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
CHEBI:16433
CAS Number
331-39-5
DrugBank ID
DB01880
TTD ID
D0V9EN
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]
Amine oxidase A (MAOA) OT8NIWMQ AOFA_HUMAN Gene/Protein Processing [5]
Amine oxidase B (MAOB) OTTDFM1O AOFB_HUMAN Gene/Protein Processing [5]
Biotin--protein ligase (HLCS) OTPDUX30 BPL1_HUMAN Gene/Protein Processing [6]
Catechol O-methyltransferase (COMT) OTPWKTQG COMT_HUMAN Biotransformations [7]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [8]
Glucose-6-phosphate 1-dehydrogenase (G6PD) OT300SMK G6PD_HUMAN Gene/Protein Processing [4]
Glutaminase kidney isoform, mitochondrial (GLS) OTGOZG2M GLSK_HUMAN Gene/Protein Processing [9]
Myeloperoxidase (MPO) OTOOXLIN PERM_HUMAN Gene/Protein Processing [10]
Nitric oxide synthase 3 (NOS3) OTLDT7NR NOS3_HUMAN Gene/Protein Processing [11]
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 Combining initro and in silico approaches to evaluate the multifunctional profile of rosmarinic acid from Blechnum brasiliense on targets related to neurodegeneration. Chem Biol Interact. 2016 Jul 25;254:135-45.
6 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.
7 Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. Mol Pharmacol. 2001 Feb;59(2):393-402. doi: 10.1124/mol.59.2.393.
8 Do wine polyphenols modulate p53 gene expression in human cancer cell lines?. Clin Biochem. 2001 Jul;34(5):415-20. doi: 10.1016/s0009-9120(01)00246-6.
9 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.
10 Differentiation between stoichiometric and anticatalytic antioxidant properties of benzoic acid analogues: a structure/redox potential relationship study. Chem Biol Interact. 2013 Nov 25;206(2):194-203.
11 A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase. Nitric Oxide. 2005 Mar;12(2):97-104.