Details of the Drug

General Information of Drug (ID: DMVZL26)

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
Disease Entry ICD 11 Status REF
Thrombocytopenia 3B64 Phase 4 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 180.16
Logarithm of the Partition Coefficient (xlogp) 1.2
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C9H8O4
IUPAC Name
(E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
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
Cross-matching ID
PubChem CID
689043
ChEBI ID
CHEMBL145
CAS Number
331-39-5
UNII
U2S3A33KVM
DrugBank ID
DB01880
TTD ID
D0V9EN
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Arachidonate 5-lipoxygenase (5-LOX) TT2J34L LOX5_HUMAN Inhibitor [2]
Macrophage migration inhibitory factor (MIF) TT2AST1 MIF_HUMAN Inhibitor [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
6-phosphogluconate dehydrogenase, decarboxylating (PGD) OTVG296F 6PGD_HUMAN Gene/Protein Processing [4]
Biotin--protein ligase (HLCS) OTPDUX30 BPL1_HUMAN Gene/Protein Processing [5]
Glutaminase kidney isoform, mitochondrial (GLS) OTGOZG2M GLSK_HUMAN Gene/Protein Processing [6]
Norrin (NDP) OTGDJ4US NDP_HUMAN Gene/Protein Processing [7]
Solute carrier family 2, facilitated glucose transporter member 2 (SLC2A2) OTBL2W7R GTR2_HUMAN Gene/Protein Processing [8]
Tyrosinase OTX54MAA TYRO_HUMAN Biotransformations [9]
UDP-glucuronosyltransferase 1-6 OTGTQ2C9 UD16_HUMAN Gene/Protein Processing [10]
UDP-glucuronosyltransferase 1A1 OTH1C8OJ UD11_HUMAN Gene/Protein Processing [10]
UDP-glucuronosyltransferase 1A10 OTOTZVEY UD110_HUMAN Gene/Protein Processing [10]
UDP-glucuronosyltransferase 1A3 OTUEOER3 UD13_HUMAN Gene/Protein Processing [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Thrombocytopenia
ICD Disease Classification 3B64
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Arachidonate 5-lipoxygenase (5-LOX) DTT ALOX5 4.15E-01 -0.06 -0.15
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 ClinicalTrials.gov (NCT02556814) Caffeic Acid Combining High-dose Dexamethasone in Management of ITP. U.S. National Institutes of Health.
2 Phenidone protects the nigral dopaminergic neurons from LPS-induced neurotoxicity. Neurosci Lett. 2008 Nov 7;445(1):1-6.
3 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
4 Investigation of the effects of some phenolic compounds on the activities of glucose-6-phosphate dehydrogenase and 6-phosphogluconate dehydrogenase from human erythrocytes. J Biochem Mol Toxicol. 2014 Nov;28(11):510-4. doi: 10.1002/jbt.21592. Epub 2014 Aug 6.
5 Resveratrol compounds inhibit human holocarboxylase synthetase and cause a lean phenotype in Drosophila melanogaster. J Nutr Biochem. 2015 Nov;26(11):1379-84. doi: 10.1016/j.jnutbio.2015.07.004. Epub 2015 Jul 26.
6 Metformin and caffeic acid regulate metabolic reprogramming in human cervical carcinoma SiHa/HTB-35ells and augment anticancer activity of Cisplatin via cell cycle regulation. Food Chem Toxicol. 2017 Aug;106(Pt A):260-272.
7 The genome-wide expression profile of Scrophularia ningpoensis-treated thapsigargin-stimulated U-87MG cells. Neurotoxicology. 2009 May;30(3):368-76.
8 Glucose absorption regulation and mechanism of the compounds in Lilium lancifolium Thunb on Caco-2?cells. Food Chem Toxicol. 2021 Mar;149:112010. doi: 10.1016/j.fct.2021.112010. Epub 2021 Jan 22.
9 Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines. Chem Biol Interact. 2010 Oct 6;188(1):1-14. doi: 10.1016/j.cbi.2010.05.018. Epub 2010 Jun 4.
10 Phloretin exhibits potential food-drug interactions by inhibiting human UDP-glucuronosyltransferases in vitro. Toxicol In Vitro. 2022 Oct;84:105447. doi: 10.1016/j.tiv.2022.105447. Epub 2022 Jul 19.