IMPPAT Phytochemical information: 
2alpha,3beta,23-trihydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopynoside
2alpha,3beta,23-trihydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopynoside
Summary

SMILES: OC[C@H]1O[C@@H](OC(=O)[C@@]23CCC(C[C@H]3C3=CC[C@H]4[C@@]([C@@]3(CC2)C)(C)CC[C@@H]2[C@]4(C)C[C@H]([C@@H]([C@@]2(C)CO)O)O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C36H58O10/c1-31(2)11-13-36(30(44)46-29-27(42)26(41)25(40)22(17-37)45-29)14-12-34(5)19(20(36)15-31)7-8-24-32(3)16-21(39)28(43)33(4,18-38)23(32)9-10-35(24,34)6/h7,20-29,37-43H,8-18H2,1-6H3/t20-,21+,22+,23+,24+,25+,26-,27+,28-,29-,32-,33-,34+,35+,36-/m0/s1
InChIKey: CJHYKSSBQRABTM-XJWBRSAFSA-N
DeepSMILES: OC[C@H]O[C@@H]OC=O)[C@]CCCC[C@H]6C=CC[C@H][C@@][C@@]6CC%14))C))C)CC[C@@H][C@]6C)C[C@H][C@@H][C@@]6C)CO)))O))O))))))))))))))C)C)))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(OC1CCCCO1)C12CCCCC1C1=CCC3C4CCCCC4CCC3C1CC2
Scaffold Graph/Node level: OC(OC1CCCCO1)C12CCCCC1C1CCC3C4CCCCC4CCC3C1CC2
Scaffold Graph level: CC(CC1CCCCC1)C12CCCCC1C1CCC3C4CCCCC4CCC3C1CC2
Functional groups: CO; CO[C@@H](OC(C)=O)C; CC=C(C)C
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:
arjunolic-acid-28-o-beta-d-glucoside, arjunglucoside ii
External chemical identifiers:
CID:CID_52951052; ChEMBL:CHEMBL3907306; ChEBI:CHEBI:67948; SureChEMBL:SCHEMBL21571936; MolPort-046-158-487
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
2alpha,3beta,23-trihydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopynoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 650.85
Log P RDKit 2.44
Topological polar surface area (Å2) RDKit 177.14
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 7
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 15
Stereochemical complexity RDKit 0.42
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 33
Shape complexity RDKit 0.92
Number of rotatable bonds RDKit 5
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
2alpha,3beta,23-trihydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopynoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.18
2alpha,3beta,23-trihydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopynoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -7.40
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