Sodium salt (5R,6S)-3-ethoxy-6-((R)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate

ID: ALA94614

PubChem CID: 44327089

Max Phase: Preclinical

Molecular Formula: C10H12NNaO5S

Molecular Weight: 259.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC1=C(C(=O)[O-])N2C(=O)[C@H]([C@@H](C)O)[C@H]2S1.[Na+]

Standard InChI:  InChI=1S/C10H13NO5S.Na/c1-3-16-10-6(9(14)15)11-7(13)5(4(2)12)8(11)17-10;/h4-5,8,12H,3H2,1-2H3,(H,14,15);/q;+1/p-1/t4-,5+,8-;/m1./s1

Standard InChI Key:  YQCOBSLIYRETMG-LAHZDFTNSA-M

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
    5.5292   -5.4917    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    4.5500   -2.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -1.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7250   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3375   -1.5792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167   -2.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7250   -1.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5792   -3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -3.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0250   -4.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875   -3.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6417   -2.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -0.4500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -1.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0542   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8792   -2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8018   -2.2135    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4003   -0.8411    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  2  1  0
  5  2  1  0
  3  6  1  0
  7  4  2  0
  8  5  1  0
  9  4  1  0
 10  5  2  0
 11  9  1  0
  8 12  1  0
 13  9  2  0
 14  7  1  0
 12 15  1  1
 16 12  1  0
 17 14  1  0
 18 17  1  0
  8  3  1  0
  6  7  1  0
  8 19  1  1
  3 20  1  6
M  CHG  2   1   1  11  -1
M  END

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: 259.28

Molecular Weight (Monoisotopic): 259.0514

AlogP: 0.19

#Rotatable Bonds: 4

Polar Surface Area: 87.07

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.81

CX Basic pKa: ┄

CX LogP: -0.14

CX LogD: -3.40

Aromatic Rings: ┄

Heavy Atoms: 17

QED Weighted: 0.70

Np Likeness Score: 0.34

References

1. Afonso A, Hon F, Fett N, Weinstein J, Ganguly AK, Naples L, Hare RS, Miller GH..  (1998)  Synthesis and antibacterial activity of 2-alkoxy penems.,  8  (19): [PMID:9873624] [10.1016/s0960-894x(98)00502-2]

Source

Source(1):

• Scientific Literature