IMPPAT Phytochemical information: 
Deacetyl asperulosidic acid methyl ester
Deacetyl asperulosidic acid methyl ester
Summary

SMILES: OCC1=C[C@@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O
InChI: InChI=1S/C17H24O11/c1-25-15(24)7-5-26-16(10-6(3-18)2-8(20)11(7)10)28-17-14(23)13(22)12(21)9(4-19)27-17/h2,5,8-14,16-23H,3-4H2,1H3/t8-,9+,10+,11-,12+,13-,14+,16-,17-/m0/s1
InChIKey: WSGPLSDARZNMCW-FCVLBCLDSA-N
DeepSMILES: OCC=C[C@@H][C@H][C@@H]5[C@@H]OC=C6C=O)OC))))))O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O)))))))))O
Scaffold Graph/Node/Bond level: C1=CC2C(C=COC2OC2CCCCO2)C1
Scaffold Graph/Node level: C1CCC(OC2OCCC3CCCC32)OC1
Scaffold Graph level: C1CCC(CC2CCCC3CCCC32)CC1
Functional groups: CO; CC(=CC)C; COC(=O)C1=CO[C@@H](O[C@@H](C)OC)CC1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Iridoids monoterpenoids
Synonymous chemical names:
methyl deacetylasperulosidate
External chemical identifiers:
CID:CID_6325021; ChEMBL:CHEMBL463096; ZINC:ZINC000038321681; MolPort-039-141-191
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Deacetyl asperulosidic acid methyl ester
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 404.37
Log P RDKit -3.26
Topological polar surface area (Å2) RDKit 175.37
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.53
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.71
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Deacetyl asperulosidic acid methyl ester
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 1
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 0.200345
Deacetyl asperulosidic acid methyl ester
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -11.22
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 No