IMPPAT Phytochemical information: 
Passisuberosin

Passisuberosin
Summary

SMILES: OC[C@H]1O[C@@H](OC2(C#N)CC(C3C2O3)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C12H17NO8/c13-3-12(1-4(15)9-10(12)20-9)21-11-8(18)7(17)6(16)5(2-14)19-11/h4-11,14-18H,1-2H2/t4?,5-,6-,7+,8-,9?,10?,11+,12?/m1/s1
InChIKey: CDFHUZRDGPRGDK-LOUUASQKSA-N
DeepSMILES: OC[C@H]O[C@@H]OCC#N))CCCC5O3)))O)))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C1CCC(OC2CCC3OC23)OC1
Scaffold Graph/Node level: C1CCC(OC2CCC3OC23)OC1
Scaffold Graph level: C1CCC(CC2CCC3CC23)CC1
Functional groups: CO; CO[C@@H](C)OC; CC#N; CC1OC1C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
passisuberosin
External chemical identifiers:
CID:CID_184130
Chemical structure download


Passisuberosin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 303.27
Log P RDKit -3.4
Topological polar surface area (Å2) RDKit 155.93
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.75
Number of sp hybridized carbon atoms RDKit 1
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 1
Number of rotatable bonds RDKit 3
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 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Passisuberosin
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 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.34


Passisuberosin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.38
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