22-epi-hippuristanol

ID: ALA458245

Chembl Id: CHEMBL458245

PubChem CID: 330750

Max Phase: Preclinical

Molecular Formula: C28H46O5

Molecular Weight: 462.67

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 22-Epi-Hippuristanol | Epihippuristanol | EPIHIPPURISTANOL|22-epi-hippuristanol|CHEMBL458245|HPHXKNOXVBFETI-FELJEYOCSA-N|BDBM50482567|NSC320006|NSC-320006|DESACETOXYHIPPURIN-1 (B710962K323)

Canonical SMILES:  C[C@H]1C[C@]2(O[C@H]3C[C@H]4[C@@H]5CC[C@H]6C[C@H](O)CC[C@]6(C)[C@H]5[C@@H](O)C[C@]4(C)[C@H]3[C@@]2(C)O)OC1(C)C

Standard InChI:  InChI=1S/C28H46O5/c1-15-13-28(33-24(15,2)3)27(6,31)23-21(32-28)12-19-18-8-7-16-11-17(29)9-10-25(16,4)22(18)20(30)14-26(19,23)5/h15-23,29-31H,7-14H2,1-6H3/t15-,16-,17+,18-,19-,20-,21-,22+,23-,25-,26-,27+,28-/m0/s1

Standard InChI Key:  HPHXKNOXVBFETI-FELJEYOCSA-N

Alternative Forms

1. Parent:

   

   ALA458245

   EPIHIPPURISTANOL

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: 462.67

Molecular Weight (Monoisotopic): 462.3345

AlogP: 4.27

#Rotatable Bonds: ┄

Polar Surface Area: 79.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.86

CX Basic pKa: ┄

CX LogP: 3.27

CX LogD: 3.27

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.50

Np Likeness Score: 3.19

References

1. Chao CH, Huang LF, Yang YL, Su JH, Wang GH, Chiang MY, Wu YC, Dai CF, Sheu JH..  (2005)  Polyoxygenated steroids from the gorgonian Isis hippuris.,  68  (6): [PMID:15974612] [10.1021/np050033y]

2. Longley RE, McConnell OJ, Essich E, Harmody D..  (1993)  Evaluation of marine sponge metabolites for cytotoxicity and signal transduction activity.,  56  (6): [PMID:8350092] [10.1021/np50096a015]

3. Poza JJ, Rodríguez J, Jiménez C..  (2010)  Synthesis of a new cytotoxic cephalostatin/ritterazine analogue from hecogenin and 22-epi-hippuristanol.,  18  (1): [PMID:19948408] [10.1016/j.bmc.2009.11.018]

4. Bordeleau ME, Mori A, Oberer M, Lindqvist L, Chard LS, Higa T, Belsham GJ, Wagner G, Tanaka J, Pelletier J..  (2006)  Functional characterization of IRESes by an inhibitor of the RNA helicase eIF4A.,  2  (4): [PMID:16532013] [10.1038/nchembio776]

5. Somaiah R, Ravindar K, Cencic R, Pelletier J, Deslongchamps P..  (2014)  Synthesis of the antiproliferative agent hippuristanol and its analogues from hydrocortisone via Hg(II)-catalyzed spiroketalization: structure-activity relationship.,  57  (6): [PMID:24588834] [10.1021/jm401799j]

Source

Source(1):

• Scientific Literature