IMPPAT Phytochemical information: 
[(1S,2R,4R,5R,6S,8R,10S,11S,12R,14R,15R,16S,19S,21R)-4,16-diacetyloxy-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-21-yl] acetate
[(1S,2R,4R,5R,6S,8R,10S,11S,12R,14R,15R,16S,19S,21R)-4,16-diacetyloxy-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-21-yl] acetate
Summary

SMILES: CC(=O)O[C@@H]1OC[C@@]23[C@H]([C@]1(C)[C@H](OC(=O)C)C[C@@H]2O)C[C@H]([C@@]1([C@@H]3C(=O)[C@H](OC(=O)C)[C@@]2([C@]31O[C@@H]3C[C@H]2c1ccoc1)C)C)O
InChI: InChI=1S/C32H40O12/c1-14(33)41-22-11-21(37)31-13-40-27(43-16(3)35)28(22,4)19(31)10-20(36)30(6)25(31)24(38)26(42-15(2)34)29(5)18(17-7-8-39-12-17)9-23-32(29,30)44-23/h7-8,12,18-23,25-27,36-37H,9-11,13H2,1-6H3/t18-,19-,20+,21-,22+,23+,25-,26-,27-,28+,29+,30+,31+,32+/m0/s1
InChIKey: JSPJNBZMTOABAW-AQFIFPCESA-N
DeepSMILES: CC=O)O[C@@H]OC[C@@][C@H][C@]6C)[C@H]OC=O)C)))C[C@@H]6O)))))C[C@H][C@@][C@@H]6C=O)[C@H]OC=O)C)))[C@@][C@@]6O[C@@H]3C[C@H]6cccoc5))))))))))C)))))C))O
Scaffold Graph/Node/Bond level: O=C1CC2C(c3ccoc3)CC3OC32C2CCC3C4CCCC3(COC4)C12
Scaffold Graph/Node level: OC1CC2C(C3CCOC3)CC3OC32C2CCC3C4CCCC3(COC4)C12
Scaffold Graph level: CC1CC2C(C3CCCC3)CC3CC32C2CCC3C4CCCC3(CCC4)C12
Functional groups: CO[C@@H](OC(C)=O)C; CC(=O)OC; CO; CC(=O)C; C[C@H]1O[C@@]1(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:
sendanin
External chemical identifiers:
CID:CID_5464491; ZINC:ZINC000255221738
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1S,2R,4R,5R,6S,8R,10S,11S,12R,14R,15R,16S,19S,21R)-4,16-diacetyloxy-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-21-yl] acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 616.66
Log P RDKit 2.04
Topological polar surface area (Å2) RDKit 171.33
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 44
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 14
Stereochemical complexity RDKit 0.44
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 7
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
[(1S,2R,4R,5R,6S,8R,10S,11S,12R,14R,15R,16S,19S,21R)-4,16-diacetyloxy-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-21-yl] acetate
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 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.287005
[(1S,2R,4R,5R,6S,8R,10S,11S,12R,14R,15R,16S,19S,21R)-4,16-diacetyloxy-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-21-yl] acetate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -9.17
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes