6-aminopenicillanic acid (CHEBI:16705)

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CHEBI:16705 - 6-aminopenicillanic acid

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ChEBI Name	6-aminopenicillanic acid

ChEBI ID	CHEBI:16705

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

Supplier Information	ZINC000001530092

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

X1E - Ideal conformer

RDKit 3D

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Time for openFile(X1E - Ideal conformer

RDKit 3D

26 27 0 0 0 0 0 0 0 0999 V2000

2.7730 1.1930 -0.9920 O 0 0 0 0 0 0 0 0 0 0 0 0

1.8150 1.0940 -0.0570 C 0 0 0 0 0 0 0 0 0 0 0 0

1.9350 1.6790 0.9940 O 0 0 0 0 0 0 0 0 0 0 0 0

0.5910 0.2550 -0.3160 C 0 0 1 0 0 0 0 0 0 0 0 0

0.9310 -1.2410 -0.0720 C 0 0 0 0 0 0 0 0 0 0 0 0

1.7970 -1.4180 1.1760 C 0 0 0 0 0 0 0 0 0 0 0 0

1.5950 -1.8680 -1.2990 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.4880 0.6750 0.5840 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.4880 1.4210 0.0810 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.5500 2.5610 -0.3290 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.4980 0.3200 0.2140 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.8460 -0.3290 -1.0570 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.4040 -0.3910 0.9930 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.7660 -1.9110 0.1890 S 0 0 0 0 0 0 0 0 0 0 0 0

3.5390 1.7430 -0.7800 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2730 0.3890 -1.3500 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2630 -1.0370 2.0470 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0170 -2.4760 1.3190 H 0 0 0 0 0 0 0 0 0 0 0 0

2.7300 -0.8670 1.0530 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5190 -1.3360 -1.5240 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8200 -2.9150 -1.0950 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9200 -1.8010 -2.1520 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5790 -0.4800 2.0650 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.3700 0.5870 0.8110 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.5070 0.2270 -1.5790 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.0200 -0.5170 -1.6050 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0

2 3 2 0

2 4 1 0

4 5 1 0

4 8 1 0

5 6 1 0

5 7 1 0

5 14 1 0

8 9 1 0

8 13 1 0

9 10 2 0

9 11 1 0

11 12 1 0

11 13 1 0

13 14 1 0

1 15 1 0

4 16 1 6

6 17 1 0

6 18 1 0

6 19 1 0

7 20 1 0

7 21 1 0

7 22 1 0

13 23 1 1

11 24 1 1

12 25 1 0

12 26 1 0

M END): 22 ms

reading 26 atoms

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1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

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26 atoms created

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Molfile

Wikipedia	License
6-APA ((+)-6-aminopenicillanic acid) is an organic compound that is used in the synthesis of β–lactam antibiotics including amoxicillin, ampicillin, oxacillin, and carbenicillin. The major commercial source of 6-APA is natural penicillin G, which contains an N-phenylacetyl substituent. The semi-synthetic penicillins derived from 6-APA are also referred to as penicillins and are considered part of the penicillin family of antibiotics.
Read full article at Wikipedia

Formulae

C8H12N2O3S
C8H12N2O3S

Net Charge

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

InChIKey

NGHVIOIJCVXTGV-ALEPSDHESA-N

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 acid 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 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	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	ChEBI
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
C02954	KEGG COMPOUND
US2941995	Patent
X1E	PDBeChem
View more database links

Registry Numbers	Types	Sources
15080	Reaxys Registry Number	Reaxys
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	Types	Sources
12569987	PubMed citation	Europe PMC
1384868	PubMed citation	Europe PMC
14687482	PubMed citation	Europe PMC
1701026	PubMed citation	Europe PMC
20970923	PubMed citation	Europe PMC
21614893	PubMed citation	Europe PMC
24293403	PubMed citation	Europe PMC
24389703	PubMed citation	Europe PMC
24631718	PubMed citation	Europe PMC
25057428	PubMed citation	Europe PMC
26852849	PubMed citation	Europe PMC
26986755	PubMed citation	Europe PMC
6166603	PubMed citation	Europe PMC

Last Modified

19 August 2024

CHEBI:16705 - 6-aminopenicillanic acid

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