3,4-dihydroxyphenylpropionic acid profile

3,4-dihydroxyphenylpropionic acid: metabolite of caffeic acid; RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

3-(3,4-dihydroxyphenyl)propanoic acid : A monocarboxylic acid that is 3-phenylpropionic acid substituted by hydroxy groups at positions 3 and 4. Also known as dihydrocaffeic acid, it is a metabolite of caffeic acid and exhibits antioxidant activity. [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	348154
CHEMBL ID	136927
CHEBI ID	48400
SCHEMBL ID	245530
MeSH ID	M0041021

Synonym
nsc624007
nsc-624007
benzenepropanoic acid, 3,4-dihydroxy-
nsc 407275
einecs 214-083-8
brn 2213449
nsc 624007
hydrocinnamic acid, 3,4-dihydroxy-
71693-95-3
3-(3,4-dihydroxyphenyl)propanoic acid
hykop
hydrocinnamic acid,4-dihydroxy-
3-(3,4-dihydroxyphenyl)propionic acid
3,4-dihydroxyhydrocinnamic acid
nsc-407275
nsc407275
hydrocaffeic acid
3,4-hpa
dihydrocaffeic acid
1078-61-1
3,4-dihydroxyphenylpropionic acid
inchi=1/c9h10o4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11h,2,4h2,(h,12,13
3,4-dihydroxyhydrocinnamic acid, 98%
3,4-dihydroxybenzenepropanoic acid
3,4-dihydroxy-beta-phenylpropionic acid
CHEBI:48400 ,
3,4-dihydroxydihydrocinnamic acid
3,4-dihydroxybenzenepropionic acid
BF0C7A6D-A5FC-4B39-819E-5ECC037C0C39
CHEMBL136927
3,4-dihydroxyhydrocinnamate
BMSE000680
A801769
unii-msw0228vub
3-10-00-01517 (beilstein handbook reference)
msw0228vub ,
FT-0613602
STL377912
AKOS015856196
S6338
SCHEMBL245530
BBL027403
DTXSID40221919
3,4-dihydroxyhydro cinnamic acid
3-[3,4-bis(oxidanyl)phenyl]propanoic acid
bdbm41957
cid_348154
AC-34200
3-(3,4-dihydroxyphenyl)propanoic acid #
3-(3,4-dihydroxyphenyl) propionic acid
3,4-dihydroxy-.beta.-phenylpropionic acid
J-510568
mfcd00002776
AS-63093
dihydrocafeate
3-(3,4-dihydroxyphenyl)propionicacid
3,4-dihydroxydihydrocinnamate
3,4-dihydroxybenzenepropionate
3,4-dihydroxy-(6ci,7ci,8ci)hydrocinnamate
3,4-dihydroxy-beta-phenylpropionate
3-(3,4-dihydroxyphenyl)propionate
3,4-dihydroxy-b-phenylpropionic acid
3,4-dihydroxyphenylpropionate
dihydrocaffeate
3,4-dihydroxy-b-phenylpropionate
3,4-dihydroxy-(6ci,7ci,8ci)hydrocinnamic acid
3,4-dihydroxy-benzenepropanoic acid
SY101000
EN300-111272
Z1255449981
Q10395580
A50643
AMY3775
HY-N2406
CS-0022607
D5901

Excerpt	Reference	Relevance
" The octyl ester of caffeic acid is nearly ten times as toxic to the leukemia cells than the widely studied phenethyl ester, CAPE."	( Mechanism of toxicity of esters of caffeic and dihydrocaffeic acids. Etzenhouser, B; Hansch, C; Kapur, S; Selassie, CD, 2001)	0.31

Excerpt	Reference	Relevance
" Several studies have shown the effect on animal models of artichoke extracts, while information on human bioavailability and metabolism of hydroxycinnamates derivatives is still lacking."	( Absorption and metabolism of bioactive molecules after oral consumption of cooked edible heads of Cynara scolymus L. (cultivar Violetto di Provenza) in human subjects: a pilot study. Azzini, E; Bugianesi, R; Catasta, G; Di Venere, D; Durazzo, A; Foddai, MS; Linsalata, V; Maiani, G; Miccadei, S; Romano, F, 2007)	0.34
" These data suggest that sulfates are the predominant hydroxycinnamic acid conjugates in humans, and that SULT mediated sulfation is a major factor determining the bioavailability of hydroxycinnamic acids in vivo."	( In vitro and in vivo conjugation of dietary hydroxycinnamic acids by UDP-glucuronosyltransferases and sulfotransferases in humans. Barron, D; Crozier, A; Glatt, HR; Meinl, W; Stalmach, A; Steiling, H; Williamson, G; Wong, CC, 2010)	0.36
" Although the bioavailability of AVAs has been investigated previously, little is known about their metabolism."	( Oat avenanthramide-C (2c) is biotransformed by mice and the human microbiota into bioactive metabolites. Chen, H; Fu, J; McBride, J; Sang, S; Wang, P; Zhu, Y, 2015)	0.42
"Although ingestion of coffee and its constituent chlorogenic acid (CGA) protects the retina from oxidative stress, the bioaccessibility and bioavailability of coffee metabolites are not well understood."	( Effects of phenolic acid metabolites formed after chlorogenic acid consumption on retinal degeneration in vivo. Ahn, HR; Choi, Y; Jang, H; Jung, SH; Lee, CY, 2015)	0.42

Role	Description
antioxidant	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
human xenobiotic metabolite	Any human metabolite produced by metabolism of a xenobiotic compound in humans.
[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
(dihydroxyphenyl)propanoic acid	A monocarboxylic acid that is propionic acid carrying a dihydroxyphenyl substituent at position 3.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
3-oxoacyl-	Pseudomonas aeruginosa	IC50 (µMol)	27.0000	2.0000	2.0000	2.0000	AID1191123
mothers against decapentaplegic homolog 3 isoform 1	Homo sapiens (human)	IC50 (µMol)	50.0000	0.0380	3.2772	10.2000	AID1058
Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)	Ki	13.0000	5.0000	7.6667	9.0000	AID1799825
Anthrax toxin receptor 2	Homo sapiens (human)	IC50 (µMol)	300.0000	0.3000	0.4535	0.6070	AID725981
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
peptidyl-proline hydroxylation to 4-hydroxy-L-proline	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
procollagen-proline 4-dioxygenase activity	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
iron ion binding	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
L-ascorbic acid binding	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
protein binding	Anthrax toxin receptor 2	Homo sapiens (human)
metal ion binding	Anthrax toxin receptor 2	Homo sapiens (human)
transmembrane signaling receptor activity	Anthrax toxin receptor 2	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
endoplasmic reticulum lumen	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
endoplasmic reticulum	Prolyl 4-hydroxylase subunit alpha-1	Gallus gallus (chicken)
extracellular region	Anthrax toxin receptor 2	Homo sapiens (human)
endoplasmic reticulum membrane	Anthrax toxin receptor 2	Homo sapiens (human)
plasma membrane	Anthrax toxin receptor 2	Homo sapiens (human)
endosome membrane	Anthrax toxin receptor 2	Homo sapiens (human)
plasma membrane	Anthrax toxin receptor 2	Homo sapiens (human)
cell surface	Anthrax toxin receptor 2	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (101)

