Echinocystic acid

ID: ALA464557

Chembl Id: CHEMBL464557

PubChem CID: 476486

Max Phase: Preclinical

Molecular Formula: C30H48O4

Molecular Weight: 472.71

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Echinocystic Acid | CHEMBL464557|YKOPWPOFWMYZJZ-RQDPUMMDSA-N|(4aR,5R,6aS,6bR,8aR,10S,12aR,12bR,14bS)-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-carboxylic acid|BDBM50434805

Canonical SMILES:  CC1(C)CC[C@]2(C(=O)O)[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/C30H48O4/c1-25(2)14-15-30(24(33)34)19(16-25)18-8-9-21-27(5)12-11-22(31)26(3,4)20(27)10-13-28(21,6)29(18,7)17-23(30)32/h8,19-23,31-32H,9-17H2,1-7H3,(H,33,34)/t19-,20+,21-,22+,23-,27+,28-,29-,30-/m1/s1

Standard InChI Key:  YKOPWPOFWMYZJZ-RQDPUMMDSA-N

Alternative Forms

1. Parent:

   

   ALA464557

   ECHINOCYSTIC ACID

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: 472.71

Molecular Weight (Monoisotopic): 472.3553

AlogP: 6.20

#Rotatable Bonds: 1

Polar Surface Area: 77.76

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.61

CX Basic pKa: ┄

CX LogP: 5.36

CX LogD: 2.64

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.40

Np Likeness Score: 3.31

References

1. Konoshima T, Yasuda I, Kashiwada Y, Cosentino LM, Lee KH..  (1995)  Anti-AIDS agents, 21. Triterpenoid saponins as anti-HIV principles from fruits of Gleditsia japonica and Gymnocladus chinensis, and a structure-activity correlation.,  58  (9): [PMID:7494144] [10.1021/np50123a006]

2. 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]

3. Wang H, Wang Q, Xiao SL, Yu F, Ye M, Zheng YX, Zhao CK, Sun DA, Zhang LH, Zhou DM..  (2013)  Elucidation of the pharmacophore of echinocystic acid, a new lead for blocking HCV entry.,  64  [PMID:23644199] [10.1016/j.ejmech.2013.03.041]

4. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

5. Ye X, Yu S, Liang Y, Huang H, Lian XY, Zhang Z..  (2014)  Bioactive triterpenoid saponins and phenolic compounds against glioma cells.,  24  (22): [PMID:25442304] [10.1016/j.bmcl.2014.09.087]

6. Wang H, Yu F, Peng Y, Wang Q, Han X, Xu R, Zhou X, Wan C, Fan Z, Jiao P, Zhang Y, Zhang L, Zhou D, Xiao S..  (2015)  Synthesis and biological evaluation of ring A and/or C expansion and opening echinocystic acid derivatives for anti-HCV entry inhibitors.,  102  [PMID:26318066] [10.1016/j.ejmech.2015.08.034]

Source

Source(1):

• Scientific Literature