 5-hydroxytryptamine receptor 1B (5-HT1B) full agonist, 10-fold selective over 5-HT1A and 1000-fold selective over 5-HT2C receptors. Centrally active following systemic administration.	2.06	1	0	maleate salt	prodrug; serotonergic agonist
rg7112 [no description available]	2.17	1	0
agar Agar: A complex sulfated polymer of galactose units, extracted from Gelidium cartilagineum, Gracilaria confervoides, and related red algae. It is used as a gel in the preparation of solid culture media for microorganisms, as a bulk laxative, in making emulsions, and as a supporting medium for immunodiffusion and immunoelectrophoresis.. agar : A complex mixture of polysaccharides extracted from species of red algae. Its two main components are agarose and agaropectin. Agarose is the component responsible for the high-strength gelling properties of agar, while agaropectin provides the viscous properties.	1.94	1	0
epiisopiloturine epiisopiloturine: an antischistosomal agent isolated from Pilocarpus microphyllus; structure in first source	2.15	1	0
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	2.99	4	0
caseins Caseins: A mixture of related phosphoproteins occurring in milk and cheese. The group is characterized as one of the most nutritive milk proteins, containing all of the common amino acids and rich in the essential ones.	2.17	1	0
oxysporidinone oxysporidinone: isolated from Fusarium oxysporum; structure in first source	2.06	1	0
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	1.95	1	0
nephrin nephrin: gene nephrin is mutated in congenital nephrotic syndrome; amino acid sequence in first source; GenBank F19541; RefSeq NM_019459 (mouse), NM_004646 (human), NM_022628 (rat)	2.15	1	0
digitonin Digitonin: A glycoside obtained from Digitalis purpurea; the aglycone is digitogenin which is bound to five sugars. Digitonin solubilizes lipids, especially in membranes and is used as a tool in cellular biochemistry, and reagent for precipitating cholesterol. It has no cardiac effects.. digitonin : A spirostanyl glycoside that is digitogenin in which the 3-hydroxy group is substituted by a beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranosyl group. It is a steroidal saponin isolated from the foxglove plant, Digitalis purpurea. It is used extensively as a mild non-ionic detergent for extracting proteins from membranes for structure and function studies.	1.95	1	0
orabase Orabase: used in therapy of oral mucosal ulcers	2.53	2	0
thromboplastin Thromboplastin: Constituent composed of protein and phospholipid that is widely distributed in many tissues. It serves as a cofactor with factor VIIa to activate factor X in the extrinsic pathway of blood coagulation.	2.04	1	0
plicamycin mithramycin A: structure given in first source	2.17	1	0
cyclic gmp Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.	2.17	1	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
deoxyguanosine [no description available]	2	1	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine monophosphate Guanosine Monophosphate: A guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature.. guanosine 5'-monophosphate : A purine ribonucleoside 5'-monophosphate having guanine as the nucleobase.	2.17	1	0	guanosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	biomarker; Escherichia coli metabolite; metabolite; mouse metabolite
guanine [no description available]	2.47	2	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine ribonucleoside : Any nucleoside where the sugar component is D-ribose.	1.95	1	0	guanosines; purines D-ribonucleoside	fundamental metabolite
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.	1.97	1	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
guanosine 5'-o-(3-thiotriphosphate) Guanosine 5'-O-(3-Thiotriphosphate): Guanosine 5'-(trihydrogen diphosphate), monoanhydride with phosphorothioic acid. A stable GTP analog which enjoys a variety of physiological actions such as stimulation of guanine nucleotide-binding proteins, phosphoinositide hydrolysis, cyclic AMP accumulation, and activation of specific proto-oncogenes.	3.51	8	0	nucleoside triphosphate analogue
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	6.46	5	2	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	2.42	2	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	2.44	2	0	guanosines	biomarker
eye [no description available]	1.96	1	0
oocydin a oocydin A: isolated from Serratia marcescens; structure in first source	2.31	1	0
metallothionein Metallothionein: A low-molecular-weight (approx. 10 kD) protein occurring in the cytoplasm of kidney cortex and liver. It is rich in cysteinyl residues and contains no aromatic amino acids. Metallothionein shows high affinity for bivalent heavy metals.	2	1	0
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	6.13	5	2
phormidolide phormidolide: a toxic metabolite from the marine cyanobacterium Phormidium sp.	2.31	1	0

Condition	Relationship Strength	Studies	Trials
Di Guglielmo Disease [description not available]	2.36	2	0
Experimental Leukemia [description not available]	1.96	1	0
Leukemia, Erythroblastic, Acute A myeloproliferative disorder characterized by neoplastic proliferation of erythroblastic and myeloblastic elements with atypical erythroblasts and myeloblasts in the peripheral blood.	2.36	2	0
Ovine Diseases [description not available]	2.11	1	0
Helminthiasis, Animal Infestation of animals with parasitic worms of the helminth class. The infestation may be experimental or veterinary.	2.11	1	0
47,XX,+21 [description not available]	2.25	1	0
Down Syndrome A chromosome disorder associated either with an extra chromosome 21 or an effective trisomy for chromosome 21. Clinical manifestations include hypotonia, short stature, brachycephaly, upslanting palpebral fissures, epicanthus, Brushfield spots on the iris, protruding tongue, small ears, short, broad hands, fifth finger clinodactyly, Simian crease, and moderate to severe INTELLECTUAL DISABILITY. Cardiac and gastrointestinal malformations, a marked increase in the incidence of LEUKEMIA, and the early onset of ALZHEIMER DISEASE are also associated with this condition. Pathologic features include the development of NEUROFIBRILLARY TANGLES in neurons and the deposition of AMYLOID BETA-PROTEIN, similar to the pathology of ALZHEIMER DISEASE. (Menkes, Textbook of Child Neurology, 5th ed, p213)	2.25	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	4.27	7	0
Innate Inflammatory Response [description not available]	5.7	17	0
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.	10.7	17	0
Angiostrongylus Infections [description not available]	1.99	1	0
Androgen-Independent Prostatic Cancer [description not available]	2.63	2	0
Prostatic Neoplasms, Castration-Resistant Tumors or cancer of the PROSTATE which can grow in the presence of low or residual amount of androgen hormones such as TESTOSTERONE.	2.63	2	0
Adenocarcinoma Of Kidney [description not available]	2.31	1	0
Cancer of Kidney [description not available]	2.31	1	0
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.	2.31	1	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	2.31	1	0
Vascular Calcification Deposition of calcium into the blood vessel structures. Excessive calcification of the vessels are associated with ATHEROSCLEROTIC PLAQUES formation particularly after MYOCARDIAL INFARCTION (see MONCKEBERG MEDIAL CALCIFIC SCLEROSIS) and chronic kidney diseases which in turn increase VASCULAR STIFFNESS.	4.92	2	1
