glycolic acid profile

glycolic acid: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

glycolic acid : A 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated. [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	757
CHEMBL ID	252557
CHEBI ID	17497
MeSH ID	M0098075

Synonym
hoch2cooh
CHEBI:17497 ,
2-hydroxyethanoic acid
alpha-hydroxyacetic acid
kyselina glykolova [czech]
kyselina hydroxyoctova [czech]
nsc 166
einecs 201-180-5
c2h4o3
brn 1209322
inchi=1/c2h4o3/c3-1-2(4)5/h3h,1h2,(h,4,5
epa pesticide chemical code 000101
ai3-15362
glycocide
glycolic acid (7ci,8ci)
caswell no. 470
glypure 70
acetic acid, hydroxy- (9ci)
hsdb 5227
glypure
GOA ,
acetic acid, hydroxy-
hydroxyethanoic acid
nsc-166
C03547
hydroxyacetic acid
C00160
nsc166 ,
glycollic acid
wln: qv1q
.alpha.-hydroxyacetic acid
glycolic acid
79-14-1
2-hydroxyacetic acid
glycolic acid, bioxtra, >=98.0% (titration)
DB03085
NCGC00160612-01
NCGC00160612-02
glycolic acid, reagentplus(r), 99%
287EB351-FF9F-4A67-B4B9-D626406C9B13
CHEMBL252557
AKOS000118921
BMSE000245
FT-0669047
G0196
G0110
polyglycolide
NCGC00257533-01
dtxsid0025363 ,
cas-79-14-1
tox21_301298
dtxcid105363
ccris 9474
unii-0wt12sx38s
0wt12sx38s ,
4-03-00-00571 (beilstein handbook reference)
kyselina glykolova
kyselina hydroxyoctova
acetic acid, 2-hydroxy-
ec 201-180-5
FT-0612572
S6272
hydroxyacetic acid-13c2
glycolic acid [vandf]
hydroxyacetic acid [hsdb]
glycolic acid [inci]
glycolic acid [mi]
glycolic acid [mart.]
glycolic acid [who-dd]
2-hydroxyl ethanoic acid
2-hydroxy-acetic acid
ho-ch2-cooh
glycolicacid
2-hydroxy acetic acid
hydroxy-acetic acid
STR00936
mfcd00004312
glycolic-2,2-d2 acid
J-509661
F2191-0224
glycolic acid, anhydrous, free-flowing, redi-dri(tm), reagentplus(r), 99%
glycolic acid, certified reference material, tracecert(r)
glycolic acid, >=97.0% (t)
glycolic acid, saj special grade, >=98.0%
glycolic acid, crystal, reagent
D78078
glycolic acid, p.a., 98%
glycolic acid, pharmaceutical secondary standard; certified reference material
glycolic acid, vetec(tm) reagent grade, 98%
hydroxyethanoate
alpha-hydroxyacetate
a-hydroxyacetic acid
a-hydroxyacetate
CS-W016683
HY-W015967
hydroxyacetic acid; hydroxyethanoic acid
Q409373
glycolic acid 100 microg/ml in acetonitrile
hydroxyacetic acid; hydroxyethanoic acid; glycollic acid
BCP28762
STL197955
o7z ,
hydroxyacetic acid solution
SB83760
2-hydroxyaceticacid
EN300-19242
glycolate standard: c2h3o3- @ 1000 microg/ml in h2o
c2h3o3-
pari 70% glycolic acid peel
usepa/opp pesticide code: 000101
village 11 factory relax day aha exfoliating body
glycolic acid (mart.)
oceanblu pre-post
oceanblu barrier
pari 30% glycolic acid peel
Z104473274

Research Excerpts

Overview

Glycolic acid (GA) is an effective way of reversing the signs of age and photodamage. In various free acid levels, it has been introduced as a topical therapy aimed at reducing pigmentation and improving skin texture, tone, and luminosity.

Excerpt	Reference	Relevance
"Glycolic acid (GA) is a commonly used superficial peel with higher concentrations and lower pH levels leading to a stronger effect despite a higher risk of adverse effects (AE), which include burning, pain, itching, erythema, and edema."	( The Efficacy and Safety of a Novel Protective Complex Combined With 50% Glycolic Acid Peel: A Double-Blinded, Split Face, Controlled Study. Artzi, O; Carasso, R; Heyman, L; Mehrabi, J, 2021)	2.3
"Glycolic acid (GA) is an effective way of reversing the signs of age and photodamage. "	( Glycolic acid adjusted to pH 4 stimulates collagen production and epidermal renewal without affecting levels of proinflammatory TNF-alpha in human skin explants. Brown, A; Fabbrocini, G; Granger, C; Narda, M; Piquero-Casals, J; Trullas, C, 2021)	3.51
"Glycolic acid is a known antioxidant; in various free acid levels, it has been introduced as a topical therapy aimed at reducing pigmentation and improving skin texture, tone, and luminosity."	( Effect of glycolic acid, phytic acid, soothing complex containing Emulsion on Hyperpigmentation and skin luminosity: A clinical evaluation. Houshmand, EB, 2021)	1.75
"Glycolic acid (GA) is an ⍺-hydroxy acid used in cosmetics, packaging, and medical industries due to its excellent properties, especially in its polymeric form. "	( Engineering Escherichia coli for glycolic acid production from D-xylose through the Dahms pathway and glyoxylate bypass. Bañares, AB; Cabulong, RB; Chung, WJ; Lee, WK; Nisola, GM; Ramos, KRM; Valdehuesa, KNG, 2018)	2.2
"Glycolic acid is an important industrial compound. "	( [Improving glycolic acid yield by metabolic engineering in Escherichia coli]. Deng, Y; Ma, N; Mao, Y; Zhu, K, 2018)	2.31
"Glycolic acid is a new substrate analog inhibitor with the value of the semi-inhibitory concentration of lipase is estimated to be 17.29 ± 0.14 mM."	( The inhibitory kinetics and mechanism of glycolic acid on lipase. Chen, QX; Liu, TT; Shen, DY; Su, WC; Zhuang, JX, 2020)	1.55
"Glycolic acid is a C2 hydroxy acid that is a widely used chemical compound. "	( Glycolic acid production in the engineered yeasts Saccharomyces cerevisiae and Kluyveromyces lactis. Barth, D; Koivistoinen, OM; Kuivanen, J; Penttilä, M; Pitkänen, JP; Richard, P; Turkia, H, 2013)	3.28
"Glycolic acid is an alpha-hydroxy acid used as a chemical peeling for more than a quarter century. "	( Effects of various concentrations of glycolic acid at the corneoxenometry and collaxenometry bioassays. Piérard, GE; Piérard-Franchimont, C; Xhauflaire-Uhoda, E, 2008)	2.06
"Glycolic acid is a member of the AHA family, which occurs naturally in foods and has been used for centuries as a cutaneous rejuvenation treatment. "	( Development of a w/o/w emulsion for chemical peeling applications containing glycolic acid. Baitokova, A; Yener, G, )	1.8
"Glycolic acid is an alpha-hydroxy acid that can be used as a topical skin peel to provide important complementary benefits to nonablative lasers, IPL, and TCA peels."	( Enhancing cosmetic outcomes by combining superficial glycolic acid (alpha-hydroxy acid) peels with nonablative lasers, intense pulsed light, and trichloroacetic acid peels. Briden, ME; Effron, C; Green, BA, 2007)	1.31
"Glycolic acid is a member of the AHA family, which occurs naturally in foods and has been used for centuries as a cutaneous rejuvenation treatment. "	( The use of glycolic acid as a peeling agent. Murad, H; Premo, PS; Shamban, AT, 1995)	2.12
"Glycolic acid is an alpha hydroxyacid that is useful as a chemical peeling agent."	( Glycolic acid peels for the treatment of wrinkles and photoaging. Moy, LS; Moy, RL; Murad, H, 1993)	3.17
"Glycolic acid peeling is an effective modality for the treatment of atrophic acne scars, but repetitive peels (at least six times) with 70% concentration are necessary to obtain evident improvement. "	( Biweekly serial glycolic acid peels vs. long-term daily use of topical low-strength glycolic acid in the treatment of atrophic acne scars. Akçali, C; Erbağci, Z, 2000)	2.1

Effects

Glycolic acid has been used extensively for the treatment of photoaging and wrinkles. It has considerable therapeutic value for acne with minimal side effects even in Asian skin.

Excerpt	Reference	Relevance
"Glycolic acid has chemical properties similar to those of formic acid. "	( High efficiency and clean separation of eucalyptus components by glycolic acid pretreatment. Cao, L; Deng, B; Hou, Y; Huang, C; Li, Y; Liang, C; Luo, Y; Qin, C; Yao, S; Zhu, J, 2021)	2.3
"Glycolic acid (GA) has been widely used in cosmetic agents and superficial chemical peeling in recent years. "	( Synergistic phototoxic effects of glycolic acid in a human keratinocyte cell line (HaCaT). Cheng, YW; Chung, JG; Hsiao, YP; Lai, WW; Wei, YH; Yang, JH, 2011)	2.09
"Glycolic acid has been added to hydroquinone formulations in the past to enhance their depigmentation effects, but may cause irritation, leading to postinflammatory hyperpigmentation."	( Safety and efficacy of 4% hydroquinone combined with 10% glycolic acid, antioxidants, and sunscreen in the treatment of melasma. Guevara, IL; Pandya, AG, 2003)	1.29
"Glycolic acid has been recognized as the major toxic agent in ethylene glycol poisoning but current methods available do not allow analysis in a clinically relevant turnaround time."	( Colorimetric and gas chromatographic procedures for glycolic acid in serum: the major toxic metabolite of ethylene glycol. Fraser, AD; MacNeil, W, 1993)	1.26
"Glycolic acid has been used extensively for the treatment of photoaging and wrinkles. "	( Glycolic acid modulation of collagen production in human skin fibroblast cultures in vitro. Howe, K; Moy, LS; Moy, RL, 1996)	3.18
"Glycolic acid has been one of the more commonly used alpha hydroxy acids for the treatment of photodamaged skin. "	( Short contact 70% glycolic acid peels as a treatment for photodamaged skin. A pilot study. Andree, C; Dobry, M; Grove, G; Hollenbach, KA; Hunt, S; Piacquadio, D, 1996)	2.07
"Glycolic acid has become important and popular for treating acne."	( The effect of glycolic acid on the treatment of acne in Asian skin. Chan, HL; Hu, CT; Huang, CL; Wang, CM, 1997)	2.1
"Glycolic acid has considerable therapeutic value for acne with minimal side effects even in Asian skin. "	( The effect of glycolic acid on the treatment of acne in Asian skin. Chan, HL; Hu, CT; Huang, CL; Wang, CM, 1997)	2.1
"Glycolic acid has also keratolytic action and could be interesting to treat acne."	( [Comparative study of the efficacy and tolerance of 12% glycolic acid cream and 0.05% retinoic acid cream for polymorphic acne]. Ezzine, N; Kamoun, F; Kamoun, MR; Kharfi, M; Mokhtar, I; Tekaya, N; Zeglaoui, F, )	1.1

Actions

Glycolic acid caused an increase in the level of skin damage in a dose- and time-dependent manner. The acid plays an intermediate role in glyoxylate metabolism.

Excerpt	Reference	Relevance
"Glycolic acid caused an increase in the level of skin damage in a dose- and time-dependent manner. "	( Effect of glycolic acid on UVB-induced skin damage and inflammation in guinea pigs. Cho, DH; Chung, SY; Hong, JT; Jung, HK; Kim, BY; Kim, DJ; Kim, EJ; Kim, HJ; Kim, HS; Nam, KT; Oh, JH; Park, KS; Song, CW; Yun, YW, )	1.98
"Glycolic acid plays and intermediate role in glyoxylate metabolism being involved in both its synthesis and degradation."	( [Determination of urinary glycolate by ion chromatography: clinical and experimental implication]. Ogawa, Y; Yamaguchi, K, 1997)	1.02

Treatment

Glycolic acid treatment is believed to reverse the photoaging process by increasing collagen synthesis in the skin. Treatment for 3 weeks had no effect on pre-existing light-induced pigmentation.

Excerpt	Reference	Relevance
"Glycolic acid treatment attenuated the UVB-induced cell cytotoxicity as well as apoptosis."	( Inhibitory effect of glycolic acid on ultraviolet B-induced c-fos expression, AP-1 activation and p53-p21 response in a human keratinocyte cell line. Ahn, KS; Chung, SY; Hong, JT; Jung, HK; Jung, KM; Kim, DJ; Lee, SH; Park, KS; Park, SM; Park, YK; Pyo, HB; Yang, KH; Yun, YP; Yun, YW, 2002)	1.35
"Glycolic acid treatment is believed to reverse the photoaging process by increasing collagen synthesis in the skin. "	( Increased in vivo collagen synthesis and in vitro cell proliferative effect of glycolic acid. Kim, DH; Kim, SJ; Maibach, HI; Park, JH; Won, YH, 1998)	1.97
"Glycolic acid treatment was compared in vivo with lactic acid (hairless mice) and in vitro to malic acid (normal human skin fibroblast culture) with controls. "	( Increased in vivo collagen synthesis and in vitro cell proliferative effect of glycolic acid. Kim, DH; Kim, SJ; Maibach, HI; Park, JH; Won, YH, 1998)	1.97
"Treatment with glycolic acid resulted in increased sensitivity of human skin to SSR, measured as an increase in erythema, DNA damage and sunburn cell formation. "	( The effects of topically applied glycolic acid and salicylic acid on ultraviolet radiation-induced erythema, DNA damage and sunburn cell formation in human skin. Barton, C; Beer, JZ; Coelho, SG; Hearing, VJ; Kaidbey, K; Kornhauser, A; Miller, SA; Takahashi, K; Wei, RR; Yamaguchi, Y, 2009)	0.99
"Treatment with glycolic acid for 3 weeks had no effect on pre-existing light-induced pigmentation."	( Effects of glycolic acid on light-induced skin pigmentation in Asian and caucasian subjects. Bowman, PH; Jee, SH; Maibach, HI; Paul, BH; Tsai, TF, 2000)	1.04

Toxicity

Glycolic acid is a commonly used superficial peel with higher concentrations and lower pH levels leading to a stronger effect despite a higher risk of adverse effects (AE), which include burning, pain, itching, erythema, and edema. A cream containing 4% hydroquinone, 10% buffered glycolic Acid, vitamins C and E, and sunscreen is safe and effective in the treatment of melasma.

Excerpt	Reference	Relevance
" A single course of q-switched ruby laser exposure is safe and efficient for the management of actinic lentigines, as it completely clears these obvious signs of aging."	( Q-switched ruby laser application is safe and effective for the management of actinic lentigo (topical glycolic acid is not). Hohenleutner, U; Kopera, D; Landthaler, M, 1996)	0.51
", this toxic effect is not accompanied by an increase in intramyocardial citrate levels."	( A 13C NMR study of 2-(13)C-chloroacetaldehyde, a metabolite of ifosfamide and cyclophosphamide, in the isolated perfused rabbit heart model. Initial observations on its cardiotoxicity and cardiac metabolism. Loqueviel, C; Malet-Martino, M; Martino, R, 1997)	0.3
" Clear evidence of maternal toxicity was demonstrated at 600 mg/kg; adverse clinical observations were statistically significantly increased (wheezing/lung noise, abnormal gait/staggering, lethargy)."	( Developmental toxicity study of glycolic acid in rats. Hurtt, ME; Kennedy, GL; Munley, SM, 1999)	0.59
"A cream containing 4% hydroquinone, 10% buffered glycolic acid, vitamins C and E, and sunscreen is safe and effective in the treatment of melasma."	( Safety and efficacy of 4% hydroquinone combined with 10% glycolic acid, antioxidants, and sunscreen in the treatment of melasma. Guevara, IL; Pandya, AG, 2003)	0.82
" Therefore, the present study suggests that combined treatment with serial glycolic acid peels, azelaic acid cream and adapalene gel should be considered as an effective and safe therapy in recalcitrant melasma."	( Efficacy and safety of serial glycolic acid peels and a topical regimen in the treatment of recalcitrant melasma. Arca, E; Erbil, H; Kurumlu, Z; Sezer, E; Taştan, B, 2007)	0.86
" These results indicate that COM, and not glyoxylate or glycolaldehyde, is the toxic metabolite responsible for the acute tubular necrosis and renal failure that is observed in EG-poisoned patients."	( Calcium oxalate, and not other metabolites, is responsible for the renal toxicity of ethylene glycol. Cenac, TA; Guo, C; Li, Y; McMartin, KE, 2007)	0.34
" Thioglycolates were slightly toxic in rat acute oral toxicity studies."	( Final amended report on the safety assessment of Ammonium Thioglycolate, Butyl Thioglycolate, Calcium Thioglycolate, Ethanolamine Thioglycolate, Ethyl Thioglycolate, Glyceryl Thioglycolate, Isooctyl Thioglycolate, Isopropyl Thioglycolate, Magnesium Thiogl Andersen, FA; Belsito, DV; Bergfeld, WF; Burnett, CL; Klaassen, CD; Marks, JG; Shank, RC; Slaga, TJ; Snyder, PW, )	0.13
" No device-related issues or adverse events were observed."	( A preclinical study of the safety and efficacy of Occlusin™ 500 Artificial Embolization Device in sheep. Biliske, JA; Griffith, IJ; Nation, PN; Owen, RJ; Polakowski, R; Tiege, PB, 2012)	0.38
" These results highlight the potential adverse effects of GA-containing cosmetic agents on human skin."	( Synergistic phototoxic effects of glycolic acid in a human keratinocyte cell line (HaCaT). Cheng, YW; Chung, JG; Hsiao, YP; Lai, WW; Wei, YH; Yang, JH, 2011)	0.65
" Nanoparticle functionalization with di-mannose (specifically carboxymethyl-α-D-mannopyranosyl-(1,2)-D-mannopyranoside), galactose (specifically carboxymethyl-β-galactoside), or glycolic acid induced no adverse effects after administration based on histopathological evaluation of liver, kidneys, and lungs."	( Safety and biocompatibility of carbohydrate-functionalized polyanhydride nanoparticles. Boggiatto, PM; Goodman, JT; Hostetter, JM; Narasimhan, B; Pohl, NL; Roychoudhury, R; Vela-Ramirez, JE; Wannemuehler, MJ, 2015)	0.61
" The glycolate complexes are selectively toxic against parasite amastigotes, with all complexes being nontoxic towards promastigotes and human fibroblast cells."	( Bismuth(III) α-hydroxy carboxylates: highly selective toxicity of glycolates towards Leishmania major. Andrews, PC; Blair, VL; Kedzierski, L; Loh, A; Ong, YC, 2015)	0.42
" Superficial chemical peeling is a skin-wounding procedure which might cause some potentially undesirable adverse events."	( Efficacy and safety of superficial chemical peeling in treatment of active acne vulgaris. Al-Khateeb, A; Al-Talib, H; Hameed, A; Murugaiah, C, )	0.13
" This clinical study demonstrated that the new synthetic resorbable membrane is safe for guided bone tissue regeneration in various dental surgery indications."	( Clinical Safety of a New Synthetic Resorbable Dental Membrane: A Case Series Study. Bourdin, D; Campard, G; Evanno, C; Hoornaert, A; Layrolle, P; Martin-Thomé, H; Morlock, JF; Saffarzadeh, A; Strube, N, 2018)	0.48
"Glycolic acid (GA) is a commonly used superficial peel with higher concentrations and lower pH levels leading to a stronger effect despite a higher risk of adverse effects (AE), which include burning, pain, itching, erythema, and edema."	( The Efficacy and Safety of a Novel Protective Complex Combined With 50% Glycolic Acid Peel: A Double-Blinded, Split Face, Controlled Study. Artzi, O; Carasso, R; Heyman, L; Mehrabi, J, 2021)	2.3
"The addition of the NPC to GA 50% peel is a highly effective, safe modality in the reduction of erythema, pain, and itching after peel application, and it provides an advantage in the post-treatment healing period."	( The Efficacy and Safety of a Novel Protective Complex Combined With 50% Glycolic Acid Peel: A Double-Blinded, Split Face, Controlled Study. Artzi, O; Carasso, R; Heyman, L; Mehrabi, J, 2021)	0.85
"Exposure to glycolic acid can be harmful and toxic to the lungs."	( Acute Toxicity in the Rat Lung Induced by Intratracheal Instillation of Glycolic Acid. Eom, IC; Kim, H; Kim, P; Kim, W; Lim, SK; Shim, I; Yoo, J; Yoon, BI, )	0.74
" No systemic adverse effect of AA-PLGA NPs was observed in our studies."	( Synthesis, characterization, and evaluation of in vitro cytotoxicity and in vivo antitumor activity of asiatic acid-loaded poly lactic-co-glycolic acid nanoparticles: A strategy of treating breast cancer. Basak, S; Chakraborty, P; Chatterjee, S; Dewanjee, S; Dutta, S; Ghosh, N; Ghosh, S; Sil, PC, 2022)	0.92

Pharmacokinetics

Excerpt	Reference	Relevance
" Pharmacokinetic parameters including Cmax, Tmax, AUC, and betat((1/2)) were determined for EG and GA."	( Dose-dependent nonlinear pharmacokinetics of ethylene glycol metabolites in pregnant (GD 10) and nonpregnant Sprague-Dawley rats following oral administration of ethylene glycol. Bartels, MJ; Carney, EW; Pottenger, LH, 2001)	0.31
" Therefore, a physiologically based pharmacokinetic (PBPK) model was developed to integrate the extensive mode of action and pharmacokinetic data on EG and GA for use in developmental risk assessments."	( Development of a physiologically based pharmacokinetic model for ethylene glycol and its metabolite, glycolic Acid, in rats and humans. Bartels, MJ; Carney, EW; Corley, RA; Gies, RA; Soelberg, JJ; Thrall, KD; Weitz, KK, 2005)	0.54
" The development and evaluation of the PBPK model was based upon previously published pharmacokinetic studies coupled with measured blood and tissue partition coefficients and rates of in vitro metabolism of glyoxylic acid to oxalic acid, glycine and other metabolites using primary hepatocytes isolated from male Wistar rats and humans."	( Extension of a PBPK model for ethylene glycol and glycolic acid to include the competitive formation and clearance of metabolites associated with kidney toxicity in rats and humans. Bartels, MJ; Corley, RA; Creim, J; Hansen, SC; McMartin, KE; Saghir, SA; Snellings, WM, 2011)	0.62

Compound-Compound Interactions

Hydroquinone 4% cream with 2% glycolic acid is safe and effective in improving photodamage on the neck and upper chest.

Excerpt	Reference	Relevance
"Hydroquinone 4% cream with 2% glycolic acid is safe and effective in improving photodamage on the neck and upper chest when used alone or in combination with salicylic acid peels."	( Efficacy of hydroquinone cream (USP 4%) used alone or in combination with salicylic acid peels in improving photodamage on the neck and upper chest. Gladstone, HB; Jeffers, M; Moy, RL; Nguyen, SL; Ottomeyer, T; Williams, R; Wortzman, M, 2000)	0.6
" In addition, well-recognized topical antiaging therapies such as superficial chemical peeling (CP) with α-hydroxy acids have been shown to be more helpful when combined with low-dose oral isotretinoin."	( Severe hyperpigmentation and scarring following glycolic acid peel treatment in combination with low-dose isotretinoin. Bölke, E; Diedrichson, E; Gerber, PA; Homey, B; Kukova, G, 2014)	0.66
"To study and compare the therapeutic efficacy and side effects of a 35% glycolic acid (GA) full face peel alone or in combination with a 10% or 20% trichloroacetic acid (TCA) spot peel for facial melasma."	( Comparative Efficacy of a 35% Glycolic Acid Peel Alone or in Combination With a 10% and 20% Trichloroacetic Acid Spot Peel for Melasma: A Randomized Control Trial. Bhalla, M; Garg, S; Kaur, J; Kumar, A; Thami, GP, 2019)	1.03
"Chemical peels with GA alone or in combination with TCA do result in a significant improvement in melasma, but the combination of the peels in the same sitting does not seem to have any additive or synergistic effect while they may increase the side effects."	( Comparative Efficacy of a 35% Glycolic Acid Peel Alone or in Combination With a 10% and 20% Trichloroacetic Acid Spot Peel for Melasma: A Randomized Control Trial. Bhalla, M; Garg, S; Kaur, J; Kumar, A; Thami, GP, 2019)	0.8
" Both medium-depth chemical peels including 15% TCA in combination with 70% GA and 35% TCA alone proved to be useful for the removal of epidermal or superficial lesions and to improve the texture of photodamaged facial skin (grade II-III Glogau photoaged skin)."	( Comparative study of 15% trichloroacetic acid peel combined with 70% glycolic acid and 35% trichloroacetic acid peel for the treatment of photodamaged facial skin in aging women. Kubiak, M; Mucha, P; Rotsztejn, H, 2020)	0.79

Bioavailability

Excerpt	Reference	Relevance
"The bioavailability of RAL into the skin after topical RALGA was studied by HPLC, and its bioconversion to RA was analysed by measuring the enzyme activity of retinaldehyde dehydrogenase and the RA content in the epidermis and dermis."	( Pharmacology of RALGA, a mixture of retinaldehyde and glycolic acid. Carraux, P; Didierjean, L; Grand, D; Kasraee, B; Saurat, JH; Sorg, O; Tran, C, 2005)	0.58
"05% alone; this indicates that the presence of GA favours the bioavailability and biotransformation of RAL into RA."	( Pharmacology of RALGA, a mixture of retinaldehyde and glycolic acid. Carraux, P; Didierjean, L; Grand, D; Kasraee, B; Saurat, JH; Sorg, O; Tran, C, 2005)	0.58
"These observations indicate that the addition of an AHA such as GA to a retinoid such as RAL results in a better bioavailability of the retinoid, thus a higher delivery of RA, which potentiates the biological activities of the retinoid."	( Pharmacology of RALGA, a mixture of retinaldehyde and glycolic acid. Carraux, P; Didierjean, L; Grand, D; Kasraee, B; Saurat, JH; Sorg, O; Tran, C, 2005)	0.58
"Nanoparticulate drug delivery systems, mucoadhesive polymers and penetration enhancers have been used individually to overcome ocular barriers and increase bioavailability to eye tissues."	( Understanding the influence of surface properties of nanoparticles and penetration enhancers for improving bioavailability in eye tissues in vivo. Katti, DS; Mahaling, B, 2016)	0.43
" The two systems were loaded with resveratrol (RSV), a hydrophobic polyphenol endowed with anti-cancerogenic, anti-inflammatory, and heart/brain protective effects, but with low bioavailability mainly due to poor aqueous solubility."	( Chitosan Oleate Coated Poly Lactic-Glycolic Acid (PLGA) Nanoparticles versus Chitosan Oleate Self-Assembled Polymeric Micelles, Loaded with Resveratrol. Bonferoni, MC; Catenacci, L; Dacarro, G; Ferrari, F; Malavasi, L; Miele, D; Rossi, S; Sandri, G; Sorrenti, M, 2019)	0.79
"The aim of this study was to improve the bioavailability of polymyxin B (PMB) in pulmonary nebulized drug delivery."	( Mucus-permeable polymyxin B-hyaluronic acid/ poly (lactic-co-glycolic acid) nanoparticle platform for the nebulized treatment of lung infections. Deng, L; Feng, Y; Li, R; Ouyang, Q; Qin, M; Sun, J; Wang, F; Wang, H; Wu, J; Yang, T; Yu, Q; Zhai, T; Zhan, Q, 2022)	0.96
" However, the poor solubility and low bioavailability limit its clinical application."	( Cannabidiol-Loaded Poly Lactic-Co-Glycolic Acid Nanoparticles with Improved Bioavailability as a Potential for Osteoarthritis Therapeutic. Jin, Z; Qin, Z; Wei, Q; Xu, S; Zhan, Y; Zheng, L, 2023)	1.19
" The current research attempted to develop poly (lactic-co-glycolic acid) nanoparticles loaded with raloxifene by modified emulsification solvent diffusion evaporation method to improve oral bioavailability by using Taguchi design."	( Formulation, optimization and characterization of raloxifene hydrochloride loaded PLGA nanoparticles by using Taguchi design for breast cancer application. Gandhi, S; Kavisri, M; Maddiboyina, B; Moovendhan, M; Nakkala, RK; Roy, H, 2023)	1.15

Dosage Studied

Paclitaxel dosage form on nanoparticles of 200-300 nm based on lactic and glycolic acid copolymer was obtained by the co-precipitation method.

Excerpt	Relevance	Reference
" Studies on the dosage design of this new delivery system of leuprorelin are summarized."	( [Once-a-month injectable microcapsules of leuprorelin acetate]. Ogawa, Y; Okada, H; Toguchi, H; Yamamoto, M, 1991)	0.28
" The peak plasma level of EG occurred at 2 hr after dosing and that of glycolate between 4-6 hr."	( Ethylene glycol and glycolate kinetics in rats and dogs. Collins, TD; Hewlett, TP; Jacobsen, D; McMartin, KE, 1989)	0.28
" Physicochemical properties, biodegradability, and biocompatibility of the polymers, and evaluations in vitro and in vivo of specific dosage forms using the polymers, are included."	( Poly(hydroxy acids) in drug delivery. Juni, K; Nakano, M, 1987)	0.27
" Ethylene glycol and commercial antifreeze were administered to experimental dogs at different dosage levels to reproduce the naturally occurring toxicosis associated with the consumption of commercial antifreeze."	( Diagnosis of ethylene glycol (antifreeze) intoxication in dogs by determination of glycolic acid in serum and urine with high pressure liquid chromatography and gas chromatography-mass spectrometry. Hewlett, TP; Ray, AC; Reagor, JC, 1983)	0.49
" A dosing regimen for the glycolic acid formulations that was tolerated by the hairless guinea pigs and significantly decreased stratum corneum turnover time was determined using the dansyl chloride staining technique."	( The effects of an alpha hydroxy acid (glycolic acid) on hairless guinea pig skin permeability. Bronaugh, RL; Hood, HL; Kraeling, ME; Robl, MG, 1999)	0.87
" Ethylene glycol was mixed in the diet at concentrations to deliver constant target dosage levels of 0, 50, 150, 500, or 1000 mg/kg/day for 16 weeks to groups of 10 male Wistar and 10 male F-344 rats based on weekly group mean body weights and feed consumption."	( Subchronic toxicity of ethylene glycol in Wistar and F-344 rats related to metabolism and clearance of metabolites. Corley, RA; Cruzan, G; Deyo, JA; Gingell, R; Hard, GC; McMartin, KE; Mertens, JJ; Snellings, WM, 2004)	0.32
" The in vivo dose-response curves were similar for all agents, with mean enhancement up to 20."	( Effect of shell type on the in vivo backscatter from polymer-encapsulated microbubbles. Forsberg, F; Goldberg, BB; Lathia, JD; Le, NT; Liu, JB; Merton, DA; Wheatley, MA, 2004)	0.32
"Paclitaxel dosage form on nanoparticles of 200-300 nm based on lactic and glycolic acid copolymer was obtained by the co-precipitation method."	( Cytotoxic effect of paclitaxel incorporated in nanoparticles based on lactic and glycolic acid copolymer. Alyautdin, RN; Balaban'yan, VY; Baranov, DS; Bojat, V; Hamdy, YM; Oganesyan, EA, 2011)	0.83
" In part B, patients with primary hyperoxaluria type 1 had a mean maximal reduction from baseline of 75% across dosing cohorts in 24-hour urinary oxalate excretion."	( Phase 1/2 Study of Lumasiran for Treatment of Primary Hyperoxaluria Type 1: A Placebo-Controlled Randomized Clinical Trial. Cochat, P; Deschênes, G; Erbe, DV; Frishberg, Y; Garg, PP; Groothoff, JW; Habtemariam, BA; Harambat, J; Haslett, P; Hulton, SA; Lieske, JC; Lorch, U; Lu, J; Magen, D; McGregor, TL; Milliner, DS; Talamudupula, S; Vaishnaw, AK; Van't Hoff, WG, 2021)	0.62
"Traditional dosage forms of granisetron (GRN) decrease patient compliance associated with repeated drug administration because of the short half-life of the drug."	( Formulation Optimization and In Vitro Characterization of Granisetronloaded Polylactic-co-glycolic Acid Microspheres Prepared by a Dropping-in-liquid Emulsification Technique. Ahmed, AMQ; Cao, QR; Chen, LQ; Du, HH; Sun, W, 2022)	0.94
" The dosage of antidotes (fomepizole or ethanol) needs to be adjusted during ECTR."	( Extracorporeal treatment for ethylene glycol poisoning: systematic review and recommendations from the EXTRIP workgroup. Bird, S; Ghannoum, M; Gosselin, S; Hassanian-Moghaddam, H; Hoffman, RS; Kallab, S; Lavergne, V; Mégarbane, B; Rif, M; Roberts, DM; Wood, DM, 2023)	0.91

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

Products

Product Category	Products
Other	5
Beauty & Personal Care	30
Baby & Kids Products	1

Product	Brand	Category	Compounds Matched from Ingredients	Date Retrieved
Acure Resurfacing Glycolic + Unicorn Root Cleanser -- 4 fl oz	Acure	Beauty & Personal Care	glyceryl oleate, decyl glucoside, ethylhexylglycerin, glycerin, glycolic acid, hemp, lactic acid, glyceryl caprylate, phenethyl alcohol	2024-11-29 10:47:42
Acure Resurfacing Inter-Gly-Lactic Exfoliator -- 4 fl oz	Acure	Beauty & Personal Care	ethylhexylglycerin, glycerin, glycolic acid, illite, kaolin, lactic acid, niacinamide, montmorillonite	2024-11-29 10:47:42
Acure Resurfacing Overnight Glycolic Treatment -- 1 fl oz	Acure	Beauty & Personal Care	citric acid, cetyl alcohol, citric acid, tocopherol, ethylhexylglycerin, tocopherol, glyceryl stearate, glycerin, glycolic acid, hemp, lactic acid, glyceryl laurate, phenethyl alcohol	2024-11-29 10:47:42
Alba Botanica Very Emollient Body Lotion Daily Shade SPF 15 -- 32 fl oz	Alba	Beauty & Personal Care	amyl cinnamal, citric acid, allantoin, ascorbic acid, benzoic acid, cetearyl alcohol, cetyl alcohol, citric acid, dehydroacetic acid, panthenol, triethyl citrate, geraniol, glycerin, glycolic acid, dimethicone, lactic acid, limonene, phenoxyethanol, phenethyl alcohol, potassium hydroxide, sodium benzoate	2024-11-29 10:47:42
Alba Botanica Very Emollient Body Lotion Maximum -- 32 fl oz	Alba	Beauty & Personal Care	amyl cinnamal, allantoin, ascorbic acid, benzoic acid, benzyl benzoate, benzyl salicylate, cetearyl alcohol, cetyl alcohol, citronellol, dehydroacetic acid, geraniol, glycerin, glycolic acid, dimethicone, hexyl cinnamal, hydroxycitronellal, lactic acid, phenoxyethanol, potassium hydroxide	2024-11-29 10:47:42
Baebody Neck Cream -- 1.7 fl oz	Baebody	Beauty & Personal Care	butylene glycol, ascorbic acid, cetearyl alcohol, cetyl alcohol, tocopherol, panthenol, dimethyl sulfone, tocopherol, glyceryl stearate, glycerin, glycolic acid, isopropyl palmitate, lactic acid, phenoxyethanol, phytic acid, squalane, potassium stearate, stearyl alcohol, ubiquinone	2024-11-29 10:47:42
CeraVe Psoriasis Cleanser with Salicylic Acid Psoriasis Wash -- 8 fl oz	CeraVe	Beauty & Personal Care	citric acid, gluconolactone, ethoxydiglycol, carbomer, ceramide NP, citric acid, disodium EDTA, ethylhexylglycerin, glycerin, glycolic acid, hexylene glycol, lactic acid, niacinamide, phenoxyethanol, phytosphingosine, laureth-9, sodium benzoate, sodium citrate, sodium lactate, urea	2024-11-29 10:47:42
Derma E Anti-Wrinkle Cleanser -- 6 fl oz	Derma E	Beauty & Personal Care	cocamidopropyl betaine, ethylhexylglycerin, glycolic acid, glyceryl laurate, phenoxyethanol, retinyl palmitate, vitamin A	2024-11-29 10:47:42
Derma E Anti-Wrinkle Scrub -- 4 oz	Derma E	Beauty & Personal Care	ascorbyl palmitate, cetearyl alcohol, cetyl alcohol, vitamin E, decyl glucoside, panthenol, provitamin B5, ethylhexylglycerin, vitamin E, glycerin, glycolic acid, phenoxyethanol, retinyl palmitate, vitamin A, stearic acid	2024-11-29 10:47:42
Derma E Essentials Overnight Peel AHAs -- 2 fl oz	Derma E	Beauty & Personal Care	ascorbyl palmitate, cetearyl alcohol, cetyl alcohol, glyceryl stearate, glycerin, glycolic acid, dimethicone, lactic acid, malic acid, phenoxyethanol, stearic acid	2024-11-29 10:47:42
Derma E Essentials Radiance Toner -- 6 fl oz	Derma E	Beauty & Personal Care	allantoin, panthenol, provitamin B5, ethylhexylglycerin, glycolic acid, phenoxyethanol, sodium hydroxide	2024-11-29 10:47:42
Derma E Even Tone Brightening Cleanser -- 6 fl oz	Derma E	Beauty & Personal Care	orange, ascorbyl palmitate, allantoin, cocamidopropyl betaine, panthenol, provitamin B5, glycolic acid, glyceryl laurate, vitamin B3, niacinamide, phenoxyethanol, retinyl palmitate, vitamin A	2024-11-29 10:47:42
Derma E Scalp Relief Rinse -- 4 fl oz	Derma E	Beauty & Personal Care	decyl glucoside, panthenol, ethylhexylglycerin, glycerin, glycolic acid, lactic acid, menthol, propanediol, salicylic acid, sodium hydroxide	2024-11-29 10:47:42
EO Bubble Bath - Rose Geranium -- 12 fl oz	EO	Beauty & Personal Care	orange, citric acid, allantoin, citric acid, panthenol, glycerin, glycolic acid, lactic acid, malic acid, tartaric acid	2024-11-29 10:47:42
Everyone 5 Star Deep Conditioner - Coconut & Lemon -- 8 fl oz	Everyone	Beauty & Personal Care	orange, citric acid, betaine, cetearyl alcohol, citric acid, tocopherol, tocopherol, glycerin, glycolic acid, lactic acid, malic acid, glyceryl caprylate, tartaric acid	2024-11-29 10:47:42
Everyone Dreamy Shampoo - Coconut + Lemon -- 12 fl oz	Everyone	Beauty & Personal Care	orange, citric acid, beta-carotene, citric acid, tocopherol, tocopherol, glycolic acid, lactic acid, malic acid, sodium lauroyl sarcosinate, tartaric acid	2024-11-29 10:47:42
Everyone Mighty Conditioner - Coconut + Lemon -- 12 fl oz	Everyone	Beauty & Personal Care	orange, citric acid, betaine, cetearyl alcohol, citric acid, tocopherol, tocopherol, glycerin, glycolic acid, lactic acid, malic acid, glyceryl caprylate, tartaric acid	2024-11-29 10:47:42
Everyone Power Rinse Clarifying Hair Cleanser - Peppermint + Tea Tree -- 8 fl oz	Everyone	Beauty & Personal Care	orange, citric acid, betaine, citric acid, glycolic acid, lactic acid, malic acid, propanediol, tartaric acid	2024-11-29 10:47:42
Everyone Super Scalp Scrub - Peppermint + Tea Tree -- 8 oz	Everyone	Beauty & Personal Care	orange, citric acid, betaine, cetearyl alcohol, citric acid, tocopherol, tocopherol, glycerin, glycolic acid, lactic acid, malic acid, glyceryl caprylate, propanediol, Sucrose, tartaric acid	2024-11-29 10:47:42
Mad Hippie AHA Exfoliating Peel -- 1.03 fl oz	Mad Hippie	Beauty & Personal Care	vitamin C, biotin, caffeine, ceramide 3, panthenol, glycerin, glycolic acid, lactic acid, melatonin, methyl cellulose, niacinamide, vitamin B5, phenoxyethanol, potassium hydroxide, squalene	2024-11-29 10:47:42
Mad Hippie Microdermabrasion Facial -- 2.1 oz	Mad Hippie	Beauty & Personal Care	caprylyl glycol, orange, cetyl alcohol, ethylhexyl glycerin, glycerin, glycolic acid, lactic acid, mandelic acid, probiotic, myristic acid, phenethyl alcohol, squalane, stearic acid	2024-11-29 10:47:42
MyChelle Dermaceuticals Brighten Perfect C Serum 17% Vitamin C -- 0.5 fl oz	MyChelle Dermaceuticals	Beauty & Personal Care	d-alpha, astaxanthin, benzyl alcohol, beta-carotene, CoQ10, tocopherol, tocopherol, glycerin, glycolic acid, aminoguanidine HCL, retinol, sodium hydroxide, tocotrienols, ubiquinone	2024-11-29 10:47:42
Pacifica Glow Baby Brightening Face Wash -- 5 fl oz	Pacifica	Beauty & Personal Care	citric acid, allantoin, vitamin C, citric acid, cocamidopropyl betaine, glycerin, glycolic acid, lactic acid, malic acid, phenoxyethanol	2024-11-29 10:47:42
Pacifica Glow Baby Brightening Peel Pads -- 60 Pads	Pacifica	Beauty & Personal Care	amylopectin, dextrin, erythritol, glycerin, glycolic acid, lactic acid, niacinamide, propanediol, salicylic acid, sodium hydroxide	2024-11-29 10:47:42
Pacifica Glowing Makeup Removing Wipes -- 30 Pre-Moistened Towelettes	Pacifica	Beauty & Personal Care	calendula, glycerin, glycolic acid	2024-11-29 10:47:42
Pacifica Rosemary Apple Cider Scalp Detox Tonic -- 5 fl oz	Pacifica	Beauty & Personal Care	cocamidopropylbetaine, panthenol, glycolic acid, lactic acid, niacinamide, propanediol, salicylic acid, sodium benzoate	2024-11-29 10:47:42
The Honest Company New Mama Care Essentials Gift Set -- 1 Set	The Honest Company	Baby & Kids Products	caprylyl glycol, citric acid, cellulose, cetearyl alcohol, cetyl alcohol, citric acid, tocopherol, tocopherol, glutamic acid, glycerin, glycolic acid, hectorite, microcrystalline cellulose, isopropyl palmitate, isostearyl alcohol, lactic acid, lauric acid, malic acid, maltodextrin, trisodium ethylenediamine disuccinate, propanediol, sodium benzoate, titanium dioxide	2024-11-29 10:47:42
The Seaweed Bath Co Calm Body Scrub - Vetiver Geranium -- 6 fl oz	The Seaweed Bath Co	Beauty & Personal Care	geranium, allantoin, kelp, carbomer, cocamidopropyl betaine, glycolic acid, vanillin	2024-11-29 10:47:42
Tree to Tub Anti Aging Green Tea Hyaluronic & Retinol Serum for Face -- 1 fl oz	Tree to Tub	Beauty & Personal Care	butylene glycol, dimethyl isosorbide, citric acid, chamomile, caffeine, citric acid, tocopherol, decyl glucoside, panthenol, ethylhexylglycerin, tocopherol, glycerin, glycolic acid, alpha-arbutin, vitamin B3, niacinamide, vitamin B5, vitamin A, sodium hydroxide, sodium metabisulfite, squalane	2024-11-29 10:47:42
TruSkin Eye Cream -- 0.5 oz	TruSkin	Beauty & Personal Care	butylene glycol, ascorbic acid, carbomer, cetostearyl alcohol, cetyl alcohol, coq10, glyceryl stearate, glycolic acid, isopropyl palmitate, lactic acid, phenoxyethanol, phytic acid, propylene glycol, potassium stearate, stearyl alcohol, thioctic acid	2024-11-29 10:47:42
Zion Health Adama Face Charcoal Mask Deep Pore Cleanser -- 4 oz	Zion Health	Beauty & Personal Care	tocopherol acetate, vitamin C, cholecalciferol, vitamin E, panthenol, vitamin E, glyceryl stearate, glycerin, glycolic acid, lactic acid, vitamin B, phenoxyethanol, retinol palmitate, salicylic acid, sorbic acid, zinc oxide	2024-11-29 10:47:42

Role	Description
metabolite	Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
keratolytic drug	A drug that softens, separates, and causes desquamation of the cornified epithelium or horny layer of skin. Keratolytic drugs are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases.
[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
2-hydroxy monocarboxylic acid
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.
[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]

Pathway	Proteins	Compounds
fatty acid u03C9-oxidation	0	8
Photosynthetic carbon reduction	0	14
Biochemical pathways: part I	0	466
GABA metabolism (aka GHB)	11	28
PCO cycle	8	24

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
DNA polymerase kappa isoform 1	Homo sapiens (human)	Potency	33.5875	0.0316	22.3146	100.0000	AID588579
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Assay ID	Title	Year	Journal	Article
AID1347082	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347083	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID311367	Permeability coefficient in human skin	2007	Bioorganic & medicinal chemistry, Nov-15, Volume: 15, Issue:22	Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	110 (11.75)	18.7374
1990's	163 (17.41)	18.2507
2000's	226 (24.15)	29.6817
2010's	275 (29.38)	24.3611
2020's	162 (17.31)	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	102 (10.33%)	5.53%
Reviews	63 (6.38%)	6.00%
Case Studies	44 (4.46%)	4.05%
Observational	1 (0.10%)	0.25%
Other	777 (78.72%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Trial	Phase	Enrollment	Study Type	Start Date	Status
Phase 2 Study of the Efficacy and Safety of a Single 70% Glycolic Acid Peel With Vitamin C for the Treatment of Photoaging [NCT02126644]	Phase 2	10 participants (Anticipated)	Interventional	2014-05-31	Not yet recruiting
"An Open-label Study of the Safety and Pharmacokinetics of the Glycolic Acid Tetrasubstituted Piceatannol (TGKP, Study Drug) With a Single Intravenous Administration With Participation of Healthy Volunteers: 3 Arms With Dose Escalation" [NCT06127381]	Phase 1	25 participants (Anticipated)	Interventional	2023-11-30	Not yet recruiting
Phase 2 Study of the The Efficacy and Safety of a Single 70% Glycolic Acid Peel With Vitamin C for the Treatment of Acne Scars [NCT02126657]	Phase 2	10 participants (Anticipated)	Interventional	2014-05-31	Not yet recruiting
Heterozygous Individuals for AGXT and Kidney Stones [NCT04430426]		4 participants (Anticipated)	Interventional	2024-01-01	Not yet recruiting
Renal Metabolism of Glycolate to Oxalate [NCT04437225]		15 participants (Anticipated)	Interventional	2020-03-12	Recruiting
Use of TCA 15% + 3% Glycolic Acid Chemical Peel for Improvement in Hand Lentigines [NCT05471947]	Phase 4	20 participants (Anticipated)	Interventional	2023-03-15	Recruiting
Acquired Epidermodysplasia Verruciformis (EV) Syndrome in HIV-infected Pediatric Patients: Prospective Treatment Trial With Topical Glycolic Acid and HPV Genotype Characterization [NCT01289171]		38 participants (Actual)	Interventional	2009-01-31	Completed
Comparing the Efficacy and Safety of Combined Glycolic Acid and Salicylic Acid Peel Versus Glycolic Acid Peel Alone in the Treatment of Melasma: A Split Face Study [NCT02812719]	Early Phase 1	0 participants (Actual)	Interventional	2018-07-31	Withdrawn(stopped due to Study did not receive funding and will not be implemented.)
Safety of Serum Containing Alpha Hydroxy Acid (AHA) and Polyglutamate Acid Derivatives for Post-Inflammatory on Hyperpigmentation Skin [NCT05998200]		34 participants (Anticipated)	Interventional	2023-07-01	Recruiting
Comparative Study Between Chemical Peeling With 70% Glycolic Acid and Intradermal Transamine for the Treatment of Melasma. [NCT05362500]	Phase 1	54 participants (Actual)	Interventional	2021-06-01	Completed
A Pilot Study Comparing the Efficacy of Glycolic Acid Peels vs. Salicylic Acid Peels for the Treatment of Melasma: A Randomized Control Trial [NCT01976286]		21 participants (Actual)	Interventional	2015-01-31	Active, not recruiting
Use Of A Novel Quantitative Tool For Evaluation of Pseudo- Acanthosis Nigricans: Acanthosis Nigricans Area And Severity Index [NCT04359485]		20 participants (Actual)	Interventional	2019-08-01	Active, not recruiting
The Efficacy of Combined Peels in Treatment of Melasma Using Modified Jessner's Solution With 20%Trichloroacetic Acid Versus 70%Glycolic Acid With 20% Trichloroacetic Acid : A Split-face Study [NCT03153852]	Phase 4	30 participants (Anticipated)	Interventional	2018-03-15	Not yet recruiting
Open Label Study to Evaluate the Efficacy and Safety of Sequential Therapy With Fluocinolone Acetonide 0.01%, Hydroquinone (HQ) 4% and Tretinoin 0.05% (TriLuma® Cream) and a Series of Glycolic Acid Peels for the Treatment of Melasma [NCT00472966]	Phase 4	20 participants (Actual)	Interventional	2006-11-30	Completed
A Multicenter, Placebo-Controlled, Randomized, Double-Blind Study of the Safety and Efficacy of Merlin (Ethanol and Glycolic Acid Mixture) for the Episodic Treatment of Recurrent Herpes Labialis [NCT01985321]	Phase 2	469 participants (Actual)	Interventional	2013-11-30	Completed
A Pilot Study Comparing the Efficacy of 1064 Q-switch Laser vs. Glycolic Acid Peels for the Treatment of Melasma: A Randomized Control Trial [NCT01976273]		20 participants (Actual)	Interventional	2013-10-31	Completed
Microneedling With Topical Glycolic Acid 35% Versus Microneedling With Topical Insulin in the Treatment of Atrophic Post-acne Scars [NCT05600075]		30 participants (Anticipated)	Interventional	2023-02-22	Not yet recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial	Outcome
NCT01976273 (1) [back to overview]	Visual Analog Scale (VAS) of Improvement Rated by a Blinded Dermatologist From at Week 10
NCT01985321 (2) [back to overview]	Clinician Assessed Duration of Complete Healing of the Herpetic Episode
NCT01985321 (2) [back to overview]	Number of Treatment Related Adverse Events

Intervention	units on a scale (Mean)
1064nm Q-switch Laser	4.37
Glycolic Acid Peels	4.62

Intervention	hours (Median)
Merlin - Ethanol/Glycolic Acid Solution	129.6
Ethanol	154.6

Intervention	participants (Number)
Merlin - Ethanol/Glycolic Acid Solution	9
Ethanol	3

Substance	Relationship Strength	Studies	Trials	Classes	Roles
chloroacetaldehyde [no description available]	1.99	1	0	organochlorine compound
alpha-ketobutyric acid alpha-ketobutyric acid: RN given refers to parent cpd; structure. 2-oxobutanoic acid : A 2-oxo monocarboxylic acid that is the 2-oxo derivative of butanoic acid.	2.39	2	0	2-oxo monocarboxylic acid; short-chain fatty acid
2-phosphoglycerate 2-phosphoglycerate: RN given refers to cpd without isomeric designation. 2-phosphoglyceric acid : A monophosphoglyceric acid having the phospho group at the 2-position.	2.31	1	0	monophosphoglyceric acid; tetronic acid derivative
2,3-diphosphoglycerate 2,3-Diphosphoglycerate: A highly anionic organic phosphate which is present in human red blood cells at about the same molar ratio as hemoglobin. It binds to deoxyhemoglobin but not the oxygenated form, therefore diminishing the oxygen affinity of hemoglobin. This is essential in enabling hemoglobin to unload oxygen in tissue capillaries. It is also an intermediate in the conversion of 3-phosphoglycerate to 2-phosphoglycerate by phosphoglycerate mutase (EC 5.4.2.1). (From Stryer Biochemistry, 4th ed, p160; Enzyme Nomenclature, 1992, p508). 2,3-bisphosphoglyceric acid : A bisphosphoglyceric acid that is glyceric acid carrying two phospho substituents at positions 2 and 3.	1.95	1	0	bisphosphoglyceric acid; tetronic acid derivative	human metabolite
3-phenylpropionic acid 3-phenylpropionic acid: RN given refers to parent cpd. 3-phenylpropionic acid : A monocarboxylic acid that is propionic acid substituted at position 3 by a phenyl group.	2.41	1	0	benzenes; monocarboxylic acid	antifungal agent; human metabolite; plant metabolite
4-hydroxyphenylacetic acid 4-hydroxyphenylacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.	3.01	1	0	monocarboxylic acid; phenols	fungal metabolite; human metabolite; mouse metabolite; plant metabolite
4-hydroxybenzoic acid 4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.	2.6	1	0	monohydroxybenzoic acid	algal metabolite; plant metabolite
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.	7.02	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
ethylene glycol Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.	10.08	81	1	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
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.	6.57	15	1	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	3.24	6	0	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
acetamide acetimidic acid : A carboximidic acid that is acetic acid in which the carbonyl oxygen is replaced by an imino group.	2.05	1	0	acetamides; carboximidic acid; monocarboxylic acid amide; N-acylammonia
adipic acid adipic acid : An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.	7.9	2	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	food acidity regulator; human xenobiotic metabolite
allantoin [no description available]	7.52	2	0	imidazolidine-2,4-dione; ureas	Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite; vulnerary
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	2.72	3	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
benzoic acid Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.	2.49	2	0	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
benzyl alcohol Benzyl Alcohol: A colorless liquid with a sharp burning taste and slight odor. It is used as a local anesthetic and to reduce pain associated with LIDOCAINE injection. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutic aid, and in perfumery and flavoring.. hydroxytoluene : Any member of the class of toluenes carrying one or more hydroxy substituents.. benzyl alcohol : An aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.. aromatic alcohol : Any alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.. aromatic primary alcohol : Any primary alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.	2.03	1	0	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
2,3-butylene glycol 2,3-butylene glycol: RN given refers to cpd without isomeric designation. butane-2,3-diol : A butanediol in which hydroxylation is at C-2 and C-3.	2.6	1	0	butanediol; glycol; secondary alcohol
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	2.03	1	0	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	2.78	3	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
cadaverine [no description available]	2.41	1	0	alkane-alpha,omega-diamine	Daphnia magna metabolite; Escherichia coli metabolite; mouse metabolite; plant metabolite
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.	3.77	3	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
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	5.71	15	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
catechol [no description available]	2.03	1	0	catechols	allelochemical; genotoxin; plant metabolite
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	2.07	1	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
chloroacetic acid chloroacetic acid: urinary metabolite of vinyl chloride; RN given refers to parent cpd; structure. chloroacetic acid : A chlorocarboxylic acid that is acetic acid carrying a 2-chloro substituent.	2.92	4	0	chlorocarboxylic acid; haloacetic acid	alkylating agent; herbicide
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.	6.64	20	3	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.	2.02	1	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	2.08	1	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	2.5	2	0	coumarins	fluorescent dye; human metabolite; plant metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	10.65	31	7	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	2.15	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
malyl-coenzyme a [no description available]	2.04	1	0
3-hydroxybutyric acid 3-Hydroxybutyric Acid: BUTYRIC ACID substituted in the beta or 3 position. It is one of the ketone bodies produced in the liver.. 3-hydroxybutyric acid : A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics.	3.14	5	0	(omega-1)-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; hydroxybutyric acid	human metabolite
bupropion Bupropion: A propiophenone-derived antidepressant and antismoking agent that inhibits the uptake of DOPAMINE.. bupropion : An aromatic ketone that is propiophenone carrying a tert-butylamino group at position 2 and a chloro substituent at position 3 on the phenyl ring.	2.05	1	0	aromatic ketone; monochlorobenzenes; secondary amino compound	antidepressant; environmental contaminant; xenobiotic
methylmalonic acid Methylmalonic Acid: A malonic acid derivative which is a vital intermediate in the metabolism of fat and protein. Abnormalities in methylmalonic acid metabolism lead to methylmalonic aciduria. This metabolic disease is attributed to a block in the enzymatic conversion of methylmalonyl CoA to succinyl CoA.. methylmalonic acid : A dicarboxylic acid that is malonic acid in which one of the methylene hydrogens is substituted by a methyl group.	1.98	1	0	C4-dicarboxylic acid	human metabolite
trimetaphosphoric acid trimetaphosphoric acid: RN given refers to parent cpd; structure. cyclotriphosphoric acid : The cyclic anhydride of triphosphoric acid.	1.99	1	0	cyclic phosphorus acid anhydride; inorganic heterocyclic compound; phosphorus oxoacid
malic acid malic acid : A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.. 2-hydroxydicarboxylic acid : Any dicarboxylic acid carrying a hydroxy group on the carbon atom at position alpha to the carboxy group.	3.78	11	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
phosphoglycolate phosphoglycolate: RN given refers to parent acid. 2-phosphoglycolic acid : The O-phospho derivative of glycolic acid.	4.61	8	0	carboxyalkyl phosphate	Escherichia coli metabolite; mouse metabolite
creatine [no description available]	3.11	1	0	glycine derivative; guanidines; zwitterion	geroprotector; human metabolite; mouse metabolite; neuroprotective agent; nutraceutical
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.	13.27	162	12	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
dihydroxyacetone phosphate Dihydroxyacetone Phosphate: An important intermediate in lipid biosynthesis and in glycolysis.. dihydroxyacetone phosphate : A member of the class of glycerone phosphates that consists of glycerone bearing a single phospho substituent.	7.41	2	0	glycerone phosphates; primary alpha-hydroxy ketone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dihydroxyacetone [no description available]	7.7	3	0	ketotriose; primary alpha-hydroxy ketone	antifungal agent; Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite; Saccharomyces cerevisiae 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.	2.02	1	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
ethanolamine [no description available]	2.69	3	0	ethanolamines; primary alcohol; primary amine	Escherichia coli metabolite; human metabolite; mouse metabolite
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	2.63	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
3-phosphoglycerate 3-phosphoglycerate : An organic anion obtained by deprotonation of at least one of the acidic groups of 3-phosphoglyceric acid.	2.66	3	0	monophosphoglyceric acid; tetronic acid derivative	algal metabolite; fundamental metabolite
glycine [no description available]	5.47	25	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
glyceraldehyde Glyceraldehyde: An aldotriose containing the propionaldehyde structure with hydroxy groups at the 2- and 3-positions. It is involved in the formation of ADVANCED GLYCOSYLATION END PRODUCTS.. glyceraldehyde : An aldotriose comprising propanal having hydroxy groups at the 2- and 3-positions. It plays role in the formation of advanced glycation end-products (AGEs), a deleterious accompaniment to ageing.. aldose : Aldehydic parent sugars (polyhydroxy aldehydes H[CH(OH)]nC(=O)H, n >= 2) and their intramolecular hemiacetals.	1.96	1	0	aldotriose	fundamental metabolite
glyceric acid glyceric acid: found in urine of patient with D-glyceric acidemia & hyperglycinaemia; RN given refers to parent cpd without isomeric designation. glycerol ether : Any ether having glyceryl as at least one of the O-substituents.. glyceric acid : A trionic acid that consists of propionic acid substituted at positions 2 and 3 by hydroxy groups.	4.9	11	0	trionic acid	fundamental metabolite
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	3.58	8	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
glycolaldehyde [no description available]	3.08	5	0	glycolaldehydes	fundamental metabolite; human metabolite
glyoxylic acid glyoxylic acid: RN given refers to parent cpd. glyoxylic acid : A 2-oxo monocarboxylic acid that is acetic acid bearing an oxo group at the alpha carbon atom.	7.25	53	0	2-oxo monocarboxylic acid; aldehydic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
carbonic acid Carbonic Acid: Carbonic acid (H2C03). The hypothetical acid of carbon dioxide and water. It exists only in the form of its salts (carbonates), acid salts (hydrogen carbonates), amines (carbamic acid), and acid chlorides (carbonyl chloride). (From Grant & Hackh's Chemical Dictionary, 5th ed)	3.06	1	0	carbon oxoacid; chalcocarbonic acid	mouse metabolite
hydrogen cyanide Hydrogen Cyanide: Hydrogen cyanide (HCN); A toxic liquid or colorless gas. It is found in the smoke of various tobacco products and released by combustion of nitrogen-containing organic materials.. hydrogen cyanide : A one-carbon compound consisting of a methine group triple bonded to a nitrogen atom	1.98	1	0	hydracid; one-carbon compound	Escherichia coli metabolite; human metabolite; poison
hydrogen carbonate Bicarbonates: Inorganic salts that contain the -HCO3 radical. They are an important factor in determining the pH of the blood and the concentration of bicarbonate ions is regulated by the kidney. Levels in the blood are an index of the alkali reserve or buffering capacity.. hydrogencarbonate : The carbon oxoanion resulting from the removal of a proton from carbonic acid.	2.67	3	0	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	4.18	5	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	10.76	24	13	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
hydroxylamine amino alcohol : An alcohol containing an amino functional group in addition to the alcohol-defining hydroxy group.	1.96	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
indole [no description available]	6.93	1	0	indole; polycyclic heteroarene	Escherichia coli metabolite
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	4.67	2	1	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
malonic acid malonic acid : An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.. dicarboxylic acid : Any carboxylic acid containing two carboxy groups.	2.45	2	0	alpha,omega-dicarboxylic acid	human metabolite
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	2.11	1	0	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	4.03	2	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
phytic acid Phytic Acid: Complexing agent for removal of traces of heavy metal ions. It acts also as a hypocalcemic agent.. myo-inositol hexakisphosphate : A myo-inositol hexakisphosphate in which each hydroxy group of myo-inositol is monophosphorylated.	3.98	2	1	inositol phosphate
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.	1.99	1	0	cyclitol; hexol
melatonin [no description available]	8.5	2	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
croton oil [no description available]	7.41	1	0	N-acyl-hexosamine
niacinamide nicotinamide : A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.	6.97	8	1	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
niacin Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.	2.03	1	0	pyridine alkaloid; pyridinemonocarboxylic acid; vitamin B3	antidote; antilipemic drug; EC 3.5.1.19 (nicotinamidase) inhibitor; Escherichia coli metabolite; human urinary metabolite; metabolite; mouse metabolite; plant metabolite; vasodilator agent
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	3.39	1	1	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
hydroxypyruvic acid hydroxypyruvic acid: RN given refers to parent cpd. 3-hydroxypyruvic acid : A 2-oxo monocarboxylic acid that is pyruvic acid in which one of the methyl hydrogens is substituted by a hydroxy group. It is an intermediate involved in the glycine and serine metabolism.	3.26	6	0	2-oxo monocarboxylic acid; 3-hydroxy monocarboxylic acid; primary alpha-hydroxy ketone	Escherichia coli metabolite; human metabolite
oxalic acid Oxalic Acid: A strong dicarboxylic acid occurring in many plants and vegetables. It is produced in the body by metabolism of glyoxylic acid or ascorbic acid. It is not metabolized but excreted in the urine. It is used as an analytical reagent and general reducing agent.. oxalic acid : An alpha,omega-dicarboxylic acid that is ethane substituted by carboxyl groups at positions 1 and 2.	6.57	38	0	alpha,omega-dicarboxylic acid	algal metabolite; human metabolite; plant metabolite
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	2.03	1	0	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
triphosphoric acid triphosphoric acid: used as water softener, peptizing agent, emulsifier & dispersing agent; ingredient of cleansers; meat preservative; RN given refers to parent cpd; structure	1.96	1	0	acyclic phosphorus acid anhydride; phosphorus oxoacid
phenol [no description available]	9.06	4	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
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.	3	4	0	phosphoric acids	algal metabolite; fertilizer; human metabolite; NMR chemical shift reference compound; solvent
phosphoenolpyruvate Phosphoenolpyruvate: A monocarboxylic acid anion derived from selective deprotonation of the carboxy group of phosphoenolpyruvic acid. It is a metabolic intermediate in GLYCOLYSIS; GLUCONEOGENESIS; and other pathways.. phosphoenolpyruvate : A monocarboxylic acid anion resuting from selective deprotonation of the carboxy group of phosphoenolpyruvic acid.. phosphoenolpyruvic acid : A monocarboxylic acid that is acrylic acid substituted by a phosphonooxy group at position 2. It is a metabolic intermediate in pathways like glycolysis and gluconeogenesis.	1.97	1	0	carboxyalkyl phosphate; monocarboxylic acid	fundamental metabolite
propylene glycol Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.	7.44	2	0	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
pyrazole 1H-pyrazole : The 1H-tautomer of pyrazole.	1.97	1	0	pyrazole
pyridoxal phosphate Pyridoxal Phosphate: This is the active form of VITAMIN B 6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (PYRIDOXAMINE).. pyridoxal 5'-phosphate : The monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal.	3.39	1	1	methylpyridines; monohydroxypyridine; pyridinecarbaldehyde; vitamin B6 phosphate	coenzyme; cofactor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyridoxine 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol: structure in first source. vitamin B6 : Any member of the group of pyridines that exhibit biological activity against vitamin B6 deficiency. Vitamin B6 deficiency is associated with microcytic anemia, electroencephalographic abnormalities, dermatitis with cheilosis (scaling on the lips and cracks at the corners of the mouth) and glossitis (swollen tongue), depression and confusion, and weakened immune function. Vitamin B6 consists of the vitamers pyridoxine, pyridoxal, and pyridoxamine and their respective 5'-phosphate esters (and includes their corresponding ionized and salt forms).	5.16	11	1	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; vitamin B6	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyruvic acid Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.	5.12	8	0	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
sarcosine cocobetaine: N-alkyl-betaine; cause of shampoo dermatitis	2.6	1	0	N-alkylglycine zwitterion; N-alkylglycine; N-methyl-amino acid; N-methylglycines	Escherichia coli metabolite; glycine receptor agonist; glycine transporter 1 inhibitor; human metabolite; mouse metabolite
sulfites Sulfites: Inorganic salts of sulfurous acid.. sulfites : Any sulfurous acid derivative that is a salt or an ester of sulfurous acid.. organosulfonate oxoanion : An organic anion obtained by deprotonation of the sufonate group(s) of any organosulfonic acid.. sulfite : A sulfur oxoanion that is the conjugate base of hydrogen sulfite (H2SO3).	2.41	2	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
spermine [no description available]	2.31	1	0	polyazaalkane; tetramine	antioxidant; fundamental metabolite; immunosuppressive agent
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	3.12	5	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
taurine [no description available]	2.25	1	0	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
thiamine thiamine(1+) : A primary alcohol that is 1,3-thiazol-3-ium substituted by (4-amino-2-methylpyrimidin-5-yl)methyl, methyl and 2-hydroxyethyl groups at positions 3, 4 and 5, respectively.	1.96	1	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	2.02	1	0	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	2.99	4	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
mandelic acid SAMMA: mandelic acid condensation polymer	5.91	7	1	2-hydroxy monocarboxylic acid; benzenes	antibacterial agent; human xenobiotic metabolite
1,10-phenanthroline 1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases	1.93	1	0	phenanthroline	EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
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.	2.5	2	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
2,4-dinitrophenol 2,4-Dinitrophenol: A toxic dye, chemically related to trinitrophenol (picric acid), used in biochemical studies of oxidative processes where it uncouples oxidative phosphorylation. It is also used as a metabolic stimulant. (Stedman, 26th ed). dinitrophenol : Members of the class of nitrophenol carrying two nitro substituents.. 2,4-dinitrophenol : A dinitrophenol having the nitro groups at the 2- and 4-positions.	1.96	1	0	dinitrophenol	allergen; antiseptic drug; bacterial xenobiotic metabolite; geroprotector; oxidative phosphorylation inhibitor
2-aminoethoxydiphenyl borate 2-aminoethoxydiphenyl borate: is a novel membrane-penetrable modulator and transient receptor potential channel blocker; structure in first source; do not confuse with 2-APB cpd. 2-aminoethoxydiphenylborane : An organoboron compound that is diphenylborane in which the borane hydrogen is replaced by a 2-aminoethoxy group.	2.07	1	0	organoboron compound; primary amino compound	calcium channel blocker; IP3 receptor antagonist; potassium channel opener
p-chloromercuribenzoic acid p-Chloromercuribenzoic Acid: An organic mercurial used as a sulfhydryl reagent.	1.96	1	0	chlorine molecular entity; mercuribenzoic acid
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.	1.99	1	0	1-pyrroline nitrones	neuroprotective agent; spin trapping reagent
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.	2.42	2	0	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	2.03	1	0	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
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.	2.03	1	0	barbiturates
antipyrine Antipyrine: An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29). antipyrine : A pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2.	2.03	1	0	pyrazolone	antipyretic; cyclooxygenase 3 inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
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.	2.03	1	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
atenolol Atenolol: A cardioselective beta-1 adrenergic blocker possessing properties and potency similar to PROPRANOLOL, but without a negative inotropic effect.. atenolol : An ethanolamine compound having a (4-carbamoylmethylphenoxy)methyl group at the 1-position and an N-isopropyl substituent.	2.03	1	0	ethanolamines; monocarboxylic acid amide; propanolamine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; sympatholytic agent; xenobiotic
azelaic acid nonanedioic acid : An alpha,omega-dicarboxylic acid that is heptane substituted at positions 1 and 7 by carboxy groups.	15.27	9	3	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	antibacterial agent; antineoplastic agent; dermatologic drug; plant metabolite
baclofen [no description available]	2.03	1	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid; monochlorobenzenes; primary amino compound	central nervous system depressant; GABA agonist; muscle relaxant
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).	2.03	1	0	barbiturates	drug allergen
benzamide benzamide : An aromatic amide that consists of benzene bearing a single carboxamido substituent. The parent of the class of benzamides.	1.97	1	0	benzamides
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.	1.99	1	0	pyrrolidines; tertiary amine	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent
2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one: from maize extracts; structure given in first source. DIMBOA : A lactol that is DIBOA in which the hydrogen at position 7 is replaced by a methoxy group. It has been isolated from the maize plants.	2.01	1	0	aromatic ether; benzoxazine; cyclic hydroxamic acid; lactol	allelochemical; plant metabolite
caffeine [no description available]	2.03	1	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
carbonyl cyanide m-chlorophenyl hydrazone Carbonyl Cyanide m-Chlorophenyl Hydrazone: A proton ionophore. It is commonly used as an uncoupling agent and inhibitor of photosynthesis because of its effects on mitochondrial and chloroplast membranes.. CCCP : A member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death.	2.01	1	0	hydrazone; monochlorobenzenes; nitrile	antibacterial agent; geroprotector; ionophore
celecoxib [no description available]	7.41	1	0	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug
chloroxylenol chloroxylenol: topical antiseptic; RN given refers to parent cpd; structure. 4-chloro-3,5-dimethylphenol : A member of the class of phenols that is 3,5-xylenol which is substituted at position 4 by chlorine. It is bactericidal against most Gram-positive bacteria but less effective against Staphylococci and Gram-negative bacteria, and often inactive against Pseudomonas species. It is ineffective against bacterial spores.	2.03	1	0	monochlorobenzenes; phenols	antiseptic drug; disinfectant; molluscicide
chlorpheniramine Chlorpheniramine: A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than PROMETHAZINE.. chlorphenamine : A tertiary amino compound that is propylamine which is substituted at position 3 by a pyridin-2-yl group and a p-chlorophenyl group and in which the hydrogens attached to the nitrogen are replaced by methyl groups. A histamine H1 antagonist, it is used to relieve the symptoms of hay fever, rhinitis, urticaria, and asthma.	2.03	1	0	monochlorobenzenes; pyridines; tertiary amino compound	anti-allergic agent; antidepressant; antipruritic drug; H1-receptor antagonist; histamine antagonist; serotonin uptake inhibitor
clofibric acid Clofibric Acid: An antilipemic agent that is the biologically active metabolite of CLOFIBRATE.. clofibric acid : A monocarboxylic acid that is isobutyric acid substituted at position 2 by a p-chlorophenoxy group. It is a metabolite of the drug clofibrate.	1.98	1	0	aromatic ether; monocarboxylic acid; monochlorobenzenes	anticholesteremic drug; antilipemic drug; antineoplastic agent; herbicide; marine xenobiotic metabolite; PPARalpha agonist
clonidine Clonidine: An imidazoline sympatholytic agent that stimulates ALPHA-2 ADRENERGIC RECEPTORS and central IMIDAZOLINE RECEPTORS. It is commonly used in the management of HYPERTENSION.. clonidine (amino form) : A clonidine that is 4,5-dihydro-1H-imidazol-2-amine in which one of the amino hydrogens is replaced by a 2,6-dichlorophenyl group.	2.03	1	0	clonidine; imidazoline
dapsone [no description available]	2.06	1	0	substituted aniline; sulfone	anti-inflammatory drug; antiinfective agent; antimalarial; leprostatic drug
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.	2.13	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
amphetamine Amphetamine: A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.. 1-phenylpropan-2-amine : A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.. amphetamine : A racemate comprising equimolar amounts of (R)-amphetamine (also known as levamphetamine or levoamphetamine) and (S)-amphetamine (also known as dexamfetamine or dextroamphetamine.	2.03	1	0	primary amine
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	2.03	1	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	2.03	1	0	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
diethylcarbamazine Diethylcarbamazine: An anthelmintic used primarily as the citrate in the treatment of filariasis, particularly infestations with Wucheria bancrofti or Loa loa.	2.03	1	0	N-carbamoylpiperazine; N-methylpiperazine
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.	2.03	1	0	pentacarboxylic acid	copper chelator
dilazep Dilazep: Coronary vasodilator with some antiarrhythmic activity.. dilazep : A member of the class of diazepanes that is 1,4-diazepane substituted by 3-[(3,4,5-trimethoxybenzoyl)oxy]propyl groups at positions 1 and 4. It is a potent adenosine uptake inhibitor that exhibits antiplatelet, antianginal and vasodilator properties.	2.01	1	0	benzoate ester; diazepane; diester; methoxybenzenes	cardioprotective agent; platelet aggregation inhibitor; vasodilator agent
erythrosine Fluoresceins: A family of spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one derivatives. These are used as dyes, as indicators for various metals, and as fluorescent labels in immunoassays.	2.38	2	0
ethacrynic acid Ethacrynic Acid: A compound that inhibits symport of sodium, potassium, and chloride primarily in the ascending limb of Henle, but also in the proximal and distal tubules. This pharmacological action results in excretion of these ions, increased urinary output, and reduction in extracellular fluid. This compound has been classified as a loop or high ceiling diuretic.. etacrynic acid : An aromatic ether that is phenoxyacetic acid in which the phenyl ring is substituted by chlorines at positions 2 and 3, and by a 2-methylidenebutanoyl group at position 4. It is a loop diuretic used to treat high blood pressure resulting from diseases such as congestive heart failure, liver failure, and kidney failure. It is also a glutathione S-transferase (EC 2.5.1.18) inhibitor.	2.03	1	0	aromatic ether; aromatic ketone; dichlorobenzene; monocarboxylic acid	EC 2.5.1.18 (glutathione transferase) inhibitor; ion transport inhibitor; loop diuretic
fenofibrate Pharmavit: a polyvitamin product, comprising vitamins A, D2, B1, B2, B6, C, E, nicotinamide, & calcium pantothene; may be a promising agent for application to human populations exposed to carcinogenic and genetic hazards of ionizing radiation; RN from CHEMLINE	2.01	1	0	aromatic ether; chlorobenzophenone; isopropyl ester; monochlorobenzenes	antilipemic drug; environmental contaminant; geroprotector; xenobiotic
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.	2.03	1	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.	5.1	10	1	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
flurbiprofen Flurbiprofen: An anti-inflammatory analgesic and antipyretic of the phenylalkynoic acid series. It has been shown to reduce bone resorption in periodontal disease by inhibiting CARBONIC ANHYDRASE.. flurbiprofen : A monocarboxylic acid that is a 2-fluoro-[1,1'-biphenyl-4-yl] moiety linked to C-2 of propionic acid. A non-steroidal anti-inflammatory, analgesic and antipyretic, it is used as a pre-operative anti-miotic as well as orally for arthritis or dental pain.	2.03	1	0	fluorobiphenyl; monocarboxylic acid	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
fomepizole Fomepizole: A pyrazole and competitive inhibitor of ALCOHOL DEHYDROGENASE that is used for the treatment of poisoning by ETHYLENE GLYCOL or METHANOL.. fomepizole : A member of the class of pyrazoles that is 1H-pyrazole substituted by a methyl group at position 4.	5.44	4	1	pyrazoles	antidote; EC 1.1.1.1 (alcohol dehydrogenase) inhibitor; protective agent
furosemide Furosemide: A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for EDEMA and chronic RENAL INSUFFICIENCY.. furosemide : A chlorobenzoic acid that is 4-chlorobenzoic acid substituted by a (furan-2-ylmethyl)amino and a sulfamoyl group at position 2 and 5 respectively. It is a diuretic used in the treatment of congestive heart failure.	2.03	1	0	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
gentamicin Gentamicins: A complex of closely related aminoglycosides obtained from MICROMONOSPORA purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit PROTEIN BIOSYNTHESIS.	7.45	2	0
