9H-purin-6-amine

• ChemBase编号: 58
• 分子式: C5H5N5
• 平均质量: 135.1267
• 单一同位素质量: 135.05449519
• SMILES: [nH]1c2c(nc1)ncnc2N
• Canonical SMILES: Nc1ncnc2c1[nH]cn2
• InChI: InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
• InChIKey: GFFGJBXGBJISGV-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 9H-purin-6-amine; 7H-purin-6-amine
• IUPAC传统名: adenine; vitamin B4
• 商标名: Pedatisectine B; Leuco-4
• 别名: 6-氨基嘌呤; 维生素 B4; 腺嘌呤; 7H-Purin-6-amine; 1H-Purin-6-aMine; 9H-Purin-6-amine; Adenine; 1,6-Dihydro-6-iminopurine; 3,6-Dihydro-6-iminopurine; 3H-Purin-6-amine; 6-Amino-1H-purine; 6-Amino-3H-purine; 6-Amino-9H-purine; 7H-Purin-6-amine; 9H-Adenine; Leuco-4; NSC 14666; Pedatisectine B; Adenine; 6-Aminopurine; Vitamin B4; 1H-Purin-6-amine; Adeninimine; Adenin; Adenine

登记号

• CAS号: 73-24-5
• EC号: 200-796-1
• MDL号: MFCD00041790
• Beilstein号: 5777
• 默克索引号: 14152
• PubChem SID: 160963521; 24891349; 46507319; 24891010; 24890691
• PubChem CID: 190
• CHEBI ID: 16708
• CHEMBL: 226345
• Chemspider ID: 185
• DrugBank ID: DB00173
• KEGG ID: D00034
• 美国药典/FDA物质标识码: JAC85A2161
• 维基百科标题: Adenine

理论计算性质

JChem

• Acid pKa: 10.293441
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): -0.7908963
• LogD (pH = 7.4): -0.57753056
• Log P: -0.57347023
• 摩尔折射率: 38.2195 cm^3
• 极化性: 13.361899 Å^3
• 极化表面积: 80.48 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.38
• LOG S: -1.07
• 溶解度: 1.15e+01 g/l

分子性质

理化性质

• 溶解度: 1.03 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; DMSO
• 外观: Off-White Solid; white, crystalline
• 熔点: >300°C; >360 °C(lit.); >360°C dec.; 360–365 °C (decomposes)
• 密度: 1.6 g/cm^3 (calculated)
• 疏水性(logP): -0.3
• pKa: 4.15 (secondary), 9.80 (primary)

安全信息

• 保存条件: -20°C; Refrigerator
• 保存注意事项: IRRITANT
• RTECS编号: AU6125000
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811; UN2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3; III
• 危险公开号: 22
• 安全公开号: 26-36; 36
• TSCA收录: false; 是
• GHS危险品标识: GHS06; GHS07
• GHS警示词: Danger
• GHS危险声明: H301; H302
• GHS警示性声明: P264-P270-P301+P312-P330-P501A; P301 + P310
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

药理学性质

• 作用靶点: Antimetabolites
• 相关基因信息: human ... AKT1(207), GSK3B(2932), LCK(3932), MAP3K1(4214), MAPK14(1432), MAPK8(5599), MAPK9(5601), MAPKAPK2(9261), PRKACA(5566), PRKCA(5578), RAF1(5894), ROCK2(9475)mouse ... Mapk1(26413)rat ... Camk2a(25400), Mapk10(25272)

产品相关信息

• 纯度: ≥99%; ≥99.0% (HPLC); 97%; 99%
• 成盐信息: Free Base
• 适用性: plant cell culture tested; suitable for cell culture
• 燃烧残渣: ≤0.05% (as SO4)
• 痕量阳离子: Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• 干燥失重: ≤0.5% loss on drying, 110 °C
• Empirical Formula (Hill Notation): C5H5N5

详细说明

DrugBank - DB00173

• Drug Groups: approved; nutraceutical
• Description: A purine base and a fundamental unit of adenine nucleotides. [PubChem]
• Indication: For nutritional supplementation, also for treating dietary shortage or imbalance
• Pharmacology: Adenine (sometimes known as vitamin B4) combines with the sugar ribose to form adenosine, which in turn can be bonded with from one to three phosphoric acid units, yielding AMP, ADP and ATP . These adenine derivatives perform important functions in cellular metabolism. Adenine is one of four nitrogenous bases utilized in the synthesis of nucleic acids. A modified form of adenosine monophosphate (cyclic AMP) is an imporant secondary messenger in the propagation of many hormonal stimuli. Adenine is an integral part of the structure of many coenzymes. Adenosine (adenine with a ribose group) causes transient heart block in the AV node of the heart. In individuals suspected of suffering from a supraventricular tachycardia (SVT), adenosine is used to help identify the rhythm. Certain SVTs can be successfully terminated with adenosine.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia

Selleck Chemicals - S1981

Research Area: Cancer
Biological Activity:
Adenine is a purine derivative and a nucleobase with a variety of roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD) and flavin adenine dinucleotide (FAD), and protein synthesis, as a chemical component of DNA and RNA. The shape of adenine is complementary to either thymine in DNA or uracil in RNA. Adenine is one of the two purine nucleobases (the other being guanine) used in forming nucleotides of the nucleic acids. In DNA, adenine binds to thymine via two hydrogen bonds to assist in stabilizing the nucleic acid structures. In RNA, which is used for protein synthesis, adenine binds to uracil. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose. Adenine forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions. [1]References on Adenine[1] http://en.wikipedia.org/wiki/Adenine, ,

Sigma Aldrich - A8626

包装
1 kg in poly bottle
1, 5, 25, 100 g in poly bottle
Application
Adenine is a purine nucleobase with a wide range of chemical and biochemical roles in vivo and in vitro. It is a regulatory molecule and a component of DNA, RNA, cofactors (NAD, FAD) and signaling molecules (cAMP).

Sigma Aldrich - A5665

Application
Adenine may be used as a plant cell culture additive. Adenine Sulphate (25mg/L) in the culture media such as Murashige & Skoog media improves the frequency of multiple shoot production and recovered the chlorotic symptoms of the leaves.

Toronto Research Chemicals - A280480

Widespread throughout animal and plant tissues combined with niacinamide, d-ribose, and phosphoric acids; a constituent of nucleic acids and coenzymes, such as codehydrase I and II, adenylic acid, coalaninedehydrase. It is used in microbial determination

参考文献

• http://en.wikipedia.org/wiki/Adenine
• Philips, et al.: J. Pharmacol. Exp. Ther., 20, 104 (1952)
• Lambertucci, C., et al.: Bioorg. Med. Chem., 17, 2812 (1952)