Arteriosclerosis, Coronary [description not available]	4.62	1	1
Diabetes Mellitus, Adult-Onset [description not available]	13.3	32	22
Diabetic Glomerulosclerosis [description not available]	6.49	5	3
Coronary Artery Disease Pathological processes of CORONARY ARTERIES that may derive from a congenital abnormality, atherosclerotic, or non-atherosclerotic cause.	4.62	1	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.	13.3	32	22
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	6.49	5	3
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	2.61	2	0
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.	2.61	2	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	5.98	38	0
Pulmonary Hypertension [description not available]	2.57	2	0
Hypertension, Pulmonary Increased VASCULAR RESISTANCE in the PULMONARY CIRCULATION, usually secondary to HEART DISEASES or LUNG DISEASES.	2.57	2	0
Disease Exacerbation [description not available]	10.53	15	13
Fatty Liver, Nonalcoholic [description not available]	2.41	1	0
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	2.41	1	0
Kahler Disease [description not available]	11.01	23	3
Multiple Myeloma A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.	11.01	23	3
Libman-Sacks Disease [description not available]	10.5	10	7
Lupus Erythematosus, Systemic A chronic, relapsing, inflammatory, and often febrile multisystemic disorder of connective tissue, characterized principally by involvement of the skin, joints, kidneys, and serosal membranes. It is of unknown etiology, but is thought to represent a failure of the regulatory mechanisms of the autoimmune system. The disease is marked by a wide range of system dysfunctions, an elevated erythrocyte sedimentation rate, and the formation of LE cells in the blood or bone marrow.	10.5	10	7
Carcinoma, Squamous Cell of Head and Neck [description not available]	2.93	3	0
Carcinoma, Epidermoid [description not available]	3.37	6	0
Cancer of Head [description not available]	2.82	3	0
Cancer of Mouth [description not available]	3.08	4	0
Squamous Cell Carcinoma of Head and Neck The most common type of head and neck carcinoma that originates from cells on the surface of the NASAL CAVITY; MOUTH; PARANASAL SINUSES, SALIVARY GLANDS, and LARYNX. Mutations in TNFRSF10B, PTEN, and ING1 genes are associated with this cancer.	2.93	3	0
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)	3.37	6	0
Head and Neck Neoplasms Soft tissue tumors or cancer arising from the mucosal surfaces of the LIP; oral cavity; PHARYNX; LARYNX; and cervical esophagus. Other sites included are the NOSE and PARANASAL SINUSES; SALIVARY GLANDS; THYROID GLAND and PARATHYROID GLANDS; and MELANOMA and non-melanoma skin cancers of the head and neck. (from Holland et al., Cancer Medicine, 4th ed, p1651)	2.82	3	0
Mouth Neoplasms Tumors or cancer of the MOUTH.	3.08	4	0
Hand Foot and Mouth Disease [description not available]	3.54	6	0
Hand, Foot and Mouth Disease A mild, highly infectious viral disease of children, characterized by vesicular lesions in the mouth and on the hands and feet. It is caused by coxsackieviruses A.	3.54	6	0
Benign Neoplasms [description not available]	10.2	34	2
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.	10.2	34	2
Malignant Melanoma [description not available]	4.85	6	1
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)	4.85	6	1
Nausea An unpleasant sensation in the stomach usually accompanied by the urge to vomit. Common causes are early pregnancy, sea and motion sickness, emotional stress, intense pain, food poisoning, and various enteroviruses.	3.8	1	1
Germinoblastoma [description not available]	3.06	4	0
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	3.06	4	0
Lassa Virus Infection [description not available]	2.41	1	0
Lassa Fever An acute febrile human disease caused by the LASSA VIRUS.	2.41	1	0
Breast Cancer [description not available]	4.54	23	0
Breast Neoplasms Tumors or cancer of the human BREAST.	4.54	23	0
Astrocytoma, Grade IV [description not available]	5.63	9	2
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.	5.63	9	2
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	3.08	4	0
Acute Liver Injury, Drug-Induced [description not available]	2.41	1	0
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	0
Granulocytic Leukemia, Chronic [description not available]	2.41	1	0
Leukemia, Myelogenous, Chronic, BCR-ABL Positive Clonal hematopoetic disorder caused by an acquired genetic defect in PLURIPOTENT STEM CELLS. It starts in MYELOID CELLS of the bone marrow, invades the blood and then other organs. The condition progresses from a stable, more indolent, chronic phase (LEUKEMIA, MYELOID, CHRONIC PHASE) lasting up to 7 years, to an advanced phase composed of an accelerated phase (LEUKEMIA, MYELOID, ACCELERATED PHASE) and BLAST CRISIS.	2.41	1	0
Enterovirus Infections Diseases caused by ENTEROVIRUS.	2.41	1	0
Foot and Mouth Disease [description not available]	2.41	1	0
Thyroid Cancer, Anaplastic [description not available]	2.6	1	0
Cancer of the Thyroid [description not available]	3.3	5	0
Thyroid Neoplasms Tumors or cancer of the THYROID GLAND.	3.3	5	0
Thyroid Carcinoma, Anaplastic An aggressive THYROID GLAND malignancy which generally occurs in IODINE-deficient areas in people with previous thyroid pathology such as GOITER. It is associated with CELL DEDIFFERENTIATION of THYROID CARCINOMA (e.g., FOLLICULAR THYROID CARCINOMA; PAPILLARY THYROID CANCER). Typical initial presentation is a rapidly growing neck mass which upon metastasis is associated with DYSPHAGIA; NECK PAIN; bone pain; DYSPNEA; and NEUROLOGIC DEFICITS.	2.6	1	0
Acute Lymphoid Leukemia [description not available]	2.6	1	0
Precursor Cell Lymphoblastic Leukemia-Lymphoma A neoplasm characterized by abnormalities of the lymphoid cell precursors leading to excessive lymphoblasts in the marrow and other organs. It is the most common cancer in children and accounts for the vast majority of all childhood leukemias.	2.6	1	0
Rheumatoid Arthritis [description not available]	2.6	1	0
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	2.6	1	0
Impaired Glucose Tolerance [description not available]	2.25	1	0
Cognitive Decline [description not available]	2.25	1	0
Acute Confusional Senile Dementia [description not available]	3.1	4	0
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)	3.1	4	0
Glucose Intolerance A pathological state in which BLOOD GLUCOSE level is less than approximately 140 mg/100 ml of PLASMA at fasting, and above approximately 200 mg/100 ml plasma at 30-, 60-, or 90-minute during a GLUCOSE TOLERANCE TEST. This condition is seen frequently in DIABETES MELLITUS, but also occurs with other diseases and MALNUTRITION.	2.25	1	0
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	2.25	1	0
Fasting Hypoglycemia HYPOGLYCEMIA expressed in the postabsorptive state, after prolonged FASTING, or an overnight fast.	5.17	3	3
Hypoglycemia A syndrome of abnormally low BLOOD GLUCOSE level. Clinical hypoglycemia has diverse etiologies. Severe hypoglycemia eventually lead to glucose deprivation of the CENTRAL NERVOUS SYSTEM resulting in HUNGER; SWEATING; PARESTHESIA; impaired mental function; SEIZURES; COMA; and even DEATH.	5.17	3	3
Weight Gain Increase in BODY WEIGHT over existing weight.	3.98	2	1
