IMPPAT Phytochemical information: 
Barbacarpan

Barbacarpan
Summary

SMILES: CC(=C)C1Oc2c(C1)c1O[C@@H]3[C@H](c1cc2)COc1c3ccc(c1)O
InChI: InChI=1S/C20H18O4/c1-10(2)17-8-14-16(23-17)6-5-12-15-9-22-18-7-11(21)3-4-13(18)20(15)24-19(12)14/h3-7,15,17,20-21H,1,8-9H2,2H3/t15-,17?,20-/m0/s1
InChIKey: MVIZRSMIUOYJNY-NUSPTKLCSA-N
DeepSMILES: CC=C)COccC5)cO[C@@H][C@H]c5cc9)))COcc6cccc6)O
Scaffold Graph/Node/Bond level: c1ccc2c(c1)OCC1c3ccc4c(c3OC21)CCO4
Scaffold Graph/Node level: C1CCC2C(C1)OCC1C3CCC4OCCC4C3OC21
Scaffold Graph level: C1CCC2C(C1)CCC1C2CC2C3CCCC3CCC21
Functional groups: C=C(C)C; cOC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Furanoisoflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Pterocarpan
Synonymous chemical names:
barbacarpan
External chemical identifiers:
CID:CID_91895478; MolPort-035-706-549
Chemical structure download


Barbacarpan
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 322.36
Log P RDKit 3.88
Topological polar surface area (Å2) RDKit 47.92
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.3
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
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 5


Barbacarpan
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 0.81


Barbacarpan
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.46
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes