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

ID: ALA96775

Chembl Id: CHEMBL96775

PubChem CID: 10224940

Max Phase: Preclinical

Molecular Formula: C20H25N3O6S

Molecular Weight: 435.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/[C@@H]2C[C@H](SC3=C(C(=O)O)N4C(=O)[C@H]([C@@H](C)O)[C@H]4[C@H]3C)CN2)on1

Standard InChI:  InChI=1S/C20H25N3O6S/c1-9-16-15(10(2)24)19(25)23(16)17(20(26)27)18(9)30-13-6-11(21-8-13)4-5-12-7-14(28-3)22-29-12/h4-5,7,9-11,13,15-16,21,24H,6,8H2,1-3H3,(H,26,27)/b5-4+/t9-,10-,11-,13+,15-,16-/m1/s1

Standard InChI Key:  PFRYIGKUAJZTNJ-VOVXVDKUSA-N

Alternative Forms

1. Parent:

   

   ALA96775

   (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(3S,5S)-5-[(E)-2-(3-methoxy-1,2-oxazol-5-yl)ethenyl]pyrrolidin-3-yl]sulfanyl-4-methyl-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: 435.50

Molecular Weight (Monoisotopic): 435.1464

AlogP: 1.31

#Rotatable Bonds: 7

Polar Surface Area: 125.13

Molecular Species: ZWITTERION

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.38

CX Basic pKa: 9.67

CX LogP: -2.57

CX LogD: -2.57

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.54

Np Likeness Score: 0.72

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]

Source

Source(1):

• Scientific Literature