Osteogenic Sarcoma [description not available]	3.51	7	0
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)	3.51	7	0
Diffuse Large B-Cell Lymphoma [description not available]	8.14	7	2
Lymphoma, Large B-Cell, Diffuse Malignant lymphoma composed of large B lymphoid cells whose nuclear size can exceed normal macrophage nuclei, or more than twice the size of a normal lymphocyte. The pattern is predominantly diffuse. Most of these lymphomas represent the malignant counterpart of B-lymphocytes at midstage in the process of differentiation.	8.14	7	2
Drug-Induced Cochlear Toxicity [description not available]	2.21	1	0
Ototoxicity Damage to the EAR or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.	2.21	1	0
Ache [description not available]	2.69	3	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2.69	3	0
Hematologic Malignancies [description not available]	3.64	1	1
Kidney Failure A severe irreversible decline in the ability of kidneys to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism.	3.94	2	1
Hepatocellular Carcinoma [description not available]	5.53	15	1
Cancer of Liver [description not available]	6.13	16	2
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.	5.53	15	1
Liver Neoplasms Tumors or cancer of the LIVER.	6.13	16	2
Hematologic Neoplasms Neoplasms located in the blood and blood-forming tissue (the bone marrow and lymphatic tissue). The commonest forms are the various types of LEUKEMIA, of LYMPHOMA, and of the progressive, life-threatening forms of the MYELODYSPLASTIC SYNDROMES.	3.64	1	1
Renal Insufficiency Conditions in which the KIDNEYS perform below the normal level in the ability to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism. Renal insufficiency can be classified by the degree of kidney damage (as measured by the level of PROTEINURIA) and reduction in GLOMERULAR FILTRATION RATE.	3.94	2	1
Cancer of Lung [description not available]	4.34	19	0
Lung Neoplasms Tumors or cancer of the LUNG.	4.34	19	0
Schistosoma mansoni Infection [description not available]	2.54	2	0
Schistosomiasis mansoni Schistosomiasis caused by Schistosoma mansoni. It is endemic in Africa, the Middle East, South America, and the Caribbean and affects mainly the bowel, spleen, and liver.	2.54	2	0
Recrudescence [description not available]	6.74	4	2
Cancer of Colon [description not available]	4.79	11	0
Invasiveness, Neoplasm [description not available]	4.11	14	0
Colonic Neoplasms Tumors or cancer of the COLON.	4.79	11	0
Protein Aggregation, Pathological A biochemical phenomenon in which misfolded proteins aggregate either intra- or extracellularly. Triggered by factors such as MUTATION; POST-TRANSLATIONAL MODIFICATIONS, and environmental stress, it is generally associated with ALZHEIMER DISEASE; PARKINSON DISEASE; HUNTINGTON DISEASE; and TYPE 2 DIABETES MELLITUS.	2.25	1	0
Candida Infection [description not available]	2.4	2	0
C gattii Infection [description not available]	2.25	1	0
Candidiasis Infection with a fungus of the genus CANDIDA. It is usually a superficial infection of the moist areas of the body and is generally caused by CANDIDA ALBICANS. (Dorland, 27th ed)	2.4	2	0
Cryptococcosis Fungal infection caused by genus CRYPTOCOCCUS.	2.25	1	0
Cancer of Pancreas [description not available]	3.82	10	0
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).	3.82	10	0
Thrombopenia [description not available]	4.55	1	1
Neutropenia A decrease in the number of NEUTROPHILS found in the blood.	4.99	2	1
Thrombocytopenia A subnormal level of BLOOD PLATELETS.	4.55	1	1
Diffuse Mixed Small and Large Cell Lymphoma [description not available]	5.85	4	2
Lymphoma, Non-Hodgkin Any of a group of malignant tumors of lymphoid tissue that differ from HODGKIN DISEASE, being more heterogeneous with respect to malignant cell lineage, clinical course, prognosis, and therapy. The only common feature among these tumors is the absence of giant REED-STERNBERG CELLS, a characteristic of Hodgkin's disease.	5.85	4	2
Cancer of Skin [description not available]	2.38	2	0
Skin Neoplasms Tumors or cancer of the SKIN.	2.38	2	0
B-Cell Chronic Lymphocytic Leukemia [description not available]	2.53	2	0
Leukemia, Lymphocytic, Chronic, B-Cell A chronic leukemia characterized by abnormal B-lymphocytes and often generalized lymphadenopathy. In patients presenting predominately with blood and bone marrow involvement it is called chronic lymphocytic leukemia (CLL); in those predominately with enlarged lymph nodes it is called small lymphocytic lymphoma. These terms represent spectrums of the same disease.	2.53	2	0
Cancer of Esophagus [description not available]	4.49	5	1
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	4.49	5	1
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	5.16	3	1
Acute Myelogenous Leukemia [description not available]	7.94	7	1
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	7.94	7	1
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	3.66	3	0
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.	2.25	1	0
Cataract, Membranous [description not available]	2.31	1	0
Cataract Partial or complete opacity on or in the lens or capsule of one or both eyes, impairing vision or causing blindness. The many kinds of cataract are classified by their morphology (size, shape, location) or etiology (cause and time of occurrence). (Dorland, 27th ed)	2.31	1	0
Bone Cancer [description not available]	3.5	7	0
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	3.5	7	0
Alloxan Diabetes [description not available]	3.97	4	0
Salivary Gland Diseases Diseases involving the SALIVARY GLANDS.	2.31	1	0
Coagulation Disorders, Blood [description not available]	2.41	1	0
Blood Coagulation Disorders Hemorrhagic and thrombotic disorders that occur as a consequence of abnormalities in blood coagulation due to a variety of factors such as COAGULATION PROTEIN DISORDERS; BLOOD PLATELET DISORDERS; BLOOD PROTEIN DISORDERS or nutritional conditions.	2.41	1	0
Herpes Simplex Virus Infection [description not available]	2.49	2	0
Herpes Simplex A group of acute infections caused by herpes simplex virus type 1 or type 2 that is characterized by the development of one or more small fluid-filled vesicles with a raised erythematous base on the skin or mucous membrane. It occurs as a primary infection or recurs due to a reactivation of a latent infection. (Dorland, 27th ed.)	2.49	2	0
Acute Kidney Failure [description not available]	5	3	1
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.52	2	0
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.	5	3	1
Diabetic Angiopathies VASCULAR DISEASES that are associated with DIABETES MELLITUS.	2.15	1	0
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	5.01	4	2
Hyperlipemia [description not available]	2.15	1	0
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	5.01	4	2
Hyperlipidemias Conditions with excess LIPIDS in the blood.	2.15	1	0
Diabetic Cardiomyopathies Diabetes complications in which VENTRICULAR REMODELING in the absence of CORONARY ATHEROSCLEROSIS and hypertension results in cardiac dysfunctions, typically LEFT VENTRICULAR DYSFUNCTION. The changes also result in myocardial hypertrophy, myocardial necrosis and fibrosis, and collagen deposition due to impaired glucose tolerance.	2.15	1	0
Colorectal Cancer [description not available]	4.87	7	1
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.	4.87	7	1
Cancer of Ovary [description not available]	4.21	16	0
