Pregnenolone

HCID 8955CAS 145-13-1

기본 정보

표준 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
분자식
C21H32O2
평균 분자량
316.5 g/mol
단동위원소 질량
316.24023026

개요

Pregnenolone is a 20-oxo steroid that is pregn-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 20. It has a role as a mouse metabolite and a human metabolite. It is a 3beta-hydroxy-Delta(5)-steroid, a 20-oxo steroid and a C21-steroid. It derives from a hydride of a pregnane.

이름 및 식별자

우선 이름
Pregnenolone
IUPAC
1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
영어명
Pregnenolone
분자식
C21H32O2
분자량
316.48

이름 및 동의어

pregnenolone145-13-13beta-Hydroxypregn-5-en-20-oneArthenoloneRegnosoneSkinostelonEneloneNatoloneBina-Skin5-Pregnen-3beta-ol-20-onedelta5-Pregnenolone5-Pregnen-3-beta-ol-20-one
이름 더 보기
3β-Hydroxypregn-5-en-20-onePregneloneprenenolone5-pregnen-3B-ol-20-one5-pregnen-3β-ol-20-oneDELTA5-PREGNEN-3BETA-OL-20-ONE5-PregZK-5553-20-oneprenolon
PregnenolonaPregnenolonumDTXSID10365413-beta-Hydroxypregn-5-en-20-onePregn-5-en-20-one, 3-hydroxy-, (3beta)-73R90F7MQ81-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanoneDTXCID9016541

데이터베이스 식별자

CAS
145-13-1
PubChem CID
8955
DTXSID
DTXSID1036541
ChEMBL
CHEMBL253363
ChEBI
CHEBI:16581
UNII
73R90F7MQ8
EC Number
205-647-4
Nikkaji
J11.381F

물성

구조 계산 물성

XLogP
4.2
극성 표면적
37.3 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
1
무거운 원자 수
23

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
SpringerMaterials PropertiesChemical shift
LogP · 2건

4.22

4.22

Solubility0.00706 mg/mL at 37 °C
Endocrine DisruptorsPotential endocrine disrupting compound

물리화학적 성질

녹는점
188 · 188-190 °C
끓는 점
395.89 °C · 395.89°C (rough estimate)
밀도
1.0382 · 1.0382 (rough estimate)
증기압
0 · 0-0Pa at 20-25℃
굴절률
1.5344 · 1.5344 (estimate)
인화점
9 ℃ · 9℃

화학적 성질

white to off-white powder

안전 및 규제

GHS 분류

GHS Classification · 5건

This chemical does not meet GHS hazard criteria for 13% (3 of 23) of reports.

Warning

H302 (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.

유해성 정보

Regulatory InformationStatus: Active Update: 29-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26422
Hazard Classes and CategoriesAcute Tox. 4 (87%)

안전 데이터

wgk
3
rtecs
TU5560700
ridadr
UN 1648 3 / PGII
HS 번호
29372900
safety_code
22-24/25
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

Pregnenolone has known human metabolites that include 1-(3,16-Dihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone, Pregn-5-en-20-on-3b-yl sulfurate, and 2-Hydroxy-1-(3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone.

Tissue LocationsAdrenal Cortex
Cellular LocationsCytoplasm
Metabolite Pathways11-beta-hydroxylase deficiency (CYP11B1)
응용 분야 · 3건

개요Pregnenolone 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.

용도Pregnenolone 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

일반 설명Pregnenolone is an endogenous steroid hormone involved in the biological synthesis of other hormones. Pregnenolone is monitored as an ancillary test for congenital adrenal hyperplasia (CAH), particularly in situations where diagnosis of 21-hydroxylase and 11-hydroxylase deficiency has been ruled out. This Certified Spiking Solution is suitable for use in LC-MS/MS testing methods as a starting material in the preparation of calibrators, controls and linearity standards.

공급사50 곳

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]

추가 설명

정의ChEBI: A 20-oxo steroid that is pregn-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 20.

관련 반응

11건

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