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

ID: ALA94455

PubChem CID: 44327134

Max Phase: Preclinical

Molecular Formula: C11H13N2NaO7S

Molecular Weight: 318.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(OCCOC(N)=O)S[C@H]12.[Na+]

Standard InChI:  InChI=1S/C11H14N2O7S.Na/c1-4(14)5-7(15)13-6(9(16)17)10(21-8(5)13)19-2-3-20-11(12)18;/h4-5,8,14H,2-3H2,1H3,(H2,12,18)(H,16,17);/q;+1/p-1/t4-,5+,8-;/m1./s1

Standard InChI Key:  USVJQYHCPDFVIZ-LAHZDFTNSA-M

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    4.2417   -5.5375    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    3.3042   -2.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -2.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -1.5250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8667   -3.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042   -3.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7792   -4.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1417   -3.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2917   -2.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4042   -2.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2792   -4.3542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -3.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -0.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042   -1.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167   -2.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6417   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5540   -2.1544    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1613   -0.7871    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 18  1  0
 11  5  2  0
 12  9  1  0
  8 13  1  0
 14  9  2  0
 15 10  2  0
 16  7  1  0
 17 10  1  0
 18 22  1  0
 13 19  1  1
 20 13  1  0
 21 16  1  0
 22 21  1  0
  8  3  1  0
  6  7  1  0
  8 23  1  1
  3 24  1  6
M  CHG  2   1   1  12  -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: 318.31

Molecular Weight (Monoisotopic): 318.0522

AlogP: -0.74

#Rotatable Bonds: 6

Polar Surface Area: 139.39

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.65

CX Basic pKa: ┄

CX LogP: -1.08

CX LogD: -4.40

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.43

Np Likeness Score: 0.39

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