rel-(1S,4R,7S,8aR)-4-((2E,4E)-6,8-dimethyldeca-2,4-dienoyloxy)-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

ID: ALA515687

Chembl Id: CHEMBL515687

PubChem CID: 11294029

Max Phase: Preclinical

Molecular Formula: C27H36O6

Molecular Weight: 456.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C=O)[C@@H]1C[C@@]2(C)C(=CC1=O)[C@H](OC(=O)/C=C/C=C/C(C)CC(C)CC)CC[C@@H]2C(=O)O

Standard InChI:  InChI=1S/C27H36O6/c1-6-17(2)13-18(3)9-7-8-10-25(30)33-24-12-11-21(26(31)32)27(5)15-20(19(4)16-28)23(29)14-22(24)27/h7-10,14,16-18,20-21,24H,4,6,11-13,15H2,1-3,5H3,(H,31,32)/b9-7+,10-8+/t17?,18?,20-,21+,24+,27+/m0/s1

Standard InChI Key:  KFNRVRQZGWBRJR-XQLFHWRFSA-N

Alternative Forms

1. Parent:

   

   ALA515687

   (1S,4R,7S,8aR)-4-[(2E,4E)-6,8-dimethyldeca-2,4-dienoyl]oxy-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid

Molecule Features

Natural Product: No

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: 456.58

Molecular Weight (Monoisotopic): 456.2512

AlogP: 4.85

#Rotatable Bonds: 10

Polar Surface Area: 97.74

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.15

CX Basic pKa: ┄

CX LogP: 5.39

CX LogD: 2.32

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.22

Np Likeness Score: 2.76

References

1. McDonald LA, Barbieri LR, Bernan VS, Janso J, Lassota P, Carter GT..  (2004)  07H239-A, a new cytotoxic eremophilane sesquiterpene from the marine-derived Xylariaceous fungus LL-07H239.,  67  (9): [PMID:15387660] [10.1021/np049924g]

Source

Source(1):

• Scientific Literature