(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(3S,5S)-5-((E)-2-isoxazol-5-yl-vinyl)-pyrrolidin-3-ylsulfanyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

ID: ALA94037

Chembl Id: CHEMBL94037

PubChem CID: 9909233

Max Phase: Preclinical

Molecular Formula: C19H23N3O5S

Molecular Weight: 405.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@@H]3CN[C@H](/C=C/c4ccno4)C3)[C@H](C)[C@H]12

Standard InChI:  InChI=1S/C19H23N3O5S/c1-9-15-14(10(2)23)18(24)22(15)16(19(25)26)17(9)28-13-7-11(20-8-13)3-4-12-5-6-21-27-12/h3-6,9-11,13-15,20,23H,7-8H2,1-2H3,(H,25,26)/b4-3+/t9-,10-,11-,13+,14-,15-/m1/s1

Standard InChI Key:  DNIPUISRDWLCOE-PCJJHXLQSA-N

Alternative Forms

1. Parent:

   

   ALA94037

   (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(3S,5S)-5-[(E)-2-(1,2-oxazol-5-yl)ethenyl]pyrrolidin-3-yl]sulfanyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-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: 405.48

Molecular Weight (Monoisotopic): 405.1358

AlogP: 1.31

#Rotatable Bonds: 6

Polar Surface Area: 115.90

Molecular Species: ZWITTERION

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.40

CX Basic pKa: 9.69

CX LogP: -3.01

CX LogD: -3.01

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: 0.75

References

1. Kim DJ, Seo KJ, Lee KS, Shin KJ, Yoo KH, Kim DC, Park SW..  (2000)  Synthesis and biological activity of 1beta-methyl-2-[5'-isoxazoloethenylpyrrolidin-3'-ylthio]carbapenems.,  10  (24): [PMID:11133095] [10.1016/s0960-894x(00)00575-8]

2. Kang YK, Lee KS, Yoo KH, Shin KJ, Kim DC, Lee CS, Kong JY, Kim DJ..  (2003)  Synthesis and biological evaluation of novel 1 beta-methylcarbapenems with isothiazoloethenyl side chains.,  13  (3): [PMID:12565951] [10.1016/s0960-894x(02)00948-4]

3. Lee KS, Kang YK, Yoo KH, Kim DC, Shin KJ, Paik YS, Kim DJ..  (2005)  Novel 1beta-methylcarbapenems with isoxazoloethenyl moieties containing carboxylic acid sodium salt.,  15  (1): [PMID:15582445] [10.1016/j.bmcl.2004.09.092]

Source

Source(1):

• Scientific Literature