Assay ID	Title	Year	Journal	Article
AID90706	Salty character at a concentration of 250 ppm (mean value)	1981	Journal of medicinal chemistry, Apr, Volume: 24, Issue:4	Dihydrochalcone sweeteners. A study of the atypical temporal phenomena.
AID715776	Pro-oxidant activity in 0.1 M potassium phosphate buffer at pH 7.4 assessed as increase of oxidation potential by cyclic voltammetry analysis	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID499286	Antioxidant activity assessed as ratio of IC50 for Trolox to compound for ABTS radical scavenging activity after 20 mins by TEAC assay	2010	Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16	Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties.
AID1592383	Antioxidant activity assessed as DPPH radical scavenging activity measured after 45 mins by UV-Visible spectrophotometric based assay
AID446272	Antihypertensive activity in Wistar rat assessed as decrease in L-NAME-induced collagen 1 level in vessel walls at 10 mg/kg/day, po for 4 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID447578	Inhibition of HDAC in human Hela cells nuclear extracts assessed as residual activity at 500 uM by fluorimetric assay	2009	Bioorganic & medicinal chemistry, Jul-15, Volume: 17, Issue:14	Molecular modifications on carboxylic acid derivatives as potent histone deacetylase inhibitors: Activity and docking studies.
AID446518	Antihypertensive activity in Wistar rat assessed as change in blood ALT level at 10 mg/kg/day, po measured after 8 weeks	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID446527	Antihypertensive activity in Wistar rat assessed as change in blood protein level at 10 mg/kg/day, po measured after 8 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID1241089	Cytotoxicity against African green monkey Vero cells after 24 hrs by MTT assay	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses.
AID446274	Antihypertensive activity in Wistar rat assessed as decrease in L-NAME-induced HNE-lysine accumulation in vessel walls at 10 mg/kg/day, po for 4 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID1191128	Inhibition of Pseudomonas aeruginosa PA14 PqsH transposon mutant assessed as extracellular level of HHQ at 250 uM after 16 hrs	2015	European journal of medicinal chemistry, Jan-27, Volume: 90	Catechol-based substrates of chalcone synthase as a scaffold for novel inhibitors of PqsD.
AID92699	Percentage of judgments reporting an aftertaste at a concentration of 250 ppm and character thereof	1981	Journal of medicinal chemistry, Apr, Volume: 24, Issue:4	Dihydrochalcone sweeteners. A study of the atypical temporal phenomena.
AID1241086	Antiviral activity against Adenovirus type 2 VR-1080 infected in human Hep2 cells assessed as inhibition of virus-induced plaque formation/cytopathogenicity	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses.
AID715803	Antiproliferative activity against human U937 cells assessed as incorporation of [3H]-methyl-thymidine after 12 hrs by scintillation counting	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID446511	Antihypertensive activity in Wistar rat assessed as change in blood glucose level at 10 mg/kg/day, po measured after 8 weeks	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID446519	Antihypertensive activity in Wistar rat assessed as change in blood creatinine level at 10 mg/kg/day, po measured after 8 weeks	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID446285	Plasma concentration in po dosed Wistar rat assessed as losartan level after 4 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID1592385	Electrochemical behavior of the compound assessed as redox potential corrected toward saturated Ag/AgCl reference electrode by cyclic voltammetry
AID548959	Antioxidant activity against AAPH-induced lipid peroxidation assessed as inhibition of conjugated diene hydroperoxide production at 0.1 mM by UV spectrophotometry	2010	Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23	Does conjugation of antioxidants improve their antioxidative/anti-inflammatory potential?
AID1241081	Antiviral activity against Poliovirus type 1 Sabin VR-1562 infected in African green monkey Vero cells assessed as inhibition of virus-induced plaque formation/cytopathogenicity	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses.
AID750752	Dissociation constant, pKa of the compound	2013	Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11	Identification of cinnamic acid derivatives as novel antagonists of the prokaryotic proton-gated ion channel GLIC.
AID715797	Induction of apoptosis in human U937 cells assessed as phosphatidylserine expression in plasma membrane at 1000 uM after 24 hrs by Annexin V-FITC double staining	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID89745	Intensity calculated on a weight basis relative to an 85500 ppm sucrose solution at a concentration of 250 ppm (mean value)	1981	Journal of medicinal chemistry, Apr, Volume: 24, Issue:4	Dihydrochalcone sweeteners. A study of the atypical temporal phenomena.
AID715791	Induction of apoptosis in human U937 cells assessed as activation of caspase-3 at 1000 uM after 48 hrs by colorimetric assay	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID647626	Antihypertensive activity against angiotensin-2-induced cell contraction in Wistar rat VSMC assessed as changes in planar cell surface area after 30 mins by planimetric technique	2012	European journal of medicinal chemistry, Apr, Volume: 50	New losartan-hydrocaffeic acid hybrids as antihypertensive-antioxidant dual drugs: Ester, amide and amine linkers.
AID647625	Antioxidant activity assessed as trolox equivalent of ABTS radical scavenging activity relative to control	2012	European journal of medicinal chemistry, Apr, Volume: 50	New losartan-hydrocaffeic acid hybrids as antihypertensive-antioxidant dual drugs: Ester, amide and amine linkers.
AID90561	Other taste character at a concentration of 250 ppm (mean value)	1981	Journal of medicinal chemistry, Apr, Volume: 24, Issue:4	Dihydrochalcone sweeteners. A study of the atypical temporal phenomena.
AID89598	Experimentally determined perceived intensity of compound at a concentration of 250 ppm (mean value)	1981	Journal of medicinal chemistry, Apr, Volume: 24, Issue:4	Dihydrochalcone sweeteners. A study of the atypical temporal phenomena.
AID733994	Antioxidant activity assessed as inhibition of lipid peroxidation after 48 hrs by ferric thiocyanate assay	2013	Bioorganic & medicinal chemistry letters, Feb-15, Volume: 23, Issue:4	Synthesis and dual biological effects of hydroxycinnamoyl phenylalanyl/prolyl hydroxamic acid derivatives as tyrosinase inhibitor and antioxidant.
AID715764	Induction of DNA damage in human U937 cells	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID446529	Antihypertensive activity in Wistar rat assessed as change in blood AST level at 10 mg/kg/day, po measured after 8 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID1241082	Antiviral activity against Coxsackie type B3 virus VR-1034 infected in African green monkey Vero cells assessed as inhibition of virus-induced plaque formation/cytopathogenicity	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses.
AID715765	Cytotoxicity against human Jurkat at 250 uM after 48 hrs by trypan blue assay	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID1241091	Cytotoxicity against human HFF1 cells after 24 hrs by MTT assay	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses.
AID715775	Induction of free radicals production in RPMI 1640 medium at pH 7.4 by electron spin resonance analysis	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID715770	Induction of apoptosis in human Jurkat cells assessed as activation of caspase-3-mediated PARP cleavage at 500 uM after 24 hrs by colorimetric assay	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID1248399	Inhibition of alpha-amylase (unknown origin) relative to control	2015	Bioorganic & medicinal chemistry, Oct-15, Volume: 23, Issue:20	From carbohydrates to drug-like fragments: Rational development of novel α-amylase inhibitors.
AID446522	Antihypertensive activity in Wistar rat assessed as change in blood K- level at 10 mg/kg/day, po measured after 8 weeks	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID1241084	Antiviral activity against Herpes simplex type 1 VR-260 infected in African green monkey Vero cells assessed as inhibition of virus-induced plaque formation/cytopathogenicity	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses.
AID715779	Induction of cell differentiation in human U937 cells assessed as increase of CD88 expression at 250 to 500 uM after 72 hrs by FACS flow cytometer analysis	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID446523	Antihypertensive activity in Wistar rat assessed as change in blood glucose level at 10 mg/kg/day, po measured after 8 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID715768	Induction of apoptosis in human Jurkat cells at 500 uM after 48 hrs by Annexin V-FITC double staining	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID446287	Plasma concentration in po dosed Wistar rat assessed as total drug level after 4 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID548958	Inhibition of soybean lipoxygenase at 0.05 mM	2010	Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23	Does conjugation of antioxidants improve their antioxidative/anti-inflammatory potential?
AID548960	Antioxidant activity of the compound assessed as reducing activity of DPPH at 0.1 mM after 20 mins	2010	Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23	Does conjugation of antioxidants improve their antioxidative/anti-inflammatory potential?
AID441921	Inhibition of Escherichia coli M15 DXR at 100 uM	2009	Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21	Coordination chemistry based approach to lipophilic inhibitors of 1-deoxy-D-xylulose-5-phosphate reductoisomerase.
AID446517	Antihypertensive activity in Wistar rat assessed as change in blood AST level at 10 mg/kg/day, po measured after 8 weeks	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID90907	Sweet character at a concentration of 250 ppm (mean value)	1981	Journal of medicinal chemistry, Apr, Volume: 24, Issue:4	Dihydrochalcone sweeteners. A study of the atypical temporal phenomena.
AID446525	Antihypertensive activity in Wistar rat assessed as change in blood triglyceride level at 10 mg/kg/day, po measured after 8 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID446526	Antihypertensive activity in Wistar rat assessed as change in blood calcium level at 10 mg/kg/day, po measured after 8 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID446524	Antihypertensive activity in Wistar rat assessed as change in blood cholesterol level at 10 mg/kg/day, po measured after 8 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID499285	Antioxidant activity assessed as ratio of IC50 for Trolox to compound for ABTS radical scavenging activity after 5 mins by TEAC assay	2010	Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16	Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties.
