(2S,3S,5R)-3-((Z)-2-Cyano-vinyl)-3-methyl-4,4,7-trioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

ID: ALA333078

Chembl Id: CHEMBL333078

PubChem CID: 9860224

Max Phase: Preclinical

Molecular Formula: C10H10N2O5S

Molecular Weight: 270.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ro-481220 | CHEMBL333078|Ro-481220|SCHEMBL1686888|BDBM50053184|(2S,3S,5R)-3-((Z)-2-Cyano-vinyl)-3-methyl-4,4,7-trioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid|(2S,3S,5R)-3-(2-Cyano-vinyl)-3-methyl-4,4,7-trioxo-4lambda 6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

Canonical SMILES:  C[C@]1(/C=C\C#N)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O

Standard InChI:  InChI=1S/C10H10N2O5S/c1-10(3-2-4-11)8(9(14)15)12-6(13)5-7(12)18(10,16)17/h2-3,7-8H,5H2,1H3,(H,14,15)/b3-2-/t7-,8+,10+/m1/s1

Standard InChI Key:  JYGFUXUBGZBBAC-BJTZKDDDSA-N

Alternative Forms

1. Parent:

   

   ALA333078

   (2S,3S,5R)-3-((Z)-2-Cyano-vinyl)-3-methyl-4,4,7-trioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-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: 270.27

Molecular Weight (Monoisotopic): 270.0310

AlogP: -0.74

#Rotatable Bonds: 2

Polar Surface Area: 115.54

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.66

CX Basic pKa: ┄

CX LogP: -0.87

CX LogD: -4.39

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.52

Np Likeness Score: 0.67

References

1. Richter HG, Angehrn P, Hubschwerlen C, Kania M, Page MG, Specklin JL, Winkler FK..  (1996)  Design, synthesis, and evaluation of 2 beta-alkenyl penam sulfone acids as inhibitors of beta-lactamases.,  39  (19): [PMID:8809160] [10.1021/jm9601967]

2. Papagiannitsis CC, Tzouvelekis LS, Tzelepi E, Miriagou V..  (2007)  Plasmid-encoded ACC-4, an extended-spectrum cephalosporinase variant from Escherichia coli.,  51  (10): [PMID:17664321] [10.1128/aac.00389-07]

3. Zioga A, Whichard JM, Kotsakis SD, Tzouvelekis LS, Tzelepi E, Miriagou V..  (2009)  CMY-31 and CMY-36 cephalosporinases encoded by ColE1-like plasmids.,  53  (3): [PMID:19104021] [10.1128/aac.01284-08]

4. Kotsakis SD, Papagiannitsis CC, Tzelepi E, Tzouvelekis LS, Miriagou V..  (2009)  Extended-spectrum properties of CMY-30, a Val211Gly mutant of CMY-2 cephalosporinase.,  53  (8): [PMID:19470510] [10.1128/aac.00219-09]

Source

Source(1):

• Scientific Literature