Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110477
Identification
Name: ATP
Description:A nucleoside triphosphate(4−) obtained by global deprotonation of the triphosphate OH groups of ATP; major species present at pH 7.3.
Structure
Thumb
Synonyms:
  • adenylpyrophosphate
  • adenosine-triphosphate
  • adenosine-5'-triphosphate
Chemical Formula: C10H12N5O13P3
Average Molecular Weight: 503.15
Monoisotopic Molecular Weight: 506.9957451569
InChI Key: ZKHQWZAMYRWXGA-KQYNXXCUSA-J
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)/p-4/t4-,6-,7-,10-/m1/s1
CAS number: 56-65-5
IUPAC Name:adenosine 5'-triphosphate(4−)
Traditional IUPAC Name: adenosine triphosphate
SMILES:C(C3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))OP(OP(=O)([O-])OP(=O)([O-])[O-])([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct Parent Purine ribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside triphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Alkyl phosphate
  • Pyrimidine
  • Imidolactam
  • Monosaccharide
  • Primary aromatic amine
  • Phosphoric acid ester
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Heteroaromatic compound
  • Oxolane
  • Azole
  • Imidazole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Amine
  • Alcohol
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mL; 862 mg/mL (magnesium salt)MERCK INDEX (1996); Human Metabolome Project (salt)
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.49 mg/mLALOGPS
logP-0.84ALOGPS
logP-6ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)0.9ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area279.13 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity95.81 m3·mol-1ChemAxon
Polarizability38.92 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Odd-Straight-Chain-234-Sat-FA + ATP + coenzyme A → Odd-Saturated-Fatty-Acyl-CoA + AMP + diphosphate
2'-deoxyribose + ATP → DEOXY-RIBOSE-5P + ADP + Hydrogen ion
ATP + dAMP → ADP + dADP
Citronellates + coenzyme A + ATP → citronellyll-CoA + AMP + diphosphate
coenzyme A + acetoacetate + ATP → acetoacetyl-CoA + diphosphate + AMP
coenzyme A + acetate + ATP → phosphate + acetyl-CoA + ADP
thiamin + ATP → Hydrogen ion + thiamin diphosphate + AMP
3-Methyl-Saturated-Fatty-Acids + coenzyme A + ATP → 3-Methyl-Saturated-Fatty-Acyl-CoA + AMP + diphosphate
pseudouridine + ATP → Hydrogen ion + pseudouridine 5'-phosphate + ADP
ATP + acetyl-CoA + Water → malonyl-CoA + ADP + phosphate + Hydrogen ion
dGMP + ATP → dGDP + ADP
Hydrogen ion + D-glycero-β-D-manno-heptose 1-phosphate + ATP → ADP-D-glycero-β-D-manno-heptose + diphosphate
ATP + DNA-N + Water → ADP + phosphate
ATP + protoporphyrin IX + MG+2 + Water → Hydrogen ion + Mg-protoporphyrin + phosphate + ADP
ATP + dIDP → ADP + dITP
beta-Alanine + (R)-pantoate + ATP → Hydrogen ion + (R)-pantothenate + phosphate + ADP
trans-cinnamate + coenzyme A + ATP → (E)-cinnamoyl-CoA + AMP + diphosphate
Deoxyadenosine + ATP → Hydrogen ion + dAMP + ADP
tRNA-uridine34 + TusE-S-sulfanylcysteine + ATP → tRNA-2-thiouridine34 + TusE-L-cysteine + AMP + diphosphate
UDP-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysine + D-Alanyl-D-alanine + ATP → Hydrogen ion + UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine + phosphate + ADP
