(4aR,5R,6aS,6bR,8aR,10S,12aR,12bR,14bS)-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)5,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

ID: ALA2386940

Chembl Id: CHEMBL2386940

Cas Number: 99633-30-4

PubChem CID: 21633122

Max Phase: Preclinical

Molecular Formula: C36H58O9

Molecular Weight: 634.85

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)[C@H](O)C[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/C36H58O9/c1-31(2)14-15-36(30(43)45-29-28(42)27(41)26(40)21(18-37)44-29)20(16-31)19-8-9-23-33(5)12-11-24(38)32(3,4)22(33)10-13-34(23,6)35(19,7)17-25(36)39/h8,20-29,37-42H,9-18H2,1-7H3/t20-,21+,22-,23+,24-,25+,26+,27-,28+,29-,33-,34+,35+,36+/m0/s1

Standard InChI Key:  VUBCDVLKKVVOTB-VDFKFUOKSA-N

Alternative Forms

1. Parent:

   

   ALA2386940

   Echinocystic acid 28-O-beta-D-glucoside

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: 634.85

Molecular Weight (Monoisotopic): 634.4081

AlogP: 3.46

#Rotatable Bonds: 3

Polar Surface Area: 156.91

Molecular Species: NEUTRAL

HBA: 9

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.19

CX Basic pKa: ┄

CX LogP: 3.10

CX LogD: 3.10

Aromatic Rings: ┄

Heavy Atoms: 45

QED Weighted: 0.20

Np Likeness Score: 3.07

References

1. Yu F, Wang Q, Zhang Z, Peng Y, Qiu Y, Shi Y, Zheng Y, Xiao S, Wang H, Huang X, Zhu L, Chen K, Zhao C, Zhang C, Yu M, Sun D, Zhang L, Zhou D..  (2013)  Development of oleanane-type triterpenes as a new class of HCV entry inhibitors.,  56  (11): [PMID:23662817] [10.1021/jm301910a]

2. 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]

Source

Source(1):

• Scientific Literature