IMPPAT Phytochemical information: 
Vanillin
Vanillin
Summary

SMILES: COc1cc(C=O)ccc1O
InChI: InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
InChIKey: MWOOGOJBHIARFG-UHFFFAOYSA-N
DeepSMILES: COcccC=O))ccc6O
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: cOC; cO; cC=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenols
ClassyFire Subclass: Methoxyphenols
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:
vanillin, 4-hydroxy-3-methoxybenzaldehyde, Vanillic aldehyde, vanillin⁄, Vanillin, vanillic aldehyde, vanillin*
External chemical identifiers:
CID:CID_1183; ChEMBL:CHEMBL13883; ChEBI:CHEBI:18346; ZINC:ZINC000002567933; FDASRS:CHI530446X; SureChEMBL:SCHEMBL1213; MolPort-000-165-443
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Vanillin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 152.15
Log P RDKit 1.21
Topological polar surface area (Å2) RDKit 46.53
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 8
Number of heavy atoms RDKit 11
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 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
Vanillin
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 2
Ghose filter RDKit Failed
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 0.647744
Vanillin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.37
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
Vanillin
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_000896ENSG00000005381MPO4353ChEMBL
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000321ENSG00000183044ABAT18BindingDB, ChEMBL, NPASS
TAR_EXP_001162ENSG00000244122UGT1A754577ChEMBL, NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216ChEMBL, NPASS
TAR_EXP_000413ENSG00000117480FAAH2166NPASS
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_000739ENSG00000148680HTR73363ChEMBL, NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000295ENSG00000159640ACE1636ChEMBL, NPASS
TAR_EXP_000679ENSG00000244734HBB3043ChEMBL, NPASS
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_001079ENSG00000197323TRIM3351592ChEMBL, NPASS
TAR_EXP_000608ENSG00000115419GLS2744NPASS
TAR_EXP_000677ENSG00000206172HBA13039ChEMBL, NPASS
TAR_EXP_001942ENSG00000012504NR1H49971NPASS
TAR_EXP_001825ENSG00000122779TRIM248805ChEMBL, NPASS
TAR_EXP_001718ENSG00000112294ALDH5A17915BindingDB, ChEMBL, NPASS
TAR_EXP_001694ENSG00000151067CACNA1C775ChEMBL
TAR_EXP_001461ENSG00000186350RXRA6256NPASS
TAR_EXP_001228ENSG00000253729PRKDC5591BindingDB, NPASS
TAR_EXP_001160ENSG00000242515UGT1A1054575ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_001165ENSG00000241119UGT1A954600ChEMBL, NPASS
TAR_EXP_001163ENSG00000167165UGT1A654578ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_000096ENSG00000173610UGT2A110941ChEMBL