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.	4.21	16	0
Adenocarcinoma, Clear Cell An adenocarcinoma characterized by the presence of varying combinations of clear and hobnail-shaped tumor cells. There are three predominant patterns described as tubulocystic, solid, and papillary. These tumors, usually located in the female reproductive organs, have been seen more frequently in young women since 1970 as a result of the association with intrauterine exposure to diethylstilbestrol. (From Holland et al., Cancer Medicine, 3d ed)	2.15	1	0
Chronic Kidney Diseases [description not available]	3.95	2	1
Renal Insufficiency, Chronic Conditions in which the KIDNEYS perform below the normal level for more than three months. Chronic kidney insufficiency is classified by five stages according to the decline in GLOMERULAR FILTRATION RATE and the degree of kidney damage (as measured by the level of PROTEINURIA). The most severe form is the end-stage renal disease (CHRONIC KIDNEY FAILURE). (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002)	3.95	2	1
Carcinoma, Anaplastic [description not available]	2.7	3	0
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.	2.7	3	0
Leucocythaemia [description not available]	2.79	3	0
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)	2.79	3	0
Carcinoma, Small Cell Lung [description not available]	2.5	2	0
Adenocarcinoma, Basal Cell [description not available]	4.68	10	0
Carcinoma, Non-Small Cell Lung [description not available]	2.15	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	4.68	10	0
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.	2.15	1	0
Small Cell Lung Carcinoma A form of highly malignant lung cancer that is composed of small ovoid cells (SMALL CELL CARCINOMA).	2.5	2	0
Diffuse Lymphocytic Lymphoma, Poorly-Differentiated [description not available]	2.17	1	0
Lymphoma, Mantle-Cell A form of non-Hodgkin lymphoma having a usually diffuse pattern with both small and medium lymphocytes and small cleaved cells. It accounts for about 5% of adult non-Hodgkin lymphomas in the United States and Europe. The majority of mantle-cell lymphomas are associated with a t(11;14) translocation resulting in overexpression of the CYCLIN D1 gene (GENES, BCL-1).	2.17	1	0
Nerve Degeneration Loss of functional activity and trophic degeneration of nerve axons and their terminal arborizations following the destruction of their cells of origin or interruption of their continuity with these cells. The pathology is characteristic of neurodegenerative diseases. Often the process of nerve degeneration is studied in research on neuroanatomical localization and correlation of the neurophysiology of neural pathways.	2.17	1	0
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	3.27	6	0
Benign Neoplasms, Brain [description not available]	6.96	10	3
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	6.96	10	3
Carcinoma, Neuroendocrine A group of carcinomas which share a characteristic morphology, often being composed of clusters and trabecular sheets of round blue cells, granular chromatin, and an attenuated rim of poorly demarcated cytoplasm. Neuroendocrine tumors include carcinoids, small (oat) cell carcinomas, medullary carcinoma of the thyroid, Merkel cell tumor, cutaneous neuroendocrine carcinoma, pancreatic islet cell tumors, and pheochromocytoma. Neurosecretory granules are found within the tumor cells. (Segen, Dictionary of Modern Medicine, 1992)	2.17	1	0
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	2.53	2	0
Inflammatory Response Syndrome, Systemic [description not available]	2.17	1	0
MODS [description not available]	2.17	1	0
Hemorrhagic Shock [description not available]	3.36	6	0
Multiple Organ Failure A progressive condition usually characterized by combined failure of several organs such as the lungs, liver, kidney, along with some clotting mechanisms, usually postinjury or postoperative.	2.17	1	0
Systemic Inflammatory Response Syndrome A systemic inflammatory response to a variety of clinical insults, characterized by two or more of the following conditions: (1) fever	2.17	1	0
Dyslipidemia [description not available]	3.59	1	1
Dyslipidemias Abnormalities in the serum levels of LIPIDS, including overproduction or deficiency. Abnormal serum lipid profiles may include high total CHOLESTEROL, high TRIGLYCERIDES, low HIGH DENSITY LIPOPROTEIN CHOLESTEROL, and elevated LOW DENSITY LIPOPROTEIN CHOLESTEROL.	3.59	1	1
Adverse Drug Event [description not available]	4.72	2	1
Drug-Related Side Effects and Adverse Reactions Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.	4.72	2	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	3.3	6	0
Allodynia [description not available]	2.8	3	0
Nerve Pain [description not available]	2.17	1	0
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.17	1	0
Experimental Hepatoma [description not available]	3.12	5	0
Asthma, Bronchial [description not available]	2.72	3	0
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	2.21	1	0
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).	2.72	3	0
Pneumonia Infection of the lung often accompanied by inflammation.	2.21	1	0
Chromosomal Translocation [description not available]	2.21	1	0
Cirrhosis [description not available]	2.83	3	0
Ureteral Obstruction Blockage in any part of the URETER causing obstruction of urine flow from the kidney to the URINARY BLADDER. The obstruction may be congenital, acquired, unilateral, bilateral, complete, partial, acute, or chronic. Depending on the degree and duration of the obstruction, clinical features vary greatly such as HYDRONEPHROSIS and obstructive nephropathy.	2.54	2	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	2.83	3	0
Adrenal Cortex Cancer [description not available]	2.21	1	0
Adrenal Cortex Neoplasms Tumors or cancers of the ADRENAL CORTEX.	2.21	1	0
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.	2.21	1	0
Degenerative Diseases, Central Nervous System [description not available]	2.08	1	0
TDP-43 Proteinopathies Diseases characterized by the presence of abnormally phosphorylated, ubiquitinated, and cleaved DNA-binding protein TDP-43 in affected brain and spinal cord. Inclusions of the pathologic protein in neurons and glia, without the presence of AMYLOID, is the major feature of these conditions, thus making these proteinopathies distinct from most other neurogenerative disorders in which protein misfolding leads to brain amyloidosis. Both frontotemporal lobar degeneration and AMYOTROPHIC LATERAL SCLEROSIS exhibit this common method of pathogenesis and thus they may represent two extremes of a continuous clinicopathological spectrum of one disease.	2.08	1	0
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.	2.08	1	0
Cancer of Prostate [description not available]	3.42	7	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	3.42	7	0
Hyperactivity, Motor [description not available]	2.08	1	0
Nociceptive Pain Dull or sharp aching pain caused by stimulated NOCICEPTORS due to tissue injury, inflammation or diseases. It can be divided into somatic or tissue pain and VISCERAL PAIN.	2.08	1	0
Pain, Chronic [description not available]	2.08	1	0
Chronic Pain Aching sensation that persists for more than a few months. It may or may not be associated with trauma or disease, and may persist after the initial injury has healed. Its localization, character, and timing are more vague than with acute pain.	2.08	1	0
