Basic information
- CAS
561-65-9- Standard SMILES
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@]2(CO)[C@@H](C(=O)CO)CC[C@@H]12- InChIKey
HFSXHZZDNDGLQN-ZVIOFETBSA-N- Molecular formula
- C21H30O5
- Average molar mass
- 362.5 g/mol
- Monoisotopic mass
- 362.20932405
Names & identifiers
- Preferred name
- 18-Hydroxycorticosterone
- IUPAC
- (8S,9S,10R,11S,13R,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-13-(hydroxymethyl)-10-methyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
- English name
- 18-Hydroxycorticosterone
- Molecular formula
- C21H30O5
- Molecular weight
- 362.47
Names & synonyms
18-HYDROXYCORTICOSTERONE561-65-94U5T0O9SI311beta,18,21-trihydroxy-pregn-4-ene-3,20-dioneCHEBI:16485DTXSID80897516Pregn-4-ene-3,20-dione, 11,18,21-trihydroxy-, (11beta)-18 Hydrocorticosterone18-HydrocorticosteroneRefChem:79365Hydroxycorticosterone, 1818 HYDROXYCORTICOSTERONE
Show more names
18-Hydroxycorticosterone-[2H4]Hydroxycorticosterone18-Hydroxycorticosterone solution4-Pregnene-11β,18,21-triol-3,20-dione4-PREGNEN-11β, 18, 21-TRIOL-3, 20-DIONE11β,18,21-Trihydroxypregn-4-ene-3,20-dione(11b)11,18,21-trihydroxy-Pregn-4-ene-3,20-dione18-Hydroxycorticosterone in Acetonitrile(10%Water)Pregn-4-ene-3,20-dione, 11,18,21-trihydroxy-, (11β)-
DTXCID601326871(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo(8.7.0.02,7.011,15)heptadec-6-en-5-one209-221-911beta,18,21-Trihydroxypregn-4-ene-3,20-dione18-hydroxy corticosterone(8S,9S,10R,11S,13R,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-13-(hydroxymethyl)-10-methyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one(8S,9S,10R,11S,13R,14S,17S)-11-Hydroxy-17-(2-hydroxyacetyl)-13-(hydroxymethyl)-10-methyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-oneUNII-4U5T0O9SI3
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 94.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 655
Experimental & physicochemical properties
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 577.8 · 577.8±50.0 °C(Predicted)
- Density
- 1.28 · 1.28±0.1 g/cm3(Predicted)
- Flash point
- 2 ℃ · 2℃
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in DMSO
- form
- Solid
- pka
- 12.98 · 12.98±0.10(Predicted)
- color
- White to off-white
- BRN
- 2631066 · 2631066
- Major Application
- clinical testing
- InChIKey
- HFSXHZZDNDGLQN-ZVIOFETBSA-N
- SMILES
- O[C@@H]1[C@H]2[C@H]([C@H]4[C@@]([C@H](CC4)C(=O)CO)(C1)CO)CCC3=CC(=O)CC[C@@]32C
- FDA UNII
- 4 U5T0O9SI3 · 4U5T0O9SI3
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；STOT SE 3 (100%)
Toxicology
Health Effects
Chronically high levels of 18-hydroxycorticosterone are associated with at least 3 inborn errors of metabolism including: Adrenal hyperplasia type 5, Corticosterone methyl oxidase I deficiency and Corticosterone methyl oxidase II deficiency.
Toxicity Summary
18-Hydroxycorticosterone is a derivative of corticosterone. It serves as an intermediate in the synthesis of aldosterone by the enzyme aldosterone synthase in the zona glomerulosa. (Wikipedia) 18-Hydroxycorticosterone (18OHB) has low affinity for the mineralocorticoid receptor and mainly originates from the conversion of corticosterone by the aldosterone synthase, although small amounts may be produced by the 11β-hydroxylase. Serum concentrations of 18OHB increase with increased aldosterone synthesis due to sodium depletion and angiotensin II infusion. (A15449) Accumulation of 18-hydroxycorticosterone in a given organ has been shown to be toxic for the body.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemistry & industry
Pharmacology
Tissue LocationsAdrenal Gland
Cellular LocationsExtracellular；Membrane
Metabolite Pathways
11-beta-hydroxylase deficiency (CYP11B1)；17-alpha-hydroxylase deficiency (CYP17)；21-hydroxylase deficiency (CYP21)；3-Beta-Hydroxysteroid Dehydrogenase Deficiency；Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency；Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency；Apparent mineralocorticoid excess syndrome；Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH；Corticosterone methyl oxidase I deficiency (CMO I)；Corticosterone methyl oxidase II deficiency - CMO II；Total 11 pathways, visit the HMDB page for details
Uses & manufacturing
UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Applications
Uses18-Hydroxycorticosterone is a derivative of Corticosterone. 18-Hydroxycorticosterone is used as an intermediate in the synthesis of Aldosterone (A514700).
Suppliers23 total
广州佳途科技股份有限公司81960175 18933936954 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
Related reactions
2 records
Compound notes
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