α-lipoic acid

Ontology mapping

Primary identifier: CHEBI:16494
Ontology label: lipoic acid

Nutritional roles

Role
VITAMIN_SOURCE
Confidence
0.8
Evidence
- Reference type
  COMPUTATIONAL_PREDICTION
  Reference text
  Inferred from curated media-role name pattern
  Curator note
  Provisional role from a curated name-pattern rule; review recommended.

Synonyms (2)

Synonym	Type	Source	Occurrences
Role: Growth factor; Properties: Organic compound, Defined component, Simple component	RAW_TEXT	CultureMech
D,L-6,8-Thioctic Acid	EXACT_SYNONYM	kg_microbe

Rejected enrichment labels (10)

Provenance-only candidates: these are not synonyms and do not resolve to this record.

Rejected label	Disposition	Source
(S)-(-)-lipoic acid	REJECTED_LABEL	kg_microbe
(S)-1,2-dithiolane-3-pentanoic acid	REJECTED_LABEL	kg_microbe
(S)-alpha-lipoic acid	REJECTED_LABEL	kg_microbe
5-[(3S)-1,2-dithiolan-3-yl]pentanoic acid	REJECTED_LABEL	kg_microbe
L-1,2-dithiolane 3-valeric acid	REJECTED_LABEL	kg_microbe
L-6,8-thioctic acid	REJECTED_LABEL	kg_microbe
L-6-thioctic acid	REJECTED_LABEL	kg_microbe
S-LA	REJECTED_LABEL	kg_microbe
SLA	REJECTED_LABEL	kg_microbe
thioctic acid l-form	REJECTED_LABEL	kg_microbe

Evidence (1)

CURATOR_JUDGMENT via MIM curation (#454)

The source label names generic or racemic lipoic/thioctic acid. No source occurrence asserts an R- or S-only enantiomer, so CHEBI:16494 is the supported ChEBI target.

Occurrence statistics

Total occurrences: 0
Distinct media: 0

Curation history

Timestamp	Curator	Action	New status	Changes
2026-03-09T06:54:18.022301+00:00	import_from_culturemech	IMPORTED	MAPPED	Initial import from CultureMech pipeline
2026-04-05T23:47:17.271583+00:00	fetch_cas_rn_with_preprocessing	ADDED_CAS_RN	MAPPED	Added CAS-RN:1077-27-6 from PubChem API (ontology label) via name preprocessing (α-lipoic acid)
2026-04-18T00:00:00+00:00	cbclaw_kg_microbe_sweep LLM	ADDED_SYNONYMS	MAPPED	Added 11 synonyms from kg-microbe P4.4 enrichment: (S)-(-)-lipoic acid, (S)-1,2-dithiolane-3-pentanoic acid, (S)-alpha-lipoic acid, 5-[(3S)-1,2-dithiolan-3-yl]pentanoic acid, D,L-6,8-Thioctic Acid, ... (6 more)
2026-05-01T07:35:37.007470+00:00	auto_classify_ingredient_type	AUTO_CLASSIFY_INGREDIENT_TYPE		set ingredient_type=SINGLE_INGREDIENT (CHEBI primary)
2026-05-01T08:08:33.104330+00:00	auto_classify_ingredient_type	AUTO_BACKFILL_CHEBI_CHEMISTRY		molecular_formula=C8H14O2S2; inchi=InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h; smiles=O=C(O)CCCC[C@H]1CCSS1
2026-05-02T03:12:19.397241+00:00	auto_classify_ingredient_type	AUTO_CLASSIFY_INGREDIENT_TYPE		set ingredient_type=SINGLE_INGREDIENT (chemical structure populated (molecular_formula))
2026-06-03T02:06:01.754161+00:00	infer_roles_from_name_lists	ANNOTATED		Added media role: VITAMIN_SOURCE (confidence: 0.80)
2026-07-20T00:00:00+00:00	migrate_media_roles_to_facets	ANNOTATED		Migrated legacy media_roles to role facets (#128): VITAMIN_SOURCE -> nutritional_roles.VITAMIN_SOURCE
2026-08-27T03:16:39.520188+00:00	refresh_occurrence_statistics	CORRECTED		occurrence_statistics 4/4 -> 11/11 (media_count/total_occurrences), derived from distinct CultureMech recipe ids in the #337 occurrence table. The prior values came from the importer retired in #453, whose media_count counted a list truncated to 50 examples (#449). [source=ingredient_occurrences.tsv culturemech_rev=15a4da5c08 rows=194137 distinct_recipes=15257]
2026-09-11T14:49:05.979520+00:00	fix_lipoic_stereochemistry	MERGED_INTO	REJECTED	Merged into CHEBI:16494 '(DL)-alpha-Lipoic acid'; the old CHEBI:43796 target was an unsupported enantiomer-specific grounding. Occurrences were transferred to the generic lipoic acid record and SSSOM rows were dropped (#454), and 10 R/S-only target synonym(s) were retained as REJECTED_LABEL provenance (#454/#634).