IMPPAT Phytochemical information: 
Hypoloside A
Hypoloside A
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@]23C=C(C)C4([C@]([C@H]3C(=O)C(C2)(C)C)(C)O)CC4)[C@@H]([C@H]([C@@H]1O)O)OC(=O)C
InChI: InChI=1S/C23H34O9/c1-11-8-23(10-20(3,4)18(28)17(23)21(5,29)22(11)6-7-22)32-19-16(30-12(2)25)15(27)14(26)13(9-24)31-19/h8,13-17,19,24,26-27,29H,6-7,9-10H2,1-5H3/t13-,14-,15+,16-,17-,19+,21-,23+/m1/s1
InChIKey: RYLFQOVBQSESBN-HOJIOWHPSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@]C=CC)C[C@][C@H]6C=O)CC9)C)C))))C)O))CC3)))))))[C@@H][C@H][C@@H]6O))O))OC=O)C
Scaffold Graph/Node/Bond level: O=C1CCC2(OC3CCCCO3)C=CC3(CC3)CC12
Scaffold Graph/Node level: OC1CCC2(OC3CCCCO3)CCC3(CC3)CC12
Scaffold Graph level: CC1CCC2(CC3CCCCC3)CCC3(CC3)CC12
Functional groups: CO; CO[C@@H](C)OC; CC(=CC)C; CC(=O)C; CC(=O)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: Sesquiterpenoids
NP Classifier Class: Illudane sesquiterpenoids
Synonymous chemical names:
hypoloside a
External chemical identifiers:
CID:CID_14313739; ZINC:ZINC000031430635
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Hypoloside A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 454.52
Log P RDKit 0.22
Topological polar surface area (Å2) RDKit 142.75
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 32
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 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 19
Shape complexity RDKit 0.83
Number of rotatable bonds RDKit 5
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 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
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 4
Hypoloside A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
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 0.346412
Hypoloside A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -9.34
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 Yes