IMPPAT Phytochemical information: 
Isocucurbitacin B
Isocucurbitacin B
Summary

SMILES: CC(=O)OC(/C=C/C(=O)[C@@]([C@H]1[C@H](O)C[C@@]2([C@]1(C)CC(=O)[C@@]1([C@H]2CC=C2[C@H]1CC(=O)[C@H](C2(C)C)O)C)C)(O)C)(C)C
InChI: InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19,21-22,25-26,35,38-39H,11,14-16H2,1-9H3/b13-12+/t19-,21-,22+,25+,26-,29+,30-,31+,32+/m1/s1
InChIKey: WTBZNVRBNJWSPF-DZEACCAPSA-N
DeepSMILES: CC=O)OC/C=C/C=O)[C@@][C@H][C@H]O)C[C@@][C@]5C)CC=O)[C@@][C@H]6CC=C[C@H]6CC=O)[C@H]C6C)C))O)))))))))C)))))C)))))O)C)))))C)C
Scaffold Graph/Node/Bond level: O=C1CCC2=CCC3C4CCCC4CC(=O)C3C2C1
Scaffold Graph/Node level: OC1CCC2CCC3C4CCCC4CC(O)C3C2C1
Scaffold Graph level: CC1CCC2CCC3C4CCCC4CC(C)C3C2C1
Functional groups: CO; COC(C)=O; C/C=C/C(C)=O; CC(=O)C; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Cucurbitacins
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Cucurbitane triterpenoids
Synonymous chemical names:
isocucurbitacin b
External chemical identifiers:
CID:CID_5352014; ZINC:ZINC000004962909; SureChEMBL:SCHEMBL10307348
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Isocucurbitacin B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 558.71
Log P RDKit 3.5
Topological polar surface area (Å2) RDKit 138.2
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 40
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.28
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 24
Shape complexity RDKit 0.75
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Isocucurbitacin B
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 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.26
Isocucurbitacin B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.92
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes