CHEBI:16705 - 6-aminopenicillanic acid

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ChEBI Name 6-aminopenicillanic acid
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:20705, CHEBI:2172
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Formulae C8H12N2O3S
Net Charge 0
Average Mass 216.260
Monoisotopic Mass 216.05686
InChI InChI=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
SMILES C([C@H]1C(S[C@@]2([C@@H](C(N12)=O)N)[H])(C)C)(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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.
(via heterocyclic antibiotic )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 base of 6-aminopenicillanate (CHEBI:30938)
6-aminopenicillanic acid (CHEBI:16705) is tautomer of 6-aminopenicillanic acid zwitterion (CHEBI:57869)
Incoming 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 acid 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)
6-amino-2,2-dimethylpenam-3α-carboxylic acid
Synonyms Sources
(+)-6-aminopenicillanic acid ChEBI
(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid IUPAC
6-Aminopenicillamine acid ChemIDplus
6-Aminopenicillanate KEGG COMPOUND
6-Aminopenicillanic acid KEGG COMPOUND
6-Apa ChemIDplus
6-Aps ChemIDplus
6β-aminopenicillanic acid ChEBI
Aminopenicillanic acid ChemIDplus
Penicin ChemIDplus
Penin ChemIDplus
Phenacyl 6-aminopenicillinate ChemIDplus
Manual Xrefs Databases
6-APA Wikipedia
US2941995 Patent
X1E PDBeChem
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Registry Numbers Types Sources
15080 Reaxys Registry Number Reaxys
15080 Beilstein Registry Number Beilstein
1876702 Gmelin Registry Number Gmelin
551-16-6 CAS Registry Number KEGG COMPOUND
551-16-6 CAS Registry Number ChemIDplus
959078 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
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Last Modified
21 November 2019