Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR3546)
Drug Name
3,4-Dihydroxycinnamic Acid
Synonyms
Caffeic acid; caffeic acid; 3,4-Dihydroxycinnamic acid; 331-39-5; 3-(3,4-dihydroxyphenyl)acrylic acid; 501-16-6; (E)-3-(3,4-dihydroxyphenyl)acrylic acid; 3,4-Dihydroxybenzeneacrylic acid; (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid; trans-caffeic acid; trans-Caffeate; 3,4-Dihydroxy-trans-cinnamate; 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-; Cinnamic acid, 3,4-dihydroxy-; 3-(3,4-Dihydroxyphenyl)propenoic acid; UNII-U2S3A33KVM; 3-(3,4-Dihydroxyphenyl)-2-propenoic acid; 4-(2-Carboxyethenyl)-1,2-dihydroxybenzene
Indication Thrombocytopenia [ICD11: 3B64] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 180.16 Topological Polar Surface Area 77.8
Heavy Atom Count 13 Rotatable Bond Count 2
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
689043
ChEBI ID
CHEBI:16433
CAS Number
331-39-5
TTD Drug ID
D0V9EN
Formula
C9H8O4
Canonical SMILES
C1=CC(=C(C=C1/C=C/C(=O)O)O)O
InChI
InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
InChIKey
QAIPRVGONGVQAS-DUXPYHPUSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
3,4-Dihydroxycinnamic Acid Metabolite M DM017699 N. A. Unclear - Unclear 1 [2]
3-(Dihydroxyphenyl)propanoic acid DM015268
348154
Reduction - Reduction 1 [4] , [2]
Caffeic acid DM003530
689043
Unclear - Unclear 1 [3]
Caffeic acid-3'-O-sulfate DM017697 N. A. Unclear - Unclear 1 [3]
Caffeic acid-4'-O-glucuronide DM017698 N. A. Unclear - Unclear 1 [3]
Caffeic acid-4'-O-sulfate DM015990
21668704
Unclear - Unclear 1 [3]
Cis-Dihydroperillic Acid DM015268
381256
Reduction - Reduction 1 [4] , [2]
FA DM015294
445858
Unclear - Unclear 1 [3]
Isoferulic acid DM015344
736186
Unclear - Unclear 1 [3]
3-(3'-Hydroxyphenyl)propionic acid DM004111
91
Oxidation - Dehydroxylation 2 [4]
4-hydroxy- 4-Hydroxyphenylpropionic acid DM006473
14340
Unclear - Unclear 2 [2]
Ferulic acid-4'-O-glucuronide DM017695 N. A. Unclear - Unclear 2 [3]
Ferulic acid-4'-O-sulfate DM015991
21668707
Unclear - Unclear 2 [3]
Isoferulic acid-3'-O-sulfate DM017696 N. A. Unclear - Unclear 2 [3]
O-quinone DM000619
95198701
Unclear - Unclear 2 [2]
3-Phenylpropionic acid DM003391
107
Oxidation - Dehydroxylation 3 [4]
FA DM015294
445858
Unclear - Unclear 3 [2]
Phenyl acetic acid DM001228
999
Oxidation - Oxidation 4 [4]
Midostaurin Metabolite P6 DM001360
243
Oxidation - Oxidation 5 [4]
Midostaurin Metabolite P6B DM001361
464
Conjugation - Glycination 6 [4]
⏷ Show the Full List of 20  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009194 3,4-Dihydroxycinnamic Acid 3-(Dihydroxyphenyl)propanoic acid Reduction - Reduction ACAD [4], [2]
MR009203 3,4-Dihydroxycinnamic Acid Ferulic acid Unclear - Unclear COMT [3]
MR009206 3,4-Dihydroxycinnamic Acid Isoferulic acid Unclear - Unclear COMT [3]
MR009208 3,4-Dihydroxycinnamic Acid Caffeic acid-3'-O-sulfate Unclear - Unclear SULT1A1 [3]
MR009209 3,4-Dihydroxycinnamic Acid Caffeic acid-4'-O-sulfate Unclear - Unclear SULT1A1 [3]
MR009210 3,4-Dihydroxycinnamic Acid Cis-Caffeic acid Unclear - Unclear Unclear [3]
MR009211 3,4-Dihydroxycinnamic Acid Caffeic acid-4'-O-glucuronide Unclear - Unclear UGT1A1 [3]
MR009212 3,4-Dihydroxycinnamic Acid 3,4-Dihydroxycinnamic Acid Metabolite M Unclear - Unclear CYP2E1 [2]
MR009195 3-(Dihydroxyphenyl)propanoic acid 3-(3'-Hydroxyphenyl)propanoic acid Oxidation - Dehydroxylation Unclear [4]
MR009200 3-(Dihydroxyphenyl)propanoic acid DHFA Unclear - Unclear COMT [2]
MR009202 3-(Dihydroxyphenyl)propanoic acid O-quinone Unclear - Unclear CYP2E1 [2]
MR009204 Ferulic acid Ferulic acid-4'-O-glucuronide Unclear - Unclear UGT1A1 [3]
MR009205 Ferulic acid Ferulic acid-4'-O-sulfate Unclear - Unclear SULT1A1 [3]
MR009207 Isoferulic acid Isoferulic acid-3'-O-sulfate Unclear - Unclear SULT1A1 [3]
MR009196 3-(3'-Hydroxyphenyl)propanoic acid 3-(phenyl)propanoic acid Oxidation - Dehydroxylation Unclear [4]
MR009201 DHFA FA Unclear - Unclear ACAD [2]
MR009197 3-(phenyl)propanoic acid 3-(phenyl)acetic acid Oxidation - Oxidation Unclear [4]
MR009198 3-(phenyl)acetic acid Benzoic acid Oxidation - Oxidation Unclear [4]
MR009199 Benzoic acid Hippuric acid Conjugation - Glycination Unclear [4]
⏷ Show the Full List of 19 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Acyl-CoA dehydrogenase (ACAD) DMEN239 Bacteroides fragilis Not Available Not Available [2]
Catechol O-methyltransferase (COMT) DME0043 Homo sapiens
COMT_HUMAN
2.1.1.6
[3] , [2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[2]
Sulfotransferase (SULT) DMEN061 . Not Available Not Available [3]
UDP-glucuronyltransferase (UGT) DMEN064 . Not Available Not Available [3]
References
1 ClinicalTrials.gov (NCT02556814) Caffeic Acid Combining High-dose Dexamethasone in Management of ITP. U.S. National Institutes of Health.
2 Metabolism of caffeic acid by isolated rat hepatocytes and subcellular fractions
3 Absorption, disposition, metabolism, and excretion of [3-(14)C]caffeic acid in rats
4 In vitro catabolism of 3',4'-dihydroxycinnamic acid by human colonic microbiota

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