(1'S,2S,2'S,4S,4'S,7'R,8'R,9'S,11'S,12'S,13'S,15'R,16'S,18'S)-4,5,5,7',9',13'-hexamethyl-5'-oxaspiro[oxolane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane]-7',11',15',16'-tetrol

ID: ALA457151

Chembl Id: CHEMBL457151

PubChem CID: 20833541

Max Phase: Preclinical

Molecular Formula: C28H46O6

Molecular Weight: 478.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1C[C@]2(O[C@H]3C[C@H]4[C@@H]5CC[C@H]6C[C@H](O)[C@H](O)C[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/C28H46O6/c1-14-11-28(34-24(14,2)3)27(6,32)23-21(33-28)10-17-16-8-7-15-9-18(29)19(30)12-25(15,4)22(16)20(31)13-26(17,23)5/h14-23,29-32H,7-13H2,1-6H3/t14-,15-,16-,17-,18-,19+,20-,21-,22+,23-,25-,26-,27+,28-/m0/s1

Standard InChI Key:  BCZIXMFNQQMCFI-LMGJWPTFSA-N

Alternative Forms

1. Parent:

   

   ALA457151

   (1S,2S,3'S,4S,6S,7R,8R,9S,11S,12S,13S,15R,16S,18S)-2',2',3',7,9,13-hexamethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,5'-oxolane]-7,11,15,16-tetrol

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: 478.67

Molecular Weight (Monoisotopic): 478.3294

AlogP: 3.24

#Rotatable Bonds: ┄

Polar Surface Area: 99.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.82

CX Basic pKa: ┄

CX LogP: 2.20

CX LogD: 2.20

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.43

Np Likeness Score: 3.09

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. 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]

Source

Source(1):

• Scientific Literature