Acute Pain Intensely discomforting, distressful, or agonizing sensation associated with trauma or disease, with well-defined location, character, and timing.	2.08	1	0
Gastric Ulcer [description not available]	2.42	2	0
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).	2.42	2	0
Blood Poisoning [description not available]	2.37	2	0
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	2.37	2	0
B16 Melanoma [description not available]	2.74	3	0
Hypovolemic [description not available]	2.08	1	0
Hypovolemia An abnormally low volume of blood circulating through the body. It may result in hypovolemic shock (see SHOCK).	2.08	1	0
Lung Adenocarcinoma [description not available]	2.48	2	0
Adenocarcinoma of Lung A carcinoma originating in the lung and the most common lung cancer type in never-smokers. Malignant cells exhibit distinct features such as glandular epithelial, or tubular morphology. Mutations in KRAS, EGFR, BRAF, and ERBB2 genes are associated with this cancer.	2.48	2	0
Peritoneal Carcinomatosis [description not available]	2.08	1	0
Peritoneal Neoplasms Tumors or cancer of the PERITONEUM.	2.08	1	0
Animal Mammary Carcinoma [description not available]	2.08	1	0
Infections, Plasmodium [description not available]	2.46	2	0
Plasmodium falciparum Malaria [description not available]	2.08	1	0
Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.	2.46	2	0
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.	2.08	1	0
Cocaine Abuse [description not available]	2.1	1	0
Drug Withdrawal Symptoms [description not available]	4.05	3	1
Substance Withdrawal Syndrome Physiological and psychological symptoms associated with withdrawal from the use of a drug after prolonged administration or habituation. The concept includes withdrawal from smoking or drinking, as well as withdrawal from an administered drug.	4.05	3	1
Cocaine-Related Disorders Disorders related or resulting from use of cocaine.	2.1	1	0
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.	3.77	11	0
Proteinuria The presence of proteins in the urine, an indicator of KIDNEY DISEASES.	2.1	1	0
Brain Stem Neoplasms, Primary [description not available]	11.33	20	16
Glial Cell Tumors [description not available]	12.47	24	17
Local Neoplasm Recurrence [description not available]	11.51	23	17
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)	12.47	24	17
Brain Stem Neoplasms Benign and malignant intra-axial tumors of the MESENCEPHALON; PONS; or MEDULLA OBLONGATA of the BRAIN STEM. Primary and metastatic neoplasms may occur in this location. Clinical features include ATAXIA, cranial neuropathies (see CRANIAL NERVE DISEASES), NAUSEA, hemiparesis (see HEMIPLEGIA), and quadriparesis. Primary brain stem neoplasms are more frequent in children. Histologic subtypes include GLIOMA; HEMANGIOBLASTOMA; GANGLIOGLIOMA; and EPENDYMOMA.	11.33	20	16
Bone Loss, Osteoclastic [description not available]	2.51	2	0
Metastase [description not available]	4.78	11	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	4.78	11	0
Canine Diseases [description not available]	2.13	1	0
Cancer of Endometrium [description not available]	2.1	1	0
Endometrial Neoplasms Tumors or cancer of ENDOMETRIUM, the mucous lining of the UTERUS. These neoplasms can be benign or malignant. Their classification and grading are based on the various cell types and the percent of undifferentiated cells.	2.1	1	0
Absence Seizure [description not available]	4.64	6	1
Seizures Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.	4.64	6	1
Complications of Diabetes Mellitus [description not available]	2.1	1	0
Angiogenesis, Pathologic [description not available]	3.32	6	0
Blood Pressure, Low [description not available]	2.46	2	0
Hypotension Abnormally low BLOOD PRESSURE that can result in inadequate blood flow to the brain and other vital organs. Common symptom is DIZZINESS but greater negative impacts on the body occur when there is prolonged depravation of oxygen and nutrients.	2.46	2	0
ADDH [description not available]	2.1	1	0
Attention Deficit Disorder with Hyperactivity A behavior disorder originating in childhood in which the essential features are signs of developmentally inappropriate inattention, impulsivity, and hyperactivity. Although most individuals have symptoms of both inattention and hyperactivity-impulsivity, one or the other pattern may be predominant. The disorder is more frequent in males than females. Onset is in childhood. Symptoms often attenuate during late adolescence although a minority experience the full complement of symptoms into mid-adulthood. (From DSM-V)	2.1	1	0
Leukemia L 1210 [description not available]	3.59	9	0
Arterial Obstructive Diseases [description not available]	2.11	1	0
Arterial Occlusive Diseases Pathological processes which result in the partial or complete obstruction of ARTERIES. They are characterized by greatly reduced or absence of blood flow through these vessels. They are also known as arterial insufficiency.	2.11	1	0
Familial Waldenstrom's Macroglobulinaemia [description not available]	2.11	1	0
Waldenstrom Macroglobulinemia A lymphoproliferative disorder characterized by pleomorphic B-LYMPHOCYTES including PLASMA CELLS, with increased levels of monoclonal serum IMMUNOGLOBULIN M. There is lymphoplasmacytic cells infiltration into bone marrow and often other tissues, also known as lymphoplasmacytic lymphoma. Clinical features include ANEMIA; HEMORRHAGES; and hyperviscosity.	2.11	1	0
Albuminuria The presence of albumin in the urine, an indicator of KIDNEY DISEASES.	4.21	3	1
Carotid Arteriopathies, Traumatic [description not available]	2.11	1	0
Neointima The new and thickened layer of scar tissue that forms on a PROSTHESIS, or as a result of vessel injury especially following ANGIOPLASTY or stent placement.	2.11	1	0
Pulmonary Arterial Remodeling [description not available]	2.11	1	0
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	2.38	2	0
Liver Steatosis [description not available]	2.53	2	0
Insulin Sensitivity [description not available]	4.21	3	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.	2.53	2	0
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.	4.21	3	1
Experimental Neoplasms [description not available]	3.47	8	0
Blood Clot [description not available]	2.11	1	0
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	2.11	1	0
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.	3.04	4	0
Disease, Pulmonary [description not available]	2.13	1	0
Lung Diseases Pathological processes involving any part of the LUNG.	2.13	1	0
Cancer of Stomach [description not available]	3.02	4	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	3.02	4	0
Ventricular Dysfunction A condition in which HEART VENTRICLES exhibit impaired function.	2.13	1	0
Cardiac Hypertrophy Enlargement of the HEART due to chamber HYPERTROPHY, an increase in wall thickness without an increase in the number of cells (MYOCYTES, CARDIAC). It is the result of increase in myocyte size, mitochondrial and myofibrillar mass, as well as changes in extracellular matrix.	2.43	2	0
Cardiomegaly Enlargement of the HEART, usually indicated by a cardiothoracic ratio above 0.50. Heart enlargement may involve the right, the left, or both HEART VENTRICLES or HEART ATRIA. Cardiomegaly is a nonspecific symptom seen in patients with chronic systolic heart failure (HEART FAILURE) or several forms of CARDIOMYOPATHIES.	2.43	2	0