gliclazide Gliclazide: An oral sulfonylurea hypoglycemic agent which stimulates insulin secretion.	2.15	1	0	N-sulfonylurea	hypoglycemic agent; insulin secretagogue; radical scavenger
glutaral Glutaral: One of the protein CROSS-LINKING REAGENTS that is used as a disinfectant for sterilization of heat-sensitive equipment and as a laboratory reagent, especially as a fixative.. glutaraldehyde : A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.	2.13	1	0	dialdehyde	cross-linking reagent; disinfectant; fixative
ethidium Ethidium: A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.. ethidium : The fluorescent compound widely used in experimental cell biology and biochemistry to reveal double-stranded DNA and RNA.	2	1	0	phenanthridines	fluorochrome; intercalator
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	2.03	1	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic
lidocaine Lidocaine: A local anesthetic and cardiac depressant used as an antiarrhythmia agent. Its actions are more intense and its effects more prolonged than those of PROCAINE but its duration of action is shorter than that of BUPIVACAINE or PRILOCAINE.. lidocaine : The monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline.	4.66	3	2	benzenes; monocarboxylic acid amide; tertiary amino compound	anti-arrhythmia drug; drug allergen; environmental contaminant; local anaesthetic; xenobiotic
ifosfamide [no description available]	1.99	1	0	ifosfamides	alkylating agent; antineoplastic agent; environmental contaminant; immunosuppressive agent; xenobiotic
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	2.03	1	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
iohexol Iohexol: An effective non-ionic, water-soluble contrast agent which is used in myelography, arthrography, nephroangiography, arteriography, and other radiographic procedures. Its low systemic toxicity is the combined result of low chemotoxicity and low osmolality.. iohexol : A benzenedicarboxamide compound having N-(2,3-dihydroxypropyl)carbamoyl groups at the 1- and 3-positions, iodo substituents at the 2-, 4- and 6-positions and an N-(2,3-dihydroxypropyl)acetamido group at the 5-position.	2.07	1	0	benzenedicarboxamide; organoiodine compound	environmental contaminant; radioopaque medium; xenobiotic
isoproterenol Isoproterenol: Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.. isoprenaline : A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.	2.03	1	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
ketoprofen Ketoprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.. ketoprofen : An oxo monocarboxylic acid that consists of propionic acid substituted by a 3-benzoylphenyl group at position 2.	2.03	1	0	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
ketorolac Ketorolac: A pyrrolizine carboxylic acid derivative structurally related to INDOMETHACIN. It is an NSAID and is used principally for its analgesic activity. (From Martindale The Extra Pharmacopoeia, 31st ed). ketorolac : A racemate comprising equimolar amounts of (R)-(+)- and (S)-(-)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid. While only the (S)-(-) enantiomer is a COX1 and COX2 inhibitor, the (R)-(+) enantiomer exhibits potent analgesic activity. A non-steroidal anti-inflammatory drug, ketorolac is mainly used (generally as the tromethamine salt) for its potent analgesic properties in the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis. It was withdrawn from the market in many countries in 1993 following association with haemorrhage and renal failure.. 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid : A member of the class of pyrrolizines that is 2,3-dihydro-1H-pyrrolizine which is substituted at positions 1 and 5 by carboxy and benzoyl groups, respectively.	2.03	1	0	amino acid; aromatic ketone; monocarboxylic acid; pyrrolizines; racemate	analgesic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
kinetin Kinetin: A furanyl adenine found in PLANTS and FUNGI. It has plant growth regulation effects.. cytokinin : A phytohormone that promote cell division, or cytokinesis, in plant roots and shoots.. kinetin : A member of the class of 6-aminopurines that is adenine carrying a (furan-2-ylmethyl) substituent at the exocyclic amino group.	6.94	1	0	6-aminopurines; furans	cytokinin; geroprotector
kojic acid [no description available]	10.81	13	4	4-pyranones; enol; primary alcohol	Aspergillus metabolite; EC 1.10.3.1 (catechol oxidase) inhibitor; EC 1.10.3.2 (laccase) inhibitor; EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; EC 1.4.3.3 (D-amino-acid oxidase) inhibitor; NF-kappaB inhibitor; skin lightening agent
meperidine Meperidine: A narcotic analgesic that can be used for the relief of most types of moderate to severe pain, including postoperative pain and the pain of labor. Prolonged use may lead to dependence of the morphine type; withdrawal symptoms appear more rapidly than with morphine and are of shorter duration.. pethidine : A piperidinecarboxylate ester that is piperidine which is substituted by a methyl group at position 1 and by phenyl and ethoxycarbonyl groups at position 4. It is an analgesic which is used for the treatment of moderate to severe pain, including postoperative pain and labour pain.	2.03	1	0	ethyl ester; piperidinecarboxylate ester; tertiary amino compound	antispasmodic drug; kappa-opioid receptor agonist; mu-opioid receptor agonist; opioid analgesic
mesalamine Mesalamine: An anti-inflammatory agent, structurally related to the SALICYLATES, which is active in INFLAMMATORY BOWEL DISEASE. It is considered to be the active moiety of SULPHASALAZINE. (From Martindale, The Extra Pharmacopoeia, 30th ed). mesalamine : A monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position.	2.06	1	0	amino acid; aromatic amine; monocarboxylic acid; monohydroxybenzoic acid; phenols	non-steroidal anti-inflammatory drug
metoprolol Metoprolol: A selective adrenergic beta-1 blocking agent that is commonly used to treat ANGINA PECTORIS; HYPERTENSION; and CARDIAC ARRHYTHMIAS.. metoprolol : A propanolamine that is 1-(propan-2-ylamino)propan-2-ol substituted by a 4-(2-methoxyethyl)phenoxy group at position 1.	2.03	1	0	aromatic ether; propanolamine; secondary alcohol; secondary amino compound	antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; geroprotector; xenobiotic
metyrapone Metyrapone: An inhibitor of the enzyme STEROID 11-BETA-MONOOXYGENASE. It is used as a test of the feedback hypothalamic-pituitary mechanism in the diagnosis of CUSHING SYNDROME.. metyrapone : An aromatic ketone that is 3,3-dimethylbutan-2-one in which the methyl groups at positions 1 and 4 are replaced by pyridin-3-yl groups. A steroid 11beta-monooxygenase (EC 1.14.15.4) inhibitor, it is used in the diagnosis of adrenal insufficiency.	2.4	2	0	aromatic ketone	antimetabolite; diagnostic agent; EC 1.14.15.4 (steroid 11beta-monooxygenase) inhibitor
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.	2.05	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
minoxidil Minoxidil: A potent direct-acting peripheral vasodilator (VASODILATOR AGENTS) that reduces peripheral resistance and produces a fall in BLOOD PRESSURE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p371). minoxidil : A pyrimidine N-oxide that is pyrimidine-2,4-diamine 3-oxide substituted by a piperidin-1-yl group at position 6.	2.03	1	0	dialkylarylamine; tertiary amino compound
mirtazapine Mirtazapine: A piperazinoazepine tetracyclic compound that enhances the release of NOREPINEPHRINE and SEROTONIN through blockage of presynaptic ALPHA-2 ADRENERGIC RECEPTORS. It also blocks both 5-HT2 and 5-HT3 serotonin receptors and is a potent HISTAMINE H1 RECEPTOR antagonist. It is used for the treatment of depression, and may also be useful for the treatment of anxiety disorders.	2.05	1	0	benzazepine; tetracyclic antidepressant	alpha-adrenergic antagonist; anxiolytic drug; H1-receptor antagonist; histamine antagonist; oneirogen; serotonergic antagonist
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	1.97	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
nadifloxacin nadifloxacin: (R)-isomer does not induce chromosomal aberrations, unlike (S)-isomer; structure given in first source	2.44	2	0	heteroarylpiperidine; hydroxypiperidine; pyridoquinoline; quinolone antibiotic	antibacterial drug
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	2.03	1	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
nitroglycerin Nitroglycerin: A volatile vasodilator which relieves ANGINA PECTORIS by stimulating GUANYLATE CYCLASE and lowering cytosolic calcium. It is also sometimes used for TOCOLYSIS and explosives.. nitroglycerol : A nitrate ester that is glycerol in which nitro group(s) replace the hydrogen(s) attached to one or more of the hydroxy groups.. nitroglycerin : A nitroglycerol that is glycerol in which the hydrogen atoms of all three hydroxy groups are replaced by nitro groups. It acts as a prodrug, releasing nitric oxide to open blood vessels and so alleviate heart pain.	2.03	1	0	nitroglycerol	explosive; muscle relaxant; nitric oxide donor; prodrug; tocolytic agent; vasodilator agent; xenobiotic
oxprenolol Oxprenolol: A beta-adrenergic antagonist used in the treatment of hypertension, angina pectoris, arrhythmias, and anxiety.	2.03	1	0	aromatic ether
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).	2.05	1	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
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.	2.03	1	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
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
prilocaine Prilocaine: A local anesthetic that is similar pharmacologically to LIDOCAINE. Currently, it is used most often for infiltration anesthesia in dentistry.. prilocaine : An amino acid amide in which N-propyl-DL-alanine and 2-methylaniline have combined to form the amide bond; used as a local anaesthetic.	4.37	2	2	amino acid amide; monocarboxylic acid amide	anticonvulsant; local anaesthetic
propidium Propidium: Quaternary ammonium analog of ethidium; an intercalating dye with a specific affinity to certain forms of DNA and, used as diiodide, to separate them in density gradients; also forms fluorescent complexes with cholinesterase which it inhibits.	2.05	1	0	phenanthridines; quaternary ammonium ion	fluorochrome; intercalator
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	2.44	2	0	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
resorcinol resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951. resorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.	2.43	2	0	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser
salicylamide salamide: a major impurity of hydrochlorothiazide; structure in first source	2.03	1	0	phenols; salicylamides	antirheumatic drug; non-narcotic analgesic
sebacic acid sebacic acid : An alpha,omega-dicarboxylic acid that is the 1,8-dicarboxy derivative of octane.	7.76	3	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	human metabolite; plant metabolite
fluoroacetic acid fluoroacetic acid: N1 same as NM; RN given refers to parent cpd. fluoroacetic acid : A haloacetic acid that is acetic acid in which one of the methyl hydrogens is substituted by fluorine.	1.98	1	0	haloacetic acid; organofluorine compound	EC 4.2.1.3 (aconitate hydratase) inhibitor
iodoacetic acid Iodoacetic Acid: A derivative of ACETIC ACID that contains one IODINE atom attached to its methyl group.. iodoacetic acid : A haloacetic acid that is acetic acid in which one of the hydrogens of the methyl group is replaced by an iodine atom.	1.96	1	0	haloacetic acid; organoiodine compound	alkylating agent
tazarotene tazarotene: a topical acetylenic retinoid; a topical kerytolytic. tazarotene : The ethyl ester of tazarotenic acid. A prodrug for tazarotenic acid, it is used for the treatment of psoriasis, acne, and sun-damaged skin.	7.02	1	0	acetylenic compound; ethyl ester; pyridines; retinoid; thiochromane	keratolytic drug; prodrug; teratogenic agent
temozolomide [no description available]	7.21	1	0	imidazotetrazine; monocarboxylic acid amide; triazene derivative	alkylating agent; antineoplastic agent; prodrug
3-hydroxyaspartic acid 3-hydroxyaspartic acid: RN given refers to cpd without isomeric designation. 3-hydroxyaspartic acid : A hydroxy-amino acid that is aspartic acid in which one of the methylene hydrogens has been replaced by a hydroxy group.	2.21	1	0	amino dicarboxylic acid; aspartic acid derivative; C4-dicarboxylic acid; hydroxy-amino acid
tranexamic acid Tranexamic Acid: Antifibrinolytic hemostatic used in severe hemorrhage.	7.31	1	0	amino acid
corticosterone [no description available]	2.03	1	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
prednisolone Prednisolone: A glucocorticoid with the general properties of the corticosteroids. It is the drug of choice for all conditions in which routine systemic corticosteroid therapy is indicated, except adrenal deficiency states.. prednisolone : A glucocorticoid that is prednisone in which the oxo group at position 11 has been reduced to the corresponding beta-hydroxy group. It is a drug metabolite of prednisone.	2.45	2	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; drug metabolite; environmental contaminant; immunosuppressive agent; xenobiotic
estriol hormonin: estrogen replacement; each tablet contains 600 ug micronized 17beta-estradiol, 270 ug estriol and 1.4 mg estrone. chlorapatite : A phosphate mineral with the formula Ca5(PO4)3Cl.	2.03	1	0	16alpha-hydroxy steroid; 17beta-hydroxy steroid; 3-hydroxy steroid	estrogen; human metabolite; human xenobiotic metabolite; mouse metabolite
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	1.98	1	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
thymidine [no description available]	2.01	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
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.	3.4	7	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
cyclobarbital cyclobarbital: was heading 1977-94 (see under BARBITURATES 1977-90); CYCLOBARBITONE, HEXEMAL, & TETRAHYDROPHENOBARBITAL were see CYCLOBARBITAL 1977-94; use BARBITURATES to search CYCLOBARBITAL 1977-94; short to intermediate duration barbiturate used as hypnotic and sedative	2.03	1	0	barbiturates
aldosterone [no description available]	2.03	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
penicillamine Penicillamine: 3-Mercapto-D-valine. The most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease.. penicillamine : An alpha-amino acid having the structure of valine substituted at the beta position with a sulfanyl group.	1.99	1	0	non-proteinogenic alpha-amino acid; penicillamine	antirheumatic drug; chelator; copper chelator; drug allergen
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	2.03	1	0	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
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.	3.83	4	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.	9.93	12	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
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	1.93	1	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.	2.91	4	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
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.	3.12	5	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.	1.93	1	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.	8.1	5	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening 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.	2.03	1	0	pyrazolone; tertiary amino compound	antipyretic; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
galactose galactopyranose : The pyranose form of galactose.	2.5	2	0	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	2.43	2	0	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	3.95	12	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
phenylethyl alcohol Phenylethyl Alcohol: An antimicrobial, antiseptic, and disinfectant that is used also as an aromatic essence and preservative in pharmaceutics and perfumery.. 2-phenylethanol : A primary alcohol that is ethanol substituted by a phenyl group at position 2.	2.03	1	0	benzenes; primary alcohol	Aspergillus metabolite; fragrance; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	2.39	2	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
lactose Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.	8.43	1	1	lactose
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	1.96	1	0	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
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.	2.03	1	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	2.03	1	0	20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; mineralocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
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.	7.17	1	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
fluocinolone acetonide Fluocinolone Acetonide: A glucocorticoid derivative used topically in the treatment of various skin disorders. It is usually employed as a cream, gel, lotion, or ointment. It has also been used topically in the treatment of inflammatory eye, ear, and nose disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p732). fluocinolone acetonide : A fluorinated steroid that is flunisolide in which the hydrogen at position 9 is replaced by fluorine. A corticosteroid with glucocorticoid activity, it is used (both as the anhydrous form and as the dihydrate) in creams, gels and ointments for the treatment of various skin disorders.	3.84	2	1	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; cyclic ketal; fluorinated steroid; glucocorticoid; organic heteropentacyclic compound; primary alpha-hydroxy ketone	anti-inflammatory drug; antipruritic drug
17-alpha-hydroxyprogesterone 17alpha-hydroxyprogesterone : A 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone.	2.03	1	0	17alpha-hydroxy-C21-steroid; 17alpha-hydroxy steroid; tertiary alpha-hydroxy ketone	human metabolite; metabolite; mouse metabolite; progestin
mannitol [no description available]	3.38	2	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
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.	7.11	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
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	2.03	1	0	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
n-pentanol n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.	2.03	1	0	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	2.13	1	0	L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid; valine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; 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.	2.45	2	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
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.	7.37	2	0	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	3.69	3	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
methylamine methyl group : An alkyl group that is the univalent group derived from methane by removal of a hydrogen atom.	7.15	1	0	methylamines; one-carbon compound; primary aliphatic amine	mouse metabolite
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	1.99	1	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
trichloroacetic acid Trichloroacetic Acid: A strong acid used as a protein precipitant in clinical chemistry and also as a caustic for removing warts.. trichloroacetic acid : A monocarboxylic acid that is acetic acid in which all three methyl hydrogens are substituted by chlorine.	10.16	23	5	monocarboxylic acid; organochlorine compound	carcinogenic agent; metabolite; mouse metabolite
triamcinolone acetonide Triamcinolone Acetonide: An esterified form of TRIAMCINOLONE. It is an anti-inflammatory glucocorticoid used topically in the treatment of various skin disorders. Intralesional, intramuscular, and intra-articular injections are also administered under certain conditions.. triamcinolone acetonide : A synthetic glucocorticoid that is the 16,17-acetonide of triamcinolone. Used to treat various skin infections.	7.46	2	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; cyclic ketal; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone	anti-allergic agent; anti-inflammatory drug
butobarbital butobarbital: Butobarbital should be distinguished from Butabarbital (a synonym for Secbutabarbital)	2.03	1	0	barbiturates
dimethyl sulfate dimethyl sulfate: RN given refers to unlabeled cpd; structure. dimethyl sulfate : The dimethyl ester of sulfuric acid.	2.05	1	0	alkyl sulfate	alkylating agent; immunosuppressive agent
acrylic acid acrylic acid: RN given refers to parent cpd. acrylic acid : A alpha,beta-unsaturated monocarboxylic acid that is ethene substituted by a carboxy group.	7.04	1	0	alpha,beta-unsaturated monocarboxylic acid	metabolite
dichloroacetic acid [no description available]	2.38	2	0	monocarboxylic acid; organochlorine compound	astringent; marine metabolite
taurocholic acid Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.	2.13	1	0	amino sulfonic acid; bile acid taurine conjugate	human metabolite
pyridoxic acid Pyridoxic Acid: The catabolic product of most of VITAMIN B 6; (PYRIDOXINE; PYRIDOXAL; and PYRIDOXAMINE) which is excreted in the urine.. 4-pyridoxic acid : A methylpyridine that is 2-methylpyridine substituted by a hydroxy group at C-3, a carboxy group at C-4, and a hydroxymethyl group at C-5. It is the catabolic product of vitamin B6 and is excreted in the urine.. 4-pyridoxate : A pyridoxate that is the conjugate base of 4-pyridoxic acid, obtained by deprotonation of the carboxy group.	3.8	2	1	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; vitamin B6	human urinary metabolite; mouse metabolite
lawsone lawsone: a molluscacide from leaves of Lawsonia inermis L. topical sunscreening agent; structure; powdered leaves of Lawsonia inermis(Lythraceae) used as brown hair dye. lawsone : 1,4-Naphthoquinone carrying a hydroxy function at C-2. It is obtained from the leaves of Lawsonia inermis.	7.6	1	0
isosorbide dinitrate Isosorbide Dinitrate: A vasodilator used in the treatment of ANGINA PECTORIS. Its actions are similar to NITROGLYCERIN but with a slower onset of action.	2.03	1	0	glucitol derivative; nitrate ester	nitric oxide donor; vasodilator agent
xylitol xylooligosaccharide: structure in first source. pentitol : An alditol obtained by reduction of any pentose.. xylooligosaccharide : An oligosaccharide comprised of xylose residues.	2.37	2	0
2,4,6-trichlorophenol [no description available]	2.03	1	0	trichlorophenol	carcinogenic agent
thymol Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.	2.03	1	0	monoterpenoid; phenols	volatile oil component
beta-glucono-1,5-lactone beta-glucono-1,5-lactone: structure. D-glucono-1,5-lactone : An aldono-1,5-lactone obtained from D-gluconic acid.	3.84	2	1	aldono-1,5-lactone; gluconolactone	animal metabolite; mouse metabolite
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	2.34	2	0	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
benzoyl peroxide Benzoyl Peroxide: A peroxide derivative that has been used topically for BURNS and as a dermatologic agent in the treatment of ACNE and POISON IVY DERMATITIS. It is used also as a bleach in the food industry.	3.69	2	0	carbonyl compound
nicotinic acid benzyl ester nicotinic acid benzyl ester: RN given refers to parent cpd; structure in Merck Index, 9th ed, #6344. benzyl nicotinate : A benzyl ester resulting from the formal condensation of the carboxy group of nicotinic acid with benzyl alcohol. It has been used as a rubefacient.	2.03	1	0	benzyl ester	vasodilator agent
3,4-dimethylphenol 3,4-dimethylphenol: RN given refers to parent cpd. 3,4-xylenol : A member of the class of phenols that is phenol substituted by methyl groups at positions 3 and 4.	2.03	1	0	phenols
dilactide dilactide: structure given in first source	2.53	2	0	dioxanes
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.	2.08	1	0	butan-4-olide	metabolite; neurotoxin
lactobionic acid [no description available]	7.05	1	0	disaccharide	antioxidant
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	0	aldehyde; furans	Maillard reaction product; metabolite
pyrrolidonecarboxylic acid Pyrrolidonecarboxylic Acid: A cyclized derivative of L-GLUTAMIC ACID. Elevated blood levels may be associated with problems of GLUTAMINE or GLUTATHIONE metabolism.. 5-oxo-L-proline : An optically active form of 5-oxoproline having L-configuration.	2.63	2	0	5-oxoproline; L-proline derivative; non-proteinogenic L-alpha-amino acid	algal metabolite
acetophenone acetophenone : A methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group.	2.02	1	0	acetophenones	animal metabolite; photosensitizing agent; xenobiotic
nitrobenzene nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.	2.03	1	0	nitroarene; nitrobenzenes
terephthalic acid terephthalic acid: RN given refers to 1,4-benzenedicarboxylic acid. terephthalic acid : A benzenedicarboxylic acid carrying carboxy groups at positions 1 and 4. One of three possible isomers of benzenedicarboxylic acid, the others being phthalic and isophthalic acids.	3.22	3	0	benzenedicarboxylic acid
styrene Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.	2.03	1	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
phenylhydrazine [no description available]	1.93	1	0	phenylhydrazines	xenobiotic
anisole anisole : A monomethoxybenzene that is benzene substituted by a methoxy group.	2.03	1	0	monomethoxybenzene	plant metabolite
4-phenylenediamine 4-phenylenediamine: agent hair dye responsible for contact dermatitis; RN given refers to parent cpd. 1,4-phenylenediamine : A phenylenediamine in which the amino functions are at positions 1 and 4 of the benzene nucleus.	2.03	1	0	phenylenediamine	allergen; dye; hapten; reagent
butane butane : A straight chain alkane composed of 4 carbon atoms.	7.02	1	0	alkane; gas molecular entity	food propellant; refrigerant
glycolonitrile glycolonitrile : An cyanohydrin that is acetonitrile in which one of the hydrogens has been replaced by a hydroxy group.	7.45	2	0	cyanohydrin
glyoxal [no description available]	8.16	5	0	dialdehyde	agrochemical; allergen; pesticide; plant growth regulator
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.46	2	0	alkane
1,3-butylene glycol 1,3-butylene glycol: RN given refers to cpd without isomeric designation. butane-1,3-diol : A butanediol compound having two hydroxy groups in the 1- and 3-positions.	1.96	1	0	butanediol; glycol
3-hydroxybutanal [no description available]	2.93	4	0
3-dimethylaminopropylamine 3-dimethylaminopropylamine: RN given refers to parent cpd; structure	2.31	1	0
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	2.02	1	0	pyrrole; secondary amine
tetrahydrofuran oxolane : A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.	6.99	1	0	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	1.94	1	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
1,4-butanediol butane-1,4-diol : A butanediol that is butane in which one hydrogen of each of the methyl groups is substituted by a hydroxy group. A colourless, water-miscible, viscous liquid at room temperature (m.p. 16degreeC) with a high boiling point (230degreeC), it is mainly used for the production of other organic chemicals, particularly the solvent oxolane (also known as tetrahydrofuran or THF).	2.6	1	0	butanediol; glycol	neurotoxin; prodrug; protic solvent
piperidine [no description available]	2.69	3	0	azacycloalkane; piperidines; saturated organic heteromonocyclic parent; secondary amine	base; catalyst; human metabolite; non-polar solvent; plant metabolite; protic solvent; reagent
morpholine [no description available]	2.92	4	0	morpholines; saturated organic heteromonocyclic parent	NMR chemical shift reference compound
n-butoxyethanol n-butoxyethanol: RN given refers to parent cpd; structure. 2-butoxyethanol : A primary alcohol that is ethanol in which one of the methyl hydrogens is replaced by a butoxy group. A high-boiling (171degreeC) colourless liquid, it is used as a solvent for paints and inks, as well as in some dry cleaning solutions.	2.03	1	0	glycol ether; primary alcohol	protic solvent
propylene propylene: structure	2.42	2	0	alkene; gas molecular entity	refrigerant; xenobiotic
trinitrotoluene Trinitrotoluene: A 2,4,6-trinitrotoluene, which is an explosive chemical that can cause skin irritation and other toxic consequences.. 2,4,6-trinitrotoluene : A trinitrotoluene having the nitro groups at positions 2, 4 and 6.	2.31	1	0	trinitrotoluene	explosive
benzoin [no description available]	1.92	1	0	benzoins; secondary alpha-hydroxy ketone	EC 3.1.1.1 (carboxylesterase) inhibitor
isoquinoline [no description available]	2.03	1	0	azaarene; isoquinolines; mancude organic heterobicyclic parent; ortho-fused heteroarene
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	2.03	1	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
nitrilotriacetic acid Nitrilotriacetic Acid: A derivative of acetic acid, N(CH2COOH)3. It is a complexing (sequestering) agent that forms stable complexes with Zn2+. (From Miall's Dictionary of Chemistry, 5th ed.)	2.03	1	0	NTA; tricarboxylic acid	carcinogenic agent; nephrotoxic agent
pregnenolone [no description available]	2.03	1	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
potassium cyanide [no description available]	1.96	1	0	cyanide salt; one-carbon compound; potassium salt	EC 1.15.1.1 (superoxide dismutase) inhibitor; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; neurotoxin
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	2.11	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
benzoxazoles 1,3-benzoxazole : A benzoxazole in which the benzene ring is fused to a 1,3-oxazole ring across positions 4 and 5.. benzoxazole : Compounds based on a fused 1,2- or 1,3-oxazole and benzene bicyclic ring skeleton.	2.01	1	0	1,3-benzoxazoles; mancude organic heterobicyclic parent
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	2.02	1	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
thiazoles [no description available]	2.93	4	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
ephedrine Ephedrine: A phenethylamine found in EPHEDRA SINICA. PSEUDOEPHEDRINE is an isomer. It is an alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used for asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists.. (-)-ephedrine : A phenethylamine alkaloid that is 2-phenylethanamine substituted by a methyl group at the amino nitrogen and a methyl and a hydroxy group at position 2 and 1 respectively.	2.03	1	0	phenethylamine alkaloid; phenylethanolamines	bacterial metabolite; environmental contaminant; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
azacitidine Azacitidine: A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.. 5-azacytidine : An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via an N-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia.	2.13	1	0	N-glycosyl-1,3,5-triazine; nucleoside analogue	antineoplastic agent
