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Pregnenolone

HCID 8955
새 노트새 반응견적 요청하기
인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
145-13-1
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

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
형식 전하
0
복잡도
550

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
Melting Point192 °C
Physical DescriptionSolid
Collision Cross Section · 4건

172.95 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

177.25 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]

174 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

214.8 Ų [M+Na]+

물리화학적 성질

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

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
스토리지 클래스
3 - Flammable liquids

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.

관련 반응

11건
반응 기록 만들기
HRID 27330 반응식
HRID 27330반응물로uspto-grants-1980_09
HRID 232791 반응식
HRID 232791반응물로uspto-grants-1997_01
HRID 354912 반응식
HRID 354912반응물로uspto-grants-1983_03
HRID 597439 반응식
HRID 597439반응물로uspto-grants-1977_03
HRID 597440 반응식
HRID 597440반응물로uspto-grants-1977_03
HRID 910002 반응식
HRID 910002반응물로uspto-grants-2011_09
HRID 1069049 반응식
HRID 1069049반응물로uspto-grants-2001_06
HRID 1385614 반응식
HRID 1385614반응물로uspto-grants-2001_07
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화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
더보기
새 노트새 반응견적 요청하기
DTXSID
DTXSID1036541
ChEMBL
CHEMBL253363
ChEBI
CHEBI:16581
UNII
73R90F7MQ8
EC Number
205-647-4
Nikkaji
J11.381F
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℃
저장 조건
Refrigerator
용해도
10 mg/mL, · 에탄올: 용해성10mg/mL, 투명, 무색 내지 희미한 노란색
물리적 상태
가루
산도 계수 (pKa)
15 · 15.00±0.70(Predicted)
색상
흰색에서 황백색까지
수용성
41 mg/L · 41mg/L(상온)
Merck
7733 · 7733
BRN
2059026 · 2059026
주요 응용
임상 시험임상 시험
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
4.4 at · 4.4 at 20℃
NIST
Pregnenolone(145-13-1)

화학적 성질

white to off-white powder

상·하류 제품 정보

상류 원료

16-데하이드로프레그네놀론Pregna-5,17(20)-diene-3,20-diol,diacetate, (3b)- (9CI)Pregn-5-en-20-one,3-hydroxy-, cyclic 1,2-ethanediyl dithioacetal, (3b)- (9CI)Difluoromethyldiphenylphosphine Oxide프레그네놀원 아세테이트20alpha-Hydroxycholesterol3-tert-부틸디메틸실릴옥시프레그네놀론Bromomethyl methyl ether베타-시토스테롤16-데하이드로프레그네놀론아세테이트

하류 제품

프로게스테론피나스테라이드가나솔론17alpha-Hydroxypregnenolone메틸3-옥소-4-안드로스텐-17베타-카르복실레이트CORTICOSTERONE1-((3R,10S,13S,17S)-3-hydroxy-3-(methoxymethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone

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.