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

Help

Find related ligands:

Chemical Details

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

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 data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
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
  • Ampicillinum
  • D-(−)-ampicillin
  • Ampicillin sodium
  • Ampicilline
  • Ampicillin
Brand Names
  • Ampicin Inj 125mg/vial
  • Ampicillin
  • Penbritin-250 Pws Im/iv 250mg/vial
  • Novo-ampicillin Pws 500mg/5ml
  • Ampicillin Trihydrate
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

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
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 6249, 7048611
ChEMBL CHEMBL174
ChEBI CHEBI:28971