IMPPAT Phytochemical information: 
Gymnemic acid xi
Gymnemic acid xi
Summary

SMILES: C/C=C(/C(=O)OC[C@@]12[C@@H](O)C[C@@]3(C(=CC[C@H]4[C@@]3(C)CC[C@@H]3[C@]4(C)CC[C@@H]([C@@]3(C)CO)O[C@@H]3O[C@H](C(=O)O)[C@H]([C@@H]([C@H]3O)O)O)[C@@H]1CC([C@H]([C@@H]2O)OC(=O)/C(=C/C)/C)(C)C)C)C
InChI: InChI=1S/C46H70O14/c1-11-23(3)38(55)57-22-46-26(19-41(5,6)36(35(46)52)60-39(56)24(4)12-2)25-13-14-28-42(7)17-16-30(58-40-33(51)31(49)32(50)34(59-40)37(53)54)43(8,21-47)27(42)15-18-44(28,9)45(25,10)20-29(46)48/h11-13,26-36,40,47-52H,14-22H2,1-10H3,(H,53,54)/b23-11+,24-12+/t26-,27+,28+,29-,30-,31-,32-,33+,34-,35-,36-,40+,42-,43-,44+,45+,46-/m0/s1
InChIKey: HXMHDLGRRVPZTP-ZIDNNZLZSA-N
DeepSMILES: C/C=C/C=O)OC[C@@][C@@H]O)C[C@@]C=CC[C@H][C@@]6C)CC[C@@H][C@]6C)CC[C@@H][C@@]6C)CO)))O[C@@H]O[C@H]C=O)O))[C@H][C@@H][C@H]6O))O))O)))))))))))))))))[C@@H]6CC[C@H][C@@H]%10O))OC=O)/C=C/C))/C)))))C)C)))))C))))))))C
Scaffold Graph/Node/Bond level: C1=C2C3CCCCC3CCC2C2CCC3CC(OC4CCCCO4)CCC3C2C1
Scaffold Graph/Node level: C1CCC(OC2CCC3C(CCC4C3CCC3C5CCCCC5CCC34)C2)OC1
Scaffold Graph level: C1CCC(CC2CCC3C(CCC4C3CCC3C5CCCCC5CCC34)C2)CC1
Functional groups: C/C=C(C)C(=O)OC; CC(=O)O; CC=C(C)C; CO; CO[C@@H](C)OC
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: Triterpenoids
NP Classifier Class: Oleanane triterpenoids
Synonymous chemical names:
gymnemic acid xi
External chemical identifiers:
CID:15674687; FDASRS:U06F13N5GR
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Gymnemic acid xi
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 847.05
Log P RDKit 3.98
Topological polar surface area (Å2) RDKit 229.74
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 46
Number of heavy atoms RDKit 60
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 17
Stereochemical complexity RDKit 0.37
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 37
Shape complexity RDKit 0.8
Number of rotatable bonds RDKit 11
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 1
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 4
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Gymnemic acid xi
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 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.0754