(5R,6S)-3-((R)-1-Amino-2-methylsulfanyl-ethyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

ID: ALA305449

PubChem CID: 13491559

Max Phase: Preclinical

Molecular Formula: C11H16N2O4S2

Molecular Weight: 304.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSC[C@@H](N)C1=C(C(=O)O)N2C(=O)[C@H]([C@@H](C)O)[C@H]2S1

Standard InChI:  InChI=1S/C11H16N2O4S2/c1-4(14)6-9(15)13-7(11(16)17)8(19-10(6)13)5(12)3-18-2/h4-6,10,14H,3,12H2,1-2H3,(H,16,17)/t4-,5-,6+,10-/m1/s1

Standard InChI Key:  YQUVZGWSJGAEAW-XTWHOAMZSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  1  0  0  0  0  0999 V2000
    4.6875   -4.8125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9625   -4.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6917   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -4.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -3.7292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7250   -5.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7875   -4.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -5.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5292   -6.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -6.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2042   -3.6917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0167   -5.1292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -2.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -5.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4292   -5.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6125   -4.4042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6917   -3.1542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8542   -3.1542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  1  0
  5  1  1  0
  6  4  1  0
  7  5  1  0
  8  2  1  0
  9  3  1  0
 10  5  2  0
  7 11  1  0
 12  8  2  0
 13  8  1  0
  9 14  1  0
 15 17  1  0
 11 16  1  1
 17  9  1  0
 18 11  1  0
 19 15  1  0
  9 20  1  1
  4 21  1  6
  7 22  1  1
  7  4  1  0
  6  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA305449

   (5R,6S)-3-[(1R)-1-amino-2-methylsulfanylethyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-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: 304.39

Molecular Weight (Monoisotopic): 304.0551

AlogP: -0.11

#Rotatable Bonds: 5

Polar Surface Area: 103.86

Molecular Species: ZWITTERION

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.79

CX Basic pKa: 8.61

CX LogP: -3.38

CX LogD: -3.40

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.61

Np Likeness Score: 0.27

References

1. Afonso A, Hon F, Weinstein J, Gentles M, Shapiro E, Ganguly A, Naples L, Hare R, Miller G.  (1993)  Penems containing amino acid derived substituents at C-2,  3  (11): [10.1016/S0960-894X(01)80921-5]

Source

Source(1):

• Scientific Literature