IMPPAT Phytochemical information: 
Lupinol A
Lupinol A
Summary

SMILES: CC(=CCc1c(O)cc2c(c1O)C(=O)[C@@]1([C@H](O2)Oc2c1ccc(c2CC=C(C)C)O)O)C
InChI: InChI=1S/C25H26O7/c1-12(2)5-7-14-18(27)11-19-20(21(14)28)23(29)25(30)16-9-10-17(26)15(8-6-13(3)4)22(16)32-24(25)31-19/h5-6,9-11,24,26-28,30H,7-8H2,1-4H3/t24-,25+/m1/s1
InChIKey: PZMHPFDAYXPEDT-RPBOFIJWSA-N
DeepSMILES: CC=CCccO)cccc6O))C=O)[C@@][C@H]O6)Occ5cccc6CC=CC)C)))))O))))))))O))))))))))C
Scaffold Graph/Node/Bond level: O=C1c2ccccc2OC2Oc3ccccc3C12
Scaffold Graph/Node level: OC1C2CCCCC2OC2OC3CCCCC3C21
Scaffold Graph level: CC1C2CCCCC2CC2CC3CCCCC3C21
Functional groups: CC=C(C)C; cO; cC(=O)C; cO[C@@H](C)Oc; 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: Coumaronochromones
Synonymous chemical names:
lupinol a, Lupinol A
External chemical identifiers:
CID:CID_101608758
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Lupinol A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 438.48
Log P RDKit 4
Topological polar surface area (Å2) RDKit 116.45
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
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 2
Stereochemical complexity RDKit 0.08
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4
Lupinol 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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.53
Lupinol A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.03
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