Ascites Accumulation or retention of free fluid within the peritoneal cavity.	2.15	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	4.66	6	1
Bowel Diseases, Inflammatory [description not available]	2.13	1	0
Inflammatory Bowel Diseases Chronic, non-specific inflammation of the GASTROINTESTINAL TRACT. Etiology may be genetic or environmental. This term includes CROHN DISEASE and ULCERATIVE COLITIS.	2.13	1	0
Cholangiocellular Carcinoma [description not available]	2.13	1	0
Cholangiocarcinoma A malignant tumor arising from the epithelium of the BILE DUCTS.	2.13	1	0
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.	3.08	5	0
Cryptogenic Fibrosing Alveolitis [description not available]	2.13	1	0
Idiopathic Pulmonary Fibrosis A common interstitial lung disease of unknown etiology, usually occurring between 50-70 years of age. Clinically, it is characterized by an insidious onset of breathlessness with exertion and a nonproductive cough, leading to progressive DYSPNEA. Pathological features show scant interstitial inflammation, patchy collagen fibrosis, prominent fibroblast proliferation foci, and microscopic honeycomb change.	2.13	1	0
Endotoxemia A condition characterized by the presence of ENDOTOXINS in the blood. On lysis, the outer cell wall of gram-negative bacteria enters the systemic circulation and initiates a pathophysiologic cascade of pro-inflammatory mediators.	3.87	2	1
Cardiometabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.	2.15	1	0
Elevated Cholesterol [description not available]	2.15	1	0
Hypercholesterolemia A condition with abnormally high levels of CHOLESTEROL in the blood. It is defined as a cholesterol value exceeding the 95th percentile for the population.	2.15	1	0
Hypertrophy General increase in bulk of a part or organ due to CELL ENLARGEMENT and accumulation of FLUIDS AND SECRETIONS, not due to tumor formation, nor to an increase in the number of cells (HYPERPLASIA).	2.38	2	0
Metabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.	2.15	1	0
Anasarca [description not available]	2.43	2	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2.43	2	0
Bites [description not available]	2.04	1	0
Aggression Behavior which may be manifested by destructive and attacking action which is verbal or physical, by covert attitudes of hostility or by obstructionism.	2.04	1	0
Coronary Restenosis Recurrent narrowing or constriction of a coronary artery following surgical procedures performed to alleviate a prior obstruction.	2.05	1	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	4.46	5	1
Atypical Mycobacterial Infection, Disseminated [description not available]	2.05	1	0
Koch's Disease [description not available]	2.05	1	0
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	2.05	1	0
Infections, Orthomyxoviridae [description not available]	2.66	3	0
Coxsackie Virus Infections [description not available]	2.64	3	0
Orthomyxoviridae Infections Virus diseases caused by the ORTHOMYXOVIRIDAE.	2.66	3	0
Idiopathic Parkinson Disease [description not available]	2.06	1	0
Parkinson Disease A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)	2.06	1	0
Cardiac Diseases [description not available]	2.06	1	0
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	2.06	1	0
Cancer of Cervix [description not available]	2.06	1	0
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	2.06	1	0
Bladder Cancer [description not available]	2.07	1	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.07	1	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.46	2	0
Leukemia, Lymphocytic, T Cell [description not available]	2.73	3	0
Leukemia, T-Cell A malignant disease of the T-LYMPHOCYTES in the bone marrow, thymus, and/or blood.	2.73	3	0
Anoxemia [description not available]	2.38	2	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	2.38	2	0
Cardiac Failure [description not available]	2.08	1	0
Heart Failure A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.	2.08	1	0
Anorexia The lack or loss of APPETITE accompanied by an aversion to food and the inability to eat. It is the defining characteristic of the disorder ANOREXIA NERVOSA.	2.01	1	0
Long Sleeper Syndrome [description not available]	4.57	6	1
Sleep Wake Disorders Abnormal sleep-wake schedule or pattern associated with the CIRCADIAN RHYTHM which affect the length, timing, and/or rigidity of the sleep-wake cycle relative to the day-night cycle.	4.57	6	1
Depression, Endogenous [description not available]	2.35	2	0
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.	2.35	2	0
Chronic Illness [description not available]	1.93	1	0
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).	1.93	1	0
Chronic Insomnia [description not available]	5.76	12	2
Sleep Initiation and Maintenance Disorders Disorders characterized by impairment of the ability to initiate or maintain sleep. This may occur as a primary disorder or in association with another medical or psychiatric condition.	5.76	12	2
Aura [description not available]	4.42	5	1
Epilepsy A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)	4.42	5	1
Anesthesia A state characterized by loss of feeling or sensation. This depression of nerve function is usually the result of pharmacologic action and is induced to allow performance of surgery or other painful procedures.	3.73	11	0
Agitation, Psychomotor [description not available]	1.93	1	0
Psychomotor Agitation A feeling of restlessness associated with increased motor activity. This may occur as a manifestation of nervous system drug toxicity or other conditions.	1.93	1	0
Encephalitis, Polio [description not available]	1.93	1	0
Poliomyelitis An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)	1.93	1	0
Asphyxia Neonatorum Respiratory failure in the newborn. (Dorland, 27th ed)	1.93	1	0
Air Sickness [description not available]	1.93	1	0
Motion Sickness Disorder caused by motion. It includes sea sickness, train sickness, roller coaster rides, rocking chair, hammock swing, car sickness, air sickness, or SPACE MOTION SICKNESS. Symptoms include nausea, vomiting and/or dizziness.	1.93	1	0
Chemical Dependence [description not available]	4.25	7	0
Substance-Related Disorders Disorders related to substance use or abuse.	4.25	7	0
Infant, Newborn, Diseases Diseases of newborn infants present at birth (congenital) or developing within the first month of birth. It does not include hereditary diseases not manifesting at birth or within the first 30 days of life nor does it include inborn errors of metabolism. Both HEREDITARY DISEASES and METABOLISM, INBORN ERRORS are available as general concepts.	2.34	2	0
Acute Hypercapnic Respiratory Failure [description not available]	1.93	1	0
Respiratory Insufficiency Failure to adequately provide oxygen to cells of the body and to remove excess carbon dioxide from them. (Stedman, 25th ed)	1.93	1	0
Autosomal Dominant Juvenile Parkinson Disease [description not available]	1.93	1	0
Parkinsonian Disorders A group of disorders which feature impaired motor control characterized by bradykinesia, MUSCLE RIGIDITY; TREMOR; and postural instability. Parkinsonian diseases are generally divided into primary parkinsonism (see PARKINSON DISEASE), secondary parkinsonism (see PARKINSON DISEASE, SECONDARY) and inherited forms. These conditions are associated with dysfunction of dopaminergic or closely related motor integration neuronal pathways in the BASAL GANGLIA.	1.93	1	0
Alcohol Abuse [description not available]	2.64	3	0
Alcoholism A primary, chronic disease with genetic, psychosocial, and environmental factors influencing its development and manifestations. The disease is often progressive and fatal. It is characterized by impaired control over drinking, preoccupation with the drug alcohol, use of alcohol despite adverse consequences, and distortions in thinking, most notably denial. Each of these symptoms may be continuous or periodic. (Morse & Flavin for the Joint Commission of the National Council on Alcoholism and Drug Dependence and the American Society of Addiction Medicine to Study the Definition and Criteria for the Diagnosis of Alcoholism: in JAMA 1992;268:1012-4)	2.64	3	0
Psychoses [description not available]	4.8	4	2
Psychotic Disorders Disorders in which there is a loss of ego boundaries or a gross impairment in reality testing with delusions or prominent hallucinations. (From DSM-IV, 1994)	4.8	4	2
Poisoning Used with drugs, chemicals, and industrial materials for human or animal poisoning, acute or chronic, whether the poisoning is accidental, occupational, suicidal, by medication error, or by environmental exposure.	2.63	3	0
Coma A profound state of unconsciousness associated with depressed cerebral activity from which the individual cannot be aroused. Coma generally occurs when there is dysfunction or injury involving both cerebral hemispheres or the brain stem RETICULAR FORMATION.	2.64	3	0
Abnormalities, Congenital [description not available]	1.93	1	0
Behavior Disorders [description not available]	3.74	2	1
Psychoses, Drug [description not available]	1.93	1	0
Mental Disorders Psychiatric illness or diseases manifested by breakdowns in the adaptational process expressed primarily as abnormalities of thought, feeling, and behavior producing either distress or impairment of function.	3.74	2	1
Amelia [description not available]	1.93	1	0
Aspergillus Infection [description not available]	1.93	1	0
Fungal Lung Diseases [description not available]	1.93	1	0
Aspergillosis Infections with fungi of the genus ASPERGILLUS.	1.93	1	0
Cardiac Death [description not available]	1.93	1	0
Phlegmon [description not available]	1.93	1	0
Asystole [description not available]	2.34	2	0
Cellulitis An acute, diffuse, and suppurative inflammation of loose connective tissue, particularly the deep subcutaneous tissues, and sometimes muscle, which is most commonly seen as a result of infection of a wound, ulcer, or other skin lesions.	1.93	1	0
Heart Arrest Cessation of heart beat or MYOCARDIAL CONTRACTION. If it is treated within a few minutes, heart arrest can be reversed in most cases to normal cardiac rhythm and effective circulation.	2.34	2	0
Cadaver A dead body, usually a human body.	2.64	3	0
Bone Fractures [description not available]	1.94	1	0
Femoral Fractures Fractures of the femur.	1.94	1	0
Birth Injuries Mechanical or anoxic trauma incurred by the infant during labor or delivery.	1.94	1	0
Fractures, Bone Breaks in bones.	1.94	1	0
Abnormalities, Drug-Induced Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.	2.87	4	0
Fibrodysplasia Ossificans Progressiva [description not available]	1.94	1	0
Myositis Ossificans A disease characterized by bony deposits or the ossification of muscle tissue.	1.94	1	0
Sarcoma 180 An experimental sarcoma of mice.	2.67	3	0
Cancer of the Vagina [description not available]	1.94	1	0
Mesenchymoma A mixed mesenchymal tumor composed of two or more mesodermal cellular elements not commonly associated, not counting fibrous tissue as one of the elements. Mesenchymomas are widely distributed in the body and about 75% are malignant. (Dorland, 27th ed; Holland et al., Cancer Medicine, 3d ed, p1866)	1.94	1	0
Vaginal Neoplasms Tumors or cancer of the VAGINA.	1.94	1	0
Rhabdomyosarcoma, Embryonal A form of RHABDOMYOSARCOMA arising primarily in the head and neck, especially the orbit, of children below the age of 10. The cells are smaller than those of other rhabdomyosarcomas and are of two basic cell types: spindle cells and round cells. This cancer is highly sensitive to chemotherapy and has a high cure rate with multi-modality therapy. (From Holland et al., Cancer Medicine, 3d ed, p2188)	1.94	1	0
Neuroses [description not available]	1.94	1	0
Neurotic Disorders Disorders in which the symptoms are distressing to the individual and recognized by him or her as being unacceptable. Social relationships may be greatly affected but usually remain within acceptable limits. The disturbance is relatively enduring or recurrent without treatment.	1.94	1	0
Bradyarrhythmia [description not available]	2.36	2	0
Bradycardia Cardiac arrhythmias that are characterized by excessively slow HEART RATE, usually below 50 beats per minute in human adults. They can be classified broadly into SINOATRIAL NODE dysfunction and ATRIOVENTRICULAR BLOCK.	2.36	2	0
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	2.39	2	0
Tachyarrhythmia [description not available]	2.02	1	0
Decerebrate Posturing [description not available]	2.02	1	0
Tachycardia Abnormally rapid heartbeat, usually with a HEART RATE above 100 beats per minute for adults. Tachycardia accompanied by disturbance in the cardiac depolarization (cardiac arrhythmia) is called tachyarrhythmia.	2.02	1	0
Body Weight, Fetal [description not available]	2.02	1	0
Experimental Mammary Neoplasms [description not available]	3.22	6	0
Anaplastic Astrocytoma [description not available]	4.64	3	2
Astrocytoma Neoplasms of the brain and spinal cord derived from glial cells which vary from histologically benign forms to highly anaplastic and malignant tumors. Fibrillary astrocytomas are the most common type and may be classified in order of increasing malignancy (grades I through IV). In the first two decades of life, astrocytomas tend to originate in the cerebellar hemispheres; in adults, they most frequently arise in the cerebrum and frequently undergo malignant transformation. (From Devita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2013-7; Holland et al., Cancer Medicine, 3d ed, p1082)	4.64	3	2
Adipocere [description not available]	2.02	1	0
Leukocytopenia [description not available]	2.44	2	0
Leukopenia A decrease in the number of LEUKOCYTES in a blood sample below the normal range (LEUKOCYTE COUNT less than 4000).	2.44	2	0
Cerebral Primitive Neuroectodermal Tumor [description not available]	3.41	1	1
Neuroectodermal Tumors, Primitive A group of malignant tumors of the nervous system that feature primitive cells with elements of neuronal and/or glial differentiation. Use of this term is limited by some authors to central nervous system tumors and others include neoplasms of similar origin which arise extracranially (i.e., NEUROECTODERMAL TUMORS, PRIMITIVE, PERIPHERAL). This term is also occasionally used as a synonym for MEDULLOBLASTOMA. In general, these tumors arise in the first decade of life and tend to be highly malignant. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, p2059)	3.41	1	1
Parasitemia The presence of parasites (especially malarial parasites) in the blood. (Dorland, 27th ed)	2.03	1	0
Drug Overdose Accidental or deliberate use of a medication or street drug in excess of normal dosage.	2.03	1	0
Anemia, Hypoplastic [description not available]	3.28	2	0
Pancytopenia Deficiency of all three cell elements of the blood, erythrocytes, leukocytes and platelets.	2.87	1	0
