5alpha-Dihydroprogesterone

HCID 92810
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
566-65-4
Standard SMILES
CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey
XMRPGKVKISIQBV-BJMCWZGWSA-N
Molecular formula
C21H32O2
Average molar mass
316.5 g/mol
Monoisotopic mass
316.24023026

Names & identifiers

Preferred name
5alpha-Dihydroprogesterone
IUPAC
(5S,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
English name
5α-Pregnane-3,20-dione
Molecular formula
C21H32O2
Molecular weight
316.48

Names & synonyms

566-65-45alpha-Pregnane-3,20-dione3,20-Allopregnanedione5-alpha-Dihydroprogesterone5alpha-Dihydroprogesterone3,20-Dioxo-5alpha-pregnane98G4S1OH0Z(5S,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-oneDTXSID301017277NSC-18319CHEBI:289525alpha DHP
Show more names
5α-dihydroprogesteronePregnane-3,20-dione5α-pregnane-3,20-dione5-Alpha-Dihydro Progesterone-d8ALLOPREGNANDIONEAllopregnanedionePregnane-3,20-dloneEstrone Impurity 235A-PREGNAN-3,20-DIONE
5alpha-DHP5beta DHP5beta-DHP5 alpha Pregnanedione5-alpha-Pregnanedione3,20 Allopregnanedione5 beta Dihydroprogesterone5 alpha Dihydroprogesterone

Database identifiers

CAS
566-65-4
PubChem CID
92810
DTXSID
DTXSID301017277
ChEMBL
CHEMBL407717
ChEBI
CHEBI:28952
UNII
98G4S1OH0Z
EC Number
209-297-3
Nikkaji
J6.519F

Properties

Computed structural properties

XLogP
4.4
Topological polar surface area
34.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
23

Experimental & physicochemical properties

Melting Point200 °C
Physical DescriptionSolid
Kovats Retention Index2665

Physicochemical properties

Melting point
200 °C · 200 °C
Boiling point
429.2 · 429.2±38.0 °C(Predicted)
Density
1.048 · 1.048±0.06 g/cm3(Predicted)
storage temp.
Sealed in dry,Room Temperature
solubility
Chloroform (Slightly), Ethyl Acetate (Slightly)
form
Solid

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.

Warning

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]；H312 (50%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H332 (50%): Harmful if inhaled [Warning Acute toxicity, inhalation]；H351 (50%): Suspected of causing cancer [Warning Carcinogenicity]；H361 (50%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]；H361fd (50%): Suspected of damaging fertility; Suspected of damaging the unborn child [Warning Reproductive toxicity]

P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 1 of 2 reports by companies.；There is 1 notification provided by 1 of 2 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (50%)；Acute Tox. 4 (50%)；Acute Tox. 4 (50%)；Carc. 2 (50%)；Repr. 2 (50%)

Safety data

wgk
3
rtecs
TU4157150
hs_code
2937.29.9095
Signal word
Warning
Symbol(GHS)
GHS07,GHS08
Hazard statements
H312-H302-H332-H351-H361fd

Chemistry & industry

Pharmacology

Tissue LocationsFibroblasts；Testis
Cellular LocationsExtracellular；Membrane
Metabolite Pathways · 1 item

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

Applications · 2 items

Description5α-Dihydroprogesterone (5α-DHP), also known as 5α-Pregnane-3,20-dione, is an endogenous progestogen and neurosteroid that is synthesized from progesterone. It is also an intermediate in the synthesis of allopregnanolone and isopregnanolone from progesterone. It is one of the mainly metabolites of progesterone in the digestive gland, the other tentatively identified as3β-hydroxy-5α-pregnan-20-one[1].

Uses(5α)-Pregnane-3,20-dione exerts neuroprotective effects in chronic autoimmune encephalomyelitis (EAE). The neuroactivity of the steroid acts as a therapeutic agent for multiple sclerosis.

Upstream & downstream products

Upstream raw materials

Suppliers100 total

Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
湖北威德利化学试剂有限公司181-6332-1995 18062128043 · [email protected]
盐城通铭生物科技有限公司15195160625 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 5alpha-pregnane-3,20-dione is a C21-steroid hormone that is 5alpha-pregnane substituted by oxo groups at positions 3 and 20. It is a metabolite of progestrone. It has a role as a human metabolite and a progestogen. It is a 20-oxo steroid, a C21-steroid hormone and a 3-oxo-5alpha-steroid. It is functionally related to a progesterone. It derives from a hydride of a 5alpha-pregnane.

Related reactions

13 records
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Compound notes

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