coenzyme A + propanoate + ATP → propanoyl-CoA + diphosphate + AMP
2-dehydro-3-deoxy-D-gluconate + ATP → Hydrogen ion + 2-dehydro-3-deoxy-D-gluconate 6-phosphate + ADP
linoleate + coenzyme A + ATP → linoleoyl-CoA + diphosphate + AMP
ATP + dCMP → ADP + dCDP
Deoxyguanosine + ATP → Hydrogen ion + dGMP + ADP
Protein-L-serine-or-L-threonine + ATP → Protein-Ser-or-Thr-phosphate + ADP + Hydrogen ion
L-Glutamine + L-aspartate + ATP + Water → Hydrogen ion + L-glutamate + L-Asparagine + diphosphate + AMP
ATP + 4-Amino-5-hydroxymethyl-2-methylpyrimidine → Hydrogen ion + ADP + 4-Amino-2-methyl-5-phosphomethylpyrimidine
ATP + α-linolenate + coenzyme A → α-linolenoyl-CoA + diphosphate + AMP
selenate + ATP + Hydrogen ion → adenosine 5'-phosphoselenate + diphosphate
oleate + coenzyme A + ATP → oleoyl-CoA + AMP + diphosphate
dATP + Water → ATP
Long-Chain-Fatty-Acids + coenzyme A + ATP → Long-Chain-Acyl-CoAs + diphosphate + AMP
Glucopyranose + ATP → D-glucopyranose-6-phosphate + ADP + Hydrogen ion
undecaprenyl-diphospho-(N-acetylglucosamine)-N-acetylmuramoyl-L-alanyl-γ-D-isoglutaminyl-N-(β-D-asparatyl)-L-lysyl-D-alanyl-D-alanine + Ammonium + ATP → Hydrogen ion + undecaprenyl-diphospho-(N-acetylglucosamine)-N-acetylmuramoyl-L-alanyl-γ-D-isoglutaminyl-N-(β-D-asparaginyl)-L-lysyl-D-alanyl-D-alanine + AMP + diphosphate
eicosapentaenoate + ATP + coenzyme A → eicosapentaenoyl-CoA + diphosphate + AMP
chlorophyllide a + ADP + phosphate → protochlorophyllide a + ATP + Water
METHYLENE-THF-GLU-N + L-glutamate + ATP → METHYLENE-THF-GLU-N + ADP + phosphate
alpha-D-Glucose + ATP → Hydrogen ion + α-D-glucose 6-phosphate + ADP
5-oxoproline + Water + ATP → Hydrogen ion + L-glutamate + phosphate + ADP
Hydrogen ion + ATP + Water → Hydrogen ion + ADP + phosphate
3-oxocholest-4-en-26-oate + ATP + coenzyme A → 3-oxocholest-4-en-26-oyl-CoA + AMP + diphosphate
alpha-N-Peptidyl-LGlutamate + L-glutamate + ATP → CPD0-2471 + ADP + phosphate + Hydrogen ion
thiamin + ATP → Hydrogen ion + thiamin phosphate + ADP
Hydrogen ion + L-Serine + ATP → diphosphate + AMP
ALGINATE + Water + ATP → ALGINATE + phosphate + ADP + Hydrogen ion
DEOXYNUCLEOTIDESM + ATP + Deoxynucleotides → AMP + diphosphate + Deoxynucleotides
CPD66-39 + coenzyme A + ATP → Saturated-Fatty-Acyl-CoA + diphosphate + AMP
phytenate + ATP + coenzyme A → phytenoyl-CoA + AMP + diphosphate
ATP → AMP + diphosphate
dADP + ATP → dATP + ADP
biotin + ATP → diphosphate + AMP
LysW-L-glutamate + ATP → LysW-L-glutamate-5-phosphate + ADP
dGDP + ATP → dGTP + ADP
phenylacetate + ATP + coenzyme A → phenylacetyl-CoA + AMP + diphosphate
ATP + cob(I)alamin → coenzyme B12 + Triphosphate
D-ALPHABETA-D-HEPTOSE-7-PHOSPHATE + ATP → Hydrogen ion + D-glycero-β-D-manno-heptose 1,7-bisphosphate + ADP
Hydrogen ion + 3'-dephospho-CoA + ATP → 2'-(5''-triphospho-α-D-ribosyl)-3'-dephospho-CoA + Adenine
(R)-4'-phosphopantothenate + L-Cysteine + ATP → Hydrogen ion + R-4'-phosphopantothenoyl-L-cysteine + diphosphate + AMP
R2OH-Straight-Chain-234-Sat-FA + ATP + coenzyme A → R2-2OH-Straight-Chain-234-Sat-FA-CoA + AMP + diphosphate
