(DL)-alpha-Lipoic acid

CHEBI:16494 chemically defined MAPPED CHEBI EXACT_MATCH

Ontology mapping

Primary identifier
CHEBI:16494
Ontology label
lipoic acid
kg-microbe node
CHEBI:16494

Nutritional roles

Synonyms (29)

SynonymTypeSourceOccurrences
Role: Growth factor; Properties: Organic compound, Defined component, Simple component RAW_TEXT CultureMech
1,2-dithiolane-3-pentanoic acid EXACT_SYNONYM kg_microbe
1,2-dithiolane-3-valeric acid EXACT_SYNONYM kg_microbe
5-(1,2-dithiolan-3-yl)pentanoic acid EXACT_SYNONYM kg_microbe
5-(1,2-dithiolan-3-yl)valeric acid EXACT_SYNONYM kg_microbe
5-(dithiolan-3-yl)valeric acid EXACT_SYNONYM kg_microbe
5-[3-(1,2-dithiolanyl)]pentanoic acid EXACT_SYNONYM kg_microbe
6,8-thioctic acid EXACT_SYNONYM kg_microbe
6,8-thiotic acid EXACT_SYNONYM kg_microbe
6-thioctic acid EXACT_SYNONYM kg_microbe
6-thiotic acid EXACT_SYNONYM kg_microbe
Acetate-replacing factor EXACT_SYNONYM kg_microbe
Biletan EXACT_SYNONYM kg_microbe
DL-6,8-thioctic acid EXACT_SYNONYM kg_microbe
DL-alpha-lipoic acid EXACT_SYNONYM kg_microbe
Thioctansaeure EXACT_SYNONYM kg_microbe
Thioctsaeure EXACT_SYNONYM kg_microbe
Thioktsaeure EXACT_SYNONYM kg_microbe
alpha-Liponsaeure EXACT_SYNONYM kg_microbe
liponic acid EXACT_SYNONYM kg_microbe
Lipoic acid EXACT_SYNONYM merged_from_duplicate_mim_record
alpha-lipoic acid EXACT_SYNONYM merged_from_duplicate_mim_record
Role: Growth factor; Properties: Defined component, Simple component, Organic compound RAW_TEXT CultureMech
Role: Vitamin; Properties: Organic compound, Defined component, Simple component RAW_TEXT CultureMech
Lipoate EXACT manual
Thioctic acid RAW_TEXT MERGED_FROM_CHEBI:30314
α-lipoic acid RAW_TEXT MERGED_FROM_CHEBI:43796
α--Lipoic acid RAW_TEXT MERGED_FROM_CHEBI:43796
D,L-6,8-Thioctic Acid RAW_TEXT MERGED_FROM_CHEBI:43796

Chemical properties

Cas rn
1077-28-7
Data source
PubChem (via CHEBI:16494)
Retrieval date
2026-04-09T00:32:50.689620+00:00
Molecular formula
C8H14O2S2
Inchi
InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
Smiles
O=C(O)CCCCC1CCSS1

Evidence (2)

DATABASE_MATCH via CultureMech

Imported from CultureMech pipeline, quality=DIRECT_MATCH

CURATOR_JUDGMENT via MIM curation (#454)

The Thioctic acid, alpha-lipoic acid, and D,L-6,8-Thioctic Acid source labels name generic or racemic lipoic/thioctic acid rather than R- or S-only lipoic acid.