Viral Diseases [description not available]	2.87	1	0
Anemia, Aplastic A form of anemia in which the bone marrow fails to produce adequate numbers of peripheral blood elements.	3.28	2	0
Virus Diseases A general term for diseases caused by viruses.	2.87	1	0
Hyperphagia Ingestion of a greater than optimal quantity of food.	1.96	1	0
Nocturnal Wandering [description not available]	1.96	1	0
Dental Plaque A film that attaches to teeth, often causing DENTAL CARIES and GINGIVITIS. It is composed of MUCINS, secreted from salivary glands, and microorganisms.	1.96	1	0
Symptom Cluster [description not available]	3.34	1	1
Syndrome A characteristic symptom complex.	3.34	1	1
Blood Pressure, High [description not available]	1.96	1	0
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	1.96	1	0
Arachnoidal Cerebellar Sarcoma, Circumscribed [description not available]	1.98	1	0
Medulloblastoma A malignant neoplasm that may be classified either as a glioma or as a primitive neuroectodermal tumor of childhood (see NEUROECTODERMAL TUMOR, PRIMITIVE). The tumor occurs most frequently in the first decade of life with the most typical location being the cerebellar vermis. Histologic features include a high degree of cellularity, frequent mitotic figures, and a tendency for the cells to organize into sheets or form rosettes. Medulloblastoma have a high propensity to spread throughout the craniospinal intradural axis. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2060-1)	1.98	1	0
Embryopathies [description not available]	1.98	1	0
Hematoma A collection of blood outside the BLOOD VESSELS. Hematoma can be localized in an organ, space, or tissue.	1.98	1	0
Anxiety Neuroses [description not available]	4.06	3	1
Anxiety Disorders Persistent and disabling ANXIETY.	4.06	3	1
Cell Transformation, Viral An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.	2.38	2	0
Cardiovascular Stroke [description not available]	1.98	1	0
Heart Disease, Ischemic [description not available]	1.98	1	0
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	1.98	1	0
Myocardial Ischemia A disorder of cardiac function caused by insufficient blood flow to the muscle tissue of the heart. The decreased blood flow may be due to narrowing of the coronary arteries (CORONARY ARTERY DISEASE), to obstruction by a thrombus (CORONARY THROMBOSIS), or less commonly, to diffuse narrowing of arterioles and other small vessels within the heart. Severe interruption of the blood supply to the myocardial tissue may result in necrosis of cardiac muscle (MYOCARDIAL INFARCTION).	1.98	1	0
Hypothermia, Accidental [description not available]	2.69	3	0
Hypothermia Lower than normal body temperature, especially in warm-blooded animals.	2.69	3	0
Bewilderment [description not available]	3.38	1	1
Daytime Sleepiness [description not available]	3.38	1	1
Disorders of Excessive Somnolence Disorders characterized by hypersomnolence during normal waking hours that may impair cognitive functioning. Subtypes include primary hypersomnia disorders (e.g., IDIOPATHIC HYPERSOMNOLENCE; NARCOLEPSY; and KLEINE-LEVIN SYNDROME) and secondary hypersomnia disorders where excessive somnolence can be attributed to a known cause (e.g., drug affect, MENTAL DISORDERS, and SLEEP APNEA SYNDROME). (From J Neurol Sci 1998 Jan 8;153(2):192-202; Thorpy, Principles and Practice of Sleep Medicine, 2nd ed, p320)	3.38	1	1
Adenoma, Prostatic [description not available]	2	1	0
Prostatic Hyperplasia Increase in constituent cells in the PROSTATE, leading to enlargement of the organ (hypertrophy) and adverse impact on the lower urinary tract function. This can be caused by increased rate of cell proliferation, reduced rate of cell death, or both.	2	1	0
Injury, Ischemia-Reperfusion [description not available]	2	1	0
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	2	1	0
Carcinoma, Oat Cell [description not available]	2	1	0
Carcinoma, Small Cell An anaplastic, highly malignant, and usually bronchogenic carcinoma composed of small ovoid cells with scanty neoplasm. It is characterized by a dominant, deeply basophilic nucleus, and absent or indistinct nucleoli. (From Stedman, 25th ed; Holland et al., Cancer Medicine, 3d ed, p1286-7)	2	1	0
Chronic Kidney Failure [description not available]	1.95	1	0
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	1.95	1	0
Amino Acid Metabolism Disorders, Inborn [description not available]	2.36	2	0
Active Hyperemia [description not available]	1.95	1	0
Hyperemia The presence of an increased amount of blood in a body part or an organ leading to congestion or engorgement of blood vessels. Hyperemia can be due to increase of blood flow into the area (active or arterial), or due to obstruction of outflow of blood from the area (passive or venous).	1.95	1	0
Cancer of Nose [description not available]	1.95	1	0
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	1.98	1	0
Atypical Ductal Hyperplasia [description not available]	1.97	1	0
Carcinoma, Intraductal, Noninfiltrating A noninvasive (noninfiltrating) carcinoma of the breast characterized by a proliferation of malignant epithelial cells confined to the mammary ducts or lobules, without light-microscopy evidence of invasion through the basement membrane into the surrounding stroma.	1.97	1	0
Cancer of Gastrointestinal Tract [description not available]	1.97	1	0
Adenoma, Basal Cell [description not available]	2.37	2	0
Adenoma A benign epithelial tumor with a glandular organization.	2.37	2	0
Anaphylactic Reaction [description not available]	1.97	1	0
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.	1.97	1	0
Abnormalities, Autosome [description not available]	1.95	1	0
Remission, Spontaneous A spontaneous diminution or abatement of a disease over time, without formal treatment.	3.33	1	1
Basal Ganglia Diseases Diseases of the BASAL GANGLIA including the PUTAMEN; GLOBUS PALLIDUS; claustrum; AMYGDALA; and CAUDATE NUCLEUS. DYSKINESIAS (most notably involuntary movements and alterations of the rate of movement) represent the primary clinical manifestations of these disorders. Common etiologies include CEREBROVASCULAR DISORDERS; NEURODEGENERATIVE DISEASES; and CRANIOCEREBRAL TRAUMA.	4.3	2	2
Porphyria [description not available]	1.94	1	0
Porphyrias A diverse group of metabolic diseases characterized by errors in the biosynthetic pathway of HEME in the LIVER, the BONE MARROW, or both. They are classified by the deficiency of specific enzymes, the tissue site of enzyme defect, or the clinical features that include neurological (acute) or cutaneous (skin lesions). Porphyrias can be hereditary or acquired as a result of toxicity to the hepatic or erythropoietic marrow tissues.	1.94	1	0
Reticulum Cell-Like Sarcoma, Yoshida [description not available]	1.95	1	0
Bovine Diseases [description not available]	1.95	1	0
Diarrhea An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight.	2.35	2	0
Dyskinesia Syndromes [description not available]	3.33	1	1
Intraocular Pressure The pressure of the fluids in the eye.	3.33	1	1
Movement Disorders Syndromes which feature DYSKINESIAS as a cardinal manifestation of the disease process. Included in this category are degenerative, hereditary, post-infectious, medication-induced, post-inflammatory, and post-traumatic conditions.	3.33	1	1

2-piperidone

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