ID: ALA617

Max Phase: Approved

First Approval: 1974

Molecular Formula: C16H16N2O6S2

Molecular Weight: 396.45

Molecule Type: Small molecule

Representations

Synonyms (1): Seffin
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)Cc3cccs3)[C@H]2SC1

Standard InChI:  InChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1

Standard InChI Key:  XIURVHNZVLADCM-IUODEOHRSA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 396.45

Molecular Weight (Monoisotopic): 396.0450

AlogP: 0.59

#Rotatable Bonds: 6

Polar Surface Area: 113.01

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.43

CX Basic pKa:

CX LogP: 0.02

CX LogD: -3.38

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.53

Np Likeness Score: -0.37

References

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23. Lartigue MF, Zinsius C, Wenger A, Bille J, Poirel L, Nordmann P..  (2007)  Extended-spectrum beta-lactamases of the CTX-M type now in Switzerland.,  51  (8): [PMID:17470647] [10.1128/aac.01614-06]

24. Suvorov M, Vakulenko SB, Mobashery S..  (2007)  Cytoplasmic-membrane anchoring of a class A beta-lactamase and its capacity in manifesting antibiotic resistance.,  51  (8): [PMID:17502412] [10.1128/aac.00011-07]

25. Pérez A, Canle D, Latasa C, Poza M, Beceiro A, Tomás Mdel M, Fernández A, Mallo S, Pérez S, Molina F, Villanueva R, Lasa I, Bou G..  (2007)  Cloning, nucleotide sequencing, and analysis of the AcrAB-TolC efflux pump of Enterobacter cloacae and determination of its involvement in antibiotic resistance in a clinical isolate.,  51  (9): [PMID:17638702] [10.1128/aac.00072-07]

26. Girlich D, Leclercq R, Naas T, Nordmann P..  (2007)  Molecular and biochemical characterization of the chromosome-encoded class A beta-lactamase BCL-1 from Bacillus clausii.,  51  (11): [PMID:17846134] [10.1128/aac.00537-07]

27. Neuwirth C, Siebor E, Robin F, Bonnet R..  (2007)  First occurrence of an IMP metallo-beta-lactamase in Aeromonas caviae: IMP-19 in an isolate from France.,  51  (12): [PMID:17938180] [10.1128/aac.01462-06]

28. Fonseca F, Sarmento AC, Henriques I, Samyn B, van Beeumen J, Domingues P, Domingues MR, Saavedra MJ, Correia A..  (2007)  Biochemical Characterization of SFC-1, a class A carbapenem-hydrolyzing beta-lactamase.,  51  (12): [PMID:17875998] [10.1128/aac.00491-07]

29. Robin F, Delmas J, Brebion A, Dubois D, Constantin JM, Bonnet R..  (2007)  TEM-158 (CMT-9), a new member of the CMT-type extended-spectrum beta-lactamases.,  51  (11): [PMID:17709463] [10.1128/aac.00614-07]

30. Power P, Di Conza J, Rodríguez MM, Ghiglione B, Ayala JA, Casellas JM, Radice M, Gutkind G..  (2007)  Biochemical characterization of PER-2 and genetic environment of blaPER-2.,  51  (7): [PMID:17438050] [10.1128/aac.01395-06]

31. Morio F, Jean-Pierre H, Dubreuil L, Jumas-Bilak E, Calvet L, Mercier G, Devine R, Marchandin H..  (2007)  Antimicrobial susceptibilities and clinical sources of Dialister species.,  51  (12): [PMID:17923492] [10.1128/aac.00538-07]

32. Meziane-Cherif D, Decré D, Høiby EA, Courvalin P, Périchon B..  (2008)  Genetic and biochemical characterization of CAD-1, a chromosomally encoded new class A penicillinase from Carnobacterium divergens.,  52  (2): [PMID:18070972] [10.1128/aac.01145-07]

33. Zong Z, Partridge SR, Iredell JR..  (2008)  RmtC 16S rRNA methyltransferase in Australia.,  52  (2): [PMID:18025117] [10.1128/aac.01399-07]

34. Cuzon G, Naas T, Demachy MC, Nordmann P..  (2008)  Plasmid-mediated carbapenem-hydrolyzing beta-lactamase KPC-2 in Klebsiella pneumoniae isolate from Greece.,  52  (2): [PMID:18056283] [10.1128/aac.01180-07]

35. Miguet L, Zervosen A, Gerards T, Pasha FA, Luxen A, Distèche-Nguyen M, Thomas A..  (2009)  Discovery of new inhibitors of resistant Streptococcus pneumoniae penicillin binding protein (PBP) 2x by structure-based virtual screening.,  52  (19): [PMID:19746934] [10.1021/jm900625q]

