6-aminopenicillanic acid

CHEBI:16705 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

penicillanic acids CHEBI:25865

Chemical structure

Computed structure properties
Molecular formula	C8H12N2O3S
Charge	0
Average mass	216.262 Da
Monoisotopic mass	216.05686 Da
Source	ChEBI
InChIKey	NGHVIOIJCVXTGV-ALEPSDHESA-N

SMILES

[H][C@]12SC(C)(C)[C@H](C(=O)O)N1C(=O)[C@H]2N

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

Also called

6-amino-2,2-dimethylpenam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
(+)-6-aminopenicillanic acid (EXACT_SYNONYM)— chebi
(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
6-APA (EXACT_SYNONYM)— chebi
6-Aminopenicillamine acid (EXACT_SYNONYM)— chebi
6-Aminopenicillanate (EXACT_SYNONYM)— chebi
6-Aminopenicillanic acid (EXACT_SYNONYM)— chebi
6-Apa (EXACT_SYNONYM)— chebi
6-Aps (EXACT_SYNONYM)— chebi
6β-aminopenicillanic acid (EXACT_SYNONYM)— chebi
Aminopenicillanic acid (EXACT_SYNONYM)— chebi
Penicin (EXACT_SYNONYM)— chebi
Penin (EXACT_SYNONYM)— chebi
Phenacyl 6-aminopenicillinate (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

beilstein:959078
cas:551-16-6
gmelin:1876702
kegg.compound:C02954
pdb-ccd:X1E
reaxys:15080

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antimicrobial agent CHEBI:33281

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:16705`	6-aminopenicillanic acid	`antibioticmech:chebi-f7d27534f9`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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