IMPPAT Phytochemical information: 
Acetovanillone
Acetovanillone
Summary

SMILES: COc1cc(ccc1O)C(=O)C
InChI: InChI=1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3
InChIKey: DFYRUELUNQRZTB-UHFFFAOYSA-N
DeepSMILES: COcccccc6O))))C=O)C
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: cC(C)=O; cO; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbonyl compounds
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
Synonymous chemical names:
4-hydroxy-3-methoxyacetophenone, 4-hydroxy-3-methoxyacetophenone (apocyanin), 4-hydroxyl-3-methoxy-acetophenone, acetoguaiacone, acetovanillone, apocynin
External chemical identifiers:
CID:2214; ChEMBL:CHEMBL346919; ChEBI:2781; ZINC:ZINC000000162515; FDASRS:B6J7B9UDTR; SureChEMBL:SCHEMBL109514; MolPort-000-000-274
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Acetovanillone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 166.18
Log P RDKit 1.6
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 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 7
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.22
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
Acetovanillone
Drug-likeness properties
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 0.6786
Acetovanillone
ADMET 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 -6.95
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
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
Acetovanillone
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000220764DECR1901
ENSP00000263341IL1B722
ENSP00000268607MAP1LC3B800
ENSP00000281537TJP1800
ENSP00000289473NCF1910
ENSP00000307786CYCS818
ENSP00000312652LEP800
ENSP00000317997DUOX1855
ENSP00000322788MMP1800
ENSP00000339527FOXO3800
ENSP00000340913TRPC6822
ENSP00000343040HMGB1786
ENSP00000353874TLR9841
ENSP00000356438PTGS2846
ENSP00000361125VEGFA825
ENSP00000362057NOX1791
ENSP00000373487KRT18786
ENSP00000373691DUOX2848
ENSP00000380450NOXO1837
ENSP00000385269ELAVL1800
ENSP00000398698TNF745
ENSP00000417517841
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.