IMPPAT Phytochemical information: 
Lupinol B
Lupinol B
Summary

SMILES: CO[C@]12[C@H](Oc3c(C1=O)c(O)c(c(c3)O)CC=C(C)C)Oc1c2ccc(c1)O
InChI: InChI=1S/C21H20O7/c1-10(2)4-6-12-14(23)9-16-17(18(12)24)19(25)21(26-3)13-7-5-11(22)8-15(13)27-20(21)28-16/h4-5,7-9,20,22-24H,6H2,1-3H3/t20-,21-/m0/s1
InChIKey: QCGOUNPNJCPCKS-SFTDATJTSA-N
DeepSMILES: CO[C@][C@H]OccC6=O))cO)ccc6)O))CC=CC)C)))))))))Occ5cccc6)O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2OC2Oc3ccccc3C12
Scaffold Graph/Node level: OC1C2CCCCC2OC2OC3CCCCC3C21
Scaffold Graph level: CC1C2CCCCC2CC2CC3CCCCC3C21
Functional groups: COC; cO[C@@H](C)Oc; cC(=O)C; cO; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Coumaronochromones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Coumaronochromones
Synonymous chemical names:
lupinol b, Lupinol B
External chemical identifiers:
CID:CID_101609099
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Lupinol B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 384.38
Log P RDKit 3.15
Topological polar surface area (Å2) RDKit 105.45
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 28
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 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 3
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 B
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 0.7
Lupinol B
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 High
Log Kp (Skin permeation, cm/s) SwissADME -5.69
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 Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No