IMPPAT Phytochemical information: 
4-Hydroxycinnamic acid
4-Hydroxycinnamic acid
Summary

SMILES: OC(=O)/C=C/c1ccc(cc1)O
InChI: InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
InChIKey: NGSWKAQJJWESNS-ZZXKWVIFSA-N
DeepSMILES: OC=O)/C=C/cccccc6))O
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: c/C=C/C(=O)O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Cinnamic acids and derivatives
ClassyFire Subclass: Hydroxycinnamic acids and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acids and derivatives
Synonymous chemical names:
hydroxycinnamate, 4-hydroxycinnamic acid, p-hydroxycinnamic acid, trans-p-coumaric acid, 4-coumaric acid, trans-p-hydroxycinnamic acid, p-hydroxycinnamate, beta coumaric acid, p-coumaric, p-coumaric acid, 4-coumarate, p-coumaric-acid, p-hydroxycinnamic, p-coumaric acids, hydroxycinnamic acid
External chemical identifiers:
CID:CID_637542; ChEMBL:CHEMBL66879; ChEBI:CHEBI:32374; ZINC:ZINC000000039811; FDASRS:IBS9D1EU3J; SureChEMBL:SCHEMBL39106; MolPort-000-860-894
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
4-Hydroxycinnamic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 164.16
Log P RDKit 1.49
Topological polar surface area (Å2) RDKit 57.53
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 9
Number of heavy atoms RDKit 12
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1
4-Hydroxycinnamic acid
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.650834
4-Hydroxycinnamic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.26
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
4-Hydroxycinnamic acid
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000104ENSG00000198610AKR1C41109ChEMBL, NPASS
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL, NPASS
TAR_EXP_001280ENSG00000198074AKR1B1057016ChEMBL, NPASS
TAR_EXP_000551ENSG00000236398TAS2R39259285ChEMBL, NPASS
TAR_EXP_001647ENSG00000077498TYR7299BindingDB, ChEMBL, NPASS
TAR_EXP_001683ENSG00000133742CA1759BindingDB, ChEMBL, NPASS
TAR_EXP_001684ENSG00000104267CA2760BindingDB, ChEMBL, NPASS
TAR_EXP_001685ENSG00000164879CA3761BindingDB, ChEMBL, NPASS
TAR_EXP_001686ENSG00000167434CA4762BindingDB, ChEMBL, NPASS
TAR_EXP_001687ENSG00000174990CA5A763BindingDB, ChEMBL, NPASS
TAR_EXP_000492ENSG00000118298CA1423632BindingDB, ChEMBL, NPASS
TAR_EXP_001688ENSG00000131686CA6765ChEMBL, NPASS
TAR_EXP_000456ENSG00000085662AKR1B1231ChEMBL, NPASS
TAR_EXP_001128ENSG00000067225PKM5315ChEMBL
TAR_EXP_001689ENSG00000168748CA7766BindingDB, ChEMBL, NPASS
TAR_EXP_001691ENSG00000074410CA12771BindingDB, ChEMBL, NPASS
TAR_EXP_001742ENSG00000070808CAMK2A815BindingDB, ChEMBL
TAR_EXP_001807ENSG00000196139AKR1C38644ChEMBL, NPASS
TAR_EXP_000397ENSG00000140009ESR22100ChEMBL, NPASS
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL, NPASS
TAR_EXP_000348ENSG00000146648EGFR1956BindingDB, NPASS
TAR_EXP_000322ENSG00000197635DPP41803ChEMBL, NPASS
TAR_EXP_000298ENSG00000151632AKR1C21646ChEMBL, NPASS
TAR_EXP_000297ENSG00000187134AKR1C11645ChEMBL, NPASS
TAR_EXP_000122ENSG00000169239CA5B11238BindingDB, ChEMBL, NPASS
TAR_EXP_001690ENSG00000107159CA9768BindingDB, ChEMBL, NPASS
TAR_EXP_000743ENSG00000182782HCAR2338442BindingDB, ChEMBL, NPASS