IMPPAT Phytochemical information: 
Pisatoside

Pisatoside
Summary

SMILES: OCC1OC(OC2C=CNC2=O)C(C(C1O)O)O
InChI: InChI=1S/C10H15NO7/c12-3-5-6(13)7(14)8(15)10(18-5)17-4-1-2-11-9(4)16/h1-2,4-8,10,12-15H,3H2,(H,11,16)
InChIKey: FHWQHJHJIXDREE-UHFFFAOYSA-N
DeepSMILES: OCCOCOCC=CNC5=O)))))))CCC6O))O))O
Scaffold Graph/Node/Bond level: O=C1NC=CC1OC1CCCCO1
Scaffold Graph/Node level: OC1NCCC1OC1CCCCO1
Scaffold Graph level: CC1CCCC1CC1CCCCC1
Functional groups: CO; COC(OC)C; O=C1CC=CN1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Amino acids and Peptides
Synonymous chemical names:
pisatoside, Pisatoside
External chemical identifiers:
CID:CID_12314351
Chemical structure download


Pisatoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 261.23
Log P RDKit -3.19
Topological polar surface area (Å2) RDKit 128.48
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 18
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.6
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Pisatoside
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 Good
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 0.36


Pisatoside
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 -9.67
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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