(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid

• ChemBase编号: 129344
• 分子式: C14H20N6O5S
• 平均质量: 384.4108
• 单一同位素质量: 384.12158877
• SMILES: O=C(O)[C@@H](N)CCSC[C@H]1O[C@@H](n2cnc3c(ncnc23)N)[C@H](O)[C@@H]1O
• Canonical SMILES: OC(=O)[C@H](CCSC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N)N
• InChI: InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1
• InChIKey: ZJUKTBDSGOFHSH-WFMPWKQPSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid
• IUPAC传统名: S-adenosyl-L-homocysteine
• 别名: AdoHcy; 2-S-adenosyl-L-homocysteine; 5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosineS-adenosylhomocysteine; SAH; S-Adenosyl-L-homocysteine; S-(5'-Deoxyadenosin-5'-yl)-L-homocysteine; L-5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosine; Adenosyl-L-homocysteine; Adenosylhomocysteine; L-S-Adenosylhomocysteine; S-Adenosyl-L-homocysteine; S-Adenosylhomocysteine; S-(5'-Adenosyl)-L-homocysteine; 5′-Deoxy-S-adenosyl-L-homocysteine; S-(5′-Deoxyadenosine-5′)-L-homocysteine; S-(5′-Adenosyl)-L-homocysteine

登记号

• CAS号: 979-92-0
• EC号: 213-560-8
• MDL号: MFCD00037388
• Beilstein号: 99188
• PubChem SID: 162223638; 24891441
• PubChem CID: 439155
• CHEBI ID: 16680
• CHEMBL: 418052
• Chemspider ID: 388301
• KEGG ID: C00021
• 医学主题词(MeSH): S-Adenosylhomocysteine
• 维基百科标题: S-Adenosyl-L-homocysteine

理论计算性质

• Acid pKa: 1.8116993
• 质子受体: 10
• 质子供体: 5
• LogD (pH = 5.5): -4.137044
• LogD (pH = 7.4): -4.026673
• Log P: -4.0272307
• 摩尔折射率: 92.7235 cm^3
• 极化性: 36.396317 Å^3
• 极化表面积: 182.63 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: crystalline; Pale Beige Solid
• 熔点: 188-190°C (dec.)

安全信息

• 保存条件: Refrigerator
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

• 纯度: ≥98.0% (HPCE)
• 产品质量级别: PREMIUM
• Empirical Formula (Hill Notation): C14H20N6O5S

详细说明

Sigma Aldrich - A9384

包装
10 mg in autosmp vl
Application
S-(5′-Adenosyl)-L-homocysteine (AdoHcy) is a component of intracellular homocysteine stress. AdoHcy is a competitive inhibitor (versus AdoMet) of DNA methyltransferases (S-adenosyl-L-methionine (AdoMet)-dependent methyltransferases) involved in epigenetics; consequently AdoHcy is used in a variety of studies on epigenetics in hyperhomocysteinemic states. S-adenosylhomocysteine (AdoHcy) is metabolized by S-adenosylhomocysteine (AdoHcy) hydrolase (AHCY).

Sigma Aldrich - 02090

Other Notes
AdoHcy is a strong inhibitor of most biological transmethylation reactions1

Toronto Research Chemicals - A291500

A novel biomarker for predicting susceptibility of a subject to a mental or neurodegenerative disorder.

参考文献

• Chamberlin, M., et al.: J. Clin. Invest., 98, 1021 (1996)
• Zoccolella, S., et al.: Neurology, 70, 222 (1996)