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CHEBI:16705 - 6-aminopenicillanic acid

ChEBI IDCHEBI:16705
ChEBI Name6-aminopenicillanic acid
Stars
DefinitionA penicillanic acid compound having a (6R)-amino substituent. The active nucleus common to all penicillins, it may be substituted at the 6-amino position to form the semisynthetic penicillins, resulting in a variety of antibacterial and pharmacologic characteristics.
Secondary ChEBI IDsCHEBI:2172, CHEBI:20705
Last Modified19 August 2024
DownloadsMolfile
FormulaC8H12N2O3S
Net Charge0
Average Mass216.262
Monoisotopic Mass216.05686
SMILES[H][C@]12SC(C)(C)[C@H](C(=O)O)N1C(=O)[C@H]2N
InChIInChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1
InChIKeyNGHVIOIJCVXTGV-ALEPSDHESA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
allergen  A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
ChEBI Ontology
Outgoing Relation(s)
6-aminopenicillanic acid (CHEBI:16705) has functional parent penicillanic acid (CHEBI:37806)
6-aminopenicillanic acid (CHEBI:16705) has role allergen (CHEBI:50904)
6-aminopenicillanic acid (CHEBI:16705) is a penicillanic acids (CHEBI:25865)
6-aminopenicillanic acid (CHEBI:16705) is conjugate acid of 6-aminopenicillanate (CHEBI:30938)
6-aminopenicillanic acid (CHEBI:16705) is tautomer of 6-aminopenicillanic acid zwitterion (CHEBI:57869)
Incoming Relation(s)
6-aminopenicilloyl-butylamine (CHEBI:55475) has functional parent 6-aminopenicillanic acid (CHEBI:16705)
6-formamidopenicillanic acid (CHEBI:59004) has functional parent 6-aminopenicillanic acid (CHEBI:16705)
penicillin (CHEBI:17334) has functional parent 6-aminopenicillanic acid (CHEBI:16705)
6-aminopenicillanate (CHEBI:30938) is conjugate base of 6-aminopenicillanic acid (CHEBI:16705)
6-aminopenicilloyl group (CHEBI:55441) is substituent group from 6-aminopenicillanic acid (CHEBI:16705)
6-aminopenicillanic acid zwitterion (CHEBI:57869) is tautomer of 6-aminopenicillanic acid (CHEBI:16705)
IUPAC Name 
6-amino-2,2-dimethylpenam-3α-carboxylic acid
Synonyms  Source
(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidIUPAC
6-Aminopenicillamine acidChemIDplus
6-AminopenicillanateKEGG COMPOUND
(+)-6-aminopenicillanic acidChEBI
6-Aminopenicillanic acidKEGG COMPOUND
6-ApaChemIDplus
Manual XrefsDatabases
6-APAWikipedia
C02954KEGG COMPOUND
US2941995Patent
X1EPDBeChem
Registry NumbersSources
Reaxys:15080Reaxys
Gmelin:1876702Gmelin
Beilstein:959078Beilstein
CAS:551-16-6KEGG COMPOUND
CAS:551-16-6ChemIDplus
Citations