IMPPAT Phytochemical information: 
(1R,2R,5R,6S,10R,11S,12R,15R,16R,18S,19R)-6-(furan-3-yl)-11,16,18-trihydroxy-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.02,10.05,9.015,19]nonadec-8-en-4-one
(1R,2R,5R,6S,10R,11S,12R,15R,16R,18S,19R)-6-(furan-3-yl)-11,16,18-trihydroxy-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.02,10.05,9.015,19]nonadec-8-en-4-one
Summary

SMILES: O[C@H]1C[C@@H](O)[C@@]2([C@H]3[C@@]1(C)[C@H]1CC(=O)[C@]4(C(=CC[C@H]4c4ccoc4)[C@]1(C)[C@@H]([C@@H]3OC2)O)C)C
InChI: InChI=1S/C26H34O6/c1-23-12-32-20-21(23)26(4,19(29)10-17(23)27)16-9-18(28)24(2)14(13-7-8-31-11-13)5-6-15(24)25(16,3)22(20)30/h6-8,11,14,16-17,19-22,27,29-30H,5,9-10,12H2,1-4H3/t14-,16-,17+,19-,20+,21-,22+,23+,24+,25-,26-/m0/s1
InChIKey: MWPUYUVXTZFYJY-CINZLWFVSA-N
DeepSMILES: O[C@H]C[C@@H]O)[C@@][C@H][C@@]6C)[C@H]CC=O)[C@]C=CC[C@H]5cccoc5))))))))[C@]6C)[C@@H][C@@H]%10OC%13)))O))))C)))))))C
Scaffold Graph/Node/Bond level: O=C1CC2C(CC3OCC4CCCC2C43)C2=CCC(c3ccoc3)C12
Scaffold Graph/Node level: OC1CC2C(CC3OCC4CCCC2C43)C2CCC(C3CCOC3)C12
Scaffold Graph level: CC1CC2C(CC3CCC4CCCC2C43)C2CCC(C3CCCC3)C12
Functional groups: CO; CC(=O)C; CC=C(C)C; coc; 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:
nimbidinin
External chemical identifiers:
CID:CID_101306757
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,2R,5R,6S,10R,11S,12R,15R,16R,18S,19R)-6-(furan-3-yl)-11,16,18-trihydroxy-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.02,10.05,9.015,19]nonadec-8-en-4-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 442.55
Log P RDKit 2.82
Topological polar surface area (Å2) RDKit 100.13
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.42
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 19
Shape complexity RDKit 0.73
Number of rotatable bonds RDKit 1
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 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
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 6
(1R,2R,5R,6S,10R,11S,12R,15R,16R,18S,19R)-6-(furan-3-yl)-11,16,18-trihydroxy-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.02,10.05,9.015,19]nonadec-8-en-4-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.578584
(1R,2R,5R,6S,10R,11S,12R,15R,16R,18S,19R)-6-(furan-3-yl)-11,16,18-trihydroxy-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.02,10.05,9.015,19]nonadec-8-en-4-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.96
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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