IMPPAT Phytochemical information: 
[(1S,2S,4R,5R,6R,9R,10S,11R,13R,14R,18S,20R)-4-acetyloxy-6-(furan-3-yl)-11,15,18-trihydroxy-5,10,14-trimethyl-3,8-dioxo-16-oxapentacyclo[12.3.3.01,13.02,10.05,9]icosan-20-yl] acetate
[(1S,2S,4R,5R,6R,9R,10S,11R,13R,14R,18S,20R)-4-acetyloxy-6-(furan-3-yl)-11,15,18-trihydroxy-5,10,14-trimethyl-3,8-dioxo-16-oxapentacyclo[12.3.3.01,13.02,10.05,9]icosan-20-yl] acetate
Summary

SMILES: CC(=O)O[C@H]1C(=O)[C@H]2[C@@]([C@@H]3[C@@]1(C)[C@H](CC3=O)c1ccoc1)(C)[C@H](O)C[C@@H]1[C@]32COC([C@]1([C@@H](C[C@@H]3O)OC(=O)C)C)O
InChI: InChI=1S/C30H38O11/c1-13(31)40-21-10-20(35)30-12-39-26(37)28(21,4)18(30)9-19(34)29(5)23-17(33)8-16(15-6-7-38-11-15)27(23,3)25(41-14(2)32)22(36)24(29)30/h6-7,11,16,18-21,23-26,34-35,37H,8-10,12H2,1-5H3/t16-,18+,19-,20+,21-,23+,24+,25+,26?,27-,28-,29+,30-/m1/s1
InChIKey: GEHGAWHOBGXBGC-QWPPDVJESA-N
DeepSMILES: CC=O)O[C@H]C=O)[C@H][C@@][C@@H][C@@]6C)[C@H]CC5=O)))cccoc5))))))))C)[C@H]O)C[C@@H][C@@]6COC[C@]6[C@@H]C[C@@H]8O)))OC=O)C))))C))O
Scaffold Graph/Node/Bond level: O=C1CC(c2ccoc2)C2CC(=O)C3C(CCC4C5CCCC43COC5)C12
Scaffold Graph/Node level: OC1CC(C2CCOC2)C2CC(O)C3C(CCC4C5CCCC43COC5)C12
Scaffold Graph level: CC1CC(C2CCCC2)C2CC(C)C3C(CCC4C5CCCC43CCC5)C12
Functional groups: CC(=O)OC; CO; CC(=O)C; COC(O)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:
isochuanliansu
External chemical identifiers:
CID:CID_101965424
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1S,2S,4R,5R,6R,9R,10S,11R,13R,14R,18S,20R)-4-acetyloxy-6-(furan-3-yl)-11,15,18-trihydroxy-5,10,14-trimethyl-3,8-dioxo-16-oxapentacyclo[12.3.3.01,13.02,10.05,9]icosan-20-yl] acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 574.62
Log P RDKit 1.51
Topological polar surface area (Å2) RDKit 169.8
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 41
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 13
Stereochemical complexity RDKit 0.43
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 22
Shape complexity RDKit 0.73
Number of rotatable bonds RDKit 5
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 4
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
[(1S,2S,4R,5R,6R,9R,10S,11R,13R,14R,18S,20R)-4-acetyloxy-6-(furan-3-yl)-11,15,18-trihydroxy-5,10,14-trimethyl-3,8-dioxo-16-oxapentacyclo[12.3.3.01,13.02,10.05,9]icosan-20-yl] acetate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.45
[(1S,2S,4R,5R,6R,9R,10S,11R,13R,14R,18S,20R)-4-acetyloxy-6-(furan-3-yl)-11,15,18-trihydroxy-5,10,14-trimethyl-3,8-dioxo-16-oxapentacyclo[12.3.3.01,13.02,10.05,9]icosan-20-yl] acetate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.48
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes