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
이름 더 보기
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
- 형식 전하
- 0
- 복잡도
- 550
실험 및 물리화학적 성질
LogP
4.22
4.22
Collision Cross Section
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
- 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
안전 및 규제
GHS 분류
GHS Classification
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
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
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.
응용 분야
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.
상·하류 제품 정보
상류 원료
하류 제품
공급사50 곳
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
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