36. Pohlmann J, Vasilevich NI, Glushkov AI, Kellenberger L, Shapiro S, Caspers P, Page MG, Danel F..  (2010)  Propenylamide and propenylsulfonamide cephalosporins as a novel class of anti-MRSA beta-lactams.,  20  (15): [PMID:20576430] [10.1016/j.bmcl.2010.05.110]

37. Girlich D, Poirel L, Nordmann P..  (2010)  Novel ambler class A carbapenem-hydrolyzing beta-lactamase from a Pseudomonas fluorescens isolate from the Seine River, Paris, France.,  54  (1): [PMID:19901091] [10.1128/aac.00961-09]

38. Doublet B, Robin F, Casin I, Fabre L, Le Fleche A, Bonnet R, Weill FX..  (2010)  Molecular and biochemical characterization of the natural chromosome-encoded class A beta-lactamase from Pseudomonas luteola.,  54  (1): [PMID:19884377] [10.1128/aac.00427-09]

39. Robin F, Aggoune-Khinache N, Delmas J, Naim M, Bonnet R..  (2010)  Novel VIM metallo-beta-lactamase variant from clinical isolates of Enterobacteriaceae from Algeria.,  54  (1): [PMID:19901092] [10.1128/aac.00017-09]

40. Girlich D, Poirel L, Nordmann P..  (2010)  First isolation of the blaOXA-23 carbapenemase gene from an environmental Acinetobacter baumannii isolate.,  54  (1): [PMID:19884362] [10.1128/aac.00861-09]

41. Poirel L, Docquier JD, De Luca F, Verlinde A, Ide L, Rossolini GM, Nordmann P..  (2010)  BEL-2, an extended-spectrum beta-lactamase with increased activity toward expanded-spectrum cephalosporins in Pseudomonas aeruginosa.,  54  (1): [PMID:19884378] [10.1128/aac.00859-09]

42. Kotsakis SD, Papagiannitsis CC, Tzelepi E, Legakis NJ, Miriagou V, Tzouvelekis LS..  (2010)  GES-13, a beta-lactamase variant possessing Lys-104 and Asn-170 in Pseudomonas aeruginosa.,  54  (3): [PMID:20065056] [10.1128/aac.01561-09]

43. Bondock S, Fadaly W, Metwally MA..  (2010)  Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety.,  45  (9): [PMID:20605657] [10.1016/j.ejmech.2010.05.018]

44. Gozalbes R, Pineda-Lucena A..  (2010)  QSAR-based solubility model for drug-like compounds.,  18  (19): [PMID:20810286] [10.1016/j.bmc.2010.08.003]

45. Mendonça N, Manageiro V, Bonnet R, Caniça M..  (2008)  Biochemical characterization of SHV-55, an extended-spectrum class A beta-lactamase from Klebsiella pneumoniae.,  52  (5): [PMID:18316524] [10.1128/aac.01525-07]

46. Carrër A, Poirel L, Yilmaz M, Akan OA, Feriha C, Cuzon G, Matar G, Honderlick P, Nordmann P..  (2010)  Spread of OXA-48-encoding plasmid in Turkey and beyond.,  54  (3): [PMID:20086157] [10.1128/aac.01312-09]

47. De Luca F, Giraud-Morin C, Rossolini GM, Docquier JD, Fosse T..  (2010)  Genetic and biochemical characterization of TRU-1, the endogenous class C beta-lactamase from Aeromonas enteropelogenes.,  54  (4): [PMID:20124004] [10.1128/aac.01252-09]

48. Nannini EC, Stryjewski ME, Singh KV, Rude TH, Corey GR, Fowler VG, Murray BE..  (2010)  Determination of an inoculum effect with various cephalosporins among clinical isolates of methicillin-susceptible Staphylococcus aureus.,  54  (5): [PMID:20211890] [10.1128/aac.01325-09]

49. Poirel L, Rodríguez-Martínez JM, Al Naiemi N, Debets-Ossenkopp YJ, Nordmann P..  (2010)  Characterization of DIM-1, an integron-encoded metallo-beta-lactamase from a Pseudomonas stutzeri clinical isolate in the Netherlands.,  54  (6): [PMID:20308383] [10.1128/aac.01456-09]

50. Mendonça N, Manageiro V, Robin F, Salgado MJ, Ferreira E, Caniça M, Bonnet R..  (2008)  The Lys234Arg substitution in the enzyme SHV-72 is a determinant for resistance to clavulanic acid inhibition.,  52  (5): [PMID:18316518] [10.1128/aac.01381-07]

