({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid

• ChemBase编号: 56
• 分子式: C10H16N5O13P3
• 平均质量: 507.181023
• 单一同位素质量: 506.99574549
• SMILES: [P@@](=O)(OC[C@H]1O[C@@H](n2c3ncnc(N)c3nc2)[C@H](O)[C@@H]1O)(O[P@](=O)(OP(=O)(O)O)O)O
• Canonical SMILES: O[C@@H]1[C@@H](CO[P@](=O)(O[P@](=O)(OP(=O)(O)O)O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
• InChIKey: ZKHQWZAMYRWXGA-KQYNXXCUSA-N

名称和登记号

名称

• IUPAC标准名: ({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
• IUPAC传统名: adenosine triphosphate
• 商标名: Adephos; Adetol; Adynol; Atipi; Atriphos; Cardenosine; Fosfobion; Glucobasin; Myotriphos; Phosphobion; Striadyne; Triadenyl; Triphosphaden
• 别名: adenosine 5'-(tetrahydrogen triphosphate); 5'-ATP; Adenosine 5'-triphosphate; Adenosine 5'-triphosphoric acid; Adenosine, 5'-(tetrahydrogen triphosphate); Adenosine-5'-triphosphate; Adenylpyrophosphoric acid; ATP; Triphosphoric acid adenosine ester; Adenosine triphosphate

登记号

• CAS号: 56-65-5
• PubChem SID: 46507614; 160963519
• PubChem CID: 5957
• CHEBI ID: 15422
• CHEMBL: 14249
• Chemspider ID: 5742
• DrugBank ID: DB00171
• IUPHAR配体索引: 1713
• KEGG ID: C00002
• 美国药典/FDA物质标识码: 8L70Q75FXE
• 维基百科标题: Adenosine_triphosphate

理论计算性质

JChem

• Acid pKa: 0.89929146
• 质子受体: 14
• 质子供体: 7
• LogD (pH = 5.5): -9.829983
• LogD (pH = 7.4): -10.469803
• Log P: -5.99769
• 摩尔折射率: 95.8143 cm^3
• 极化性: 38.64708 Å^3
• 极化表面积: 279.13 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: -0.84
• LOG S: -2.05
• 溶解度: 4.49e+00 g/l

分子性质

理化性质

• 溶解度: 1000 mg/mL [MERCK INDEX (1996); freely soluble]
• 熔点: 187 °C (disodium salt) ; decomposes
• 密度: 1.04 g/cm^3 (disodium salt)
• 疏水性(logP): -5.5
• pKa: 6.5

详细说明

DrugBank - DB00171

• Drug Groups: approved; nutraceutical
• Description: An adenine nucleotide containing three phosphate groups esterified to the sugar moiety. In addition to its crucial roles in metabolism adenosine triphosphate is a neurotransmitter. [PubChem]
• Indication: For nutritional supplementation, also for treating dietary shortage or imbalance
• Pharmacology: Adenosine triphosphate (ATP) is the nucleotide known in biochemistry as the "molecular currency" of intracellular energy transfer; that is, ATP is able to store and transport chemical energy within cells. ATP also plays an important role in the synthesis of nucleic acids. The total quantity of ATP in the human body is about 0.1 mole. The energy used by human cells requires the hydrolysis of 200 to 300 moles of ATP daily. This means that each ATP molecule is recycled 2000 to 3000 times during a single day. ATP cannot be stored, hence its consumption must closely follow its synthesis.
• Toxicity: Oral LD₅₀ in rats is > 2 g/kg.
• Affected Organisms: Humans and other mammals
• References: Gajewski E, Steckler DK, Goldberg RN: Thermodynamics of the hydrolysis of adenosine 5'-triphosphate to adenosine 5'-diphosphate. J Biol Chem. 1986 Sep 25;261(27):12733-7. [Pubmed] ; Storer AC, Cornish-Bowden A: Concentration of MgATP2- and other ions in solution. Calculation of the true concentrations of species present in mixtures of associating ions. Biochem J. 1976 Oct 1;159(1):1-5. [Pubmed] ; Wilson JE, Chin A: Chelation of divalent cations by ATP, studied by titration calorimetry. Anal Biochem. 1991 Feb 15;193(1):16-9. [Pubmed] ; Garfinkel L, Altschuld RA, Garfinkel D: Magnesium in cardiac energy metabolism. J Mol Cell Cardiol. 1986 Oct;18(10):1003-13. [Pubmed] ; Parsons M: Glycosomes: parasites and the divergence of peroxisomal purpose. Mol Microbiol. 2004 Aug;53(3):717-24. [Pubmed]
• External Links: Wikipedia

参考文献

• Gajewski E, Steckler DK, Goldberg RN: Thermodynamics of the hydrolysis of adenosine 5'-triphosphate to adenosine 5'-diphosphate. J Biol Chem. 1986 Sep 25;261(27):12733-7. Pubmed
• Storer AC, Cornish-Bowden A: Concentration of MgATP2- and other ions in solution. Calculation of the true concentrations of species present in mixtures of associating ions. Biochem J. 1976 Oct 1;159(1):1-5. Pubmed
• Wilson JE, Chin A: Chelation of divalent cations by ATP, studied by titration calorimetry. Anal Biochem. 1991 Feb 15;193(1):16-9. Pubmed
• Garfinkel L, Altschuld RA, Garfinkel D: Magnesium in cardiac energy metabolism. J Mol Cell Cardiol. 1986 Oct;18(10):1003-13. Pubmed
• Parsons M: Glycosomes: parasites and the divergence of peroxisomal purpose. Mol Microbiol. 2004 Aug;53(3):717-24. Pubmed