Pregnenolon
3β-Hydroxypregn-5-en-20-one · Pregnelone · prenenolone · 5-pregnen-3B-ol-20-one · 5-pregnen-3β-ol-20-one · DELTA5-PREGNEN-3BETA-OL-20-ONE · 5-Preg · ZK-5553
Identifikatoren & physikalische Daten
| CAS No. | 145-13-1 |
|---|---|
| Summenformel | C21H32O2 |
| Durchschnittliche Molmasse | 316,5 g/mol |
| Monoisotopische Masse | 316,24023026 g/mol |
| SMILES | CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C |
| InChIKey | ORNBQBCIOKFOEO-QGVNFLHTSA-N |
| PubChem CID | 8955 |
| ChEMBL | CHEMBL253363 |
| ChEBI | CHEBI:16581 |
| EC No. | 205-647-4 |
| DTXSID | DTXSID1036541 |
| Lokaler Name | Pregnenolon |
Chemische & physikalische Eigenschaften
| XLogP | 4,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 37,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 23 |
| Formalladung | 0 |
| Komplexität | 550 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Lipide | Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203] |
| SpringerMaterials Properties | Chemical shift |
| LogP (Verteilungskoeffizient) | 4.22 |
| Löslichkeit | 0.00706 mg/mL at 37 °Cethanol: soluble10mg/mL, clear, colorless to faintly yellow41mg/L(room temperature) |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 192 °C188-190 °C |
| Physical Description | Solid |
| Collision Cross Section | 172.95 Ų [M+H-H2O]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]177.25 Ų [M+H]+ [CCS Type: DTMethod: stepped-field]174 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]214.8 Ų [M+Na]+ |
| Siedepunkt | 395.89°C (rough estimate) |
| Dichte | 1.0382 (rough estimate) |
| Dampfdruck | 0-0Pa at 20-25℃ |
| Brechungsindex | 1.5344 (estimate) |
| Flammpunkt | 9℃ |
| Lagerbedingungen | Refrigerator |
| Aggregatzustand | Powder |
| pKa (Säurekonstante) | 15.00±0.70(Predicted) |
| Farbe | White to off-white |
| Merck | 7733 |
| BRN | 2059026 |
| Hauptanwendungen | clinical testingclinical testing |
| InChI | 1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1 |
| InChIKey | ORNBQBCIOKFOEO-QGVNFLHTSA-N |
| SMILES | O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@]([C@H](CC4)C(=O)C)(CC3)C)CC=C2C1)C |
| LogP (Verteilungskoeffizient) | 4.4 at 20℃ |
| CAS Datenbank | 145-13-1(CAS DataBase Reference) |
| NIST chemische Informationen | Pregnenolone(145-13-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 13% (3 of 23) of reports.WarningH302 (87%): Harmful if swallowed [Warning Acute toxicity, oral]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 23 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 29-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26422 |
| Hazard Classes and Categories | Acute Tox. 4 (87%) |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 1648 3 / PGII |
| Zollcode | 29372900 |
| RTECS-Nr. | TU5560700 |
| Sicherheitshinweise (S) | 22-24/25 |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrenklasse | Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2 |
Anwendungen & Verwendung
Beschreibung
Pregnenolone serves as the common precursor in the formation of the adrenocorticoids and other steroid hormones. This C21 steroid is converted via enzymatic oxidations and isomerization of the double bond to a number of physiologically active C21 steroids, including the female sex hormone progesterone and the adrenocorticoids hydrocortisone (cortisol), corticosterone, and aldosterone. Oxidative cleavage of the two-carbon side chain of pregnenolone and subsequent enzymatic oxidations and isomerization lead to C19 steroids, including the androgens testosterone and dihydrotestosterone. The final group of steroids, the C18 female sex hormones, are derived from oxidative aromatization of the A ring of androgens to produce estrogens.
Verwenden
Pregnenolone is a steroid hormone involved in the steroidogenesis of progesterone, mineralocorticoids, glucocorticoids, androgens, and estrogens. As such it is a prohormone. Pregnenolone is a GABAA an tagonist and increases neurogenesis in the hippocampus. It is a modulator of cytochrome P 450-3A