51. Naas T, Cuzon G, Villegas MV, Lartigue MF, Quinn JP, Nordmann P..  (2008)  Genetic structures at the origin of acquisition of the beta-lactamase bla KPC gene.,  52  (4): [PMID:18227185] [10.1128/aac.01451-07]

52. Poirel L, Mansour W, Bouallegue O, Nordmann P..  (2008)  Carbapenem-resistant Acinetobacter baumannii isolates from Tunisia producing the OXA-58-like carbapenem-hydrolyzing oxacillinase OXA-97.,  52  (5): [PMID:18299404] [10.1128/aac.00978-07]

53. Marchiaro P, Tomatis PE, Mussi MA, Pasteran F, Viale AM, Limansky AS, Vila AJ..  (2008)  Biochemical characterization of metallo-beta-lactamase VIM-11 from a Pseudomonas aeruginosa clinical strain.,  52  (6): [PMID:18362187] [10.1128/aac.01025-07]

54. Manageiro V, Ferreira E, Albuquerque L, Bonnet R, Caniça M..  (2010)  Biochemical study of a new inhibitor-resistant beta-lactamase, SHV-84, produced by a clinical Escherichia coli strain.,  54  (5): [PMID:20211886] [10.1128/aac.01442-09]

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56. Meziane-Cherif D, Lambert T, Dupêchez M, Courvalin P, Galimand M..  (2008)  Genetic and biochemical characterization of OXA-63, a new class D beta-lactamase from Brachyspira pilosicoli BM4442.,  52  (4): [PMID:18212108] [10.1128/aac.00684-07]

57. Doi Y, Poirel L, Paterson DL, Nordmann P..  (2008)  Characterization of a naturally occurring class D beta-lactamase from Achromobacter xylosoxidans.,  52  (6): [PMID:18362192] [10.1128/aac.01463-07]

58. Stoczko M, Frère JM, Rossolini GM, Docquier JD..  (2008)  Functional diversity among metallo-beta-lactamases: characterization of the CAR-1 enzyme of Erwinia carotovora.,  52  (7): [PMID:18443127] [10.1128/aac.01062-07]

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60. Pränting M, Negrea A, Rhen M, Andersson DI..  (2008)  Mechanism and fitness costs of PR-39 resistance in Salmonella enterica serovar Typhimurium LT2.,  52  (8): [PMID:18519732] [10.1128/aac.00205-08]

61. Samuelsen Ø, Castanheira M, Walsh TR, Spencer J..  (2008)  Kinetic characterization of VIM-7, a divergent member of the VIM metallo-beta-lactamase family.,  52  (8): [PMID:18559652] [10.1128/aac.00166-08]

62. Petrella S, Ziental-Gelus N, Mayer C, Renard M, Jarlier V, Sougakoff W..  (2008)  Genetic and structural insights into the dissemination potential of the extremely broad-spectrum class A beta-lactamase KPC-2 identified in an Escherichia coli strain and an Enterobacter cloacae strain isolated from the same patient in France.,  52  (10): [PMID:18625772] [10.1128/aac.00163-08]

63. Dubois V, Poirel L, Demarthe F, Arpin C, Coulange L, Minarini LA, Bezian MC, Nordmann P, Quentin C..  (2008)  Molecular and biochemical characterization of SHV-56, a novel inhibitor-resistant beta-lactamase from Klebsiella pneumoniae.,  52  (10): [PMID:18663019] [10.1128/aac.00387-08]

64. Picão RC, Poirel L, Demarta A, Petrini O, Corvaglia AR, Nordmann P..  (2008)  Expanded-spectrum beta-lactamase PER-1 in an environmental Aeromonas media isolate from Switzerland.,  52  (9): [PMID:18644966] [10.1128/aac.00770-08]

65. Mammeri H, Galleni M, Nordmann P..  (2009)  Role of the Ser-287-Asn replacement in the hydrolysis spectrum extension of AmpC beta-lactamases in Escherichia coli.,  53  (1): [PMID:19001118] [10.1128/aac.00608-08]

66. Cattoir V, Poirel L, Nordmann P..  (2008)  Plasmid-mediated quinolone resistance pump QepA2 in an Escherichia coli isolate from France.,  52  (10): [PMID:18644958] [10.1128/aac.00638-08]

67. Rodríguez MM, Power P, Sader H, Galleni M, Gutkind G..  (2010)  Novel chromosome-encoded CTX-M-78 beta-lactamase from a Kluyvera georgiana clinical isolate as a putative origin of CTX-M-25 subgroup.,  54  (7): [PMID:20421403] [10.1128/aac.01615-09]