AID446286	Plasma concentration in po dosed Wistar rat assessed as EXP-3174 level after 4 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID446520	Antihypertensive activity in Wistar rat assessed as change in blood urea level at 10 mg/kg/day, po measured after 8 weeks	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID715782	Induction of cell differentiation in human U937 cells assessed as increase of CD11b and CD14 expression at 250 to 500 uM after 72 hrs by FACS flow cytometer analysis	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID446533	Antihypertensive activity in Wistar rat assessed as change in blood Na+ level at 10 mg/kg/day, po measured after 8 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID446530	Antihypertensive activity in Wistar rat assessed as change in blood ALT level at 10 mg/kg/day, po measured after 8 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID1592386	Electrochemical behavior of the compound assessed as redox potential corrected toward saturated Ag/AgCl reference electrode by differential pulse voltammetry
AID715796	Induction of apoptosis in human U937 cells assessed as reduction of normal cells at 1000 uM after 24 hrs by Annexin V-FITC double staining	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID750756	Antagonist activity at Gloeobacter violaceus ligand-gated ion channel expressed in Xenopus oocytes assessed as inhibition of MES buffer pH 5.5 -induced currents after 30 secs by voltage clamp technique	2013	Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11	Identification of cinnamic acid derivatives as novel antagonists of the prokaryotic proton-gated ion channel GLIC.
AID446513	Antihypertensive activity in Wistar rat assessed as change in blood triglyceride level at 10 mg/kg/day, po measured after 8 weeks	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID1191123	Inhibition of Pseudomonas aeruginosa recombinant PqsD expressed in Escherichia coli BL21 (lambdaDE3) using ACoA/beta-ketodecanoic acid as substrate after 10 mins	2015	European journal of medicinal chemistry, Jan-27, Volume: 90	Catechol-based substrates of chalcone synthase as a scaffold for novel inhibitors of PqsD.
AID715771	Pro-oxidant activity in human U937 cells assessed as DCF-DA oxidation at 10 to 250 uM after 48 hrs by fluorescence assay	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID715804	Induction of cell differentiation in human U937 cells assessed as increase of rhC5a-induced response at 250 to 500 uM after 72 hrs by FACS flow cytometer analysis	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID446534	Antihypertensive activity in Wistar rat assessed as change in blood K- level at 10 mg/kg/day, po measured after 8 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID90539	Bitter character at a concentration of 250 ppm (mean value)	1981	Journal of medicinal chemistry, Apr, Volume: 24, Issue:4	Dihydrochalcone sweeteners. A study of the atypical temporal phenomena.
AID1058583	Antioxidant activity assessed as DPPH radical scavenging activity	2013	Bioorganic & medicinal chemistry, Dec-15, Volume: 21, Issue:24	Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity.
AID715774	Induction of free radicals production in carbonate buffer at pH 9 by electron spin resonance analysis	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID1241085	Antiviral activity against Herpes simplex type 2 VR-734 infected in African green monkey Vero cells assessed as inhibition of virus-induced plaque formation/cytopathogenicity	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses.
AID715800	Inhibition of clonogenic activity in human U937 cells assessed as reduction of colony formation in soft agar at 100 to 250 uM after 24 hrs using crystal violet staining	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID446531	Antihypertensive activity in Wistar rat assessed as change in blood creatinine level at 10 mg/kg/day, po measured after 8 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID446512	Antihypertensive activity in Wistar rat assessed as change in blood cholesterol level at 10 mg/kg/day, po measured after 8 weeks	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID446516	Antihypertensive activity in Wistar rat assessed as change in blood LDH level at 10 mg/kg/day, po measured after 8 weeks	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID499287	Antioxidant activity assessed as ratio of IC50 for Trolox to compound for DPPH radical scavenging activity by TEAC assay	2010	Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16	Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties.
AID548957	Inhibition of soybean lipoxygenase at 0.1 mM	2010	Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23	Does conjugation of antioxidants improve their antioxidative/anti-inflammatory potential?
AID89575	Intensity calculated on a molar basis relative to a 0.25 M sucrose solution at a concentration of 250 ppm (mean value)	1981	Journal of medicinal chemistry, Apr, Volume: 24, Issue:4	Dihydrochalcone sweeteners. A study of the atypical temporal phenomena.
AID446273	Antihypertensive activity in Wistar rat assessed as decrease in L-NAME-induced fibronectin content in vessel walls at 10 mg/kg/day, po for 4 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID446521	Antihypertensive activity in Wistar rat assessed as change in blood Na+ level at 10 mg/kg/day, po measured after 8 weeks	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID715763	Induction of apoptosis in human Jurkat cells assessed as activation of caspase-3 at 500 uM after 24 hrs by colorimetric assay	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID548961	Antioxidant activity of the compound assessed as reducing activity of DPPH at 0.1 mM after 60 mins	2010	Bioorganic & medicinal chemistry, Dec-01, Volume: 18, Issue:23	Does conjugation of antioxidants improve their antioxidative/anti-inflammatory potential?
AID89778	Number of taste judgments per compound	1981	Journal of medicinal chemistry, Apr, Volume: 24, Issue:4	Dihydrochalcone sweeteners. A study of the atypical temporal phenomena.
AID1058582	Antiviral activity against Influenza A/PR8/H1N1 virus infected in MDCK cells assessed as inhibition of virus yield after 48 hrs	2013	Bioorganic & medicinal chemistry, Dec-15, Volume: 21, Issue:24	Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity.
AID90728	Sour character at a concentration of 250 ppm (mean value)	1981	Journal of medicinal chemistry, Apr, Volume: 24, Issue:4	Dihydrochalcone sweeteners. A study of the atypical temporal phenomena.
AID1241088	Antiviral activity against Cytomegalovirus VR-538 infected in human HFF1 cells assessed as inhibition of virus-induced plaque formation/cytopathogenicity	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses.
AID499283	Antioxidant activity assessed as inhibition of AAPH-induced lipid peroxidation in liposomes measured as Trolox equivalent antioxidant capacity	2010	Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16	Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties.
AID750755	Inhibition of Gloeobacter violaceus ligand-gated ion channel expressed in Xenopus laevis oocytes assessed as inhibition of MES buffer pH 5.5 -induced currents at 1 mM after 30 secs by voltage clamp technique	2013	Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11	Identification of cinnamic acid derivatives as novel antagonists of the prokaryotic proton-gated ion channel GLIC.
AID88199	Cytotoxic effect of compound measured as cell density of HeLa cells 72 hrs after incubation with compound compared to a initial density of 5E6 cells/mL	2003	Journal of medicinal chemistry, Dec-04, Volume: 46, Issue:25	Anticancer activity of phenolic acids of natural or synthetic origin: a structure-activity study.
AID1241083	Antiviral activity against Human echovirus type 9 VR-1050 infected in African green monkey Vero cells assessed as inhibition of virus-induced plaque formation/cytopathogenicity	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses.
AID446515	Antihypertensive activity in Wistar rat assessed as change in blood protein level at 10 mg/kg/day, po measured after 8 weeks	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID446514	Antihypertensive activity in Wistar rat assessed as change in blood calcium level at 10 mg/kg/day, po measured after 8 weeks	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID592088	Antihemorrhagic activity in ddY mouse assessed as inhibition of Protobothrops flavoviridis venom-induced hemorrhage incubated with compound for 10 mins measured after 24 hrs	2011	Bioorganic & medicinal chemistry, Apr-01, Volume: 19, Issue:7	Contribution of cinnamic acid analogues in rosmarinic acid to inhibition of snake venom induced hemorrhage.
AID446532	Antihypertensive activity in Wistar rat assessed as change in blood urea level at 10 mg/kg/day, po measured after 8 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID1241087	Antiviral activity against Adenovirus type 5 VR-1523 infected in human Hep2 cells assessed as inhibition of virus-induced plaque formation/cytopathogenicity	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses.
AID499282	Redox potential at pH 7.3 by differential pulse and cyclic voltametry	2010	Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16	Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties.
AID715802	Cytotoxicity against human U937 cells after 48 hrs by trypan blue assay	2012	Bioorganic & medicinal chemistry, Sep-15, Volume: 20, Issue:18	Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action.
AID1592384	Antioxidant activity assessed as ABTS radical scavenging activity measured after 15 mins by UV-Visible spectrophotometric based assay
AID725981	Inhibition of CMG2 (40 to 217) C175A and R40C double mutant (unknown origin) interaction to full length PA E733C mutant expressed in Escherichia coli by FRET assay	2013	Journal of medicinal chemistry, Mar-14, Volume: 56, Issue:5	1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose inhibits angiogenesis via inhibition of capillary morphogenesis gene 2.
AID90878	Sweet / Bitter character at a concentration of 250 ppm (mean value); 0/100	1981	Journal of medicinal chemistry, Apr, Volume: 24, Issue:4	Dihydrochalcone sweeteners. A study of the atypical temporal phenomena.
AID446528	Antihypertensive activity in Wistar rat assessed as change in blood LDH level at 10 mg/kg/day, po measured after 8 weeks in presence of losartan	2009	Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22	Losartan-antioxidant hybrids: novel molecules for the prevention of hypertension-induced cardiovascular damage.