fluocinonide Fluocinonide: A topical glucocorticoid used in the treatment of ECZEMA.	2.03	1	0	organic molecular entity
betamethasone Betamethasone: A glucocorticoid given orally, parenterally, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. Its lack of mineralocorticoid properties makes betamethasone particularly suitable for treating cerebral edema and congenital adrenal hyperplasia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p724)	2.03	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	anti-asthmatic agent; anti-inflammatory drug; immunosuppressive agent
hydantoins Hydantoins: Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS.. imidazolidine-2,4-dione : An imidazolidinone with oxo groups at position 2 and 4.	1.98	1	0	imidazolidine-2,4-dione
limestone Calcium Carbonate: Carbonic acid calcium salt (CaCO3). An odorless, tasteless powder or crystal that occurs in nature. It is used therapeutically as a phosphate buffer in hemodialysis patients and as a calcium supplement.. calcium carbonate : A calcium salt with formula CCaO3.	2.02	1	0	calcium salt; carbonate salt; inorganic calcium salt; one-carbon compound	antacid; fertilizer; food colouring; food firming agent
indophenol Indophenol: A deep blue dye (with the formula OC6H4NC6H4OH) used to detect AMMONIA in a common test called the Berthelot's reaction and to detect PARACETAMOL by spectrophotometry.. indophenol : A quinone imine obtained by formal condensation of one of the keto groups of benzoquinone with the amino group of 4-hydroxyaniline.	1.93	1	0	quinone imine	dye
caprolactone hexano-6-lactone : A epsilon-lactone that is oxepane substituted by an oxo group at position 2.	2.05	1	0	epsilon-lactone
4-hydroxybutyric acid 4-hydroxybutyric acid: was an entry term to Sodium Oxybate (74-98). 4-hydroxybutyric acid : A 4-hydroxy monocarboxylic acid that is butyric acid in which one of the hydrogens at position 4 is replaced by a hydroxy group.	2.02	1	0	4-hydroxy monocarboxylic acid; hydroxybutyric acid	general anaesthetic; GHB receptor agonist; neurotoxin; sedative
1,3-propanediol propane-1,3-diol : The simplest member of the class of propane-1,3-diols, consisting of propane in which one hydrogen from each methyl group is substituted by a hydroxy group. A colourless, viscous, water-miscible liquid with a high (210degreeC) boiling point, it is used in the synthesis of certain polymers and as a solvent and antifreeze.	2.05	1	0	propane-1,3-diols	metabolite; protic solvent
thiazolidines Thiazolidines: Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES.	1.98	1	0	thiazolidine
suberic acid suberic acid: used in plastics industry; inhibits activity of some enzymes; RN given refers to parent cpd; structure. suberic acid : An alpha,omega-dicarboxylic acid that is the 1,6-dicarboxy derivative of hexane.	2	1	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	human metabolite
copper gluconate Gluconates: Derivatives of gluconic acid (the structural formula HOCH2(CHOH)4COOH), including its salts and esters.	3.84	2	1	organic molecular entity
cellobiose beta-cellobiose : A cellobiose with beta configuration at the reducing-end glucose residue.	7.31	1	0	cellobiose	epitope
delta-valerolactone [no description available]	3.06	1	0	delta-lactone
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	1	0	dialdehyde	biomarker
glycyl-glycyl-glycine glycyl-glycyl-glycine : A tripeptide in which three glycine units are linked via peptide bonds in a linear sequence.	2.13	1	0	tripeptide zwitterion; tripeptide
2-hydroxybutyric acid 2-hydroxybutyric acid: RN given refers to cpd without isomeric designation. hydroxybutyric acid : Any compound comprising a butyric acid core carrying at least one hydroxy substituent.. 2-hydroxybutyric acid : A hydroxybutyric acid having a single hydroxyl group located at position 2; urinary secretion of 2-hydroxybutyric acid is increased with alcohol ingestion or vigorous physical exercise and is associated with lactic acidosis and ketoacidosis in humans and diabetes in animals.	2.37	2	0	2-hydroxy monocarboxylic acid; hydroxybutyric acid	algal metabolite; human metabolite
2-hydroxyisobutyric acid 2-hydroxyisobutyric acid : A 2-hydroxy monocarboxylic acid that is isobutyric acid bearing a hydroxy substituent at position 2. It is a metabolite of methyl tertiary-butyl ether.	2.42	2	0	2-hydroxy monocarboxylic acid	human xenobiotic metabolite
ethylmalonic acid ethylmalonic acid: don't confuse with diethyl malonate, which is a diester. ethylmalonate : A dicarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of ethylmalonic acid.. ethylmalonic acid : A dicarboxylic acid obtained by substitution of one of the methylene hydrogens of malonic acid by an ethyl group.	2	1	0	dicarboxylic acid; dicarboxylic fatty acid	human metabolite
dansyl chloride dansyl chloride: RN given refers to unlabeled cpd	2	1	0	aminonaphthalene; sulfonic acid derivative
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.41	2	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
5-methyl-2-furfural 5-methyl-2-furfural: RN given refers to cpd with locants as specified	2	1	0	aldehyde; furans	EC 2.2.1.6 (acetolactate synthase) inhibitor; flavouring agent; human metabolite; Maillard reaction product
3-hydroxybenzeneacetic acid 3-hydroxybenzeneacetic acid: metabolite of L-dopa; structure. 3-hydroxyphenylacetic acid : A monocarboxylic acid that is phenylacetic acid in which the hydrogen at position 3 on the benzene ring is replaced by a hydroxy group.	2.9	2	0	monocarboxylic acid; phenols	human xenobiotic metabolite
methoxyacetic acid methoxyacetic acid: RN given refers to parent cpd. methoxyacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by a methoxy group.	2.47	2	0	ether; monocarboxylic acid	antineoplastic agent; apoptosis inducer; human xenobiotic metabolite; mutagen
ethoxyacetic acid [no description available]	2.11	1	0	carboxylic acid
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.	3.35	1	0	cyclic ketone; erythromycin
n-nitrosodiethanolamine [no description available]	2.03	1	0	nitroso compound
durapatite Durapatite: The mineral component of bones and teeth; it has been used therapeutically as a prosthetic aid and in the prevention and treatment of osteoporosis.. hydroxylapatite : A phosphate mineral with the formula Ca5(PO4)3(OH).	3.45	7	0
vanadium pentoxide [no description available]	2.08	1	0	vanadium oxide
hydrofluoric acid Hydrofluoric Acid: Hydrofluoric acid. A solution of hydrogen fluoride in water. It is a colorless fuming liquid which can cause painful burns.. hydrogen fluoride : A diatomic molecule containing covalently bonded hydrogen and fluorine atoms.. organofluorine compound : An organofluorine compound is a compound containing at least one carbon-fluorine bond.	2	1	0	hydrogen halide; mononuclear parent hydride	NMR chemical shift reference compound
vancomycin Vancomycin: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear.. vancomycin : A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.	3.16	3	0	glycopeptide	antibacterial drug; antimicrobial agent; bacterial metabolite
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	5.51	8	2	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
beta-hydroxymyristic acid beta-hydroxymyristic acid: RN given refers to cpd without isomeric designation. 3-hydroxytetradecanoic acid : A 3-hydroxy fatty acid that is tetradecanoic (myristic) acid substituted at position 3 by a hydroxy group	2.15	1	0	3-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; long-chain fatty acid	bacterial metabolite; human metabolite
betamethasone valerate Betamethasone Valerate: The 17-valerate derivative of BETAMETHASONE. It has substantial topical anti-inflammatory activity and relatively low systemic anti-inflammatory activity.. betamethasone valerate : A steroid ester that is betamethasone in which the hydroxy group at the 17alpha position has been converted to the corresponding pentanoate ester.	3.81	2	1	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; fluorinated steroid; primary alpha-hydroxy ketone; steroid ester	anti-inflammatory drug
fluorescein Fluorescein: A phthalic indicator dye that appears yellow-green in normal tear film and bright green in a more alkaline medium such as the aqueous humor.. fluorescein (lactone form) : A xanthene dye that is highly fluorescent, detectable even when present in minute quantities. Used forensically to detect traces of blood, in analytical chemistry as an indicator in silver nitrate titrations and in microscopy.	2.38	2	0	2-benzofurans; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; polyphenol; xanthene dye	fluorescent dye; radioopaque medium
n,n-dimethylacrylamide [no description available]	2.1	1	0
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	1	0	fluorescein isothiocyanate
mannose mannopyranose : The pyranose form of mannose.	2.87	3	0	D-aldohexose; D-mannose; mannopyranose	metabolite
nafenopin Nafenopin: A peroxisome proliferator that is used experimentally to promote liver tumors. It has been used as an antihyperlipoproteinemic agent.. nafenopin : A racemate comprising equimolar amounts of (R)- and (S)-nafenopin. It is a peroxisome proliferator that is used experimentally to promote liver tumors. It has been used as an hypolipidemic agent.. 2-methyl-2-[4-(1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy]propanoic acid : A monocarboxylic acid that is 2-hydroxy-2-methylpropanoic acid in which ther tertiary hydroxy group has been converted into the corresponding p-(1,2,3,4-tetrahydronaphthalen-1-yl)phenyl ether.	1.97	1	0	aromatic ether; monocarboxylic acid
carbonates Carbonates: Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed). carbonates : Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.	2.46	2	0	carbon oxoanion
3-phenylbutyric acid 3-phenylbutyric acid : A monocarboxylic acid that is butanoic acid substituted by a phenyl group at position 3.	2	1	0	benzenes; monocarboxylic acid	antibacterial agent; bacterial xenobiotic metabolite
norleucine Norleucine: An unnatural amino acid that is used experimentally to study protein structure and function. It is structurally similar to METHIONINE, however it does not contain SULFUR.. L-norleucine : A non-proteinogenic L-alpha-amino acid comprising hexanoic acid carrying an amino group at C-2. It does not occur naturally.	2.41	1	0	2-aminohexanoic acid; L-alpha-amino acid zwitterion; non-proteinogenic L-alpha-amino acid
lanthanum [no description available]	2.13	1	0	f-block element atom; lanthanoid atom; scandium group element 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.	2.13	1	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
molybdenum Molybdenum: A metallic element with the atomic symbol Mo, atomic number 42, and atomic weight 95.95. It is an essential trace element, being a component of the enzymes xanthine oxidase, aldehyde oxidase, and nitrate reductase.	7.75	3	0	chromium group element atom	micronutrient
neodymium Neodymium: An element of the rare earth family of metals. It has the atomic symbol Nd, atomic number 60, and atomic weight 144.24, and is used in industrial applications.	8.45	1	1	f-block element atom; lanthanoid atom
scandium Scandium: An element of the rare earth family of metals. It has the atomic symbol Sc, atomic number 21, and atomic weight 45.	1.94	1	0	d-block element atom; rare earth metal atom; scandium group element atom
thorium Thorium: A radioactive element of the actinide series of metals. It has an atomic symbol Th, atomic number 90, and atomic weight 232.04. It is used as fuel in nuclear reactors to produce fissionable uranium isotopes. Because of its radioopacity, various thorium compounds are used to facilitate visualization in roentgenography.	1.94	1	0	actinoid atom; f-block 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.	8.26	6	0	titanium group element atom
argon Argon: A noble gas with the atomic symbol Ar, atomic number 18, and atomic weight 39.948. It is used in fluorescent tubes and wherever an inert atmosphere is desired and nitrogen cannot be used.	2.61	2	0	monoatomic argon; noble gas atom; p-block element atom	food packaging gas; neuroprotective agent
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.	2.49	2	0	cadmium molecular entity; zinc group element atom
europium Europium: An element of the rare earth family of metals. It has the atomic symbol Eu, atomic number 63, and atomic weight 152. Europium is used in the form of its salts as coatings for cathode ray tubes and in the form of its organic derivatives as shift reagents in NMR spectroscopy.	2.05	1	0	f-block element atom; lanthanoid atom
gadolinium Gadolinium: An element of the rare earth family of metals. It has the atomic symbol Gd, atomic number 64, and atomic weight 157.25. Its oxide is used in the control rods of some nuclear reactors.	1.99	1	0	f-block element atom; lanthanoid atom
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	7.48	2	0	copper group element atom; elemental gold
holmium Holmium: An element of the rare earth family of metals. It has the atomic symbol Ho, atomic number 67, and atomic weight 164.93.	2.6	1	0	f-block element atom; lanthanoid atom
uranium Uranium: A radioactive element of the actinide series of metals. It has an atomic symbol U, atomic number 92, and atomic weight 238.03. U-235 is used as the fissionable fuel in nuclear weapons and as fuel in nuclear power reactors.	1.94	1	0	actinoid atom; f-block element atom; monoatomic uranium
vanadium Vanadium: A metallic element with the atomic symbol V, atomic number 23, and atomic weight 50.94. It is used in the manufacture of vanadium steel. Prolonged exposure can lead to chronic intoxication caused by absorption usually via the lungs.	7.47	2	0	elemental vanadium; vanadium group element atom	micronutrient
yttrium Yttrium: An element of the rare earth family of metals. It has the atomic symbol Y, atomic number 39, and atomic weight 88.91. In conjunction with other rare earths, yttrium is used as a phosphor in television receivers and is a component of the yttrium-aluminum garnet (YAG) lasers.	8.45	1	1	d-block element atom; rare earth metal atom; scandium group element atom
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	7.37	2	0	titanium group element atom
aluminum chloride Aluminum Chloride: A compound with the chemical formula AlCl3; the anhydrous salt is used as a catalyst in organic chemical synthesis, and hydrated salts are used topically as antiperspirants, and for the management of HYPERHYDROSIS.	2.02	1	0	aluminium coordination entity	Lewis acid
phosphoric acid, trisodium salt [no description available]	2.03	1	0	sodium phosphate
zinc sulfate Zinc Sulfate: A compound given in the treatment of conditions associated with zinc deficiency such as acrodermatitis enteropathica. Externally, zinc sulfate is used as an astringent in lotions and eye drops. (Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Englewood, CO, 1995). zinc sulfate : A metal sulfate compound having zinc(2+) as the counterion.	1.99	1	0	metal sulfate; zinc molecular entity	fertilizer
sodium sulfite [no description available]	1.98	1	0	inorganic sodium salt; sulfite salt	food preservative; reducing agent
calcium phosphate, monobasic, anhydrous calcium phosphate, monobasic: MW 234.05	2.03	1	0	calcium phosphate	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.	10.04	9	1	calcium phosphate
silver nitrate Silver Nitrate: A silver salt with powerful germicidal activity. It has been used topically to prevent OPHTHALMIA NEONATORUM.	2.46	2	0	inorganic nitrate salt; silver salt	astringent
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	1.98	1	0	dihydrogen
molybdate ion molybdate : A divalent inorganic anion obtained by removal of both protons from molybdic acid	2.02	1	0	divalent inorganic anion; molybdenum oxoanion	Escherichia coli metabolite
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	3.19	1	0
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.	2.03	1	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
ferric sulfate ferric sulfate: RN given refers to Fe(+3)[3:2] salt). iron(3+) sulfate : A compound of iron and sulfate in which the ratio of iron(3+) to sulfate ions is 3:2.	2.02	1	0	iron molecular entity; metal sulfate	astringent; catalyst; mordant
strontium nitrate [no description available]	3.39	1	1
beta-hydroxyethoxyacetic acid beta-hydroxyethoxyacetic acid: metabolite of both dioxane and diethylene glycol	2.11	1	0
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.	2.46	2	0	titanium oxides	food colouring
fluorides [no description available]	2.38	2	0	halide anion; monoatomic fluorine
homocitric acid [no description available]	2.17	1	0	tricarboxylic acid
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.	5.14	48	0	benzenes; phenyl acetates
pyrrolidine [no description available]	2.4	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.	2.17	1	0	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
carbamide peroxide Carbamide Peroxide: A urea peroxide compound that is commonly used in tooth whitening agents; topical anti-infective agents, and earwax remover.. urea hydrogen peroxide : A mixture obtained by combining equimolar amounts of hydrogen peroxide and urea.	2.25	1	0	mixture	disinfectant; oxidising agent; reagent
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.	2.03	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
alkenes [no description available]	2.74	3	0
calcium oxalate Calcium Oxalate: The calcium salt of oxalic acid, occurring in the urine as crystals and in certain calculi.. calcium oxalate : The calcium salt of oxalic acid, which in excess in the urine may lead to formation of oxalate calculi (kidney stones).	5.24	16	0	organic calcium salt
poly-n,n-dimethyl-n,n-diallylammonium chloride diallyldimethylammonium chloride: structure in first source	2.41	1	0
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	1.93	1	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	3.37	6	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	3.1	1	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
sufentanil Sufentanil: An opioid analgesic that is used as an adjunct in anesthesia, in balanced anesthesia, and as a primary anesthetic agent.. sufentanil : An anilide resulting from the formal condensation of the aryl amino group of 4-(methoxymethyl)-N-phenyl-1-[2-(2-thienyl)ethyl]piperidin-4-amine with propanoic acid.	2.03	1	0	anilide; ether; piperidines; thiophenes	anaesthesia adjuvant; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
nicorandil Nicorandil: A derivative of the NIACINAMIDE that is structurally combined with an organic nitrate. It is a potassium-channel opener that causes vasodilatation of arterioles and large coronary arteries. Its nitrate-like properties produce venous vasodilation through stimulation of guanylate cyclase.. nicorandil : A pyrimidinecarboxamide that is nicotinamide in which one of the hydrogens attached to the carboxamide nitrogen is replaced by a 2-(nitrooxy)ethyl group. It has both nitrate-like and ATP-sensitive potassium channel activator properties, and is used for the prevention and treatment of angina pectoris.	2.03	1	0	nitrate ester; pyridinecarboxamide	potassium channel opener; vasodilator agent
lovastatin Lovastatin: A fungal metabolite isolated from cultures of Aspergillus terreus. The compound is a potent anticholesteremic agent. It inhibits 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It also stimulates the production of low-density lipoprotein receptors in the liver.. lovastatin : A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom).	7.17	1	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	anticholesteremic drug; antineoplastic agent; Aspergillus metabolite; prodrug
raloxifene hydrochloride Raloxifene Hydrochloride: A second generation selective estrogen receptor modulator (SERM) used to prevent osteoporosis in postmenopausal women. It has estrogen agonist effects on bone and cholesterol metabolism but behaves as a complete estrogen antagonist on mammary gland and uterine tissue.. raloxifene hydrochloride : A hydrochloride salt resulting from the reaction of equimolar amounts of raloxifene and hydrogen chloride.	2.6	1	0	hydrochloride	bone density conservation agent; estrogen antagonist; estrogen receptor modulator
adapalene Adapalene: A naphthalene derivative that has specificity for RETINOIC ACID RECEPTORS. It is used as a DERMATOLOGIC AGENT for the treatment of ACNE.. adapalene : A naphthoic acid that is CD437 in which the phenolic hydroxy group has been converted to its methyl ether.	6.1	4	2	adamantanes; monocarboxylic acid; naphthoic acid	dermatologic drug; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor; non-steroidal anti-inflammatory drug
gadolinium chloride gadolinium chloride: a macrophage inhibitor; reduces pulmonary injury and inflammatory mediator production induced by inhaled ozone	1.99	1	0	gadolinium coordination entity	TRP channel blocker
musk xylene musk xylene : A C-nitro compound that is m-xylene bearing three nitro substituents at positions 2, 4 and 6 as well as a tert-butyl group at position 5.	2	1	0	C-nitro compound	carcinogenic agent; explosive; fragrance
epsilon-decalactone [no description available]	3.06	1	0	lactone
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	2.05	1	0	D-glucopyranose	epitope; mouse metabolite
fenofibric acid fenofibric acid: RN given refers to parent cpd without isomeric designation; structure. fenofibric acid : A monocarboxylic acid that is 2-methylpropanoic acid substituted by a 4-(4-chlorobenzoyl)phenoxy group at position 2. It is a metabolite of the drug fenofibrate.	2.01	1	0	aromatic ketone; chlorobenzophenone; monocarboxylic acid	drug metabolite; marine xenobiotic metabolite
3-aminoisobutyric acid 3-aminoisobutyric acid: RN given refers to cpd without isomeric designation. 3-aminoisobutyric acid : A beta-amino-acid that is isobutyric acid in which one of the methyl hydrogens is substituted by an amino group.	2.41	1	0	amino acid zwitterion; beta-amino acid	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.	2.01	1	0	organic bromide salt	colorimetric reagent; dye
n,n-bis(trimethylsilyl)-2,2,2-trifluoroacetamide [no description available]	2.02	1	0
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	2.41	1	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
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.	2.06	1	0	cephalosporin	fungal metabolite
1,7-phenanthroline [no description available]	2.36	2	0	phenanthroline
phenylacetylglycine phenylacetylglycine : A N-acylglycine that is glycine substituted on nitrogen with a phenylacetyl group.	3.01	1	0	monocarboxylic acid amide; monocarboxylic acid; N-acylglycine	human metabolite; mouse metabolite
hydracrylic acid 3-hydroxypropionic acid : A 3-hydroxy monocarboxylic acid that is propionic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group.	1.97	1	0	3-hydroxy monocarboxylic acid; omega-hydroxy-short-chain fatty acid	Escherichia coli metabolite; human metabolite
glycolamide [no description available]	2.05	1	0	acetamides
beta-hydroxyisovaleric acid 3-hydroxyisovaleric acid : A 3-hydroxy monocarboxylic acid that is isovaleric acid substituted at position 3 by a hydroxy group. Used as indicator of biotin deficiency.	2	1	0	3-hydroxy monocarboxylic acid	human metabolite
tocophersolan tocophersolan: RN given refers to parent cpd	2.41	1	0	tocol
2-carboxythiazolidine-4-carboxylic acid 2-carboxythiazolidine-4-carboxylic acid: hepatoprotective drug; structure given in first source	1.98	1	0	organonitrogen compound; organooxygen compound
uroporphyrin i uroporphyrin I: RN given refers to parent cpd	1.97	1	0
glucose-1,6-bisphosphate alpha-D-glucose 1,6-bisphosphate : A D-glucose 1,6-bisphosphate in which both phosphate groups are monophosphates.	1.96	1	0	D-glucose 1,6-bisphosphate	Escherichia coli metabolite; human metabolite
ketorolac tromethamine Ketorolac Tromethamine: A pyrrolizine carboxylic acid derivative structurally related to INDOMETHACIN. It is a non-steroidal anti-inflammatory agent used for analgesia for postoperative pain and inhibits cyclooxygenase activity.. ketorolac tromethamine : An organoammonium salt resulting from the mixture of equimolar amounts of ketorolac and tromethamine (tris). It has potent non-sedating analgesic and moderate anti-inflammatory effects. It is used in the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis.	2.02	1	0	organoammonium salt	analgesic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor
thifluzamide thifluzamide: a fungicide; structure in first source. thifluzamide : An aromatic amide obtained by formal condensation of the carboxy group of 2-methyl-4-(trifluoromethyl)thiazole-5-carboxylic acid with the amino group of 2,6-dibromo-4-(trifluoromethoxy)aniline. Used to control Rhizoctonia spp. diseases on rice, potatoes, maize, grass and other crops.	7.6	1	0	1,3-thiazoles; anilide fungicide; aromatic amide; aromatic ether; dibromobenzene; organofluorine compound	antifungal agrochemical; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor
coenzyme a [no description available]	2.02	1	0	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	2.36	2	0	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
cadmium telluride cadmium telluride: used in radiation monitoring device	2.46	2	0
glycidyl nitrate glycidyl nitrate: a nitric oxide donor; structure in first source. peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids.	1.98	1	0
pyrimidine dimers Pyrimidine Dimers: Dimers found in DNA chains damaged by ULTRAVIOLET RAYS. They consist of two adjacent PYRIMIDINE NUCLEOTIDES, usually THYMINE nucleotides, in which the pyrimidine residues are covalently joined by a cyclobutane ring. These dimers block DNA REPLICATION.	2.05	1	0
cortisol octanoate [no description available]	2.03	1	0	corticosteroid hormone
alpha-tocopherol phosphate alpha-tocopherol phosphate: RN given refers to (2R(4R,8R*))-(+-)-isomer	2.15	1	0
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	2.02	1	0	D-glucuronic acid	algal metabolite
2-hydroxy-1,2-bis(methoxyphenyl)ethanone 2-hydroxy-1,2-bis(methoxyphenyl)ethanone: structure given in first source	1.92	1	0
3,4-dihydroxybutanoic acid gamma-lactone 3-hydroxy-gamma-butyrolactone: structure in first source	2.08	1	0
coumarin 6 coumarin 6: structure in first source	2.13	1	0	7-aminocoumarins	fluorochrome
calcium phosphate, dibasic, dihydrate calcium phosphate, dibasic, dihydrate: Molecular formula CaHPO(4)-2(H2O)	2.73	3	0	calcium salt; hydrate
vitamin b 6 Vitamin B 6: VITAMIN B 6 refers to several PICOLINES (especially PYRIDOXINE; PYRIDOXAL; & PYRIDOXAMINE) that are efficiently converted by the body to PYRIDOXAL PHOSPHATE which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, and aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into PYRIDOXAMINE phosphate. Although pyridoxine and Vitamin B 6 are still frequently used as synonyms, especially by medical researchers, this practice is erroneous and sometimes misleading (EE Snell; Ann NY Acad Sci, vol 585 pg 1, 1990). Most of vitamin B6 is eventually degraded to PYRIDOXIC ACID and excreted in the urine.	2.02	1	0
valerates Valerates: Derivatives of valeric acid, including its salts and esters.	2	1	0	short-chain fatty acid anion; straight-chain saturated fatty acid anion	plant metabolite
asiatic acid [no description available]	7.41	1	0	monocarboxylic acid; pentacyclic triterpenoid; triol	angiogenesis modulating agent; metabolite
4-hydroxypyrazole [no description available]	1.96	1	0
caprylates Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.	2	1	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
3-quinuclidinyl-4-iodobenzilate [no description available]	1.98	1	0
ribulose-1,5 diphosphate ribulose-1,5 diphosphate: RN given refers to cpd without isomeric designation. D-ribulose 1,5-bisphosphate : A ribulose phosphate that is D-ribulose attached to phosphate groups at positions 1 and 5. It is an intermediate in photosynthesis.	2.42	2	0	ribulose phosphate	Escherichia coli metabolite; plant metabolite
3-deoxyglycero-galacto-nonulosonic acid 3-deoxyglycero-galacto-nonulosonic acid: deaminated neuraminic acid from rainbow trout; structure given in first source	2.08	1	0	L-alpha-D-Hepp-(1->7)-L-alpha-D-Hepp-(1->3)-L-alpha-D-Hepp-(1->5)-alpha-Kdo
polytrimethylene carbonate trimethylene carbonate: structure in first source	2.52	2	0
lhrh, leu(6)-n-et-glynh2(10)- [no description available]	1.97	1	0
4-fluorothreonine 4-fluorothreonine: from Streptomyces cattleya	1.98	1	0	amino acid zwitterion; fluoroamino acid; L-threonine derivative; non-proteinogenic L-alpha-amino acid
n',n''-diacetylspermine N',N''-diacetylspermine: intermediate in polyamine catabolism	2.31	1	0	acetamides
xylose xylopyranose: structure in first source	4.92	10	0	D-xylose
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	2.77	3	0	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
naproxen Naproxen: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.. naproxen : A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.	2.03	1	0	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	2.71	3	0	oxygen hydride; oxygen radical; reactive oxygen species
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.	3.1	1	0	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
peroxymonosulfate peroxymonosulfate: oxidizing agent in prevention of tooth discoloration; RN given refers to ion(2-)	2.49	2	0	sulfur oxide; sulfur oxoanion
fenton's reagent Fenton's reagent: used for oxidizing sugars & alcohols	2.02	1	0
palmitoyl dihydroxyacetone phosphate [no description available]	1.97	1	0	1-acylglycerone 3-phosphate
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	7.17	1	0	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
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.	2.03	1	0
lignin Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.	2.93	4	0
sorafenib [no description available]	2.41	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
cholic acid Cholic Acid: A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.. cholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12.	7.21	1	0	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
fumagillol fumagillol: from Penicillium jensenii; FR 65814 is an analog; structure given in first source. fumagillol : A sesquiterpenoid with antimicrobial properties.	2.02	1	0	secondary alcohol; sesquiterpenoid; spiro-epoxide	antimicrobial agent
cortisone [no description available]	2.03	1	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
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.	2.01	1	0	monohydroxypyrrolidine; organonitrogen heterocyclic antibiotic	anticoronaviral agent; antimicrobial agent; antineoplastic agent; antiparasitic agent; bacterial metabolite; DNA synthesis inhibitor; protein synthesis inhibitor
metribolone Metribolone: A synthetic non-aromatizable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors.. 17beta-hydroxy-17-methylestra-4,9,11-trien-3-one : A synthetic non-aromatisable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors.	2.02	1	0	17beta-hydroxy steroid; 3-oxo steroid; anabolic androgenic steroid	androgen
