IMPPAT Phytochemical information: 
3-(3,4-Dihydroxyphenyl)-2-oxopropyl caffeate
3-(3,4-Dihydroxyphenyl)-2-oxopropyl caffeate
Summary

SMILES: O=C(/C=C/c1ccc(c(c1)O)O)OCC(=O)Cc1ccc(c(c1)O)O
InChI: InChI=1S/C18H16O7/c19-13(7-12-2-5-15(21)17(23)9-12)10-25-18(24)6-3-11-1-4-14(20)16(22)8-11/h1-6,8-9,20-23H,7,10H2/b6-3+
InChIKey: VMNHBRAHVFOYGK-ZZXKWVIFSA-N
DeepSMILES: O=C/C=C/cccccc6)O))O)))))))OCC=O)Ccccccc6)O))O
Scaffold Graph/Node/Bond level: O=C(COC(=O)C=Cc1ccccc1)Cc1ccccc1
Scaffold Graph/Node level: OC(COC(O)CCC1CCCCC1)CC1CCCCC1
Scaffold Graph level: CC(CCC(C)CC1CCCCC1)CCC1CCCCC1
Functional groups: c/C=C/C(=O)OC; cO; CC(C)=O
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:
petasiphenol
External chemical identifiers:
CID:CID_6438779
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
3-(3,4-Dihydroxyphenyl)-2-oxopropyl caffeate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 344.32
Log P RDKit 1.88
Topological polar surface area (Å2) RDKit 124.29
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 7
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 16
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.11
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2
3-(3,4-Dihydroxyphenyl)-2-oxopropyl caffeate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.36
3-(3,4-Dihydroxyphenyl)-2-oxopropyl caffeate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -6.89
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
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