IMPPAT Phytochemical information: 
Limonin 17-beta-D-glucopyranoside
Limonin 17-beta-D-glucopyranoside
Summary

SMILES: OC[C@H]1O[C@@H](O[C@H]([C@]2(C)CC[C@H]3[C@@]([C@@]42O[C@@H]4C(=O)O)(C)C(=O)C[C@@H]2[C@]43COC(=O)C[C@@H]4OC2(C)C)c2cocc2)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C32H42O14/c1-28(2)17-9-18(34)30(4)16(31(17)13-42-20(35)10-19(31)45-28)5-7-29(3,32(30)25(46-32)26(39)40)24(14-6-8-41-12-14)44-27-23(38)22(37)21(36)15(11-33)43-27/h6,8,12,15-17,19,21-25,27,33,36-38H,5,7,9-11,13H2,1-4H3,(H,39,40)/t15-,16+,17+,19+,21-,22+,23-,24+,25-,27+,29+,30+,31-,32-/m1/s1
InChIKey: FYIKIBQJAJRKQM-WNCNYDOCSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@H][C@]C)CC[C@H][C@@][C@]6O[C@@H]3C=O)O)))))C)C=O)C[C@@H][C@@]6COC=O)C[C@@H]6OC9C)C)))))))))))))))))ccocc5)))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1CC2OCC3CC(=O)C4C(CCC(C(OC5CCCCO5)c5ccoc5)C45CO5)C32CO1
Scaffold Graph/Node level: OC1CC2OCC3CC(O)C4C(CCC(C(OC5CCCCO5)C5CCOC5)C45CO5)C32CO1
Scaffold Graph level: CC1CCC23C(CCC2CC(C)C2C3CCC(C(CC3CCCCC3)C3CCCC3)C23CC3)C1
Functional groups: CO; CO[C@@H](C)OC; C[C@]1(C)O[C@@H]1C(=O)O; CC(=O)C; COC(=O)C; COC; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Limonoids
Synonymous chemical names:
17-β-d-glucopyranosides of limonin, limonin-17-beta-d-glucopyranoside, limonin-17beta-d-glucoside
External chemical identifiers:
CID:CID_24820753; ChEBI:CHEBI:16063; ZINC:ZINC000087493118; FDASRS:9553Q8Z7PF
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Limonin 17-beta-D-glucopyranoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 650.67
Log P RDKit 0.48
Topological polar surface area (Å2) RDKit 214.95
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 46
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 14
Stereochemical complexity RDKit 0.44
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 0.78
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Limonin 17-beta-D-glucopyranoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.21
Limonin 17-beta-D-glucopyranoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.70
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