(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(3S,5S)-5-(2-methoxycarbonyl-ethylcarbamoyl)-pyrrolidin-3-ylsulfanyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

ID: ALA43620

PubChem CID: 44289075

Max Phase: Preclinical

Molecular Formula: C19H27N3O7S

Molecular Weight: 441.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CCNC(=O)[C@@H]1C[C@H](SC2=C(C(=O)O)N3C(=O)[C@H]([C@@H](C)O)[C@H]3[C@H]2C)CN1

Standard InChI:  InChI=1S/C19H27N3O7S/c1-8-14-13(9(2)23)18(26)22(14)15(19(27)28)16(8)30-10-6-11(21-7-10)17(25)20-5-4-12(24)29-3/h8-11,13-14,21,23H,4-7H2,1-3H3,(H,20,25)(H,27,28)/t8-,9-,10+,11+,13-,14-/m1/s1

Standard InChI Key:  RYGXBRDMAQZVLA-BSTSDWCZSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  1  0  0  0  0  0999 V2000
    2.8500   -2.9250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -3.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500   -2.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -2.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500   -2.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4125   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -3.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667   -2.6167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -2.9167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -2.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125   -2.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -3.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3250   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4875   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7250   -2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9750   -2.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -4.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4042   -1.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792   -1.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9292   -2.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3250   -3.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -4.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4500   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0042   -2.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7250   -1.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -2.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0000   -2.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -1.7250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -1.7250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  2  0
  5  1  1  0
  6  5  1  0
  7  5  1  0
  8  2  1  0
  9  4  1  0
 10 23  1  0
 11 14  1  0
 11 12  1  1
 13  3  2  0
 14 16  1  0
 15 18  1  0
 16  9  1  1
 17  6  1  0
 18 25  1  0
 19  8  2  0
 20 12  2  0
 21 15  2  0
 22 12  1  0
 23 16  1  0
 24  8  1  0
 25 22  1  0
  7 26  1  1
 27 15  1  0
 17 28  1  1
 29 17  1  0
 30 27  1  0
  6 31  1  1
  5 32  1  6
  4  7  1  0
  6  3  1  0
 10 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA43620

   (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(3S,5S)-5-[(3-methoxy-3-oxopropyl)carbamoyl]pyrrolidin-3-yl]sulfanyl-4-methyl-7-oxo-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: 441.51

Molecular Weight (Monoisotopic): 441.1570

AlogP: -0.72

#Rotatable Bonds: 8

Polar Surface Area: 145.27

Molecular Species: ZWITTERION

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.35

CX Basic pKa: 9.35

CX LogP: -4.72

CX LogD: -4.72

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.28

Np Likeness Score: 0.51

References

1. Shin KJ, Yoo KH, Kim DJ, Park SW, Ko BS, Lee SJ, Huh JD, Park SY..  (1998)  Synthesis and biological properties of new 1 beta-methylcarbapenems.,  8  (13): [PMID:9873399] [10.1016/s0960-894x(98)00270-4]

Source

Source(1):

• Scientific Literature