sorbinil sorbinil: aldose reductase inhibitor. sorbinil : An azaspiro compound having a monofluoro-substituted chromane skeleton spiro-linked to an imidazolidinedione ring.	1.98	1	0	azaspiro compound; chromanes; imidazolidinone; organofluorine compound; oxaspiro compound	antioxidant; EC 1.1.1.21 (aldehyde reductase) inhibitor
carboplatin [no description available]	7.6	1	0
glycerate 1,3-biphosphate 3-phospho-D-glyceroyl dihydrogen phosphate : The (R)-enantiomer of 3-phosphoglyceroyl dihydrogen phosphate.	2.03	1	0	2,3-bisphosphoglyceric acid; acyl monophosphate	Escherichia coli metabolite; mouse metabolite
n-acetylneuraminic acid N-Acetylneuraminic Acid: An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518). N-acetylneuraminic acid : An N-acylneuraminic acid where the N-acyl group is specified as acetyl.	1.98	1	0	N-acetylneuraminic acids	antioxidant; bacterial metabolite; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; human metabolite; mouse metabolite
fibrin Fibrin: A protein derived from FIBRINOGEN in the presence of THROMBIN, which forms part of the blood clot.	2.01	1	0	peptide
hexacyanoferrate iii hexacyanoferrate III: RN given refers to parent cpd	2.36	2	0
elastin [no description available]	2.7	3	0	oligopeptide
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.	1.98	1	0	2,6-diaminopimelic acid; amino acid zwitterion	Escherichia coli metabolite
oxytocin Oxytocin: A nonapeptide hormone released from the neurohypophysis (PITUITARY GLAND, POSTERIOR). It differs from VASOPRESSIN by two amino acids at residues 3 and 8. Oxytocin acts on SMOOTH MUSCLE CELLS, such as causing UTERINE CONTRACTIONS and MILK EJECTION.. oxytocin : A cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is believed to influence social cognition and behaviour.	2.51	2	0	heterodetic cyclic peptide; peptide hormone	oxytocic; vasodilator agent
ouabain Ouabain: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE.. cardiac glycoside : Steroid lactones containing sugar residues that act on the contractile force of the cardiac muscles.. ouabain : A steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+)/K(+)-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus.	2.03	1	0	11alpha-hydroxy steroid; 14beta-hydroxy steroid; 5beta-hydroxy steroid; alpha-L-rhamnoside; cardenolide glycoside; steroid hormone	anti-arrhythmia drug; cardiotonic drug; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; ion transport inhibitor; plant metabolite
tartaric acid tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.	4.46	5	1	tartaric acid	Escherichia coli metabolite
n-glycolylneuraminic acid N-glycolylneuraminic acid: RN given refers to (all-D)-isomer	7.41	2	0	N-acylneuraminic acid
cortodoxone Cortodoxone: 17,21-Dihydroxypregn-4-ene-3,20-dione. A 17-hydroxycorticosteroid with glucocorticoid and anti-inflammatory activities.. 11-deoxycortisol : A deoxycortisol that is cortisol in which the hydroxy group at position 11 has been replaced by a hydrogen.	2.03	1	0	deoxycortisol; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
arbutin hydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.	2.71	3	0	beta-D-glucoside; monosaccharide derivative	Escherichia coli metabolite; plant metabolite
cellulase Cellulase: An endocellulase with specificity for the hydrolysis of 1,4-beta-glucosidic linkages in CELLULOSE, lichenin, and cereal beta-glucans.. beta-cellotriose : A cellotriose with a beta-configuration at the anomeric position.	2.15	1	0	cellotriose
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.	1.93	1	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.	2.03	1	0	1-benzofurans; antibiotic antifungal drug; benzofuran antifungal drug; organochlorine compound; oxaspiro compound	antibacterial agent; Penicillium metabolite
digitoxin Digitoxin: A cardiac glycoside sometimes used in place of DIGOXIN. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. (From Martindale, The Extra Pharmacopoeia, 30th ed, p665). digitoxin : A cardenolide glycoside in which the 3beta-hydroxy group of digitoxigenin carries a 2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl trisaccharide chain.	2.03	1	0	cardenolide glycoside	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor
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.	13.69	35	13	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
fumaric acid fumaric acid: see also record for ferrous fumarate; use FUMARATES for general fumaric acid esters. fumaric acid : A butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.	2.41	2	0	butenedioic acid	food acidity regulator; fundamental metabolite; geroprotector
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	2.79	3	0	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
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).	4.75	6	1	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	2.21	1	0	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	2.6	1	0	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
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.	2.02	1	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
clindamycin Clindamycin: An antibacterial agent that is a semisynthetic analog of LINCOMYCIN.. clindamycin : A carbohydrate-containing antibiotic that is the semisynthetic derivative of lincomycin, a natural antibiotic.	10.4	3	1
zithromax Azithromycin: A semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis.. azithromycin : A macrolide antibiotic useful for the treatment of bacterial infections.	4.45	1	1	macrolide antibiotic	antibacterial drug; environmental contaminant; xenobiotic
drf 2725 ragaglitazar: a phenoxazine analogue of phenyl propanoic acid; Ragaglitazar is a coligand of PPARalpha and PPARgamma	2.02	1	0
imidazolidines [no description available]	1.98	1	0	azacycloalkane; imidazolidines; saturated organic heteromonocyclic parent
decitabine [no description available]	2.13	1	0	2'-deoxyribonucleoside
sodium bicarbonate Sodium Bicarbonate: A white, crystalline powder that is commonly used as a pH buffering agent, an electrolyte replenisher, systemic alkalizer and in topical cleansing solutions.	4.09	3	1	one-carbon compound; organic sodium salt	antacid; food anticaking agent
potassium bicarbonate potassium hydrogencarbonate : A potassium salt that is the monopotassium salt of carbonic acid. It has fungicidal properties and is used in organic farming for the control of powdery mildew and apple scab.	1.96	1	0	organic salt; potassium salt	antifungal agrochemical; buffer; food acidity regulator; raising agent
bromochloroacetic acid Keratins: A class of fibrous proteins or scleroproteins that represents the principal constituent of EPIDERMIS; HAIR; NAILS; horny tissues, and the organic matrix of tooth ENAMEL. Two major conformational groups have been characterized, alpha-keratin, whose peptide backbone forms a coiled-coil alpha helical structure consisting of TYPE I KERATIN and a TYPE II KERATIN, and beta-keratin, whose backbone forms a zigzag or pleated sheet structure. alpha-Keratins have been classified into at least 20 subtypes. In addition multiple isoforms of subtypes have been found which may be due to GENE DUPLICATION.. bromochloroacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by bromine while a second is replaced by chlorine. A low-melting (27.5-31.5degreeC), hygroscopic crystalline solid, it can be formed during the disinfection (by chlorination) of water that contains bromide ions and organic matter, so can occur in drinking water as a byproduct of the disinfection process.	4.08	3	1	2-bromocarboxylic acid; monocarboxylic acid; organochlorine compound
glycosides [no description available]	2.37	2	0
retinaldehyde Retinaldehyde: A diterpene derived from the carotenoid VITAMIN A which functions as the active component of the visual cycle. It is the prosthetic group of RHODOPSIN (i.e., covalently bonded to ROD OPSIN as 11-cis-retinal). When stimulated by visible light, rhodopsin transforms this cis-isomer of retinal to the trans-isomer (11-trans-retinal). This transformation straightens-out the bend of the retinal molecule and causes a change in the shape of rhodopsin triggering the visual process. A series of energy-requiring enzyme-catalyzed reactions convert the 11-trans-retinal back to the cis-isomer.. all-trans-retinal : A retinal in which all four exocyclic double bonds have E- (trans-) geometry.	7.49	11	4	retinal; vitamin A	gap junctional intercellular communication inhibitor; human metabolite; mouse metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.91	4	0	stilbene
phenyl-n-tert-butylnitrone phenyl-N-tert-butylnitrone: a spin-trapping agent	1.99	1	0
flavin-adenine dinucleotide Flavin-Adenine Dinucleotide: A condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972)	1.93	1	0	flavin adenine dinucleotide; vitamin B2	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; prosthetic group
cannabidiol Cannabidiol: Compound isolated from Cannabis sativa extract.. cannabidiol : An cannabinoid that is cyclohexene which is substituted by a methyl group at position 1, a 2,6-dihydroxy-4-pentylphenyl group at position 3, and a prop-1-en-2-yl group at position 4.	7.6	1	0	olefinic compound; phytocannabinoid; resorcinols	antimicrobial agent; plant metabolite
etorphine [no description available]	2.03	1	0	alcohol; morphinane alkaloid	opioid analgesic; opioid receptor agonist; sedative
leuprolide Leuprolide: A potent synthetic long-acting agonist of GONADOTROPIN-RELEASING HORMONE that regulates the synthesis and release of pituitary gonadotropins, LUTEINIZING HORMONE and FOLLICLE STIMULATING HORMONE.. leuprolide : An oligopeptide comprising pyroglutamyl, histidyl, tryptophyl, seryl, tyrosyl, D-leucyl, leucyl, arginyl, and N-ethylprolinamide residues joined in sequence. It is a synthetic nonapeptide analogue of gonadotropin-releasing hormone, and is used as a subcutaneous hydrogel implant (particularly as the acetate salt) for the treatment of prostate cancer and for the suppression of gonadal sex hormone production in children with central precocious puberty.	3.77	3	0	oligopeptide	anti-estrogen; antineoplastic agent; gonadotropin releasing hormone agonist
sesquiterpenes [no description available]	2.02	1	0
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	3.84	9	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
sulindac Sulindac: A sulfinylindene derivative prodrug whose sulfinyl moiety is converted in vivo to an active NSAID analgesic. Specifically, the prodrug is converted by liver enzymes to a sulfide which is excreted in the bile and then reabsorbed from the intestine. This helps to maintain constant blood levels with reduced gastrointestinal side effects.. sulindac : A monocarboxylic acid that is 1-benzylidene-1H-indene which is substituted at positions 2, 3, and 5 by methyl, carboxymethyl, and fluorine respectively, and in which the phenyl group of the benzylidene moiety is substituted at the para position by a methylsulfinyl group. It is a prodrug for the corresponding sulfide, a non-steroidal anti-inflammatory drug, used particularly in the treatment of acute and chronic inflammatory conditions.	2.03	1	0	monocarboxylic acid; organofluorine compound; sulfoxide	analgesic; antineoplastic agent; antipyretic; apoptosis inducer; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug; tocolytic agent
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
D-fructopyranose [no description available]	2.25	1	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
n-methyl-n-(tert-butyldimethylsilyl)trifluoroacetamide N-(tert-butyldimethylsilyl)-N-methyltrifluoroacetamide : An N-silyl compound that is N-methyltrifluoroacetamide in which the amide nitrogen is replaced by a tert-butyldimethylsilyl group.	2.25	1	0	monocarboxylic acid amide; N-silyl compound; trifluoroacetamide	chromatographic reagent
capsazepine capsazepine: modified capsaicin molecule; a capsaicin receptor antagonist. capsazepine : A benzazepine that is 2,3,4,5-tetrahydro-1H-2-benzazepine which is substituted by hydroxy groups at positions 7 and 8 and on the nitrogen atom by a 2-(p-chlorophenyl)ethylaminothiocarbonyl group. A synthetic analogue of capsaicin, it was the first reported capsaicin receptor antagonist.	2.05	1	0	benzazepine; catechols; monochlorobenzenes; thioureas	capsaicin receptor antagonist
nadp [no description available]	3.07	5	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)	1.99	1	0
valinomycin Valinomycin: A cyclododecadepsipeptide ionophore antibiotic produced by Streptomyces fulvissimus and related to the enniatins. It is composed of 3 moles each of L-valine, D-alpha-hydroxyisovaleric acid, D-valine, and L-lactic acid linked alternately to form a 36-membered ring. (From Merck Index, 11th ed) Valinomycin is a potassium selective ionophore and is commonly used as a tool in biochemical studies.. valinomycin : A twelve-membered cyclodepsipeptide composed of three repeating D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl units joined in sequence. An antibiotic found in several Streptomyces strains.	1.97	1	0	cyclodepsipeptide; macrocycle	antimicrobial agent; antiviral agent; bacterial metabolite; potassium ionophore
laccase Laccase: A copper-containing oxidoreductase enzyme that catalyzes the oxidation of 4-benzenediol to 4-benzosemiquinone. It also has activity towards a variety of O-quinols and P-quinols. It primarily found in FUNGI and is involved in LIGNIN degradation, pigment biosynthesis and detoxification of lignin-derived products.	2.15	1	0
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.	2.48	2	0	alkali metal atom
biomer biomer: segmented polyether polyurethane with properties similar to lycra	1.98	1	0
sodium dodecyl sulfate Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.	3.8	2	1	organic sodium salt	detergent; protein denaturant
osteoprotegerin Osteoprotegerin: A secreted member of the TNF receptor superfamily that negatively regulates osteoclastogenesis. It is a soluble decoy receptor of RANK LIGAND that inhibits both CELL DIFFERENTIATION and function of OSTEOCLASTS by inhibiting the interaction between RANK LIGAND and RECEPTOR ACTIVATOR OF NUCLEAR FACTOR-KAPPA B.	7.05	1	0	long-chain fatty acid
2-mercaptoacetate 2-mercaptoacetate: RN given refers to parent cpd	2.13	1	0	monocarboxylic acid anion
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.	2.46	2	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
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.	4.45	1	1	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	2.01	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
vitamin k semiquinone radical vitamin K semiquinone radical: found in active preparations of vitamin K-dependent carboxylase. vitamin K : Any member of a group of fat-soluble 2-methyl-1,4-napthoquinones that exhibit biological activity against vitamin K deficiency. Vitamin K is required for the synthesis of prothrombin and certain other blood coagulation factors.	1.98	1	0
myricetin [no description available]	7.41	1	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
maytansine Maytansine: An ansa macrolide isolated from the MAYTENUS genus of East African shrubs.. maytansine : An organic heterotetracyclic compound and 19-membered macrocyclic lactam antibiotic originally isolated from the Ethiopian shrub Maytenus serrata but also found in other Maytenus species. It exhibits cytotoxicity against many tumour cell lines.	2.03	1	0	alpha-amino acid ester; carbamate ester; epoxide; maytansinoid; organic heterotetracyclic compound; organochlorine compound	antimicrobial agent; antimitotic; antineoplastic agent; plant metabolite; tubulin modulator
soraphen a [no description available]	2.03	1	0	cyclic hemiketal; ether; macrolide; olefinic compound	bacterial metabolite; EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor; teratogenic agent
isotretinoin Isotretinoin: A topical dermatologic agent that is used in the treatment of ACNE VULGARIS and several other skin diseases. The drug has teratogenic and other adverse effects.. isotretinoin : A retinoic acid that is all-trans-retinoic acid in which the double bond which is alpha,beta- to the carboxy group is isomerised to Z configuration. A synthetic retinoid, it is used for the treatment of severe cases of acne and other skin diseases.	7.1	1	0	retinoic acid	antineoplastic agent; keratolytic drug; teratogenic agent
zinostatin Zinostatin: An enediyne that alkylates DNA and RNA like MITOMYCIN does, so it is cytotoxic.	2	1	0
sphingosine 1-phosphate sphingosine 1-phosphate: RN given refers to (R-(R,S-(E)))-isomer; RN for cpd without isomeric designation not available 8/89. sphingosine 1-phosphate : A phosphosphingolipid that consists of sphingosine having a phospho group attached at position 1	2.6	1	0	sphingoid 1-phosphate	mouse metabolite; signalling molecule; sphingosine-1-phosphate receptor agonist; T-cell proliferation inhibitor; vasodilator agent
codeine [no description available]	2.03	1	0	morphinane alkaloid; organic heteropentacyclic compound	antitussive; drug allergen; environmental contaminant; opioid analgesic; opioid receptor agonist; prodrug; xenobiotic
hydromorphone Hydromorphone: An opioid analgesic made from MORPHINE and used mainly as an analgesic. It has a shorter duration of action than morphine.. hydromorphone : A morphinane alkaloid that is a hydrogenated ketone derivative of morphine. A semi-synthetic drug, it is a centrally acting pain medication of the opioid class.	2.03	1	0	morphinane alkaloid; organic heteropentacyclic compound	mu-opioid receptor agonist; opioid analgesic
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.	3.01	2	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
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	2.03	1	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
xylulose [no description available]	2.13	1	0	xylulose	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
fosbretabulin fosbretabulin: a microtubule destabilizing agent isolated from Combretum caffrum; structure in first source	2.41	1	0
muconic acid muconic acid: a metabolite of benzene; reported to be a reliable indicator of occupational exposure to benzene; structure given in first source. trans,trans-muconic acid : The trans,trans-isomer of muconic acid. It is metabolite of benzene in humans and serves as a biomarker of occupational exposure to benzene.. muconic acid : A hexadienedioic acid with unsaturation at positions 2 and 4.	7.6	1	0	muconic acid	biomarker; human xenobiotic metabolite
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	1.97	1	0	boron group element atom; elemental aluminium; metal atom
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.	3.39	1	1	alkaline earth metal atom
bismuth Bismuth: A metallic element that has the atomic symbol Bi, and atomic number 83. Its principal isotope is Bismuth 209.	7.87	3	0	metal atom; pnictogen
dihydromorphine Dihydromorphine: A semisynthetic analgesic used in the study of narcotic receptors.	2.03	1	0	morphinane alkaloid
dextromethorphan Dextromethorphan: Methyl analog of DEXTRORPHAN that shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist (RECEPTORS, N-METHYL-D-ASPARTATE) and acts as a non-competitive channel blocker. It is one of the widely used ANTITUSSIVES, and is also used to study the involvement of glutamate receptors in neurotoxicity.. dextromethorphan : A 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the sterocenters at positions 4a, 10 and 10a have S-configuration. It is a prodrug of dextrorphan and used as an antitussive drug for suppressing cough.	2.03	1	0	6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene	antitussive; environmental contaminant; neurotoxin; NMDA receptor antagonist; oneirogen; prodrug; xenobiotic
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	9.62	4	0	chalcogen; nonmetal atom	macronutrient
plastoquinone [no description available]	2.01	1	0	plastoquinone
deoxyribose [no description available]	1.99	1	0	deoxypentose	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	2.41	2	0	butenedioate; C4-dicarboxylate	human metabolite; metabolite; Saccharomyces cerevisiae metabolite
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	3.28	6	0	cysteinium	fundamental metabolite
phosphorus Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.	3.11	5	0	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
iodoresiniferatoxin iodoresiniferatoxin: a vanilloid receptor 1 antagonist	2.05	1	0
tellurium Tellurium: An element that is a member of the chalcogen family. It has the atomic symbol Te, atomic number 52, and atomic weight 127.60. It has been used as a coloring agent and in the manufacture of electrical equipment. Exposure may cause nausea, vomiting, and CNS depression.	2.46	2	0	chalcogen; metalloid 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.	10.27	62	3
bafilomycin a1 bafilomycin A1: from Streptomyces griseus; structure given in first source. bafilomycin A1 : The most used of the bafilomycins, a family of toxic macrolide antibiotics derived from Streptomyces griseus.	2.03	1	0	cyclic hemiketal; macrolide antibiotic; oxanes	apoptosis inducer; autophagy inhibitor; bacterial metabolite; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.14 (H(+)-transporting two-sector ATPase) inhibitor; ferroptosis inhibitor; fungicide; potassium ionophore; toxin
concanamycin a concanamycin A: from Streptomyces diastatochromogenes S-45; inhibits vacuolar H+ ATPase. concanamycin A : A concanamycin in which the lactone ring contains 4 double bonds and is substituted by 4 methyl groups, 2 hydroxy groups, 2 methoxy groups and an ethyl group.	2.03	1	0	carbamate ester; concanamycin	antifungal agent; EC 3.6.3.14 (H(+)-transporting two-sector ATPase) inhibitor; metabolite
D-xylonic acid xylonic acid: sugar acid that can be obtained by the complete oxidation of xylose. xylonic acid : A pentonic acid resulting from the formal oxidation of the aldehyde group of aldehydo-xylose to the corresponding carboxylic acid.. D-xylonic acid : A xylonic acid with D configuration.	2.25	1	0	xylonic acid
chlorhexidine Chlorhexidine: A disinfectant and topical anti-infective agent used also as mouthwash to prevent oral plaque.. chlorhexidine : A bisbiguanide compound with a structure consisting of two (p-chlorophenyl)guanide units linked by a hexamethylene bridge.	3.08	4	0	biguanides; monochlorobenzenes	antibacterial agent; antiinfective agent
formazans Formazans: Colored azo compounds formed by the reduction of tetrazolium salts. Employing this reaction, oxidoreductase activity can be determined quantitatively in tissue sections by allowing the enzymes to act on their specific substrates in the presence of tetrazolium salts.	2	1	0
capryloyl salicylic acid [no description available]	9.37	2	2
psd 502 Lidocaine, Prilocaine Drug Combination: A topical local anesthetic preparation that is composed of a mixture of lidocaine and prilocaine. It is used to provide anesthesia during minor surgery and for the treatment of PREMATURE EJACULATION.	4.37	2	2
cediranib [no description available]	2.11	1	0	aromatic ether
zeolites [no description available]	7.41	1	0
medrogestone Medrogestone: 6,17-Dimethylpregna-4,6-diene-3,20-dione. A synthetic progestational hormone with actions similar to those of progesterone. It is used in the treatment of menstrual irregularities and has also been employed in the treatment of prostatic hypertrophy and endometrial carcinoma.	3.37	1	1	corticosteroid hormone
ribose ribopyranose : The pyranose form of ribose.	1.93	1	0	D-ribose; ribopyranose
Dihydrotanshinone I dihydrotanshinone I: extracted from Radix Salviae	7.17	1	0	abietane diterpenoid	anticoronaviral agent
losartan potassium Erythropoietin: Glycoprotein hormone, secreted chiefly by the KIDNEY in the adult and the LIVER in the FETUS, that acts on erythroid stem cells of the BONE MARROW to stimulate proliferation and differentiation.	2.21	1	0
zaragozic acid c zaragozic acid C: structure given in first source; a fungal metabolite. zaragozic acid C : A polyketide isolated from fungi that is a potent inhibitor of fungal and mammalian squalene synthase.	2.04	1	0	acetate ester; cyclic ketal; oxabicycloalkane; polyketide; tertiary alcohol; tricarboxylic acid	EC 2.5.1.21 (squalene synthase) inhibitor; fungal metabolite
alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-D-GlcpNAc Sialyl Lewis X Antigen: A sialylated version of Lewis X antigen expressed on cell surfaces. It is a ligand for SELECTINS.. alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-D-GlcpNAc : A branched amino tetrasaccharide consisting of a sialyl residue, linked (2->3) to a galactosyl residue that in turn is linked (1->4) to a glucosaminyl residue, which is also carrying a fucosyl residue at the 3-position.	1.98	1	0	amino tetrasaccharide; glucosamine oligosaccharide	epitope
scopolamine hydrobromide [no description available]	2.03	1	0
ethidium homodimer ethidium homodimer: structure	2	1	0
acid phosphatase Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.	1.98	1	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	3.36	7	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	9.29	5	0	glycoside
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.69	3	0	1,2-diacyl-sn-glycero-3-phosphocholine
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	2.13	1	0	chlorophyll; methyl ester	cofactor
chitosan [no description available]	3.8	10	0
sodium oxybate Sodium Oxybate: The sodium salt of 4-hydroxybutyric acid. It is used for both induction and maintenance of ANESTHESIA.	2.69	2	0
sodium hypochlorite Sodium Hypochlorite: It is used as an oxidizing and bleaching agent and as a disinfectant. (From Grant & Hackh's Chemical Dictionary, 5th ed). sodium hypochlorite : An inorganic sodium salt in which hypochlorite is the counterion. It is used as a bleaching and disinfecting agent and is commonly found in household bleach.	3.16	3	0	inorganic sodium salt	bleaching agent; disinfectant
arabinogalactan [no description available]	1.98	1	0
mannans [no description available]	2.54	2	0
nitrogenase Nitrogenase: An enzyme system that catalyzes the fixing of nitrogen in soil bacteria and blue-green algae (CYANOBACTERIA). EC 1.18.6.1.	2.17	1	0
phosphinothricin phosphinothricin: RN given refers to parent cpd with unspecified isomeric designation; structure. phosphinothricin(1-) : Conjugate base of phosphinothricin arising from deprotonation of the phosphinate function.	2.25	1	0	organic anion
piperidines Piperidines: A family of hexahydropyridines.	2.69	3	0
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	2.63	2	0
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.	7.1	1	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.	13.88	20	4	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
tetracycline Tetracycline: A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.. tetracycline : A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.	3.37	1	1
salicylates Salicylates: The salts or esters of salicylic acids, or salicylate esters of an organic acid. Some of these have analgesic, antipyretic, and anti-inflammatory activities by inhibiting prostaglandin synthesis.. hydroxybenzoate : Any benzoate derivative carrying a single carboxylate group and at least one hydroxy substituent.. salicylates : Any salt or ester arising from reaction of the carboxy group of salicylic acid, or any ester resulting from the condensation of the phenolic hydroxy group of salicylic acid with an organic acid.. salicylate : A monohydroxybenzoate that is the conjugate base of salicylic acid.	8.29	12	5	monohydroxybenzoate	plant metabolite
dicumarol Dicumarol: An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.	1.99	1	0	hydroxycoumarin	anticoagulant; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; Hsp90 inhibitor; vitamin K antagonist
piroxicam [no description available]	2.03	1	0	benzothiazine; monocarboxylic acid amide; pyridines	analgesic; antirheumatic drug; cyclooxygenase 1 inhibitor; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
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.	2.59	2	0	benzenes; hydroxycoumarin; methyl ketone
calca protein, human CALCA protein, human: RefSeq NM_001741	2.07	1	0
clay Clay: A naturally-occurring rock or soil constituent characterized by particles with a diameter of less than 0.005 mm. It is composed primarily of hydrous aluminum silicates, trace amounts of metal OXIDES, and organic matter.	7.31	1	0
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.	2.05	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.	2.57	2	0
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	2	1	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.	2.08	1	0
bafilomycin b1 bafilomycin B1: structure given in first source	2.03	1	0
benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone: an interleukin-1beta converting enzyme (ICE)-like protease inhibitor	2.02	1	0
vitamin b 12 Vitamin B 12: A cobalt-containing coordination compound produced by intestinal micro-organisms and found also in soil and water. Higher plants do not concentrate vitamin B 12 from the soil and so are a poor source of the substance as compared with animal tissues. INTRINSIC FACTOR is important for the assimilation of vitamin B 12.	2.03	1	0
flavin mononucleotide Flavin Mononucleotide: A coenzyme for a number of oxidative enzymes including NADH DEHYDROGENASE. It is the principal form in which RIBOFLAVIN is found in cells and tissues.	2.36	2	0
muramidase Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.	2.44	2	0
ansamitocins ansamitocins: maytansinoid antibiotics produced by an actinomycete strain Norcardia sp. No. C-15003 (N-1); P-1 & P-2 identified with maytanacine & maytansinol propionate, respectively; structures for ansamitocins P-0, P-1, P-2, P-3, P-3', P-4 in second source	2.03	1	0
chondroitin sulfates Chondroitin Sulfates: Derivatives of chondroitin which have a sulfate moiety esterified to the galactosamine moiety of chondroitin. Chondroitin sulfate A, or chondroitin 4-sulfate, and chondroitin sulfate C, or chondroitin 6-sulfate, have the sulfate esterified in the 4- and 6-positions, respectively. Chondroitin sulfate B (beta heparin; DERMATAN SULFATE) is a misnomer and this compound is not a true chondroitin sulfate.	1.99	1	0
acyclovir Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.	2.43	2	0	2-aminopurines; oxopurine	antimetabolite; antiviral drug
hypoxanthine [no description available]	3.01	1	0	nucleobase analogue; oxopurine; purine nucleobase	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.	2.82	2	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
pheophytin a pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S,11S),4beta,21beta))-isomer	2.13	1	0
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.	1.97	1	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	2.17	1	0

