(3E,5E,9E)-11-[(2R,3S)-2-Carbamoyl-3-((S)-1-hydroxy-ethyl)-oxiranyl]-2-eth-(E)-ylidene-4,10-dimethyl-11-oxo-undeca-3,5,9-trienoic acid methyl ester

ID: ALA184955

Chembl Id: CHEMBL184955

PubChem CID: 11132935

Max Phase: Preclinical

Molecular Formula: C21H29NO6

Molecular Weight: 391.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H29NO6/c1-6-16(19(25)27-5)12-13(2)10-8-7-9-11-14(3)17(24)21(20(22)26)18(28-21)15(4)23/h6,8,10-12,15,18,23H,7,9H2,1-5H3,(H2,22,26)/b10-8+,13-12+,14-11+,16-6+/t15-,18-,21-/m0/s1

Standard InChI Key:  JUHJLIGNRVAWDN-JFGBVNEWSA-N

Alternative Forms

1. Parent:

   

   ALA184955

   methyl (2E,3E,5E,9E)-11-[(2R,3S)-2-carbamoyl-3-[(1S)-1-hydroxyethyl]oxiran-2-yl]-2-ethylidene-4,10-dimethyl-11-oxoundeca-3,5,9-trienoate

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: 391.46

Molecular Weight (Monoisotopic): 391.1995

AlogP: 1.91

#Rotatable Bonds: 10

Polar Surface Area: 119.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.88

CX LogD: 2.88

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.15

Np Likeness Score: 1.80

References

1. Nagumo Y, Kakeya H, Yamaguchi J, Uno T, Shoji M, Hayashi Y, Osada H..  (2004)  Structure-activity relationships of epolactaene derivatives: structural requirements for inhibition of Hsp60 chaperone activity.,  14  (17): [PMID:15357965] [10.1016/j.bmcl.2004.06.054]

Source

Source(1):

• Scientific Literature