AID1241090	Cytotoxicity against human Hep2 cells after 24 hrs by MTT assay	2015	Bioorganic & medicinal chemistry, Sep-01, Volume: 23, Issue:17	Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses.
AID1799825	Inhibition Assay from Article : \\Partial identity of the 2-oxoglutarate and ascorbate binding sites of prolyl 4-hydroxylase.\\	1986	The Journal of biological chemistry, Jun-15, Volume: 261, Issue:17	Partial identity of the 2-oxoglutarate and ascorbate binding sites of prolyl 4-hydroxylase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	8 (8.99)	18.7374
1990's	2 (2.25)	18.2507
2000's	28 (31.46)	29.6817
2010's	38 (42.70)	24.3611
2020's	13 (14.61)	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	3 (3.37%)	5.53%
Reviews	1 (1.12%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	85 (95.51%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
2,3-dihydroxybenzoic acid 2,3-dihydroxybenzoic acid: RN given refers to parent cpd. dihydroxybenzoic acid : Any member of the class of hydroxybenzoic acids carrying two phenolic hydroxy groups on the benzene ring and its derivatives.. 2,3-dihydroxybenzoic acid : A dihydroxybenzoic acid that is benzoic acid substituted by hydroxy groups at positions 2 and 3. It occurs naturally in Phyllanthus acidus and in the aquatic fern Salvinia molesta.	2.94	4	0	dihydroxybenzoic acid	human xenobiotic metabolite; plant metabolite
protocatechuic acid protocatechuic acid: RN given refers to parent cpd; structure. 3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.	3.29	6	0	catechols; dihydroxybenzoic acid	antineoplastic agent; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; human xenobiotic metabolite; plant metabolite
dihydro-3-coumaric acid dihydro-3-coumaric acid: intermediate in biosynthesis of dihydrophenanthrenes from phenylalanine. 3-(3-hydroxyphenyl)propanoic acid : A monocarboxylic acid that is propionic acid carrying a 3-hydroxyphenyl substituent at C-3.	2.69	3	0	monocarboxylic acid	Escherichia coli metabolite; human xenobiotic 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.	2.02	1	0	benzenes; monocarboxylic acid	antifungal agent; human metabolite; plant metabolite
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	2.05	1	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
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.	2.73	3	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.	2.7	3	0	monohydroxybenzoic acid	algal metabolite; plant metabolite
anthranilic acid anthranilic acid: RN given refers to parent cpd; structure in Negwer, 5th ed, #565. anthranilic acid : An aminobenzoic acid that is benzoic acid having a single amino substituent located at position 2. It is a metabolite produced in L-tryptophan-kynurenine pathway in the central nervous system.	2.05	1	0	aminobenzoic acid	human metabolite; mouse metabolite
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.	2.02	1	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
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.	2.05	1	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
catechol [no description available]	4.07	4	0	catechols	allelochemical; genotoxin; plant metabolite
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	2.05	1	0	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental 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).	2.4	2	0	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
digallic acid digallic acid: structure given in first source	2.08	1	0	benzoate ester; gallate ester
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	2.93	4	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
hippuric acid hippuric acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #4591. N-benzoylglycine : An N-acylglycine in which the acyl group is specified as benzoyl.	2.45	2	0	N-acylglycine	human blood serum metabolite; uremic toxin
3,4-dihydroxyphenylacetic acid 3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.	3.62	9	0	catechols; dihydroxyphenylacetic acid	human metabolite
fosmidomycin fosmidomycin: from Streptomyces lavendulae; RN given refers to parent cpd; structure in second source. fosmidomycin : Propylphosphonic acid in which one of the hydrogens at position 3 is substituted by a formyl(hydroxy)amino group. An antibiotic obtained from Streptomyces lavendulae, it specifically inhibits DXP reductoisomerase (EC 1.1.1.267), a key enzyme in the non-mevalonate pathway of isoprenoid biosynthesis.	2.05	1	0	hydroxamic acid; phosphonic acids	antimicrobial agent; bacterial metabolite; EC 1.1.1.267 (1-deoxy-D-xylulose-5-phosphate reductoisomerase) inhibitor
glucono-1,4-lactone [no description available]	1.96	1	0	gamma-lactone
hydroquinone [no description available]	1.96	1	0	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
dihydroxyphenylalanine Dihydroxyphenylalanine: A beta-hydroxylated derivative of phenylalanine. The D-form of dihydroxyphenylalanine has less physiologic activity than the L-form and is commonly used experimentally to determine whether the pharmacological effects of LEVODOPA are stereospecific.. dopa : A hydroxyphenylalanine carrying hydroxy substituents at positions 3 and 4 of the benzene ring.	2.39	2	0	hydroxyphenylalanine; non-proteinogenic alpha-amino acid; tyrosine derivative	human metabolite
hydroxide ion [no description available]	2.06	1	0	oxygen hydride	mouse metabolite
4-aminobenzoic acid 4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.	2.01	1	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
phenol [no description available]	2.02	1	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phenylacetic acid phenylacetic acid : A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.	2.69	3	0	benzenes; monocarboxylic acid; phenylacetic acids	allergen; Aspergillus metabolite; auxin; EC 6.4.1.1 (pyruvate carboxylase) inhibitor; Escherichia coli metabolite; human metabolite; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite; toxin
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	2.05	1	0	saturated fatty acid; short-chain fatty acid	antifungal drug
pyrogallol benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.	1.96	1	0	benzenetriol; phenolic donor	plant metabolite
spermidine [no description available]	2.04	1	0	polyazaalkane; triamine	autophagy inducer; fundamental metabolite; geroprotector
spermine [no description available]	2.05	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.	2.05	1	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
vanilmandelic acid Vanilmandelic Acid: A 3-O-methyl ether of 3,4-dihydroxymandelic acid. It is an end-stage metabolite of CATECHOLAMINES; EPINEPHRINE; and NOREPINEPHRINE.. vanillylmandelic acid : An aromatic ether that is the 3-O-methyl ether of 3,4-dihydroxymandelic acid.	2.04	1	0	2-hydroxy monocarboxylic acid; aromatic ether; phenols	human metabolite
mandelic acid SAMMA: mandelic acid condensation polymer	2.4	2	0	2-hydroxy monocarboxylic acid; benzenes	antibacterial agent; human xenobiotic metabolite
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.	2.98	4	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
beta-resorcylic acid beta-resorcylic acid: RN given refers to parent cpd; structure	1.96	1	0
homovanillic acid Homovanillic Acid: A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.. homovanillate : A hydroxy monocarboxylic acid anion which is obtained by deprotonation of the carboxy group of homovanillic acid.. homovanillic acid : A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.	2.04	1	0	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
oxyquinoline Oxyquinoline: An antiseptic with mild fungistatic, bacteriostatic, anthelmintic, and amebicidal action. It is also used as a reagent and metal chelator, as a carrier for radio-indium for diagnostic purposes, and its halogenated derivatives are used in addition as topical anti-infective agents and oral antiamebics.. quinolin-8-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes.	2.05	1	0	monohydroxyquinoline	antibacterial agent; antifungal agrochemical; antiseptic drug; iron chelator
baclofen [no description available]	2.05	1	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid; monochlorobenzenes; primary amino compound	central nervous system depressant; GABA agonist; muscle relaxant
caffeine [no description available]	2.48	2	0	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
4-cresol 4-cresol: RN given refers to parent cpd. p-cresol : A cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals.	2.06	1	0	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
valproic acid Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.	2.05	1	0	branched-chain fatty acid; branched-chain saturated fatty acid	anticonvulsant; antimanic drug; EC 3.5.1.98 (histone deacetylase) inhibitor; GABA agent; neuroprotective agent; psychotropic drug; teratogenic agent
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.	2.02	1	0
2,5-dihydroxybenzoic acid 2,5-dihydroxybenzoic acid: RN given refers to parent cpd; a oxidative product of saligenin. 2,5-dihydroxybenzoic acid : A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.	1.96	1	0	dihydroxybenzoic acid	EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; fungal metabolite; human metabolite; MALDI matrix material; mouse metabolite
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.	2.05	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
kojic acid [no description available]	2.05	1	0	4-pyranones; enol; primary alcohol	Aspergillus metabolite; EC 1.10.3.1 (catechol oxidase) inhibitor; EC 1.10.3.2 (laccase) inhibitor; EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; EC 1.4.3.3 (D-amino-acid oxidase) inhibitor; NF-kappaB inhibitor; skin lightening agent
kynurenic acid Kynurenic Acid: A broad-spectrum excitatory amino acid antagonist used as a research tool.. kynurenic acid : A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by a hydroxy group at C-4.	2.04	1	0	monohydroxyquinoline; quinolinemonocarboxylic acid	G-protein-coupled receptor agonist; human metabolite; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist; Saccharomyces cerevisiae metabolite
3-phenyllactic acid 3-phenyllactic acid: alpha-hydroxy analog of phenylalanine; RN given refers to cpd without isomeric designation. 3-phenyllactic acid : A 2-hydroxy monocarboxylic acid that is lactic acid in which one of the methyl hydrogens is substituted by a phenyl group.	2.08	1	0	2-hydroxy monocarboxylic acid	human metabolite
losartan Losartan: An antagonist of ANGIOTENSIN TYPE 1 RECEPTOR with antihypertensive activity due to the reduced pressor effect of ANGIOTENSIN II.. losartan : A biphenylyltetrazole where a 1,1'-biphenyl group is attached at the 5-position and has an additional trisubstituted imidazol-1-ylmethyl group at the 4'-position	2.8	3	0	biphenylyltetrazole; imidazoles	angiotensin receptor antagonist; anti-arrhythmia drug; antihypertensive agent; endothelin receptor antagonist
