9H-purin-6-amine

• ChemBase ID: 58
• Molecular Formular: C5H5N5
• Molecular Mass: 135.1267
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 9H-purin-6-amine; 7H-purin-6-amine
• IUPAC Traditional name: adenine; vitamin B4
• Brand Name: Pedatisectine B; Leuco-4
• Synonyms: 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; 6-氨基嘌呤; 维生素 B4; 腺嘌呤

Database IDs

• CAS Number: 73-24-5
• EC Number: 200-796-1
• MDL Number: MFCD00041790
• Beilstein Number: 5777
• Merck Index: 14152
• PubChem SID: 46507319; 24891010; 24890691; 160963521; 24891349
• PubChem CID: 190
• CHEBI ID: 16708
• CHEMBL: 226345
• Chemspider ID: 185
• DrugBank ID: DB00173
• KEGG ID: D00034
• Unique Ingredient Identifier: JAC85A2161
• Wikipedia Title: Adenine

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.293441
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.7908963
• LogD (pH = 7.4): -0.57753056
• Log P: -0.57347023
• Molar Refractivity: 38.2195 cm^3
• Polarizability: 13.361899 Å^3
• Polar Surface Area: 80.48 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.38
• LOG S: -1.07
• Solubility (Water): 1.15e+01 g/l

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: -20°C; Refrigerator
• Storage Warning: IRRITANT
• RTECS: AU6125000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2811; UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 22
• Safety Statements: 26-36; 36
• TSCA Listed: false; 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301; H302
• GHS Precautionary statements: P264-P270-P301+P312-P330-P501A; P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Target: Antimetabolites
• Gene Information: 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)

Product Information

• Purity: ≥99%; ≥99.0% (HPLC); 97%; 99%
• Salt Data: Free Base
• Suitability: plant cell culture tested; suitable for cell culture
• Ignition Residue: ≤0.05% (as SO4)
• Cation Traces: 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
• Loss on Drying: ≤0.5% loss on drying, 110 °C
• Empirical Formula (Hill Notation): C5H5N5

DETAILS

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

REFERENCES

• 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)