IMPPAT Phytochemical information: 
Artepillin A
Artepillin A
Summary

SMILES: OCC(C1Cc2c(O1)c(CC=C(C)C)cc(c2)/C=C/C(=O)O)C
InChI: InChI=1S/C19H24O4/c1-12(2)4-6-15-8-14(5-7-18(21)22)9-16-10-17(13(3)11-20)23-19(15)16/h4-5,7-9,13,17,20H,6,10-11H2,1-3H3,(H,21,22)/b7-5+
InChIKey: IJQHPPUNNDWTDR-FNORWQNLSA-N
DeepSMILES: OCCCCccO5)cCC=CC)C))))ccc6)/C=C/C=O)O)))))))))))C
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CCO2
Scaffold Graph/Node level: C1CCC2OCCC2C1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: CO; cOC; CC=C(C)C; c/C=C/C(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Cinnamic acids and derivatives
ClassyFire Subclass: Cinnamic acids
NP Classifier Biosynthetic pathway: Terpenoids
Synonymous chemical names:
artepillin a
External chemical identifiers:
CID:CID_21626500; SureChEMBL:SCHEMBL5790015
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Artepillin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 316.4
Log P RDKit 3.23
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 19
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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
Artepillin A
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.62
Artepillin A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.40
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No