IMPPAT Phytochemical information: 
Swietenolide-3-acetate
Swietenolide-3-acetate
Summary

SMILES: COC(=O)C([C@H]1C(C)(C)[C@@H](OC(=O)C)[C@H]2C(=O)[C@]1(C)C1CC[C@@]3(C(=C1C2)CC(=O)O[C@H]3c1ccoc1)C)O
InChI: InChI=1S/C29H36O9/c1-14(30)37-25-17-11-16-18(29(5,23(17)33)22(27(25,2)3)21(32)26(34)35-6)7-9-28(4)19(16)12-20(31)38-24(28)15-8-10-36-13-15/h8,10,13,17-18,21-22,24-25,32H,7,9,11-12H2,1-6H3/t17-,18?,21?,22+,24+,25+,28-,29-/m1/s1
InChIKey: LUDUHKJIKKLONS-AEXLHLMCSA-N
DeepSMILES: COC=O)C[C@H]CC)C)[C@@H]OC=O)C)))[C@H]C=O)[C@]6C)CCC[C@@]C=C6C%10))CC=O)O[C@H]6cccoc5))))))))))C)))))))))))O
Scaffold Graph/Node/Bond level: O=C1CC2=C3CC4CCCC(C4=O)C3CCC2C(c2ccoc2)O1
Scaffold Graph/Node level: OC1CC2C3CC4CCCC(C4O)C3CCC2C(C2CCOC2)O1
Scaffold Graph level: CC1CC(C2CCCC2)C2CCC3C4CCCC(CC3C2C1)C4C
Functional groups: COC(C)=O; coc; CO; CC(=O)OC; CC(=O)C; CC(=C(C)C)C
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:
swietenolide and its acetate
External chemical identifiers:
CID:CID_6708550; SureChEMBL:SCHEMBL12998447
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Swietenolide-3-acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 528.6
Log P RDKit 3.7
Topological polar surface area (Å2) RDKit 129.34
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.28
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 19
Shape complexity RDKit 0.66
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Swietenolide-3-acetate
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 0.353194
Swietenolide-3-acetate
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 High
Log Kp (Skin permeation, cm/s) SwissADME -7.92
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 No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes