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

ID: ALA2111569

Chembl Id: CHEMBL2111569

PubChem CID: 71450816

Max Phase: Preclinical

Molecular Formula: C21H25N3O7S

Molecular Weight: 463.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc(/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/C21H25N3O7S/c1-9-16-15(10(2)25)19(26)24(16)17(20(27)28)18(9)32-13-6-11(22-8-13)4-5-12-7-14(23-31-12)21(29)30-3/h4-5,7,9-11,13,15-16,22,25H,6,8H2,1-3H3,(H,27,28)/b5-4-/t9-,10-,11-,13+,15-,16-/m1/s1

Standard InChI Key:  MVFIICWBKUPEBL-VZFQYJDLSA-N

Alternative Forms

1. Parent:

   

   ALA2111569

   (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(3S,5S)-5-[(Z)-2-(3-methoxycarbonyl-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: 463.51

Molecular Weight (Monoisotopic): 463.1413

AlogP: 1.09

#Rotatable Bonds: 7

Polar Surface Area: 142.20

Molecular Species: ZWITTERION

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.38

CX Basic pKa: 9.67

CX LogP: -2.62

CX LogD: -2.62

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.40

Np Likeness Score: 0.65

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