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

ID: ALA306713

Cas Number: 95415-91-1

PubChem CID: 72445

Max Phase: Preclinical

Molecular Formula: C11H14N2O6S2

Molecular Weight: 334.38

Molecule Type: Small molecule

Names and Identifiers

Synonyms: SCH-34343 | Sch 34343|Sch-34343|95415-91-1|SCH34343|2-Carbamoyloxyethylthio-6-(1-hydroxyethyl)penem-3-carboxylic acid|WM2TR07VX3|(5R,6S)-3-(2-carbamoyloxyethylsulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid|4-Thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-((aminocarbonyl)oxy)ethyl)thio)-6-(1-hydroxyethyl)-7-oxo-, monosodium salt, (5R-(5alpha,6alpha))-|UNII-WM2TR07VX3|CHEMBL306713|SCHEMBL10396007|SCH-34343 FREE ACID|DTXSID60873378|(5R,6SShow More⌵

Canonical SMILES:  C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O)=C(SCCOC(N)=O)S[C@H]12

Standard InChI:  InChI=1S/C11H14N2O6S2/c1-4(14)5-7(15)13-6(9(16)17)10(21-8(5)13)20-3-2-19-11(12)18/h4-5,8,14H,2-3H2,1H3,(H2,12,18)(H,16,17)/t4-,5+,8-/m1/s1

Standard InChI Key:  LVCPLOQIOKEULU-GLDDHUGJSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  1  0  0  0  0  0999 V2000
    3.3042   -2.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -2.6042    0.0000 C   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
    4.1000   -1.5292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -1.7792    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
    7.8750   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9000   -3.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4042   -2.2042    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7875   -4.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9000   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1500   -3.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2875   -2.9292    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
    7.0500   -3.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1125   -0.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8125   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1000   -1.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6375   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5540   -2.1586    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1594   -0.7910    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  3  2  0
  2  6  1  0
  7  4  1  0
  8  3  1  0
  9 17  1  0
 10  4  2  0
 11  5  1  0
 12  8  1  0
  7 13  1  0
 14  8  2  0
 15  9  2  0
 16  9  1  0
 17 21  1  0
 13 18  1  1
 19 11  1  0
 20 13  1  0
 21 19  1  0
  7  2  1  0
  6  5  1  0
  7 22  1  1
  2 23  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA306713

   Sch-34343

2. Alternative Forms:

   

   ALA306713

   SH1V2Hhm4V

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: 334.38

Molecular Weight (Monoisotopic): 334.0293

AlogP: -0.02

#Rotatable Bonds: 6

Polar Surface Area: 130.16

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.76

CX Basic pKa: ┄

CX LogP: -0.55

CX LogD: -3.83

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.46

Np Likeness Score: 0.12

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]

2. Varma MV, Feng B, Obach RS, Troutman MD, Chupka J, Miller HR, El-Kattan A..  (2009)  Physicochemical determinants of human renal clearance.,  52  (15): [PMID:19445515] [10.1021/jm900403j]

3. Jolivette LJ, Ward KW..  (2005)  Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.,  94  (7): [PMID:15920768] [10.1002/jps.20373]

4. Obach RS, Lombardo F, Waters NJ..  (2008)  Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.,  36  (7): [PMID:18426954] [10.1124/dmd.108.020479]

5. Yeh CH, Walsh SI, Craney A, Tabor MG, Voica AF, Adhikary R, Morris SE, Romesberg FE..  (2018)  Optimization of a β-Lactam Scaffold for Antibacterial Activity via the Inhibition of Bacterial Type I Signal Peptidase.,  9  (4): [PMID:29670704] [10.1021/acsmedchemlett.8b00064]

Source

Source(1):

• Scientific Literature