IMPPAT Phytochemical information: 
methyl (1R,2S,3R,6R,8S,11S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4-oxo-11-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
methyl (1R,2S,3R,6R,8S,11S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4-oxo-11-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
Summary

SMILES: OC[C@H]1O[C@@H](O[C@H]2C=C(C)[C@H]3[C@@]([C@@H]2O)(C)[C@H]2[C@@H](O)[C@H](O)[C@@]4([C@H]5[C@@]2([C@@H](C3)OC(=O)[C@@H]5OC(=O)C=C(C)C)CO4)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C32H44O16/c1-11(2)6-17(34)48-22-24-31-10-44-32(24,29(42)43-5)26(40)21(38)23(31)30(4)13(8-16(31)47-27(22)41)12(3)7-14(25(30)39)45-28-20(37)19(36)18(35)15(9-33)46-28/h6-7,13-16,18-26,28,33,35-40H,8-10H2,1-5H3/t13-,14-,15+,16+,18+,19-,20+,21+,22+,23+,24+,25+,26-,28+,30-,31+,32-/m0/s1
InChIKey: IZUDZNKPPXKFJY-DXMXMRDXSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@H]C=CC)[C@H][C@@][C@@H]6O))C)[C@H][C@@H]O)[C@H]O)[C@@][C@H][C@@]6[C@@H]C%10)OC=O)[C@@H]6OC=O)C=CC)C)))))))))CO5))))C=O)OC)))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1CC2C3CCC4C5CC(OC6CCCCO6)C=CC5CC(O1)C24CO3
Scaffold Graph/Node level: OC1CC2C3CCC4C5CC(OC6CCCCO6)CCC5CC(O1)C24CO3
Scaffold Graph level: CC1CC2CC3CCC(CC4CCCCC4)CC3C3CCC4CCC23C4C1
Functional groups: CO; CO[C@@H](C)OC; CC(=CC)C; COC(=O)C; CC(C)=CC(=O)OC; COC; COC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Quassinoids
Synonymous chemical names:
yadanzioside e
External chemical identifiers:
CID:CID_101659160; ZINC:ZINC000085542189
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
methyl (1R,2S,3R,6R,8S,11S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4-oxo-11-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 684.69
Log P RDKit -2.78
Topological polar surface area (Å2) RDKit 248.2
Number of hydrogen bond acceptors RDKit 16
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 48
Number of heteroatoms RDKit 16
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 17
Stereochemical complexity RDKit 0.53
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 0.78
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
methyl (1R,2S,3R,6R,8S,11S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4-oxo-11-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
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 0.0646973
methyl (1R,2S,3R,6R,8S,11S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4-oxo-11-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
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 -11.50
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No