3b-Allotetrahydrocortisol (BioCAD00000019590)
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Metabolite Card
Chinese Name: 四氢皮质醇
Formula: C21H34O5 (366.2406)
SMILES:
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12CSynonyms [en]
3beta-Allotetrahydrocortisol; 3b-Allotetrahydrocortisol; 2-hydroxy-1-[(3S,5S,8S,9S,10S,11S,13S,14S,17R)-3,11,17-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone; Allo-3-beta-tetrahydrocortisol; 3beta,5alpha-tetrahydrocortisol; Reichstein's substance V
Note
3b-Allotetrahydrocortisol is one of the tetrahydrometabolites of cortisol. The 11-beta-hydroxysteroid dehydrogenase (11beta-HSD) is responsible for the interconversion of both the hormonally inactive cortisone and the active cortisol, which has implications in the pathogenesis of numerous diseases, as reflected in the ratio of tetrahydrometabolites of cortisol. (PMID: 16310418). The daily excretion of allotetrahydrocortisol is above normal in hyperthyroid patients; In contrast, in hyperthyroidism the excretion is diminished below normal levels to approximately half that of normal subjects. (PMID 13906284). A decreased activity of the enzyme 11beta-HSD produces a pattern of urinary steroid metabolites with an abnormal elevation of tetrahydrocortisol and allo-tetrahydrocortisol compared to tetrahydrocortisone; this pattern of steroid excretion is essential for the diagnosis of the syndrome of apparent mineralocorticoid excess type 1. (PMID: 8834992).
DBLinks
- CAS Registry Number: 651-43-4
- PubChem CID: 12444612
- ChEBI: 166779
- HMDB: HMDB0000314
- LipidMaps: LMST02030139
- KEGG:
- BioCyc:
- NCBI MeSH:
- Wikipedia:
Other DBLinks
- CAS Registry Number: 53-02-1
- CAS Registry Number: 651-43-4
- PubChem: 12444612
- ChEBI: ChEBI:166779
- HMDB: HMDB0000314
- HMDB: HMDB00314
- LipidMaps: LMST02030139
- RefMet: RM0125974
- Metlin: METLIN_57839
- metaboanalyst: 6e53dabb69bb019d7921d8fb33dcbc1e
Class / Ontology
- WishartLab ClassyFire: [Hydroxysteroids] Hydroxysteroids
- RefMet: [C21 steroids] C21 steroids
- LipidMaps: [C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]] C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
- ChEBI: [CHEBI:166779] 3beta-Allotetrahydrocortisol