IMPPAT Phytochemical information: 
(1R,2S,3S)-2,3-dihydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclopentane-1-carbonitrile
(1R,2S,3S)-2,3-dihydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclopentane-1-carbonitrile
Summary

SMILES: OC[C@H]1O[C@H](O[C@@]2(C#N)CC[C@@H]([C@@H]2O)O)[C@@H]([C@H]([C@H]1O)O)O
InChI: InChI=1S/C12H19NO8/c13-4-12(2-1-5(15)10(12)19)21-11-9(18)8(17)7(16)6(3-14)20-11/h5-11,14-19H,1-3H2/t5-,6+,7-,8-,9+,10-,11+,12+/m0/s1
InChIKey: GVFAYMLCFVOLFT-VVKLXUGQSA-N
DeepSMILES: OC[C@H]O[C@H]O[C@@]C#N))CC[C@@H][C@@H]5O))O))))))[C@@H][C@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: C1CCC(OC2CCCC2)OC1
Scaffold Graph/Node level: C1CCC(OC2CCCC2)OC1
Scaffold Graph level: C1CCC(CC2CCCC2)CC1
Functional groups: CO; CO[C@H](C)OC; CC#N
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
passiguatemalin
External chemical identifiers:
CID:CID_636565
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,2S,3S)-2,3-dihydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclopentane-1-carbonitrile
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 305.28
Log P RDKit -3.42
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 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 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 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
(1R,2S,3S)-2,3-dihydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclopentane-1-carbonitrile
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 0.31
(1R,2S,3S)-2,3-dihydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclopentane-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 -10.01
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