IMPPAT Phytochemical information: 
Spirasineol B
Spirasineol B
Summary

SMILES: COc1cc(O)c2-c3ccc4c(c3CCc2c1Cc1ccc(cc1)O)CCC(O4)(C)C
InChI: InChI=1S/C27H28O4/c1-27(2)13-12-19-18-8-9-21-22(14-16-4-6-17(28)7-5-16)25(30-3)15-23(29)26(21)20(18)10-11-24(19)31-27/h4-7,10-11,15,28-29H,8-9,12-14H2,1-3H3
InChIKey: QIXBWUHRQJSXBR-UHFFFAOYSA-N
DeepSMILES: COcccO)c-cccccc6CCc%10c%14Ccccccc6))O)))))))))))CCCO6)C)C
Scaffold Graph/Node/Bond level: c1ccc(Cc2cccc3c2CCc2c-3ccc3c2CCCO3)cc1
Scaffold Graph/Node level: C1CCC(CC2CCCC3C2CCC2C4CCCOC4CCC32)CC1
Scaffold Graph level: C1CCC(CC2CCCC3C2CCC2C4CCCCC4CCC23)CC1
Functional groups: cO; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Naphthopyrans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenanthrenoids
NP Classifier Class: Phenanthrenes
Synonymous chemical names:
spirasineol b, Spirasineol B
External chemical identifiers:
CID:CID_14583242; ZINC:ZINC000014713481
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Spirasineol B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 416.52
Log P RDKit 5.57
Topological polar surface area (Å2) RDKit 58.92
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.33
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
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
Spirasineol B
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 0.59
Spirasineol B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.58
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes