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56-65-5 molecular structure
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({[({[(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 and InChIs

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

Cite this record

CBID:56 http://www.chembase.cn/molecule-56.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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
adenosine 5'-(tetrahydrogen triphosphate)
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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 0.89929146  H Acceptors 14 
H Donor LogD (pH = 5.5) -9.829983 
LogD (pH = 7.4) -10.469803  Log P -5.99769 
Molar Refractivity 95.8143 cm3 Polarizability 38.64708 Å3
Polar Surface Area 279.13 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P -0.84  LOG S -2.05 
Solubility (Water) 4.49e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
1000 mg/mL [MERCK INDEX (1996); freely soluble] expand Show data source
Melting Point
187 °C (disodium salt)
decomposes
expand Show data source
Density
1.04 g/cm3 (disodium salt) expand Show data source
Hydrophobicity(logP)
-5.5 expand Show data source
pKa
6.5 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00171 external link
Item Information
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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PATENTS

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