IMPPAT Phytochemical information: 
2-Butenoic acid, 2-methyl-, (2R,3aS,5R,6aR,6bR,7S,9R,9aR,11aR,11bR,12S,12aR)-7,9-bis(acetyloxy)-2-(3-furanyl)-3,3a,6,6a,6b,7,8,9,9a,10,11a,11b,12,12a-tetradecahydro-5-hydroxy-1,6b,9a,12a-tetramethyl-2H,5H-cyclopent(a)isobenzofuro(7,1-gh)(3)benzoxepin-12-yl ester, (2E)-
2-Butenoic acid, 2-methyl-, (2R,3aS,5R,6aR,6bR,7S,9R,9aR,11aR,11bR,12S,12aR)-7,9-bis(acetyloxy)-2-(3-furanyl)-3,3a,6,6a,6b,7,8,9,9a,10,11a,11b,12,12a-tetradecahydro-5-hydroxy-1,6b,9a,12a-tetramethyl-2H,5H-cyclopent(a)isobenzofuro(7,1-gh)(3)benzoxepin-12-yl ester, (2E)-
Summary

SMILES: C/C=C(/C(=O)O[C@@H]1[C@@H]2OC[C@]3([C@H]2[C@](C2[C@]1(C)C1=C(C)[C@@H](CC1OC(C2)O)c1ccco1)(C)C(CC3OC(=O)C)OC(=O)C)C)\C
InChI: InChI=1S/C35H46O10/c1-9-17(2)32(39)45-31-29-30-33(6,16-41-29)25(42-19(4)36)15-26(43-20(5)37)34(30,7)24-14-27(38)44-23-13-21(22-11-10-12-40-22)18(3)28(23)35(24,31)8/h9-12,21,23-27,29-31,38H,13-16H2,1-8H3/b17-9+/t21-,23?,24?,25?,26?,27?,29-,30+,31-,33-,34+,35-/m1/s1
InChIKey: AMWGLRNNROPNBO-JKXNYECQSA-N
DeepSMILES: C/C=C/C=O)O[C@@H][C@@H]OC[C@][C@H]5[C@]C[C@]9C)C=CC)[C@@H]CC5OCC%10)O)))))cccco5))))))))))C)CCC6OC=O)C)))))OC=O)C))))))C))))))))\C
Scaffold Graph/Node/Bond level: C1=C2C(CC1c1ccco1)OCCC1C2CC2OCC3CCCC1C32
Scaffold Graph/Node level: C1COC(C2CC3OCCC4C(CC5OCC6CCCC4C65)C3C2)C1
Scaffold Graph level: C1CCC(C2CC3CCCC4C(CC5CCC6CCCC4C65)C3C2)C1
Functional groups: C/C=C(\C)C(=O)OC; COC(C)=O; COC; CC(=C(C)C)C; COC(O)C; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Tricarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Limonoids
Synonymous chemical names:
nimbolinin b
External chemical identifiers:
CID:CID_6440564
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
2-Butenoic acid, 2-methyl-, (2R,3aS,5R,6aR,6bR,7S,9R,9aR,11aR,11bR,12S,12aR)-7,9-bis(acetyloxy)-2-(3-furanyl)-3,3a,6,6a,6b,7,8,9,9a,10,11a,11b,12,12a-tetradecahydro-5-hydroxy-1,6b,9a,12a-tetramethyl-2H,5H-cyclopent(a)isobenzofuro(7,1-gh)(3)benzoxepin-12-yl ester, (2E)-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 626.74
Log P RDKit 5
Topological polar surface area (Å2) RDKit 130.73
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 35
Number of heavy atoms RDKit 45
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.34
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 24
Shape complexity RDKit 0.69
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
2-Butenoic acid, 2-methyl-, (2R,3aS,5R,6aR,6bR,7S,9R,9aR,11aR,11bR,12S,12aR)-7,9-bis(acetyloxy)-2-(3-furanyl)-3,3a,6,6a,6b,7,8,9,9a,10,11a,11b,12,12a-tetradecahydro-5-hydroxy-1,6b,9a,12a-tetramethyl-2H,5H-cyclopent(a)isobenzofuro(7,1-gh)(3)benzoxepin-12-yl ester, (2E)-
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 Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.21
2-Butenoic acid, 2-methyl-, (2R,3aS,5R,6aR,6bR,7S,9R,9aR,11aR,11bR,12S,12aR)-7,9-bis(acetyloxy)-2-(3-furanyl)-3,3a,6,6a,6b,7,8,9,9a,10,11a,11b,12,12a-tetradecahydro-5-hydroxy-1,6b,9a,12a-tetramethyl-2H,5H-cyclopent(a)isobenzofuro(7,1-gh)(3)benzoxepin-12-yl ester, (2E)-
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 -7.38
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
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