Grundinformationen
- CAS
387-79-1- Standard-SMILES
CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C- InChIKey
JERGUCIJOXJXHF-TVWVXWENSA-N- Summenformel
- C21H32O3
- Durchschnittliche Molmasse
- 332,5 g/mol
- Monoisotopische Masse
- 332,23514488
Überblick
17alpha-hydroxypregnenolone is a hydroxypregnenolone carrying an alpha-hydroxy group at position 17. It has a role as a mouse metabolite and a human metabolite. It is a 17alpha-hydroxy-C21-steroid, a tertiary alpha-hydroxy ketone, a 3beta-hydroxy-Delta(5)-steroid, a 17alpha-hydroxy steroid and a hydroxypregnenolone.
Namen und Bezeichner
- Bevorzugter Name
- 17-Hydroxypregnenolone
- IUPAC
- 1-[(3S,8R,9S,10R,13S,14S,17R)-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]ethanone
- Lokaler Name
- 3-β,17-α-Dihydroxypregn-5-en-20-on
- Englischer Name
- 17alpha-Hydroxypregnenolone
- Summenformel
- C21H32O3
- Molmasse
- 332.48
Namen und Synonyme
17alpha-Hydroxypregnenolone17-Hydroxypregnenolone387-79-117-alpha-Hydroxypregnenolone17-OH-pregnenolone17-Hydroxy-delta5-pregnenolone5-Pregnen-3beta,17alpha-diol-20-one17alpha Hydroxypregnenolone3-beta,17-Dihydroxypregn-5-en-20-onePregn-5-en-20-one, 3-beta,17-dihydroxy-DTXSID208949883beta,17alpha-dihydroxypregn-5-en-20-one
Weitere Namen anzeigen
17α-HydroxypregnenoloneNSC 6385317-OH PREG17alpha-Hydroxy17-OH PregnenoloneDronedarone HCl-d6Hydroxypregnenolone17a-Hydroxypregnolone17A-HYDROXYPREGENOLONE
Pregn-5-en-20-one, 3beta,17-dihydroxy-77ME40334SPregn-5-en-20-one, 3,17-dihydroxy-, (3beta)-CHEBI:28750NSC-6385317 Hydroxypregnenolone17 alpha Hydroxypregnenolone17 alpha-Hydroxypregnenolone
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,1
- Polarare Oberfläche (TPSA)
- 57,5 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 24
- Formalladung
- 0
- Komplexität
- 596
Experimentelle und physikochemische Eigenschaften
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
SpringerMaterials PropertiesChemical shift
Melting Point266 - 271 °C
Physical DescriptionSolid
Collision Cross Section190.45 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
Physikochemische Eigenschaften
- Schmelzpunkt
- 273 ℃ · 273℃
- Flammpunkt
- 9 ℃ · 9℃
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- Chloroform (Slightly), DMSO (Slightly, Heated, Sonicated)
- Aggregatzustand
- Solid
- Siedepunkt
- 478.4 · 478.4±45.0 °C(Predicted)
- Dichte
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Gefahrenhinweise
Hazard Classes and CategoriesCarc. 2 (100%)
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN1230 - class 3 - PG 2 - Methanol
- RTECS-Nr.
- TU5548000
- risk_code
- 11-23/24/25-39/23/24/25
- hazard_code
- F,T
- safety_code
- 7-16-36/37-45
- Speicherklasse
- 3 - Flammable liquids
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
Chemie und Industrie
Pharmakologische Informationen
Tissue LocationsAdrenal Cortex
Cellular LocationsCytoplasm
Metabolite Pathways11-beta-hydroxylase deficiency (CYP11B1)
Anwendungen
Beschreibung17α-hydroxy Pregnenolone is a metabolite of pregnenolone and a precursor in the biosynthesis of dehydroepiandrosterone (DHEA; ). It is formed from pregnenolone by cytochrome P450 (CYP) isoform CYP17A1 hydroxylase activity and then converted to dehydroepiandrosterone by CYP17A1-mediated 17,20-lyase activity. Plasma levels of 17α-hydroxy pregnenolone are elevated in patients with type II 3β-hydroxysteroid dehydrogenase deficiency, a form of congenital adrenal hyperplasia.
Verwenden17α-hydroxypregnenolone has been used as a substrate for the enzyme 3β‐hydroxysteroid dehydrogenase (3β‐HSD) expressed in COS1 cells.
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