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(5R,6Z)-7-oxo-6-{[5-(pyridin-3-ylmethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)]methylene}-7oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid sodium salt

ID: ALA211143

PubChem CID: 23673798

Max Phase: Preclinical

Molecular Formula: C20H16N3NaO3S2

Molecular Weight: 411.51

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C([O-])C1=CS[C@@H]2/C(=C\c3cc4c(s3)CCN(Cc3cccnc3)C4)C(=O)N12.[Na+]

Standard InChI:  InChI=1S/C20H17N3O3S2.Na/c24-18-15(19-23(18)16(11-27-19)20(25)26)7-14-6-13-10-22(5-3-17(13)28-14)9-12-2-1-4-21-8-12;/h1-2,4,6-8,11,19H,3,5,9-10H2,(H,25,26);/q;+1/p-1/b15-7-;/t19-;/m1./s1

Standard InChI Key:  SQIIBGAETATCOD-KFLCVYELSA-M

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    6.7667    0.9708    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    9.8730   -1.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6745   -0.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6774   -0.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4789   -0.0067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5407    0.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7773    1.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2439    0.4997    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.3795   -1.2366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4445   -1.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2442    1.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9707    0.8593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2197    2.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6197   -1.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1496   -1.0100    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1218   -2.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3425   -2.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3597   -1.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6566   -0.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9319   -1.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9147   -2.0433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6222   -2.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1914   -2.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4861   -2.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5054   -1.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8009   -0.7622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0766   -1.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0612   -1.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7663   -2.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7549   -0.5882    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 18  1  0
  5  6  1  0
  6  7  2  0
 14 15  1  0
 17 16  1  0
 16 14  2  0
 17 18  2  0
  7  8  1  0
  4  8  1  0
  4  5  1  0
  3  9  2  0
  2  3  1  0
  2 10  2  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
  3  5  1  0
 24 25  2  0
 11 12  1  0
 25 26  1  0
 11 13  2  0
 26 27  2  0
  6 11  1  0
 27 28  1  0
  4  2  1  0
 28 29  2  0
 29 24  1  0
 10 14  1  0
  4 30  1  6
M  CHG  2   1   1  12  -1
M  END

Associated Targets(non-human)

Serratia marcescens (3237 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterobacter cloacae (7976 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
bla Beta-lactamase TEM (457 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ccrA Beta-lactamase type II (170 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ampC Beta-lactamase (730 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
nmcA Imipenem-hydrolyzing beta-lactamase (46 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 411.51Molecular Weight (Monoisotopic): 411.0711AlogP: 2.93#Rotatable Bonds: 4
Polar Surface Area: 73.74Molecular Species: ACIDHBA: 6HBD: 1
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 3.45CX Basic pKa: 6.96CX LogP: -0.74CX LogD: -1.16
Aromatic Rings: 2Heavy Atoms: 28QED Weighted: 0.62Np Likeness Score: -1.04

References

1. Venkatesan AM, Agarwal A, Abe T, Ushirogochi H, Yamamura I, Ado M, Tsuyoshi T, Dos Santos O, Gu Y, Sum FW, Li Z, Francisco G, Lin YI, Petersen PJ, Yang Y, Kumagai T, Weiss WJ, Shlaes DM, Knox JR, Mansour TS..  (2006)  Structure-activity relationship of 6-methylidene penems bearing 6,5 bicyclic heterocycles as broad-spectrum beta-lactamase inhibitors: evidence for 1,4-thiazepine intermediates with C7 R stereochemistry by computational methods.,  49  (15): [PMID:16854068] [10.1021/jm060021p]

Source