Cortolone
Basic information
- CAS
516-42-7- Standard SMILES
C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)[C@@H](O)CO- InChIKey
JXCOSKURGJMQSG-AZQJGLEESA-N- Molecular formula
- C21H34O5
- Average molar mass
- 366.5 g/mol
- Monoisotopic mass
- 366.24062418
Overview
Cortolone is a 21-hydroxy steroid.
Names & identifiers
- Preferred name
- Cortolone
- IUPAC
- (3R,5R,8S,9S,10S,13S,14S,17R)-17-[(1S)-1,2-dihydroxyethyl]-3,17-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-11-one
- English name
- ALPHA-CORTOLONE
- Molecular formula
- C21H34O5
- Molecular weight
- 366.49
Names & synonyms
Cortolonealpha-CortoloneCortolon516-42-720alpha-Cortolone3J9D9J550ANSC-59872DTXSID10904343Pregnan-11-one, 3,17,20,21-tetrahydroxy-, (3alpha,5beta,20S)-RefChem:919083DTXCID5013334995beta-11-oxo-pregnane-3alpha, 11beta,17, 20S, 21-tetrol
Show more names
α-Cortoloneα-Cortolone-d5Alpha Cortolone D5A-cortolone crystalline5β-Pregnane-3α,17α,20α,21-tetrol-11-one5β-Pregnan-3α, 17, 20α, 21-Tetrol-11-One3α,17α,20α,21-Tetrahydroxy-5β-pregnan-11-one(20S)-3α,17,20,21-Tetrahydroxy-5β-pregnan-11-one
3 alpha,17 alpha,20 alpha,21-tetrahydroxy-5 beta-pregnan-11-one.alpha.-Cortolone20.alpha.-Cortolone(3R,5R,8S,9S,10S,13S,14S,17R)-17-[(1S)-1,2-dihydroxyethyl]-3,17-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-11-one3alpha,17alpha,20alpha,21-Tetrahydroxy-5beta-pregnan-11-oneUNII-3J9D9J550Aa-CortoloneNSC 59872
Properties
Computed structural properties
- XLogP
- 1.8
- Topological polar surface area
- 98 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 593
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 208 · 208-209°
- alpha
- 25 · D25 +44° (c = 0.5 in ethanol); D28 +34.2° (ethanol)
- Boiling point
- 564.1 · 564.1±50.0 °C(Predicted)
- Density
- 1.248 · 1.248±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
- solubility
- DMSO (Slightly), Methanol (Slightly), Pyridine (Slightly)
- pka
- 13.95 · 13.95±0.70(Predicted)
- form
- Solid
- color
- White to Off-White
- Stability
- Hygroscopic
- FDA UNII
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
Usesα-Cortolone is a human urinary metabolite of Cortisol ((H714615), a steroid hormone, more specifically a glucocorticoid, produced by the zona fasciculata of the adrenal gland. Cortisol is released in response to stress and a low level of blood glucocorticoids. Its primary functions are to increase blood sugar through gluconeogenesis; suppress the immune system; and aid in fat, protein and carbohydrate metabolism.
Additional notes
DefinitionChEBI: Cortolone is a 21-hydroxy steroid.
Related reactions
0 records
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Compound notes
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