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

ID: ALA306916

PubChem CID: 13491553

Max Phase: Preclinical

Molecular Formula: C12H18N2O4S2

Molecular Weight: 318.42

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H18N2O4S2/c1-5(15)7-10(16)14-8(12(17)18)9(20-11(7)14)6(13)3-4-19-2/h5-7,11,15H,3-4,13H2,1-2H3,(H,17,18)/t5-,6-,7+,11-/m1/s1

Standard InChI Key:  BKEZMVHISYYHTL-FHZUQPTBSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  1  0  0  0  0  0999 V2000
    4.5917   -5.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750   -5.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8667   -4.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6000   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -5.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -4.1042    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -6.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1875   -5.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6917   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1875   -3.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4292   -6.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -6.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1042   -4.0667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1000   -5.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3292   -6.2167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4000   -2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9250   -5.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -3.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1542   -6.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6917   -4.7814    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8428   -4.7369    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4454   -3.3662    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
  4  6  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
 15 10  1  0
 16 18  1  0
 11 17  1  1
 18 15  1  0
 19 11  1  0
 20 16  1  0
 10 21  1  1
  7  4  1  0
  6  3  1  0
  7 22  1  1
  4 23  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA306916

   (5R,6S)-3-[(1R)-1-amino-3-methylsulfanylpropyl]-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: 318.42

Molecular Weight (Monoisotopic): 318.0708

AlogP: 0.28

#Rotatable Bonds: 6

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: 3.86

CX Basic pKa: 8.93

CX LogP: -3.17

CX LogD: -3.17

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.60

Np Likeness Score: 0.19

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