IMPPAT Phytochemical information: 
Coleoside B
Coleoside B
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccccc2)[C@]([C@H]([C@]1(O)C(C)C)O)(O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C21H32O12/c1-10(2)20(28)13(9-23)32-19(30-11-6-4-3-5-7-11)21(29,18(20)27)33-17-16(26)15(25)14(24)12(8-22)31-17/h3-7,10,12-19,22-29H,8-9H2,1-2H3/t12-,13-,14-,15+,16-,17+,18+,19-,20+,21-/m1/s1
InChIKey: CLEXUMAQDPYDCU-UTCUZKGZSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6)))))))[C@][C@H][C@]6O)CC)C)))O))O)O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: c1ccc(OC2OCCCC2OC2CCCCO2)cc1
Scaffold Graph/Node level: C1CCC(OC2OCCCC2OC2CCCCO2)CC1
Scaffold Graph level: C1CCC(CC2CCCCC2CC2CCCCC2)CC1
Functional groups: CO; cO[C@H](OC)[C@](O)(O[C@@H](C)OC)C
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: Terpenoids
Synonymous chemical names:
coleoside b
External chemical identifiers:
CID:CID_179289
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Coleoside B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 476.48
Log P RDKit -2.96
Topological polar surface area (Å2) RDKit 198.76
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.48
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.71
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Coleoside B
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 1
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 0.19
Coleoside B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.24
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 No