Occurrence statistics

Total occurrences
1,748
Distinct media
1,747

Curation history

TimestampCuratorActionNew statusChanges
2026-03-09T06:54:18.022301+00:00 import_from_culturemech IMPORTED MAPPED Initial import from CultureMech pipeline
2026-04-05T19:51:03.959053+00:00 fetch_cas_rn_from_pubchem ADDED_CAS_RN MAPPED Added CAS-RN:1077-28-7 from PubChem API via name lookup (alpha-lipoic acid)
2026-04-05T21:48:45.295350+00:00 fetch_cas_rn_from_culturebot_csv ADDED_CAS_RN MAPPED Added CAS-RN:1077-28-7 from CultureBotHT compounds_to_cas.csv (matched: Lipoic acid)
2026-04-09T00:32:50.689620+00:00 enrich_mim_cas_rn_batch CAS_RN_ADDED MAPPED Added CAS-RN 1077-28-7 from PubChem (via CHEBI:16494)
2026-04-17T12:00:00+00:00 synonym_expansion_cbclaw LLM ADDED_SYNONYMS MAPPED Added 1 synonym for unmapped CultureMech surface form
2026-04-18T00:00:00+00:00 cbclaw_kg_microbe_sweep LLM ADDED_SYNONYMS MAPPED Added 19 synonyms from kg-microbe P4.4 enrichment: 1,2-dithiolane-3-pentanoic acid, 1,2-dithiolane-3-valeric acid, 5-(1,2-dithiolan-3-yl)pentanoic acid, 5-(1,2-dithiolan-3-yl)valeric acid, 5-(dithiolan-3-yl)valeric acid, ... (14 more)
2026-04-18T00:00:00+00:00 cbclaw_kg_microbe_sweep LLM ADDED_SYNONYMS MAPPED Added 20 synonyms from kg-microbe P4.4 enrichment: (DL)-alpha-Lipoic acid, 1,2-dithiolane-3-pentanoic acid, 1,2-dithiolane-3-valeric acid, 5-(1,2-dithiolan-3-yl)pentanoic acid, 5-(1,2-dithiolan-3-yl)valeric acid, ... (15 more)
2026-04-18T00:00:00+00:00 cbclaw_kg_microbe_sweep LLM ADDED_SYNONYMS MAPPED Added 19 synonyms from kg-microbe P4.4 enrichment: (DL)-alpha-Lipoic acid, 1,2-dithiolane-3-pentanoic acid, 1,2-dithiolane-3-valeric acid, 5-(1,2-dithiolan-3-yl)pentanoic acid, 5-(1,2-dithiolan-3-yl)valeric acid, ... (14 more)
2026-04-19T07:39:23.955331+00:00 audit_mim_merge MERGED_FROM_DUPLICATES MAPPED Absorbed 4 duplicate MIM record(s) into this one: Lipoic_Acid.yaml, Alpha-lipoic_Acid.yaml, Dl-68-thioctic_Acid.yaml, Dl-alpha-lipoic_Acid_2.yaml. Synonyms, curation_history, and occurrence counts were unioned/summed; winner selected by highest occurrence count with preferred_term readability tie-break.
2026-05-01T07:35:33.335201+00:00 auto_classify_ingredient_type AUTO_CLASSIFY_INGREDIENT_TYPE set ingredient_type=SINGLE_INGREDIENT (CHEBI primary)
2026-05-01T08:08:29.303356+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)CCCCC1CCSS1
2026-05-02T03:12:14.110613+00:00 auto_classify_ingredient_type AUTO_CLASSIFY_INGREDIENT_TYPE set ingredient_type=SINGLE_INGREDIENT (chemical structure populated (molecular_formula))
2026-05-29T23:35:36.110999+00:00 extract_roles_from_synonyms ANNOTATED Added media role: VITAMIN_SOURCE (confidence: 1.00)
2026-06-09T05:23:46.757782+00:00 correct_stale_ontology_labels.py CORRECTED ontology_label '(DL)-alpha-Lipoic acid' -> 'lipoic acid': synced to canonical CHEBI label (preferred_term '(DL)-alpha-Lipoic acid' unchanged).
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
2026-08-27T03:16:39.518756+00:00 refresh_occurrence_statistics CORRECTED occurrence_statistics 157/1399 -> 1700/1701 (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_FROM_MAPPED_RECORD MAPPED Absorbed generic/racemic Thioctic acid and alpha-lipoic acid records from CHEBI:30314/CHEBI:43796; carried 4 observed source label(s), kept R/S-only target synonyms as REJECTED_LABEL provenance on the tombstones, moved 47/47 occurrences, and retargeted 2 component reference(s) (#454/#634).