glycolic acid

Description

Cross-References

Synonyms (116)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Occurs in Manufacturing (36 Product(s))

Product Categories

Products

Roles (2)

Drug Classes (2)

Pathways (5)

Protein Targets (1)

Potency Measurements

Bioassays (4)

Research

Studies (936)

Market Indicators

Research Demand Index: 75.47

Study Types

Clinical Trials (17)

Trial Overview

Trial Outcomes

Visual Analog Scale (VAS) of Improvement Rated by a Blinded Dermatologist From at Week 10

Clinician Assessed Duration of Complete Healing of the Herpetic Episode

glycolic acid

Description

Cross-References

Synonyms (116)

Research Excerpts

Overview

Effects

Actions

Treatment

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Occurs in Manufacturing (36 Product(s))

Product Categories

Products

Roles (2)

Drug Classes (2)

Pathways (5)

Protein Targets (1)

Potency Measurements

Bioassays (4)

Research

Studies (936)

Market Indicators

Research Demand Index: 75.47

Study Types

Clinical Trials (17)

Trial Overview

Trial Outcomes

Visual Analog Scale (VAS) of Improvement Rated by a Blinded Dermatologist From at Week 10

Clinician Assessed Duration of Complete Healing of the Herpetic Episode

Number of Treatment Related Adverse Events

Related Drugs (570)

Related Conditions (335)