AIC

(2S,5R,6R)-6-{[(2R)-2-AMINO-2-PHENYLETHANOYL]AMINO}-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID

Created:2001-02-17
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count43
Chiral Atom Count4
Bond Count45
Aromatic Bond Count6
2D diagram of AIC

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Chemical Component Summary

Name(2S,5R,6R)-6-{[(2R)-2-AMINO-2-PHENYLETHANOYL]AMINO}-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID
SynonymsAMPICILLIN; D(-)-ALPHA-AMINOBENZYLPENICILLIN; 6-[D(-)-ALPHA-AMINOPHENYLLACETAMIDO]PENICILLANIC ACID
Systematic Name (OpenEye OEToolkits)(2S,5R,6R)-6-[[(2R)-2-amino-2-phenyl-ethanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
FormulaC16 H19 N3 O4 S
Molecular Weight349.405
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs10.04O=C(O)C2N3C(=O)C(NC(=O)C(c1ccccc1)N)C3SC2(C)C
SMILESCACTVS3.341CC1(C)S[CH]2[CH](NC(=O)[CH](N)c3ccccc3)C(=O)N2[CH]1C(O)=O
SMILESOpenEye OEToolkits1.5.0CC1(C(N2C(S1)C(C2=O)NC(=O)C(c3ccccc3)N)C(=O)O)C
Canonical SMILESCACTVS3.341 CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(O)=O
Canonical SMILESOpenEye OEToolkits1.5.0 CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](c3ccccc3)N)C(=O)O)C
InChIInChI1.03 InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
InChIKeyInChI1.03 AVKUERGKIZMTKX-NJBDSQKTSA-N

Drug Info: DrugBank

DrugBank IDDB00415 
NameAmpicillin
Groups
  • approved
  • vet_approved
DescriptionAmpicillin is a semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.
Synonyms
  • D-(−)-6-(α-aminophenylacetamido)penicillanic acid
  • Ampicillinum
  • Anhydrous ampicillin
  • Ampicilina
  • AP
Brand Names
  • Ampicillin
  • Ampicillin and Sulbactam
  • Teva-ampicillin
  • Pro Ampi 500 Cap 500mg
  • Penbritin Cap 500mg
IndicationFor treatment of infection (Respiratory, GI, UTI and meningitis) due to E. coli, P. mirabilis, enterococci, Shigella, S. typhosa and other Salmonella, nonpenicillinase-producing N. gononhoeae, H. influenzae, staphylococci, streptococci including streptoc
Categories
  • Amides
  • Aminopenicillins
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
ATC-Code
  • J01CR50
  • J01CA51
  • J01CA01
  • S01AA19
CAS number69-53-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Penicillin-binding protein 2aMKLDKLFEKFLSLFKKETSELEDSDSTILRRSRSDRKKLAQVGPIRKFWR...unknowninhibitor
Penicillin-binding protein 1bMQNQLNELKRKMLEFFQQKQKNKKSARPGKKGSSTKKSKTLDKSAIFPAI...unknowninhibitor
Penicillin-binding protein 3MKKIFLTLLTVSLLGGASTAVAQDFTIAAKHAIAVEANTGKILYEKDATQ...unknowninhibitor
Penicillin-binding protein 1AMNKPTILRLIKYLSISFLSLVIAAIVLGGGVFFYYVSKAPSLSESKLVAT...unknowninhibitor
Penicillin-binding protein 2BMRKFNSHSIPIRLNLLFSIVILLFMTIIGRLLYMQVLNKDFYEKKLASAS...unknowninhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 7048611, 6249
ChEMBL CHEMBL174
ChEBI CHEBI:28971