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

ID: ALA304748

PubChem CID: 44309099

Max Phase: Preclinical

Molecular Formula: C10H14N2O4S

Molecular Weight: 258.30

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H14N2O4S/c1-3(11)7-6(10(15)16)12-8(14)5(4(2)13)9(12)17-7/h3-5,9,13H,11H2,1-2H3,(H,15,16)/t3-,4+,5-,9+/m0/s1

Standard InChI Key:  FGNWGTHEWZWVES-PGRQXVTRSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  1  0  0  0  0  0999 V2000
    4.4792   -4.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2625   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4875   -3.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -4.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -2.9792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -3.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -5.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -4.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5792   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167   -5.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -5.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9917   -2.9417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2875   -1.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9875   -4.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2750   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4042   -3.6542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500   -2.4042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792   -2.4042    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  5  2  0
 10  3  1  0
  7 11  1  0
 12  8  2  0
 13  8  1  0
 10 14  1  0
 11 15  1  1
 16 10  1  0
 17 11  1  0
 10 18  1  6
  7 19  1  1
  4 20  1  6
  4  7  1  0
  6  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA304748

   (5R,6S)-3-[(1S)-1-aminoethyl]-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: 258.30

Molecular Weight (Monoisotopic): 258.0674

AlogP: -0.46

#Rotatable Bonds: 3

Polar Surface Area: 103.86

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.75

CX Basic pKa: 8.89

CX LogP: -3.82

CX LogD: -3.83

Aromatic Rings: ┄

Heavy Atoms: 17

QED Weighted: 0.59

Np Likeness Score: 0.44

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