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-2
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-2
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; CC(C)=C(C)C; COC; COC(C)=O; COC(C)O; 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: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-2
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-2
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 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.2062
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-2
ADMET 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 0.0
Number of Brenk structural alerts SwissADME 3.0
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