IMPPAT Phytochemical information: 
(1S)-4-hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclopent-2-ene-1-carbonitrile
(1S)-4-hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclopent-2-ene-1-carbonitrile
Summary

SMILES: OCC1OC(O[C@]2(C#N)C=CC(C2)O)C(C(C1O)O)O
InChI: InChI=1S/C12H17NO7/c13-5-12(2-1-6(15)3-12)20-11-10(18)9(17)8(16)7(4-14)19-11/h1-2,6-11,14-18H,3-4H2/t6?,7?,8?,9?,10?,11?,12-/m1/s1
InChIKey: JRCWYCAEAZEYNW-WTVGNPTKSA-N
DeepSMILES: OCCOCO[C@]C#N))C=CCC5)O))))))CCC6O))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; COC(OC)C; 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:
epivolkenin
External chemical identifiers:
CID:CID_5459113
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1S)-4-hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclopent-2-ene-1-carbonitrile
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 287.27
Log P RDKit -2.61
Topological polar surface area (Å2) RDKit 143.4
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.58
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
(1S)-4-hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclopent-2-ene-1-carbonitrile
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 0.36
(1S)-4-hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclopent-2-ene-1-carbonitrile
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 -9.69
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