68. Cuzon G, Naas T, Bogaerts P, Glupczynski Y, Huang TD, Nordmann P..  (2008)  Plasmid-encoded carbapenem-hydrolyzing beta-lactamase OXA-48 in an imipenem-susceptible Klebsiella pneumoniae strain from Belgium.,  52  (9): [PMID:18644970] [10.1128/aac.00543-08]

69. Juan C, Beceiro A, Gutiérrez O, Albertí S, Garau M, Pérez JL, Bou G, Oliver A..  (2008)  Characterization of the new metallo-beta-lactamase VIM-13 and its integron-borne gene from a Pseudomonas aeruginosa clinical isolate in Spain.,  52  (10): [PMID:18644957] [10.1128/aac.00465-08]

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71. PubChem BioAssay data set, 

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73. Wolter DJ, Kurpiel PM, Woodford N, Palepou MF, Goering RV, Hanson ND..  (2009)  Phenotypic and enzymatic comparative analysis of the novel KPC variant KPC-5 and its evolutionary variants, KPC-2 and KPC-4.,  53  (2): [PMID:19015357] [10.1128/aac.00734-08]

74. Cui L, Neoh HM, Shoji M, Hiramatsu K..  (2009)  Contribution of vraSR and graSR point mutations to vancomycin resistance in vancomycin-intermediate Staphylococcus aureus.,  53  (3): [PMID:19124662] [10.1128/aac.01173-08]

75. Nagano Y, Nagano N, Wachino J, Ishikawa K, Arakawa Y..  (2009)  Novel chimeric beta-lactamase CTX-M-64, a hybrid of CTX-M-15-like and CTX-M-14 beta-lactamases, found in a Shigella sonnei strain resistant to various oxyimino-cephalosporins, including ceftazidime.,  53  (1): [PMID:18955524] [10.1128/aac.00227-08]

76. Rodríguez-Martínez JM, Poirel L, Nordmann P..  (2009)  Extended-spectrum cephalosporinases in Pseudomonas aeruginosa.,  53  (5): [PMID:19258272] [10.1128/aac.01410-08]

77. Papp-Wallace KM, Taracila M, Hornick JM, Hujer AM, Hujer KM, Distler AM, Endimiani A, Bonomo RA..  (2010)  Substrate selectivity and a novel role in inhibitor discrimination by residue 237 in the KPC-2 beta-lactamase.,  54  (7): [PMID:20421396] [10.1128/aac.00197-10]

78. Pradel N, Delmas J, Wu LF, Santini CL, Bonnet R..  (2009)  Sec- and Tat-dependent translocation of beta-lactamases across the Escherichia coli inner membrane.,  53  (1): [PMID:18981261] [10.1128/aac.00642-08]

79. Poirel L, Rodriguez-Martinez JM, Plésiat P, Nordmann P..  (2009)  Naturally occurring Class A ss-lactamases from the Burkholderia cepacia complex.,  53  (3): [PMID:19075063] [10.1128/aac.00946-08]

80. Zioga A, Whichard JM, Kotsakis SD, Tzouvelekis LS, Tzelepi E, Miriagou V..  (2009)  CMY-31 and CMY-36 cephalosporinases encoded by ColE1-like plasmids.,  53  (3): [PMID:19104021] [10.1128/aac.01284-08]

81. Zeba B, De Luca F, Dubus A, Delmarcelle M, Simporé J, Nacoulma OG, Rossolini GM, Frère JM, Docquier JD..  (2009)  IND-6, a highly divergent IND-type metallo-beta-lactamase from Chryseobacterium indologenes strain 597 isolated in Burkina Faso.,  53  (10): [PMID:19651915] [10.1128/aac.01607-08]

82. Duval V, Nicoloff H, Levy SB..  (2009)  Combined inactivation of lon and ycgE decreases multidrug susceptibility by reducing the amount of OmpF porin in Escherichia coli.,  53  (11): [PMID:19721064] [10.1128/aac.00787-09]

83. Dalley AJ, Deans R, Lipman J, Venkatesh B, Rudd M, Roberts MS, Cross SE..  (2009)  Unbound cephalothin pharmacokinetics in adult burn patients are related to the elapsed time after injury.,  53  (12): [PMID:19752272] [10.1128/aac.01600-08]

84. Yong D, Toleman MA, Giske CG, Cho HS, Sundman K, Lee K, Walsh TR..  (2009)  Characterization of a new metallo-beta-lactamase gene, bla(NDM-1), and a novel erythromycin esterase gene carried on a unique genetic structure in Klebsiella pneumoniae sequence type 14 from India.,  53  (12): [PMID:19770275] [10.1128/aac.00774-09]

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Source

Source(9):

• Scientific Literature
• PubChem BioAssays
• Open TG-GATEs
• TP-search Transporter Database
• Gene Expression Atlas Compounds
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6