IMPPAT Phytochemical information: 
[(1R,2R,5R,6R,10R,11S,15R,16R,18S)-16,18-diacetyloxy-6-(furan-3-yl)-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.02,10.05,9.015,19]nonadec-8-en-11-yl] (E)-3-phenylprop-2-enoate
[(1R,2R,5R,6R,10R,11S,15R,16R,18S)-16,18-diacetyloxy-6-(furan-3-yl)-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.02,10.05,9.015,19]nonadec-8-en-11-yl] (E)-3-phenylprop-2-enoate
Summary

SMILES: O=C(O[C@@H]1C2OC[C@]3(C2[C@]([C@@H]2[C@]1(C)C1=CC[C@H]([C@]1(CC2)C)c1cocc1)(C)[C@H](C[C@H]3OC(=O)C)OC(=O)C)C)/C=C/c1ccccc1
InChI: InChI=1S/C39H46O8/c1-23(40)45-30-20-31(46-24(2)41)39(6)29-16-18-36(3)27(26-17-19-43-21-26)13-14-28(36)38(29,5)35(33-34(39)37(30,4)22-44-33)47-32(42)15-12-25-10-8-7-9-11-25/h7-12,14-15,17,19,21,27,29-31,33-35H,13,16,18,20,22H2,1-6H3/b15-12+/t27-,29-,30+,31-,33?,34?,35+,36+,37+,38-,39-/m0/s1
InChIKey: GQNAMBZGINRMBH-IBOKIDTJSA-N
DeepSMILES: O=CO[C@@H]COC[C@]C5[C@][C@@H][C@]9C)C=CC[C@H][C@]5CC9))C))ccocc5)))))))))))C)[C@H]C[C@H]6OC=O)C)))))OC=O)C))))))C)))))))/C=C/cccccc6
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1C2OCC3CCCC(C4CCC5C(=CCC5c5ccoc5)C41)C32
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1C2OCC3CCCC(C4CCC5C(C6CCOC6)CCC5C41)C32
Scaffold Graph level: CC(CCC1CCCCC1)CC1C2CCC3CCCC(C4CCC5C(C6CCCC6)CCC5C41)C32
Functional groups: c/C=C/C(=O)OC; CC(=O)OC; COC; CC=C(C)C; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Limonoids
Synonymous chemical names:
nimbolin a
External chemical identifiers:
CID:CID_101650373
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1R,2R,5R,6R,10R,11S,15R,16R,18S)-16,18-diacetyloxy-6-(furan-3-yl)-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.02,10.05,9.015,19]nonadec-8-en-11-yl] (E)-3-phenylprop-2-enoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 642.79
Log P RDKit 7.05
Topological polar surface area (Å2) RDKit 101.27
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 39
Number of heavy atoms RDKit 47
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.28
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 22
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
[(1R,2R,5R,6R,10R,11S,15R,16R,18S)-16,18-diacetyloxy-6-(furan-3-yl)-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.02,10.05,9.015,19]nonadec-8-en-11-yl] (E)-3-phenylprop-2-enoate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
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 0.143069
[(1R,2R,5R,6R,10R,11S,15R,16R,18S)-16,18-diacetyloxy-6-(furan-3-yl)-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.02,10.05,9.015,19]nonadec-8-en-11-yl] (E)-3-phenylprop-2-enoate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -5.31
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes