IMPPAT Phytochemical information: 
Lupinisol C

Lupinisol C
Summary

SMILES: CC(=CCc1c(O)cc2c(c1O)c(=O)c(co2)c1ccc(c(c1O)CC(C(=C)C)O)O)C
InChI: InChI=1S/C25H26O7/c1-12(2)5-6-15-20(28)10-21-22(24(15)30)25(31)17(11-32-21)14-7-8-18(26)16(23(14)29)9-19(27)13(3)4/h5,7-8,10-11,19,26-30H,3,6,9H2,1-2,4H3
InChIKey: YGIMNZIIYOGVNP-UHFFFAOYSA-N
DeepSMILES: CC=CCccO)cccc6O))c=O)cco6))cccccc6O))CCC=C)C))O))))O))))))))))))))C
Scaffold Graph/Node/Bond level: O=c1c(-c2ccccc2)coc2ccccc12
Scaffold Graph/Node level: OC1C(C2CCCCC2)COC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CCC1C1CCCCC1
Functional groups: CC=C(C)C; cO; c=O; coc; C=C(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Isoflavans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavones
Synonymous chemical names:
Lupinisol C, lupinisol c
External chemical identifiers:
CID:CID_14237670
Chemical structure download


Lupinisol C
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 438.48
Log P RDKit 4.27
Topological polar surface area (Å2) RDKit 131.36
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.04
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.24
Number of rotatable bonds RDKit 6
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 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
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 3


Lupinisol C
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.36


Lupinisol C
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 No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -5.34
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No