IMPPAT Phytochemical information: 
2-Cyclopentene-1-carbonitrile, 1-(beta-D-glucopyranosyloxy)-4,5-dihydroxy-,(1alpha,4alpha,5beta)-
2-Cyclopentene-1-carbonitrile, 1-(beta-D-glucopyranosyloxy)-4,5-dihydroxy-,(1alpha,4alpha,5beta)-
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@]2(C#N)C=C[C@@H]([C@H]2O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C12H17NO8/c13-4-12(2-1-5(15)10(12)19)21-11-9(18)8(17)7(16)6(3-14)20-11/h1-2,5-11,14-19H,3H2/t5-,6+,7+,8-,9+,10+,11-,12+/m0/s1
InChIKey: HASDUOHKNMHNJA-GDLVSTOPSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@]C#N))C=C[C@@H][C@H]5O))O))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=CC(OC2CCCCO2)CC1
Scaffold Graph/Node level: C1CCC(OC2CCCC2)OC1
Scaffold Graph level: C1CCC(CC2CCCC2)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:
gynocardin, Gynocardin
External chemical identifiers:
CID:CID_441466; ChEBI:CHEBI:5578; ZINC:ZINC000004097526
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
2-Cyclopentene-1-carbonitrile, 1-(beta-D-glucopyranosyloxy)-4,5-dihydroxy-,(1alpha,4alpha,5beta)-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 303.27
Log P RDKit -3.64
Topological polar surface area (Å2) RDKit 163.63
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 6
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 8
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 9
Shape complexity RDKit 0.82
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 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
2-Cyclopentene-1-carbonitrile, 1-(beta-D-glucopyranosyloxy)-4,5-dihydroxy-,(1alpha,4alpha,5beta)-
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 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 0.29
2-Cyclopentene-1-carbonitrile, 1-(beta-D-glucopyranosyloxy)-4,5-dihydroxy-,(1alpha,4alpha,5beta)-
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 -10.09
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