Sodium salt (1S,5S,8aS,8bR)-1-((R)-1-hydroxy-ethyl)-5-methoxy-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylate

ID: ALA295691

Cas Number: 141611-76-9

PubChem CID: 23669766

Max Phase: Unknown

Molecular Formula: C14H18NNaO5

Molecular Weight: 281.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Sanfetrinem sodium | GV 104326B | GV-104326B | Sanfetrinem sodium|Sanfetrinem sodium [USAN]|141611-76-9|UNII-R0OS2S9G4U|R0OS2S9G4U|GV 104326B|Sanfetrinem (sodium)|GV-104326B|Sanfetrinem sodium (USAN)|Sodium (1S,5S,8aS,8bR)-1,2,5,6,7,8,8a,8b-octahydro-1-((R)-1-hydroxyethyl)-5-methoxy-2-oxoazeto(2,1-a)isoindole-4-carboxylate|Azeto(2,1-a)isoindole-4-carboxylic acid, 1,2,5,6,7,8,8a,8b-octahydro-1-(1-hydroxyethyl)-5-methoxy-2-oxo-, sodium salt, (1S-(1alpha(S(sup *)),5alpha,8aalpha,8balpha))-|sodium;(Show More⌵

Canonical SMILES:  CO[C@H]1CCC[C@H]2C1=C(C(=O)[O-])N1C(=O)[C@H]([C@@H](C)O)[C@@H]21.[Na+]

Standard InChI:  InChI=1S/C14H19NO5.Na/c1-6(16)9-11-7-4-3-5-8(20-2)10(7)12(14(18)19)15(11)13(9)17;/h6-9,11,16H,3-5H2,1-2H3,(H,18,19);/q;+1/p-1/t6-,7+,8+,9-,11-;/m1./s1

Standard InChI Key:  YXEMRWDSRDEZLB-KOKFPPFCSA-M

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    2.2125   -2.6500    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   -0.8333   -0.5500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1625   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792    0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1625    0.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333    0.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3125    0.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -1.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167    0.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2958    1.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -2.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375   -2.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292    2.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -0.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2958    2.6208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9375    2.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000    1.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4083    0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792    0.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3652    1.7311    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9610    1.6876    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0147    0.1726    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  2  1  0
  5  3  2  0
  6  7  1  0
  7  2  1  0
  8  7  1  0
  9  3  1  0
 10  4  2  0
 11  5  1  0
 12  6  1  0
 13  9  1  0
 14  9  2  0
  8 15  1  0
 11 16  1  6
 12 17  1  1
 18 15  1  0
 19 11  1  0
 20 12  1  0
 21 16  1  0
  8  5  1  0
  4  6  1  0
 18 19  1  0
  8 22  1  6
  7 23  1  6
  6 24  1  1
M  CHG  2   1   1  13  -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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 281.31

Molecular Weight (Monoisotopic): 281.1263

AlogP: 0.36

#Rotatable Bonds: 3

Polar Surface Area: 87.07

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.84

CX Basic pKa: ┄

CX LogP: -0.54

CX LogD: -3.79

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.73

Np Likeness Score: 1.03

References

1. Tranquillini ME, Araldi GL, Donati D, Pentassuglia G, Pezzoli A, Ursini A.  (1996)  Synthesis and antimicrobial activity of 4-amino trinems,  6  (14): [10.1016/0960-894X(96)00292-2]

2. Hanessian S, Griffin AM, Rozema MJ.  (1997)  Tricyclic -lactams: Total synthesis and antibacterial activity of 5-methoxyethyl and 5-hydroxyethyl trinems,  7  (14): [10.1016/S0960-894X(97)00326-0]

3. Andreotti D, Biondi S, Fabio RD, Donati D, Piga E, Rossi T.  (1996)  Synthesis and biological evaluation of 4-alkoxy substituted trinems. Part I,  6  (16): [10.1016/0960-894X(96)00359-9]

4. Gehanne S, Piga E, Andreotti D, Biondi S, Pizzi D.  (1996)  Synthesis and antibacterial, activity of 4-ureido trinems,  6  (22): [10.1016/S0960-894X(96)00515-X]

5. Kwak HJ, Pyun DK, Kim JH, Kim EJ, Jeong HJ, Kim BJ, Lee CH..  (2000)  Synthesis and antibacterial activity of 2alpha-functionalized 1beta-methylcarbapenems related to KR-21012.,  10  (4): [PMID:10714493] [10.1016/s0960-894x(99)00692-7]

6. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

7. Fernandes GFS, Thompson AM, Castagnolo D, Denny WA, Dos Santos JL..  (2022)  Tuberculosis Drug Discovery: Challenges and New Horizons.,  65  (11.0): [PMID:35612311] [10.1021/acs.jmedchem.2c00227]

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names