IMPPAT Phytochemical information: 
Crispioside B
Crispioside B
Summary

SMILES: OC[C@H]1O[C@@H](OC(=O)[C@]2(C)CCC[C@@]3([C@@H]2CC[C@]24[C@H]3CC[C@H](C2)[C@@](C4)(O)CO)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C26H42O9/c1-23-7-3-8-24(2,22(32)35-21-20(31)19(30)18(29)15(11-27)34-21)16(23)6-9-25-10-14(4-5-17(23)25)26(33,12-25)13-28/h14-21,27-31,33H,3-13H2,1-2H3/t14-,15-,16+,17+,18-,19+,20-,21+,23-,24-,25+,26+/m1/s1
InChIKey: XKXZHTWOHXJEOL-HMQRFDIMSA-N
DeepSMILES: OC[C@H]O[C@@H]OC=O)[C@]C)CCC[C@@][C@@H]6CC[C@][C@H]6CC[C@H]C6)[C@@]C7)O)CO)))))))))))C))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(OC1CCCCO1)C1CCCC2C1CCC13CCC(CCC21)C3
Scaffold Graph/Node level: OC(OC1CCCCO1)C1CCCC2C1CCC13CCC(CCC21)C3
Scaffold Graph level: CC(CC1CCCCC1)C1CCCC2C1CCC13CCC(CCC21)C3
Functional groups: CO; CO[C@@H](OC(C)=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Norkaurane diterpenoids
Synonymous chemical names:
crispioside b
External chemical identifiers:
CID:CID_23635315; ChEMBL:CHEMBL3357412; ZINC:ZINC000139456124
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Crispioside B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 498.61
Log P RDKit 0.47
Topological polar surface area (Å2) RDKit 156.91
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.46
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 0.96
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Crispioside B
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.303169
Crispioside B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -8.21
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