({[({[(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 ID: 56
• Molecular Formular: C10H16N5O13P3
• Molecular Mass: 507.181023
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[(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 Traditional name: adenosine triphosphate
• Brand Name: Adephos; Adetol; Adynol; Atipi; Atriphos; Cardenosine; Fosfobion; Glucobasin; Myotriphos; Phosphobion; Striadyne; Triadenyl; Triphosphaden
• Synonyms: 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

Database IDs

• CAS Number: 56-65-5
• PubChem SID: 46507614; 160963519
• PubChem CID: 5957
• CHEBI ID: 15422
• CHEMBL: 14249
• Chemspider ID: 5742
• DrugBank ID: DB00171
• IUPHAR ligand ID: 1713
• KEGG ID: C00002
• Unique Ingredient Identifier: 8L70Q75FXE
• Wikipedia Title: Adenosine_triphosphate

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.89929146
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): -9.829983
• LogD (pH = 7.4): -10.469803
• Log P: -5.99769
• Molar Refractivity: 95.8143 cm^3
• Polarizability: 38.64708 Å^3
• Polar Surface Area: 279.13 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.84
• LOG S: -2.05
• Solubility (Water): 4.49e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1000 mg/mL [MERCK INDEX (1996); freely soluble]
• Melting Point: 187 °C (disodium salt) ; decomposes
• Density: 1.04 g/cm^3 (disodium salt)
• Hydrophobicity(logP): -5.5
• pKa: 6.5

DETAILS

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

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