IMPPAT Phytochemical information: 
Pilosanol C
Pilosanol C
Summary

SMILES: CCCC(=O)c1c(O)c(Cc2c(O)cc(c3c2O[C@@H]([C@H](C3)O)c2ccc(c(c2)O)O)O)c(c(c1OC)C)O
InChI: InChI=1S/C28H30O10/c1-4-5-18(30)23-25(36)16(24(35)12(2)26(23)37-3)9-14-19(31)11-20(32)15-10-22(34)27(38-28(14)15)13-6-7-17(29)21(33)8-13/h6-8,11,22,27,29,31-36H,4-5,9-10H2,1-3H3/t22-,27+/m0/s1
InChIKey: UYBMYSLWGHMDRE-WXVAWEFUSA-N
DeepSMILES: CCCC=O)ccO)cCccO)cccc6O[C@@H][C@H]C6)O))cccccc6)O))O)))))))))O))))))ccc6OC)))C))O
Scaffold Graph/Node/Bond level: c1ccc(Cc2cccc3c2OC(c2ccccc2)CC3)cc1
Scaffold Graph/Node level: C1CCC(CC2CCCC3CCC(C4CCCCC4)OC32)CC1
Scaffold Graph level: C1CCC(CC2CCCC3CCC(C4CCCCC4)CC32)CC1
Functional groups: cOC; cC(C)=O; cO; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavans
NP Classifier Biosynthetic pathway: Polyketides|Shikimates and Phenylpropanoids
NP Classifier Superclass: Phloroglucinols|Flavonoids
NP Classifier Class: Dimeric phloroglucinols|Flavan-3-ols
Synonymous chemical names:
pilosanol c+, pilosanol c
External chemical identifiers:
CID:CID_44257098; ChEMBL:CHEMBL3908614; ZINC:ZINC000014656300
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Pilosanol C
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 526.54
Log P RDKit 3.85
Topological polar surface area (Å2) RDKit 177.14
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
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
Pilosanol C
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.176699
Pilosanol C
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -6.65
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No