deoxyepinephrine Deoxyepinephrine: Sympathomimetic, vasoconstrictor agent.	2.06	1	0	catecholamine
masoprocol nordihydroguaretic acid: antioxidant compound found in the creosote bush (Larrea tridentata)	2.05	1	0	catechols; lignan; tetrol	antioxidant; ferroptosis inhibitor; geroprotector; plant metabolite
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	2.41	2	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
4-phenylbutyric acid 4-phenylbutyric acid: RN refers to the parent cpd. 4-phenylbutyric acid : A monocarboxylic acid the structure of which is that of butyric acid substituted with a phenyl group at C-4. It is a histone deacetylase inhibitor that displays anticancer activity. It inhibits cell proliferation, invasion and migration and induces apoptosis in glioma cells. It also inhibits protein isoprenylation, depletes plasma glutamine, increases production of foetal haemoglobin through transcriptional activation of the gamma-globin gene and affects hPPARgamma activation.	2.05	1	0	monocarboxylic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor; prodrug
propyl gallate Propyl Gallate: Antioxidant for foods, fats, oils, ethers, emulsions, waxes, and transformer oils.	2.08	1	0	trihydroxybenzoic acid
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.	1.96	1	0	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser
4-phenylbutyric acid, sodium salt sodium phenylbutyrate : The organic sodium salt of 4-phenylbutyric acid. A prodrug for phenylacetate, it is used to treat urea cycle disorders.	2.05	1	0	organic sodium salt	EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector; neuroprotective agent; orphan drug; prodrug
vorinostat Vorinostat: A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME.. vorinostat : A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL).	2.05	1	0	dicarboxylic acid diamide; hydroxamic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	2.25	1	0	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
tyramine [no description available]	2.15	1	0	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
xanthurenic acid xanthurenic acid : A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by hydroxy groups at C-4 and C-8.	2.04	1	0	dihydroxyquinoline; quinolinemonocarboxylic acid	animal metabolite; iron chelator; metabotropic glutamate receptor agonist; vesicular glutamate transport inhibitor
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.04	1	0	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	2.25	1	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
kanamycin a Kanamycin: Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components.. kanamycin : Kanamycin is a naturally occurring antibiotic complex from Streptomyces kanamyceticus that consists of several components: kanamycin A, the major component (also usually designated as kanamycin), and kanamycins B, C, D and X the minor components.	2.05	1	0	kanamycins	bacterial metabolite
galactose galactopyranose : The pyranose form of galactose.	2.06	1	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	2.05	1	0	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	1.97	1	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
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.	2.01	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
carbaryl Carbaryl: A carbamate insecticide and parasiticide. It is a potent anticholinesterase agent belonging to the carbamate group of reversible cholinesterase inhibitors. It has a particularly low toxicity from dermal absorption and is used for control of head lice in some countries.. carbaryl : A carbamate ester obtained by the formal condensation of 1-naphthol with methylcarbamic acid.	2.03	1	0	carbamate ester; naphthalenes	acaricide; agrochemical; carbamate insecticide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; plant growth retardant
ampicillin Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.	2.05	1	0	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
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.	2.05	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
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	2.88	3	0
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.	2.31	1	0	alpha,beta-unsaturated monocarboxylic acid	metabolite
isobutyric acid isobutyric acid: RN given refers to parent cpd. isobutyric acid : A branched fatty acid comprising propanoic acid carrying a methyl branch at C-2.	2.05	1	0	branched-chain saturated fatty acid; fatty acid 4:0; methyl-branched fatty acid	Daphnia magna metabolite; plant metabolite; volatile oil component
cumene hydroperoxide cumene hydroperoxide: RN given refers to parent cpd. cumene hydroperoxide : A peroxol that is cumene in which the alpha-hydrogen is replaced by a hydroperoxy group.	2.06	1	0	peroxol	environmental contaminant; Mycoplasma genitalium metabolite; oxidising agent
1-naphthol 1-naphthol: RN given refers to parent cpd. 1-naphthol : A naphthol carrying a hydroxy group at position 1.. hydroxynaphthalene : Any member of the class of naphthalenes that is naphthalene carrying one or more hydroxy groups.	2.03	1	0	naphthol	genotoxin; human xenobiotic metabolite
2-naphthoic acid 2-naphthoic acid: RN given refers to parent cpd. 2-naphthoic acid : A naphthoic acid that is naphthalene carrying a carboxy group at position 2.	2.08	1	0	naphthoic acid	mouse metabolite; xenobiotic metabolite
propylparaben Parabens: Methyl, propyl, butyl, and ethyl esters of p-hydroxybenzoic acid. They have been approved by the FDA as antimicrobial agents for foods and pharmaceuticals. (From Hawley's Condensed Chemical Dictionary, 11th ed, p872)	2.45	2	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
3-hydroxybenzoic acid 3-hydroxybenzoic acid: RN given refers to parent cpd. 3-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid substituted by a hydroxy group at position 3. It has been isolated from Taxus baccata. It is used as an intermediate in the synthesis of plasticisers, resins, pharmaceuticals, etc.	1.96	1	0	monohydroxybenzoic acid	bacterial metabolite; plant metabolite
alpha-resorcylic acid alpha-resorcylic acid: RN given refers to parent cpd. 3,5-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 5.	1.96	1	0	dihydroxybenzoic acid; resorcinols	metabolite
methyl gallate methyl gallate: has both immunosuppressive and phytogenic antineoplastic activities; isolated from Acer saccharinum. methyl 3,4,5-trihydroxybenzoate : A gallate ester obtained by the formal condensation of gallic acid with methanol. It exhibits anti-oxidant, anti-tumor, anti-microbial and anti-inflammatory properties.	2.08	1	0	gallate ester	anti-inflammatory agent; antioxidant; plant metabolite
n-pentanoic acid n-pentanoic acid: RN given refers to unlabeled parent cpd. valeric acid : A straight-chain saturated fatty acid containing five carbon atoms.	2.05	1	0	short-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
scoparone scoparone: structure. scoparone : A member of the class of coumarins that is esculetin in which the two hydroxy groups at positions 6 and 7 are replaced by methoxy groups. It is a major constituent of the Chinese herbal medicine Yin Chen Hao, and exhibits a variety of pharmacological activities such as anti-inflammatory, anti-allergic, and anti-tumor activities.	2.07	1	0	aromatic ether; coumarins	anti-allergic agent; anti-inflammatory agent; antihypertensive agent; antilipemic drug; immunosuppressive agent; plant metabolite
2-naphthalenesulfonic acid naphthalene-2-sulfonic acid : A naphthalenesulfonic acid in which the sulfo group is linked to position 2 of the naphthalene ring.	2.08	1	0	naphthalenesulfonic acid	environmental contaminant; xenobiotic
vanillic acid Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.	2.76	3	0	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
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
mequinol mequinol: depigmenting agent; RN given refers to parent cpd	2.01	1	0	methoxybenzenes; phenols	metabolite
adamantane Adamantane: A tricyclo bridged hydrocarbon.	2.03	1	0	adamantanes; polycyclic alkane
thiazoles [no description available]	2.01	1	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
gamma-resorcylic acid [no description available]	1.96	1	0	dihydroxybenzoic acid	metabolite
4-methylcatechol [no description available]	2.06	1	0	methylcatechol	antioxidant; carcinogenic agent; hapten; human metabolite; plant metabolite
phloretic acid phloretic acid: structure. N-hydroxysuccinimide ester : An ester of N-hydroxysuccinimide.. phloretic acid : A hydroxy monocarboxylic acid consisting of propionic acid having a 4-hydroxyphenyl group at the 3-position.	2.48	2	0	hydroxy monocarboxylic acid	plant metabolite
isovaleric acid isovaleric acid: structure. isovaleric acid : A C5, branched-chain saturated fatty acid.	2.05	1	0	branched-chain saturated fatty acid; methylbutyric acid; short-chain fatty acid	mammalian metabolite; plant metabolite
hesperidin Hesperidin: A flavanone glycoside found in CITRUS fruit peels.. hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.44	2	0	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
syringic acid syringic acid: RN given refers to parent cpd; structure in third source. syringic acid : A dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid.	2.07	1	0	benzoic acids; dimethoxybenzene; phenols	plant metabolite
coumarin-3-carboxylic acid coumarin-3-carboxylic acid: structure given in first source	2.08	1	0	coumarins
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.	2.05	1	0	2-hydroxy monocarboxylic acid; hydroxybutyric acid	algal metabolite; human metabolite
3-hydroxyflavone 3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.	2.21	1	0	flavonols; monohydroxyflavone
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.	2.44	2	0	monocarboxylic acid; phenols	human xenobiotic metabolite
dihydroferulic acid dihydroferulic acid: structure in first source. dihydroferulic acid : A monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 3 has been replaced by a 4-hydroxy-3-methoxyphenyl group.	3.45	7	0	guaiacols; monocarboxylic acid; phenylpropanoid	antioxidant; human xenobiotic metabolite; mouse metabolite; plant metabolite
2-amino-4-phenylphenol [no description available]	2.05	1	0	biphenyls
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	2.7	3	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
3,5-di-tert-butyl-4-hydroxybenzoic acid [no description available]	2.07	1	0
alpha-methyldopamine [no description available]	2.06	1	0	amphetamines
phenoxyacetic acid phenoxyacetic acid : A monocarboxylic acid that is the O-phenyl derivative of glycolic acid. A metabolite of 2-phenoxyethanol, it is used in the manufacture of pharmaceuticals, pesticides, fungicides and dyes.	2.08	1	0	aromatic ether; monocarboxylic acid	allergen; Aspergillus metabolite; human xenobiotic metabolite; plant growth retardant
3-phenylbutyric acid 3-phenylbutyric acid : A monocarboxylic acid that is butanoic acid substituted by a phenyl group at position 3.	2.07	1	0	benzenes; monocarboxylic acid	antibacterial agent; bacterial xenobiotic metabolite
terbium Terbium: An element of the rare earth family of metals. It has the atomic symbol Tb, atomic number 65, and atomic weight 158.92.	2.03	1	0	f-block element atom; lanthanoid atom
chromium Chromium: A trace element that plays a role in glucose metabolism. It has the atomic symbol Cr, atomic number 24, and atomic weight 52. According to the Fourth Annual Report on Carcinogens (NTP85-002,1985), chromium and some of its compounds have been listed as known carcinogens.. chromium ion : An chromium atom having a net electric charge.. chromium atom : A chromium group element atom that has atomic number 24.	2.02	1	0	chromium group element atom; metal allergen	micronutrient
amoxicillin Amoxicillin: A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.. amoxicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group.	2.21	1	0	penicillin allergen; penicillin	antibacterial drug
ribavirin Rebetron: Rebetron is tradename	2.08	1	0	1-ribosyltriazole; aromatic amide; monocarboxylic acid amide; primary carboxamide	anticoronaviral agent; antiinfective agent; antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	2.45	2	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
vanillyl alcohol vanillyl alcohol: structure. vanillyl alcohol : A monomethoxybenzene that is 2-methoxyphenol substituted by a hydroxymethyl group at position 4.	2.06	1	0	benzyl alcohols; guaiacols	plant metabolite
3-(2'-spiroadamantane)-4-methoxy-4-(3''-phosphoryloxy)phenyl-1,2-dioxetane 3-(2'-spiroadamantane)-4-methoxy-4-(3''-phosphoryloxy)phenyl-1,2-dioxetane: chemiluminescent substrate for alkaline phosphatase	2.03	1	0
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	2.83	3	0	D-glucopyranose	epitope; mouse metabolite
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	2.11	1	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
metaperiodate Periodic Acid: A strong oxidizing agent.	1.97	1	0	iodine oxoacid
1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose pentagalloylglucose: pentahydroxy gallic acid ester of glucose; a phytogenic antineoplastic agent and antibacterial agent. 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose : A galloyl-beta-D-glucose compound having five galloyl groups in the 1-, 2-, 3-, 4- and 6-positions.	2.5	2	0	gallate ester; galloyl beta-D-glucose	anti-inflammatory agent; antineoplastic agent; geroprotector; hepatoprotective agent; plant metabolite; radiation protective agent; radical scavenger
benzeneboronic acid [no description available]	2.25	1	0	boronic acids
2-pyrone 2-pyrone: structure in first source. pyranone : Any of a class of cyclic chemical compounds that contain an unsaturated six-membered ring with one ring oxygen atom and an oxo substituent.	2.07	1	0	2-pyranones
epicatechin (-)-epicatechin : A catechin with (2R,3R)-configuration.	2.5	2	0	catechin; polyphenol	antioxidant
gallocatechol (-)-epigallocatechin : A flavan-3,3',4',5,5',7-hexol having (2R,3R)-configuration.	2.08	1	0	catechin; flavan-3,3',4',5,5',7-hexol	antioxidant; food component; plant metabolite
hesperetin [no description available]	2.44	2	0	3'-hydroxyflavanones; 4'-methoxyflavanones; monomethoxyflavanone; trihydroxyflavanone	antineoplastic agent; antioxidant; plant metabolite
indole-2-carboxylic acid [no description available]	2.05	1	0	indolyl carboxylic acid
(-)-catechin (-)-catechin : The (-)-enantiomer of catechin.	2.11	1	0	catechin	metabolite
3-(3,4-dimethoxyphenyl)propanoic acid 3-(3,4-dimethoxyphenyl)propanoic acid : A monocarboxylic acid that is propanoic acid substituted by a 3,4-dimethoxyphenyl group at position 3.	2.49	2	0	dimethoxybenzene; monocarboxylic acid
methyl 3-(4-hydroxyphenyl)propionate methyl 3-(4-hydroxyphenyl)propionate: a root-exuded compound responsible for biological nitrification inhibition by sorghum (Sorghum bicolor); structure in first source. methyl 3-(4-hydroxyphenyl)propionate : A methyl ester resulting from the formal condensation of the carboxy group of phloretic acid with methanol. It is a nitrification inhibitor and a plant growth regulator.	2.5	2	0	methyl ester; phenols	nitrification inhibitor; plant growth regulator
3,4-dihydroxymandelic acid 3,4-dihydroxymandelic acid: metabolite of L-dopa; RN given refers to parent cpd without isomeric designation. 3,4-dihydroxymandelic acid : A catechol that is the 3,4-dihydroxy derivative of mandelic acid; a metabolite of L-dopa.	1.96	1	0	2-hydroxy monocarboxylic acid; catechols	antioxidant; drug metabolite; human metabolite; mouse metabolite
irgarol 1051 irgarol 1051: a booster biocide; structure given in first source. irgarol 1051 : A diamino-1,3,5-triazine that is 1,3,5-triazine-2,4-diamine carrying a N-tert-butyl, N'-cyclopropyl and a methylsulfanyl group at position 6.	2.03	1	0	aryl sulfide; cyclopropanes; diamino-1,3,5-triazine	antifouling biocide; environmental contaminant; xenobiotic
7-amino-4-methylcoumarin 7-amino-4-methylcoumarin: RN given refers to parent cpd	2.07	1	0	7-aminocoumarins	fluorochrome
parinaric acid parinaric acid: long-chain polyenoic fatty acid; RN given refers to cpd without isomeric designation. parinaric acid : An octadecatetraenoic acid containing a conjugated system of double bonds at positions 9, 11, 13 and 15.	2.02	1	0	octadecatetraenoic acid
exp3174 losartan carboxylic acid: structure given in first source. losartan carboxylic acid : A biphenylyltetrazole that is losartan with the hydroxymethyl group at position 5 on the imidazole ring replaced with a carboxylic acid.	2.07	1	0	biphenylyltetrazole; imidazoles; organochlorine compound	metabolite
phenoxy radical phenoxy radical : An organic radical generated from phenol.	2.01	1	0	organic radical
4-hydroxyhippuric acid p-hydroxyhippuric acid : An N-acylglycine that is the 4-hydroxy derivative of hippuric acid.	2.05	1	0	N-acylglycine	human blood serum metabolite
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	2.01	1	0	oxygen hydride; oxygen radical; reactive oxygen species
vanillactic acid vanillactic acid: metabolite of catecholamines	2.06	1	0	2-oxo monocarboxylic acid
metaperiodate metaperiodate: RN given refers to periodic acid, Na salt; structure. periodate : A monovalent inorganic anion obtained by deprotonation of periodic acid.	1.97	1	0	iodine oxoanion; monovalent inorganic anion
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	2.07	1	0	amino acid zwitterion; angiotensin II	human metabolite
N-hydroxy-2-phenylacetamide [no description available]	2.05	1	0	acetamides
methyl 3,4-dihydroxybenzoate [no description available]	2.08	1	0	catechols; methyl ester	antioxidant; neuroprotective agent; plant metabolite
hexacyanoferrate iii hexacyanoferrate III: RN given refers to parent cpd	2	1	0
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	2.46	2	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
scopolin [no description available]	2.08	1	0	beta-D-glucoside; coumarins; monosaccharide derivative	plant metabolite
tartaric acid tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.	2.05	1	0	tartaric acid	Escherichia coli 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.	2.5	2	0	beta-D-glucoside; monosaccharide derivative	Escherichia coli metabolite; plant metabolite
naringin [no description available]	2.11	1	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
malvidin-3-glucoside malvidin 3-O-beta-D-glucoside : An anthocyanin cation consisting of malvidin having a beta-D-glucosyl residue attached at the 3-hydroxy position.	2.58	2	0	anthocyanin cation; aromatic ether; beta-D-glucoside	metabolite
acarbose [no description available]	2.11	1	0	amino cyclitol; glycoside
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	2.99	4	0	cinnamic acid	plant metabolite
trichostatin a trichostatin A: chelates zinc ion in the active site of histone deacetylases, resulting in preventing histone unpacking so DNA is less available for transcription; do not confuse with TRICHOSANTHIN which is a protein; found in STREPTOMYCES	2.05	1	0	antibiotic antifungal agent; hydroxamic acid; trichostatin	bacterial metabolite; EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector
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.	2.05	1	0	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	6.31	13	1	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
crotonic acid crotonic acid: a stereospecific unsaturated carboxylic acid found in CROTON OIL. butenoic acid : Any C4, straight-chain fatty acid containing one double bond.. crotonic acid : A but-2-enoic acid with a trans- double bond at C-2. It has been isolated from Daucus carota.	2.06	1	0	2-butenoic acid	plant metabolite
cinnamaldehyde 3-phenylprop-2-enal : A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer.. (E)-cinnamaldehyde : The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.	2.06	1	0	3-phenylprop-2-enal; cinnamaldehydes	antifungal agent; EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor; flavouring agent; hypoglycemic agent; plant metabolite; sensitiser; vasodilator agent
methyl cinnamate methyl cinnamate: RN given refers to cpd without isomeric designation. methyl cinnamate : A methyl ester resulting from the formal condensation of methyl cinnamic acid with methanol. It is found naturally in the essential oils of Alpinia and Basil leaf oil, and widely used in the flavor and perfume industries.. methyl trans-cinnamate : The E (trans) isomer of methyl cinnamate.	2.49	2	0	methyl cinnamate	antibacterial agent; fungal metabolite; nematicide; plant metabolite
2-hydroxycinnamic acid trans-2-coumaric acid : The trans-isomer of 2-coumaric acid.. 2-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring.	2.06	1	0	2-coumaric acid; phenols	antioxidant; metabolite
3-coumaric acid 3-coumaric acid: RN given refers to cpd without isomeric designation in Chemline. trans-3-coumaric acid : A 3-coumaric acid that is phenol substituted with trans-2-propenoic acid at position C-3.. 3-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-3 of the phenyl ring.	2.97	4	0	3-coumaric acid
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	3.18	5	0	4-coumaric acid	food component; mouse metabolite; plant metabolite
glycosides [no description available]	2.52	2	0
chalcone trans-chalcone : The trans-isomer of chalcone.	2.11	1	0	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
sinapinic acid sinapinic acid: a matrix for matrix-assisted laser desorption technique for protein MW determination; a constituent of propolis. trans-sinapic acid : A sinapic acid in which the double bond has trans-configuration.	2.5	2	0	sinapic acid	MALDI matrix material; plant metabolite
