5-Hydroxy-4-{5-[2-((1R,2R,4aS,8aS)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalen-1-yl)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-5H-furan-2-one

ID: ALA111739

Chembl Id: CHEMBL111739

PubChem CID: 10386285

Max Phase: Preclinical

Molecular Formula: C25H36O4

Molecular Weight: 400.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CCC[C@H]2[C@](C)(CCC3=CCC(C4=CC(=O)OC4O)OC3)[C@H](C)CC[C@]12C

Standard InChI:  InChI=1S/C25H36O4/c1-16-6-5-7-21-24(16,3)12-10-17(2)25(21,4)13-11-18-8-9-20(28-15-18)19-14-22(26)29-23(19)27/h8,14,17,20-21,23,27H,1,5-7,9-13,15H2,2-4H3/t17-,20?,21-,23?,24-,25-/m1/s1

Standard InChI Key:  CVAZWHZRZNYCOV-ILKJNQADSA-N

Alternative Forms

1. Parent:

   

   ALA111739

   CACOSPONGIONOLIDE B

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: 400.56

Molecular Weight (Monoisotopic): 400.2614

AlogP: 5.08

#Rotatable Bonds: 4

Polar Surface Area: 55.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.19

CX Basic pKa: ┄

CX LogP: 5.04

CX LogD: 4.98

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: 3.64

References

1. De Rosa M, Giordano S, Scettri A, Sodano G, Soriente A, Pastor PG, Alcaraz MJ, Payá M..  (1998)  Synthesis and comparison of the antiinflammatory activity of manoalide and cacospongionolide B analogues.,  41  (17): [PMID:9703468] [10.1021/jm980027h]

2. De Rosa S, Crispino A, De Giulio A, Iodice C, Pronzato R, Zavodnik N..  (1995)  Cacospongionolide B, a new sesterterpene from the sponge Fasciospongia cavernosa.,  58  (11): [PMID:8594155] [10.1021/np50125a024]

3. De Rosa S, Crispino A, De Giulio A, Iodice C, Benrezzouk R, Terencio MC, Ferrándiz ML, Alcaraz MJ, Payá M..  (1998)  A new cacospongionolide inhibitor of human secretory phospholipase A2 from the Tyrrhenian sponge Fasciospongia cavernosa and absolute configuration of cacospongionolides.,  61  (7): [PMID:9677277] [10.1021/np980122t]

Source

Source(1):

• Scientific Literature