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6-(6,7-dihydro-4H-thieno[3,2-c]pyran-2-ylmethylene)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid sodium salt

ID: ALA380061

PubChem CID: 44413920

Max Phase: Preclinical

Molecular Formula: C21H17N2NaO4S3

Molecular Weight: 458.59

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(c3cc5c(s3)CCOC5)C4)C(=O)N12.[Na+]

Standard InChI:  InChI=1S/C21H18N2O4S3.Na/c24-19-14(20-23(19)15(10-28-20)21(25)26)7-13-5-11-8-22(3-1-16(11)29-13)18-6-12-9-27-4-2-17(12)30-18;/h5-7,10,20H,1-4,8-9H2,(H,25,26);/q;+1/p-1/b14-7-;/t20-;/m1./s1

Standard InChI Key:  KFRUINCRKCXKEP-KOQARVEBSA-M

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    5.0239   -4.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5438   -3.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5436   -4.7380    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7577   -4.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7587   -3.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0514   -3.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -3.6606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3378   -4.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0495   -4.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2772   -3.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0787   -3.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0816   -2.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8831   -2.3942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9449   -1.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1815   -1.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6481   -1.8878    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7837   -3.6241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8487   -4.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6484   -1.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3749   -1.5282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6239   -0.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6253   -3.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5406   -2.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8703   -3.5803    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3198   -2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7358   -2.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3271   -1.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4992   -1.5324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9152   -2.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5049   -2.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1591   -2.9757    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8917   -1.9708    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
 14 15  2  0
 15 16  1  0
 12 16  1  0
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 11 17  2  0
 10 11  1  0
 10 18  2  0
 11 13  1  0
 19 20  1  0
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 14 19  1  0
 12 10  1  0
 18  1  1  0
 13 14  1  0
  7 22  1  0
 22 23  2  0
  2  5  1  0
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 25 24  1  0
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  1  2  2  0
  4  3  1  0
  3  1  1  0
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 25 30  1  0
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 27 28  1  0
 28 29  1  0
 29 30  1  0
 12 31  1  6
M  CHG  2  20  -1  32   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
ampC Beta-lactamase (730 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ccrA Beta-lactamase type II (170 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: 458.59Molecular Weight (Monoisotopic): 458.0429AlogP: 3.67#Rotatable Bonds: 3
Polar Surface Area: 70.08Molecular Species: ACIDHBA: 7HBD: 1
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 3.61CX Basic pKa: CX LogP: 3.32CX LogD: -0.02
Aromatic Rings: 2Heavy Atoms: 30QED Weighted: 0.56Np Likeness Score: -0.45

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