3-ヒドロキシ-2-メトキシエストラ-1,3,5(10)-トリエン-17-オン

2-Methoxyestrone

HCID 440624CAS 362-08-3

基本情報

標準SMILES: COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
InChIKey: WHEUWNKSCXYKBU-QPWUGHHJSA-N
分子式: C19H24O3
平均分子量: 300.4 g/mol

概要

2-methoxyestrone is a 17-oxo steroid that is estrone in which the hydrogen at position 2 has been replaced by a methoxy group. It has a role as a mouse metabolite and a human metabolite. It is a phenolic steroid, a 17-oxo steroid, a member of phenols, an aromatic ether, an alicyclic ketone and a 3-hydroxy steroid. It is functionally related to an estrone.

名称と識別子

優先名称: 2-Methoxyestrone
IUPAC: (8R,9S,13S,14S)-3-hydroxy-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
現地名: 3-ヒドロキシ-2-メトキシエストラ-1,3,5(10)-トリエン-17-オン
英語名: 2-METHOXYESTRONE
分子式: C19H24O3
分子量: 300.39

名称と別名

2-METHOXYESTRONE362-08-33-Hydroxy-2-methoxyestra-1,3,5(10)-trien-17-oneSJ5857RRL3(8R,9S,13S,14S)-3-hydroxy-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-oneCHEBI:1189GSS-332-methoxy,3-hydroxy-estra-1,3,5(10)-trien-17-one(8R,9S,13S,14S)-3-hydroxy-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta(a)phenanthren-17-oneRefChem:879062-MeOE12-OMeE1

名称をさらに表示

3-ヒドロキシ-2-メトキシエストラ-1,3,5(10)-トリエン-17-オン2-メトキシ-3-ヒドロキシエストラ-1(10),2,4-トリエン-17-オン3-ヒドロキシ-2-メトキシエストラ-1(10),2,4-トリエン-17-オン2-メトキシエストロン2-メトキシ-3-ヒドロキシ-1(10),2,4-エストラトリエン-17-オン(3aS,3bR,9bS,11aS)-7-ヒドロキシ-8-メトキシ-11a-メチル-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-シクロペンタ[a]フェナントレン-1-オンC05299GSS 33Estrone Impurity 3DL-2-METHOXYESTRONEEstrone 2-Methoxy Impurity2-Methoxy-[13C,2H3]-estrone2-Methoxyestrone (Standard)2-Methoxyestrone, 10 mM in DMSO

2-MeE1(1S,10R,11S,15S)-5-hydroxy-4-methoxy-15-methyltetracyclo(8.7.0.02,7.011,15)heptadeca-2(7),3,5-trien-14-one206-645-62-Methoxy Estrone2-Hydroxyestrone 2-methyl etherEstrone, 2-methoxy-2-Methoxyestrone?2-Methoxy-3-hydroxyestra-1,3,5(10)-trien-17-one

データベース識別子

CAS: 362-08-3
PubChem CID: 440624
ChEMBL: CHEMBL425194
ChEBI: CHEBI:1189
UNII: SJ5857RRL3
EC Number: 206-645-6
Nikkaji: J101.999F

物性

構造計算による物性

XLogP: 3.1
極性表面積: 46.5 Å²
水素結合供与体数: 1
水素結合受容体数: 3
回転可能結合数: 1
重原子数: 22
形式電荷: 0
複雑度: 462

実験および物理化学的性質

Chemical ClassesBiological Agents -> Other Biomolecules

LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C18 steroids (estrogens) and derivatives [ST0201]

Melting Point187.0 - 189.5 °C

Physical Description · 2 件

Solid; [Sigma-Aldrich MSDS]

Solid

Collision Cross Section · 2 件

184.55 Å² [M-H]- [CCS Type: DT; Method: stepped-field]

183.9 Å² [M-H]-

物理化学的性質

融点: 187 · 187.0-189.5 °C
沸点: 463.5 · 463.5±45.0 °C(Predicted)
比重(密度): 1.172 · 1.172±0.06 g/cm3(Predicted)
貯蔵温度: 2 · 2-8°C
溶解性: Chloroform: slightly soluble
酸解離定数(Pka): 10.27 · 10.27±0.40(Predicted)
外見: Solid
色: White to off-white
由来生物: synthetic
InChI: 1S/C19H24O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,20H,3-8H2,1-2H3/t12-,13+,15-,19-/m0/s1
InChIKey: WHEUWNKSCXYKBU-QPWUGHHJSA-N
SMILES: C[C@@]12[C@](CCC2=O)([H])[C@]3([H])CCC4=CC(O)=C(OC)C=C4[C@@]3([H])CC1

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazards SummaryMay cause irritation; Possible carcinogen; [Sigma-Aldrich MSDS]

Hazard Classes and CategoriesCarc. 2 (100%)

安全データ

wgk: 3
ridadr: UN3077 9/PG 3
risk_code: 40-50/53
hazard_code: Xn,N
safety_code: 22-36-61-60
Hazard Classifications: Aquatic Acute 1Aquatic Chronic 1Carc. 2
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

Metabolism/Metabolites2-Methoxyestrone has known human metabolites that include (8R,9S,13S,14S)-2-Methoxy-13-methyl-3-[(2R,3R,4S,5S,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one.

Cellular LocationsExtracellular

Metabolite PathwaysEstrone Metabolism

応用分野

使用2-Methoxyestrone is a endogenous estrogen metabolite. 2-Methoxyestrone detection can be used as a breast cancer biomarker and help assess the risk-factors for development of breast cancer.