Methylenedioxycinnamic acid [no description available]	2.08	1	0	hydroxycinnamic acid
sorbic acid Sorbic Acid: Mold and yeast inhibitor. Used as a fungistatic agent for foods, especially cheeses.. (2E,4E)-hexa-2,4-dienoic acid : A sorbic acid having trans-double bonds at positions 2 and 4; a food preservative that can induce cutaneous vasodilation and stinging upon topical application to humans. It is the most thermodynamically stable of the four possible geometric isomers possible, as well as the one with the highest antimicrobial activity.. sorbic acid : A hexadienoic acid with double bonds at C-2 and C-4; it has four geometrical isomers, of which the trans,trans-form is naturally occurring.	2.46	2	0	alpha,beta-unsaturated monocarboxylic acid; sorbic acid
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	4.78	30	0	caffeic acid	geroprotector; mouse metabolite
methyl caffeate methyl caffeate: from plant Gaillardia pulchella. methyl caffeate : An alkyl caffeate ester formed by the formal condensation of caffeic acid with methyl alcohol.	3	4	0	alkyl caffeate ester; methyl ester
3-(3,4-dimethoxyphenyl)propenoic acid 3-(3,4-dimethoxyphenyl)propenoic acid: structure given in first source; RN given refers to parent cpd. 3,4-dimethoxycinnamic acid : A methoxycinnamic acid that is trans-cinnamic acid substituted by methoxy groups at positions 3' and 4' respectively.	2.98	4	0	methoxycinnamic acid
isoferulic acid isoferulic acid: isomer of ferulic acid; structure. isoferulic acid : A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 4 and 3 respectively on the phenyl ring.	2.99	4	0	ferulic acids	antioxidant; biomarker; metabolite
4-(4-(4-chloro-phenyl)thiazol-2-ylamino)phenol [no description available]	2.11	1	0	substituted aniline
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.	2.25	1	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
beta-styrylacrylic acid beta-styrylacrylic acid: RN given refers to parent cpd; structure	2.06	1	0
cinnamonitrile cinnamonitrile: RN given refers to cpd without isomeric designation	2.08	1	0
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	5.22	11	1	cinnamate ester; tannin	food component; plant metabolite
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.	2.01	1	0
sodium butyrate [no description available]	2.05	1	0	organic sodium salt	EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector
fraxetin fraxetin : A hydroxycoumarin that is 6-methoxycoumarin in which the hydrogens at positions 7 and 8 have been replaced by hydroxy groups.	2.07	1	0	aromatic ether; hydroxycoumarin	anti-inflammatory agent; antibacterial agent; antimicrobial agent; antioxidant; apoptosis inducer; apoptosis inhibitor; Arabidopsis thaliana metabolite; hepatoprotective agent; hypoglycemic agent
quercetin [no description available]	2.45	2	0	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	2.11	1	0	trihydroxyflavone	antineoplastic agent; metabolite
quercitrin [no description available]	2.11	1	0	alpha-L-rhamnoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	antileishmanial agent; antioxidant; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; plant metabolite
scopoletin [no description available]	2.49	2	0	hydroxycoumarin	plant growth regulator; plant metabolite
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	2.15	1	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
hymecromone Hymecromone: A coumarin derivative possessing properties as a spasmolytic, choleretic and light-protective agent. It is also used in ANALYTICAL CHEMISTRY TECHNIQUES for the determination of NITRIC ACID.	2.07	1	0	hydroxycoumarin	antineoplastic agent; hyaluronic acid synthesis inhibitor
luteolin-7-glucoside luteolin-7-glucoside: has both antiasthmatic and antineoplastic activities; has 3C protease inhibitory activity; isolated from Ligustrum lucidum. luteolin 7-O-beta-D-glucoside : A glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	2.11	1	0	beta-D-glucoside; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antioxidant; plant metabolite
quercetin 3-o-glucopyranoside quercetin 3-O-glucopyranoside: structure in first source. quercetin 3-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells	2.11	1	0	beta-D-glucoside; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antineoplastic agent; antioxidant; antipruritic drug; bone density conservation agent; geroprotector; histamine antagonist; osteogenesis regulator; plant metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	2.11	1	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
genistein [no description available]	3.99	1	1	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
esculetin esculetin: used in filters for absorption of ultraviolet light; structure. esculetin : A hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light.	2.49	2	0	hydroxycoumarin	antioxidant; plant metabolite; ultraviolet filter
esculin [no description available]	2.11	1	0	beta-D-glucoside; hydroxycoumarin	antioxidant; metabolite
chrysin chrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.	2.11	1	0	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant metabolite
myricetin [no description available]	2.08	1	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
cynarine cynarine: active principle of the artichoke; functions primarily as a cholagogue and choleretic and also as antilipemic agent	2.11	1	0	alkyl caffeate ester; quinic acid	plant metabolite
rosmarinic acid rosmarinic acid: RN given refers to parent cpd; promote OT project. (R)-rosmarinic acid : A stereoisomer of rosmarinic acid having (R)-configuration.. rosmarinic acid : The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid.	2.49	2	0	rosmarinic acid	geroprotector; plant metabolite
acitretin Acitretin: An oral retinoid effective in the treatment of psoriasis. It is the major metabolite of ETRETINATE with the advantage of a much shorter half-life when compared with etretinate.. acitretin : A retinoid that consists of 3,7-dimethylnona-2,4,6,8-tetraenoic acid having a 4-methoxy-2,3,6-trimethylphenyl group attached at position 9.	2.05	1	0	acitretin; alpha,beta-unsaturated monocarboxylic acid; retinoid	keratolytic drug
cinnamyl alcohol cinnamyl alcohol: RN given refers to parent cpd without isomeric designation. (E)-cinnamyl alcohol : The E (trans) stereoisomer of cinnamyl alcohol.. cinnamyl alcohol : A primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified).	2.06	1	0	cinnamyl alcohol	plant metabolite
ethyl caffeate (E)-ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate: structure in first source. ethyl trans-caffeate : An ethyl ester resulting from the formal condensation of the carboxy group of trans-caffeic acid with ethanol.	2.08	1	0	alkyl caffeate ester; ethyl ester; hydroxycinnamic acid	anti-inflammatory agent; antineoplastic agent; metabolite
kukoamine a kukoamine A: inhibits Crithidia fasciculata trypanothione reductase; structure given in first source	2.05	1	0	amine
4-methylesculetin 4-methylesculetin: has antiinflammatory activity. 6,7-dihydroxy-4-methylcoumarin : A hydroxycoumarin that is 4-methylcuomarin which is substituted by hydroxy groups at positions 3 and 4. A hyaluronan synthesis inhibitor. It has also been used as a fluorescent sensor to monitor the consumption of a boronic acid in Suzuki coupling reactions; fluorescence is readily detectable by the naked eye using a standard 365 nm UV lamp.	2.07	1	0	hydroxycoumarin	anti-inflammatory agent; antioxidant; hyaluronan synthesis inhibitor
methyl-p-coumarate methyl-p-coumarate: structure in first source. 4-coumaric acid methyl ester : A cinnamate ester that is the methyl ester of 4-coumaric acid.	2.11	1	0	4-coumaric acid methyl ester
5,7-dihydroxy-4-methylcoumarin [no description available]	2.07	1	0	hydroxycoumarin
7,8-dihydroxy-4-methylcoumarin 7,8-dihydroxy-4-methylcoumarin: possess strong antioxidant and radical scavenging activities; structure in first source	2.07	1	0	hydroxycoumarin
7-hydroxy-4-methyl-1H-quinolin-2-one [no description available]	2.07	1	0	hydroxyquinoline; quinolone
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	2.08	1	0	cysteinium	fundamental metabolite
3-methyl-2-benzothiazolone hydrazone 3-methyl-2-benzothiazolone hydrazone: RN given refers to parent cpd	2.01	1	0
oxalates Oxalates: Derivatives of OXALIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that are derived from the ethanedioic acid structure.	1.97	1	0
indigo carmine 3,5-di-O-(E)-caffeoylquinic acid: from roots of Lychnophora ericoides; structure in first source. 3,5-di-O-caffeoyl quinic acid : A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.	2.11	1	0
avenanthramide b avenanthramide B : A monohydroxybenzoic acid resulting from the formal condensation of the carboxy group of ferulic acid with the amino group of 2-amino-5-hydroxybenzoic acid. It is an oat phytoalexin produced in response to pathogen attack and elicitation.	2.11	1	0	amidobenzoic acid; cinnamamides; monohydroxybenzoic acid; monomethoxybenzene; phenols; secondary carboxamide	antineoplastic agent; apoptosis inducer; phytoalexin
malvidin-3-glucoside oenin: pigment found in red wine	2.25	1	0
aspalathin aspalathin: structure in first source. aspalathin : A member of the class of dihydrochalcones that is the 2-C-beta-D-glucopyranide of phloroglucinol and which is substituted at position 4 by a 3-(3,4-dihydroxyphenyl)propanoyl group. A metabolite of red bush, Aspalathus linearis (and present in the herbal tea made from the leaves), aspalathin exhibits significant hypoglycemic activity.	2.25	1	0	C-glycosyl compound; catechols; dihydrochalcones; polyketide; polyphenol	antioxidant; EC 1.17.3.2 (xanthine oxidase) inhibitor; hypoglycemic agent; plant metabolite
tannins gallotannin : A class of hydrolysable tannins obtained by condensation of the carboxy group of gallic acid (and its polymeric derivatives) with the hydroxy groups of a monosaccharide (most commonly glucose).	2.08	1	0	tannin
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.1	1	0	1,2-diacyl-sn-glycero-3-phosphocholine
chitosan [no description available]	3.17	4	0
sodium lactate Sodium Lactate: The sodium salt of racemic or inactive lactic acid. It is a hygroscopic agent used intravenously as a systemic and urinary alkalizer.. sodium lactate : An organic sodium salt having lactate as the counterion.	2.05	1	0	lactate salt; organic sodium salt	food acidity regulator; food preservative
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.72	3	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
4-hydroxy-6-methyl-2-pyrone 4-hydroxy-6-methyl-2-pyrone: structure in first source	2.07	1	0	2-pyranones
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.	2.08	1	0	benzenes; hydroxycoumarin; methyl ketone
6-o-palmitoylascorbic acid [no description available]	2.11	1	0	fatty acid ester

