IMPPAT Phytochemical information: 
Passibiflorin
Passibiflorin
Summary

SMILES: OC[C@H]1O[C@@H](O[C@]2(C#N)C=C[C@@H](C2)O[C@@H]2O[C@H](C)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C18H27NO11/c1-7-10(21)12(23)14(25)16(27-7)28-8-2-3-18(4-8,6-19)30-17-15(26)13(24)11(22)9(5-20)29-17/h2-3,7-17,20-26H,4-5H2,1H3/t7-,8+,9-,10-,11-,12+,13+,14-,15-,16+,17+,18-/m1/s1
InChIKey: WSDAOKMCDDRLAL-OZCVSGGTSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@]C#N))C=C[C@@H]C5)O[C@@H]O[C@H]C)[C@H][C@@H][C@H]6O))O))O)))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=CC(OC2CCCCO2)CC1OC1CCCCO1
Scaffold Graph/Node level: C1CCC(OC2CCC(OC3CCCCO3)C2)OC1
Scaffold Graph level: C1CCC(CC2CCC(CC3CCCCC3)C2)CC1
Functional groups: CO; CO[C@@H](C)OC; CC#N; CC=CC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
passibiflorin
External chemical identifiers:
CID:CID_101182023
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Passibiflorin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 433.41
Log P RDKit -3.76
Topological polar surface area (Å2) RDKit 202.32
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.67
Number of sp hybridized carbon atoms RDKit 1
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.88
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Passibiflorin
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 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.20897
Passibiflorin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -11.36
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes