18-Hydroxy-11-Deoxycorticosterone
Basic information
- CAS
379-68-0- Standard SMILES
C[C@]12CCC(=O)C=C1CC[C@H]1[C@@H]3CC[C@H](C(=O)CO)[C@@]3(CO)CC[C@@H]12- InChIKey
VPJHREHKRNIYDB-TZGXILGRSA-N- Molecular formula
- C21H30O4
- Average molar mass
- 346.5 g/mol
- Monoisotopic mass
- 346.21440943
Overview
18-hydroxydeoxycorticosterone is a 21-hydroxy steroid, a 18-hydroxy steroid, a 20-oxo steroid and a 3-oxo-Delta(4) steroid.
Names & identifiers
- Preferred name
- 18-Hydroxy-11-Deoxycorticosterone
- IUPAC
- (8R,9S,10R,13R,14S,17S)-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-HYDROXY-11-DEOXYCORTICOSTERONE
- Molecular formula
- C21H30O4
- Molecular weight
- 346.46
Names & synonyms
379-68-018-Hydroxy-11-deoxycorticosterone18-HydroxydeoxycorticosteroneDTXSID9095892018,21-dihydroxy-4-pregnene-3,20-dioneRefChem:388745DTXCID501386812206-834-318,21-Dihydroxypregn-4-ene-3,20-dione11-Deoxy-18-hydroxycorticosterone(8R,9S,10R,13R,14S,17S)-17-(2-hydroxyacetyl)-13-(hydroxymethyl)-10-methyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-onePregn-4-ene-3,20-dione, 18,21-dihydroxy-
Show more names
18-HYDROXY DOC4-PREGNEN-18,21-DIOL-3,20-DIONE4-PREGNENE-18,21-DIOL-3,20-DIONE18,20-EPOXY-20,21-DIHYDROXY-4-PREGNEN-3-ONE
18,21-dihydroxyprogesterone18-Hydroxydesoxycorticosterone(1S,3aS,3bR,9aR,9bS,11aR)-1-(2-hydroxyacetyl)-11a-(hydroxymethyl)-9a-methyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-oneEINECS 206-834-318-OH-DOCSCHEMBL927204orb2283106CHEBI:195166
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 74.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 623
Physicochemical properties
- Melting point
- 171 · 171-173 °C
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly, Sonicated), Methanol (Slightly, Heated)
- form
- Solid
- color
- White to Off-White
- LogP
- 1.571 · 1.571 (est)
- Safety Statements
- 22 · 22-24/25
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- safety_code
- 22-24/25
Chemistry & industry
Applications
Description18-hydroxy-11-deoxy Corticosterone (18-OH-DOC) is a mineralocorticoid secreted by the zona fasciculata of the adrenal gland. Its biosynthesis is regulated by adrenocorticotropic hormone (ACTH; ) as well as angiotensin II , which increases 18-OH-DOC production in isolated human adrenal glomerulosa cells. 18-OH-DOC can be formed via conversion of 11-deoxy corticosterone (DOC; ) in human SK-MEL188 melanoma cells. 18-OH-DOC is an intermediate in the metabolism of progesterone and can be converted to aldosterone by the capsular portion of rat adrenal glands. Continuous infusion of 18-OH-DOC (200 μg/rat per day) increases systolic blood pressure in uninephrectomized saline-drinking rats. Plasma levels of 18-OH-DOC are elevated in a db/db mouse model of type 2 diabetes.
Uses11-Deoxy-18-hydroxycorticosterone is an analog of Corticosterone (C695700); a glucocorticoid and intermediate in the biosynthesis of Aldosterone (A514700) which is an adrenocortical steroid isolated from the adrenal cortex.
Additional notes
DefinitionChEBI: 18-hydroxydeoxycorticosterone is a 21-hydroxy steroid, a 3-oxo-Delta(4) steroid, a 20-oxo steroid and a 18-hydroxy steroid.
Suppliers
Loading…
Open inquiries
Loading…
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…