16-Dehydropregnenolone

HCID 92871
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Basic information

CAS
1162-53-4
Standard SMILES
CC(=O)C1=CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey
YLFRRPUBVUAHSR-RRPFGEQOSA-N
Molecular formula
C21H30O2
Average molar mass
314.5 g/mol
Monoisotopic mass
314.2245802

Overview

16,17-didehydropregnenolone is a 3beta-hydroxy-5-steroid that is pregnenolone with a double bond between positions 16 and 17. It is a 3beta-hydroxy-Delta(5)-steroid, a 20-oxo steroid and an enone. It is functionally related to a pregnenolone.

Names & identifiers

Preferred name
16-Dehydropregnenolone
IUPAC
1-[(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
English name
16-Dehydropregnenolone
Molecular formula
C21H30O2
Molecular weight
314.46

Names & synonyms

16-Dehydropregnenolone1162-53-416-Dehydropregnolone3beta-Hydroxypregna-5,16-dien-20-one16,17-Didehydropregnenolonedelta16-Pregnenolone(-)-PregnadienoloneDelta(16)-pregnenolonePregna-5,16-dien-20-one, 3-hydroxy-, (3beta)-(3beta)-3-hydroxypregna-5,16-dien-20-one5,16-Pregnadien-3beta-ol-20-oneNSC-15467
Show more names
16-DPA5,16-PREGNADIEN-3B-ACETOXY-20-ONEDPA16-biseneolonePregnadienoloneDon't progesteroneDehydropregnenoloneAllopregnanolone-001
1-[(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone7349506P5SCHEBI:27486DTXSID401016789Pregna-5,16-dien-20-one, 3beta-hydroxy-1-((3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta(a)phenanthren-17-yl)ethanoneRefChem:78964DTXCID801474987

Database identifiers

CAS
1162-53-4
PubChem CID
92871
DTXSID
DTXSID401016789
ChEBI
CHEBI:27486
UNII
7349506P5S
EC Number
214-602-8
Nikkaji
J22.717J

Properties

Computed structural properties

XLogP
3.9
Topological polar surface area
37.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
23

Experimental & physicochemical properties

LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point
212 · 212-214 °C
Boiling point
456.6 · 456.6±45.0 °C(Predicted)
Density
1.11 · 1.11±0.1 g/cm3(Predicted)
storage temp.
-20 °C · -20°C Freezer, Under inert atmosphere
solubility
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)
pka
14.7 · 14.70±0.70(Predicted)

Chemistry & industry

Applications

Uses16-Dehydropregnolone is a novel antihyperlipidemic agent. It can be used in chemotherapeutic drug development.

Upstream & downstream products

Upstream raw materials

Suppliers61 total

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]
上海科骊科生物技术有限公司021-34975789 18721102763
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
广州隽唐科技有限公司020-36607679 13502246435 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 16,17-didehydropregnenolone is a 3beta-hydroxy-Delta(5)-steroid that is pregnenolone with a double bond between positions 16 and 17. It is a 20-oxo steroid, an enone and a 3beta-hydroxy-Delta(5)-steroid. It is functionally related to a pregnenolone.

Related reactions

3 records
New reaction record

Compound notes

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