Details of the Drug

General Information of Drug (ID: DM340FH)

Drug Name
cinnamic acid
Synonyms
CINNAMIC ACID; TRANS-CINNAMIC ACID; 140-10-3; 621-82-9; (E)-Cinnamic acid; trans-3-Phenylacrylic acid; 3-Phenylacrylic acid; Phenylacrylic acid; Zimtsaeure; (2E)-3-phenylprop-2-enoic acid; 3-phenylprop-2-enoic acid; E-Cinnamic Acid; 3-Phenylpropenoic acid; (E)-3-phenylprop-2-enoic acid; trans-beta-Carboxystyrene; Benzenepropenoic acid; trans-Cinnamate; (E)-3-Phenyl-2-propenoic acid; (E)-cinnamate; Benzeneacrylic acid; trans-3-Phenyl-2-propenoic acid; Cinnamylic acid; Cinnamic acid, (E)-; t-Cinnamic acid; (2E)-3-Phenyl-2-propenoic
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 148.16
Logarithm of the Partition Coefficient (xlogp) 2.1
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C9H8O2
IUPAC Name
(E)-3-phenylprop-2-enoic acid
Canonical SMILES
C1=CC=C(C=C1)/C=C/C(=O)O
InChI
InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
InChIKey
WBYWAXJHAXSJNI-VOTSOKGWSA-N
Cross-matching ID
PubChem CID
444539
ChEBI ID
CHEBI:35697
CAS Number
140-10-3
TTD ID
D0T2QL
INTEDE ID
DR2499

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Nicotinic acid receptor (HCAR2) TTWNV8U HCAR2_HUMAN Agonist [2]
Phosphomevalonate kinase (PMVK) TTXMI0C PMVK_HUMAN Inhibitor [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2 (HSD3B2) OT02MSKN 3BHS2_HUMAN Gene/Protein Processing [4]
Cytochrome P450 2A6 (CYP2A6) OT52TWG3 CP2A6_HUMAN Gene/Protein Processing [4]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [4]
Cytochrome P450 2C8 (CYP2C8) OTHCWT42 CP2C8_HUMAN Gene/Protein Processing [4]
Cytochrome P450 2C9 (CYP2C9) OTGLBN29 CP2C9_HUMAN Gene/Protein Processing [4]
Cytochrome P450 2D6 (CYP2D6) OTZJC802 CP2D6_HUMAN Gene/Protein Processing [4]
Cytochrome P450 2E1 (CYP2E1) OTHQ17JG CP2E1_HUMAN Gene/Protein Processing [4]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [4]
Hydroxycarboxylic acid receptor 2 (HCAR2) OTZM930L HCAR2_HUMAN Protein Interaction/Cellular Processes [5]
Nitric oxide synthase 3 (NOS3) OTLDT7NR NOS3_HUMAN Gene/Protein Processing [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 3203).
2 Phenolic acids suppress adipocyte lipolysis via activation of the nicotinic acid receptor GPR109A (HM74a/PUMA-G). J Lipid Res. 2009 May;50(5):908-14.
3 Inhibition of rat liver mevalonate pyrophosphate decarboxylase and mevalonate phosphate kinase by phenyl and phenolic compounds. Biochem J. 1979 Jul 1;181(1):143-51.
4 Cinnamic acid based thiazolidinediones inhibit human P450c17 and 3beta-hydroxysteroid dehydrogenase and improve insulin sensitivity independent of PPARgamma agonist activity. J Mol Endocrinol. 2004 Apr;32(2):425-36.
5 Structure-activity relationships of trans-substituted-propenoic acid derivatives on the nicotinic acid receptor HCA2 (GPR109A). Bioorg Med Chem Lett. 2011 May 1;21(9):2736-9. doi: 10.1016/j.bmcl.2010.11.091. Epub 2010 Nov 25.
6 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.