Condition	Relationship Strength	Studies	Trials
Adenocarcinoma, Basal Cell [description not available]	2.01	1	0
Breast Cancer [description not available]	2.41	2	0
Cancer of Cervix [description not available]	2.01	1	0
Leukemia, Lymphocytic [description not available]	2.01	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.01	1	0
Breast Neoplasms Tumors or cancer of the human BREAST.	2.41	2	0
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	2.01	1	0
Leukemia, Lymphoid Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.	2.01	1	0
Blood Pressure, High [description not available]	2.46	2	0
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	2.05	1	0
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	2.46	2	0
Anasarca [description not available]	2.05	1	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2.05	1	0
Bleeding [description not available]	2.06	1	0
Hemorrhage Bleeding or escape of blood from a vessel.	2.06	1	0
Angiogenesis, Pathologic [description not available]	2.08	1	0
Infections, RNA Virus [description not available]	2.11	1	0
DNA Virus Infections Diseases caused by DNA VIRUSES.	2.11	1	0
Adverse Drug Event [description not available]	2.6	1	0
Drug-Related Side Effects and Adverse Reactions Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.	2.6	1	0
Diabetes Mellitus, Adult-Onset [description not available]	3.97	2	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	3.97	2	1
Cirrhosis [description not available]	2.6	1	0
Chronic Kidney Failure [description not available]	2.6	1	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	2.6	1	0
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	2.6	1	0
Cancer of Colon [description not available]	2.25	1	0
Colonic Neoplasms Tumors or cancer of the COLON.	2.25	1	0
Chronic Illness [description not available]	2.25	1	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.04	4	0
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	2.25	1	0
Benign Neoplasms [description not available]	2.31	1	0
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	2.31	1	0
Innate Inflammatory Response [description not available]	2.17	1	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	2.58	2	0
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	2.17	1	0
Cerebral Ischemia [description not available]	2.11	1	0
Brain Ischemia Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.	2.11	1	0
Retinal Degeneration A retrogressive pathological change in the retina, focal or generalized, caused by genetic defects, inflammation, trauma, vascular disease, or aging. Degeneration affecting predominantly the macula lutea of the retina is MACULAR DEGENERATION. (Newell, Ophthalmology: Principles and Concepts, 7th ed, p304)	2.11	1	0
Acute Confusional Senile Dementia [description not available]	2.13	1	0
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	2.13	1	0
Elevated Cholesterol [description not available]	2.05	1	0
Hypercholesterolemia A condition with abnormally high levels of CHOLESTEROL in the blood. It is defined as a cholesterol value exceeding the 95th percentile for the population.	2.05	1	0
Leukemia L 1210 [description not available]	2	1	0

3,4-dihydroxyphenylpropionic acid

Description

Cross-References

Synonyms (76)

Research Excerpts

Toxicity

Bioavailability

Roles (2)

Drug Classes (1)

Protein Targets (4)

Inhibition Measurements

Biological Processes (1)

Molecular Functions (6)

Ceullar Components (7)

Bioassays (101)

Research

Studies (89)

Market Indicators

Research Demand Index: 26.56

Study Types

3,4-dihydroxyphenylpropionic acid

Description

Cross-References

Synonyms (76)

Research Excerpts

Toxicity

Bioavailability

Roles (2)

Drug Classes (1)

Protein Targets (4)

Inhibition Measurements

Biological Processes (1)

Molecular Functions (6)

Ceullar Components (7)

Bioassays (101)

Research

Studies (89)

Market Indicators

Research Demand Index: 26.56

Study Types

Related Drugs (211)

Related Conditions (44)