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Allotetrahydrodeoxycorticosterone

HCID 101771
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Basic information

CAS
567-02-2
Standard SMILES
C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C(=O)CO)CC[C@@H]12
InChIKey
CYKYBWRSLLXBOW-GDYGHMJCSA-N
Molecular formula
C21H34O3
Average molar mass
334.5 g/mol
Monoisotopic mass
334.25079494

Overview

5-alpha-THDOC is a 21-hydroxy steroid.

Names & identifiers

Preferred name
Allotetrahydrodeoxycorticosterone
IUPAC
2-hydroxy-1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
English name
21-Hydroxyallopregnanolone
Molecular formula
C21H34O3
Molecular weight
334.49

Names & synonyms

567-02-23alpha,21-Dihydroxy-5alpha-pregnan-20-oneAllotetrahydrodeoxycorticosteroneRefChem:915422209-300-821-Hydroxyallopregnanolone5alpha-THDOC5-alpha-THDOC3|A,21-Dihydroxy-5|A-pregnan-20-one2-hydroxy-1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanoneCHEMBL12567603alpha,21-dihydroxy-5alpha-pregnane-20-one
Show more names
3α,21-Dihydroxy-5α-pregnan-20-one3α,21-dihydroxy-5α-pregnan-20-oneTDOC5α-THDOCALLO TH DOC3α,5α-THDOCALLOTETRAHYDRO DOCALLOTETRAHYDROCORTEXONE1-HYDROXYALLOPREGNANOLONE
3?,21-dihydroxy-5?-pregnan-20-one2-Hydroxy-1-((3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanoneA8ZEINECS 209-300-83beta,21-Dihydroxy-5alpha-pregnan-20-one3a,21-dihydroxy-5a-pregnan-20-oneBiomol-NT_000267ALLOPREGNANOLONE_met006

Properties

Computed structural properties

XLogP
4.2
Topological polar surface area
57.5 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
24
Formal charge
0
Complexity
517

Experimental & physicochemical properties

LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid
Collision Cross Section191.43 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
150 oC · >150oC (dec.)
storage temp.
Refrigerator
solubility
Chloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
form
Solid
color
White to Off-White
InChI
1S/C21H34O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h13-18,22-23H,3-12H2,1-2H3/t13-,14+,15-,16-,17-,18+,20-,21-/m0/s1

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

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
Storage Class
11 - Combustible Solids

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 3 items

Agents capable of inducing a total or partial loss of sensation, especially tactile sensation and pain. They may act to induce general ANESTHESIA, in which an unconscious state is achieved, or may act locally to induce numbness or lack of sensation at a targeted site.

Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.

Endogenous compounds or drugs that affect neuronal excitability through modulation of specific ionotropic receptors (e.g., GABA-A RECEPTORS). Endogenous neurosteroids are steroid hormones de novo synthesized by neurons and glial cells from steroid metabolite precursors (e.g., PREGNENOLONE).

Cellular LocationsExtracellular
Applications · 2 items

Uses3α,21-Dihydroxy-5α-pregnan-20-one (THDOC) has been used:as an γ-aminobutyric acid type A receptor (γ-GABAA) agonist in voltage-clamp measurements studies in Xenopus oocytesto test its effect on the spike-wave discharges (SWD) finasteride-treated ratsin electrophysiological studies with dentate granule cells (DGCs) post controlled cortical impact (CCI) -induced brain injury

General Description3α21-Dihydroxy-5α-pregnan-20-one (THDOC) is a neurosteroid. It is synthesized in a two-step process from deoxycorticosterone (DOC) via 5α-dihydrodeoxycorticosterone (DHDOC) intermediate with enzymes 5α-reductase and 3α-hydroxysteroid oxidoreductase catalyzing these steps respectively.

Additional notes

DefinitionChEBI: 5-alpha-THDOC is a 21-hydroxy steroid.

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
567-02-2、567-03-3
PubChem CID
101771
DTXSID
DTXSID801017258
ChEMBL
CHEMBL1256760
ChEBI
CHEBI:34461
EC Number
209-300-8
Nikkaji
J188.433F
InChIKey
CYKYBWRSLLXBOW-GDYGHMJCSA-N
SMILES
[H][C@@]12CC[C@@]3([H])[C@]4([H])CC[C@H](C(=O)CO)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC[C@@H](O)C2
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
PPE
95 · Eyeshields, Gloves, type N95 (US)
WGK Germany
3 · 3
Storage Class
11 · 11 - Combustible Solids