IMPPAT Phytochemical information: 
Abrusoside A
Abrusoside A
Summary

SMILES: OC[C@H]1O[C@@H](O[C@H]2CC[C@]34[C@H]([C@]2(C)C(=O)O)CC[C@@H]2[C@@]4(C3)CC[C@]3([C@@]2(C)CC[C@@H]3[C@@H]([C@@H]2CC=C(C(=O)O2)C)C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C36H54O10/c1-18-6-7-21(44-29(18)41)19(2)20-10-12-33(4)23-8-9-24-34(5,31(42)43)25(46-30-28(40)27(39)26(38)22(16-37)45-30)11-13-35(24)17-36(23,35)15-14-32(20,33)3/h6,19-28,30,37-40H,7-17H2,1-5H3,(H,42,43)/t19-,20+,21-,22+,23-,24-,25-,26+,27-,28+,30-,32+,33-,34-,35+,36-/m0/s1
InChIKey: CJHYXUPCGHKJOO-AYOTXDKCSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@H]CC[C@@][C@H][C@]6C)C=O)O)))CC[C@@H][C@@]6C7)CC[C@][C@@]6C)CC[C@@H]5[C@@H][C@@H]CC=CC=O)O6))C)))))C))))))C))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1C=CCC(CC2CCC3C2CCC24CC25CCC(OC2CCCCO2)CC5CCC34)O1
Scaffold Graph/Node level: OC1CCCC(CC2CCC3C2CCC24CC25CCC(OC2CCCCO2)CC5CCC34)O1
Scaffold Graph level: CC1CCCC(CC2CCC3C2CCC24CC25CCC(CC2CCCCC2)CC5CCC34)C1
Functional groups: CO; CC1=CCCOC1=O; CO[C@@H](C)OC; CC(=O)O
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: Cycloartane triterpenoids
Synonymous chemical names:
abrusoside a, abrusoside-a
External chemical identifiers:
CID:CID_6857683; ChEMBL:CHEMBL471718; ChEBI:CHEBI:2364; ZINC:ZINC000008234231
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Abrusoside A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 646.82
Log P RDKit 3.57
Topological polar surface area (Å2) RDKit 162.98
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 36
Number of heavy atoms RDKit 46
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 16
Stereochemical complexity RDKit 0.44
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 32
Shape complexity RDKit 0.89
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 5
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Abrusoside A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.21
Abrusoside A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -6.50
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