IMPPAT Phytochemical information: 
Vanillic acid
Vanillic acid
Summary

SMILES: COc1cc(ccc1O)C(=O)O
InChI: InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
InChIKey: WKOLLVMJNQIZCI-UHFFFAOYSA-N
DeepSMILES: COcccccc6O))))C=O)O
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: cOC; cO; cC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Benzoic acids and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenolic acids (C6-C1)|Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acids and derivatives|Simple phenolic acids
Synonymous chemical names:
vanillic-acid, vanillic acid, Vanillic acid, vanillic, 4-hydroxy-3-methoxy-benzoic-acid, 4-hydroxy-3-methoxybenzoic acid
External chemical identifiers:
CID:CID_8468; ChEMBL:CHEMBL120568; ChEBI:CHEBI:30816; ZINC:ZINC000000338275; FDASRS:GM8Q3JM2Y8; SureChEMBL:SCHEMBL26179; MolPort-000-871-610
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Vanillic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 168.15
Log P RDKit 1.1
Topological polar surface area (Å2) RDKit 66.76
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 8
Number of heavy atoms RDKit 12
Number of heteroatoms RDKit 4
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 7
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.12
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
Vanillic 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 0.693399
Vanillic 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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.31
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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
Vanillic 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_000770ENSG00000171105INSR3643BindingDB
TAR_EXP_001230ENSG00000100030MAPK15594BindingDB
TAR_EXP_000439ENSG00000068078FGFR32261BindingDB
TAR_EXP_001222ENSG00000147099HDAC855869ChEMBL
TAR_EXP_001078ENSG00000113721PDGFRB5159BindingDB
TAR_EXP_001075ENSG00000061273HDAC751564ChEMBL
TAR_EXP_001074ENSG00000134853PDGFRA5156BindingDB
TAR_EXP_000994ENSG00000162733DDR24921BindingDB
TAR_EXP_000874ENSG00000105976MET4233BindingDB
TAR_EXP_001363ENSG00000165731RET5979BindingDB
TAR_EXP_000841ENSG00000062524LTK4058BindingDB
TAR_EXP_000750ENSG00000140443IGF1R3480BindingDB
TAR_EXP_000685ENSG00000196591HDAC23066ChEMBL
TAR_EXP_000684ENSG00000116478HDAC13065ChEMBL
TAR_EXP_000683ENSG00000197386HTT3064NPASS
TAR_EXP_000509ENSG00000097007ABL125BindingDB
TAR_EXP_000498ENSG00000171094ALK238BindingDB
TAR_EXP_000461ENSG00000102755FLT12321BindingDB
TAR_EXP_000810ENSG00000128052KDR3791BindingDB
TAR_EXP_001625ENSG00000137364TPMT7172NPASS
TAR_EXP_001648ENSG00000092445TYRO37301BindingDB
TAR_EXP_001726ENSG00000163517HDAC1179885ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL, NPASS
TAR_EXP_000438ENSG00000077782FGFR12260BindingDB
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000005ENSG00000108840HDAC510014ChEMBL
TAR_EXP_000031ENSG00000135446CDK41019BindingDB
TAR_EXP_000034ENSG00000105810CDK61021BindingDB
TAR_EXP_000054ENSG00000153208MERTK10461BindingDB
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000166ENSG00000163297ANTXR2118429NPASS
TAR_EXP_000348ENSG00000146648EGFR1956BindingDB
TAR_EXP_000353ENSG00000142627EPHA21969BindingDB
TAR_EXP_000388ENSG00000178568ERBB42066BindingDB
TAR_EXP_001930ENSG00000170312CDK1983BindingDB
TAR_EXP_001928ENSG00000068024HDAC49759ChEMBL
TAR_EXP_001926ENSG00000048052HDAC99734ChEMBL
TAR_EXP_001831ENSG00000171720HDAC38841ChEMBL
TAR_EXP_001761ENSG00000100429HDAC1083933ChEMBL, NPASS
TAR_EXP_000456ENSG00000085662AKR1B1231ChEMBL, NPASS
TAR_EXP_000440ENSG00000066468FGFR22263BindingDB