beta-D-Pyranoglucosyl 3beta-Hydroxyolean-12-en-28-oate

ID: ALA510111

Chembl Id: CHEMBL510111

Cas Number: 14162-53-9

PubChem CID: 14189384

Max Phase: Preclinical

Molecular Formula: C36H58O8

Molecular Weight: 618.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC[C@]2(C(=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1

Standard InChI:  InChI=1S/C36H58O8/c1-31(2)14-16-36(30(42)44-29-28(41)27(40)26(39)22(19-37)43-29)17-15-34(6)20(21(36)18-31)8-9-24-33(5)12-11-25(38)32(3,4)23(33)10-13-35(24,34)7/h8,21-29,37-41H,9-19H2,1-7H3/t21-,22+,23-,24+,25-,26+,27-,28+,29-,33-,34+,35+,36-/m0/s1

Standard InChI Key:  KMKFOIBUKYMVRJ-YHFBEQRYSA-N

Alternative Forms

1. Parent:

   

   ALA510111

   oleanolic acid beta-D-glucopyranosyl ester

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 618.85

Molecular Weight (Monoisotopic): 618.4132

AlogP: 4.49

#Rotatable Bonds: 3

Polar Surface Area: 136.68

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.20

CX Basic pKa: ┄

CX LogP: 4.33

CX LogD: 4.33

Aromatic Rings: ┄

Heavy Atoms: 44

QED Weighted: 0.23

Np Likeness Score: 3.04

References

1. Wen X, Sun H, Liu J, Cheng K, Zhang P, Zhang L, Hao J, Zhang L, Ni P, Zographos SE, Leonidas DD, Alexacou KM, Gimisis T, Hayes JM, Oikonomakos NG..  (2008)  Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: synthesis, structure-activity relationships, and X-ray crystallographic studies.,  51  (12): [PMID:18517260] [10.1021/jm8000949]

2. Chan HH, Hwang TL, Reddy MV, Li DT, Qian K, Bastow KF, Lee KH, Wu TS..  (2011)  Bioactive constituents from the roots of Panax japonicus var. major and development of a LC-MS/MS method for distinguishing between natural and artifactual compounds.,  74  (4): [PMID:21417387] [10.1021/np100851s]

3. Wang WW, Xu SH, Zhao YZ, Zhang C, Zhang YY, Yu BY, Zhang J..  (2017)  Microbial hydroxylation and glycosylation of pentacyclic triterpenes as inhibitors on tissue factor procoagulant activity.,  27  (4): [PMID:28109788] [10.1016/j.bmcl.2016.12.066]

4. Vinh LB, Jang HJ, Phong NV, Cho K, Park SS, Kang JS, Kim YH, Yang SY..  (2019)  Isolation, structural elucidation, and insights into the anti-inflammatory effects of triterpene saponins from the leaves of Stauntonia hexaphylla.,  29  (8): [PMID:30808589] [10.1016/j.bmcl.2019.02.022]

Source

Source(1):

• Scientific Literature