1,6-anhydro-N-acetyl-β-muramate + ATP + Water → Hydrogen ion + N-acetyl-β-muramate 6-phosphate + ADP
ATP → ADP
cob(II)yrinate c-monoamide + L-Glutamine + ATP + Water → cob(II)yrinate a,c-diamide + L-glutamate + ADP + phosphate + Hydrogen ion
ATP + acetyl-CoA + Hydrogen carbonate → Hydrogen ion + malonyl-CoA + phosphate + ADP
CTP + ATP → diphosphate
cobyrinate + L-Glutamine + ATP + Water → cob(II)yrinate c-monoamide + L-glutamate + ADP + phosphate + Hydrogen ion
(15Z)-tetracosenoate + coenzyme A + ATP → (Z)-15-tetracosenoyl-CoA + diphosphate + AMP
ATP → ADP + phosphate
Water + ATP → Hydrogen ion + phosphate + ADP
O-ureidohomoserine + L-aspartate + ATP → Hydrogen ion + canavaninosuccinate + AMP + diphosphate
cobyrinate + L-Glutamine + ATP + Water → cob(II)yrinate a,c-diamide + L-glutamate + ADP + phosphate + Hydrogen ion
palmitate + coenzyme A + ATP → palmitoyl-CoA + diphosphate + AMP
Nucleoside-Diphosphates + ATP → Nucleoside-Triphosphates + ADP
L-Glutamine + ATP + Water → L-glutamate + phosphate + ADP + Hydrogen ion
Xenobiotic + Water + ATP → Xenobiotic + phosphate + ADP
3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate + ATP + coenzyme A → 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoyl-CoA + AMP + diphosphate
L-glutamate + ATP + Hydrogen ion → AMP + diphosphate
pristanate + coenzyme A + ATP → pristanoyl-CoA + diphosphate + AMP
UDP-N-acetyl-α-D-muramate + L-alanyl-γ-D-glutamyl-meso-diaminopimelate + ATP → Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + ADP + phosphate
L-glutamate + LysW-C-Terminal-L-Glutamate + ATP → LysW-L-glutamate + ADP + phosphate + Hydrogen ion
cis-geranyl-CoA + Hydrogen carbonate + ATP → 3-(4-methylpent-3-en-1-yl)-pent-2-enedioyl-CoA + phosphate + ADP + Hydrogen ion
NAD+ + ATP → Hydrogen ion + NADP+ + ADP
glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate + ATP → Hydrogen ion + glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate + ADP
ATP + Water + K+ → ADP + phosphate + K+ + Hydrogen ion
2-Me-Branched-234-Sat-FA + coenzyme A + ATP → 2-Me-Branched-234-Sat-Fatty-Acyl-CoA + diphosphate + AMP
tRNAs-Asp-with-queuosine + ATP + L-glutamate → tRNAs-with-glutamylated-queuosine + AMP + diphosphate + Hydrogen ion
glucosyl-(heptosyl)2-Kdo2-lipid A + ATP → Hydrogen ion + glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate + ADP
ATP + IDP → ITP + ADP
L-1-PHOSPHATIDYL-GLYCEROL + ATP → L-1-PHOSPHATIDYL-GLYCEROL-P + ADP + Hydrogen ion
ATP + 4-methyl-5-(β-hydroxyethyl)thiazole → Hydrogen ion + ADP + 4-methyl-5-(2-phosphonooxyethyl)thiazole
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientific ) , Negativesplash10-0a4i-0131190000-316dbdca27f38ad8ee57View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientific ) , Negativesplash10-004i-0000900000-f5ffc4694dfd302fd52dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientific ) , Negativesplash10-0a4i-0000900000-e9a09b9360491c310280View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
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  • Gottlieb C, Svanborg K, Eneroth P, Bygdeman M: Effect of prostaglandins on human sperm function in vitro and seminal adenosine triphosphate content. Fertil Steril. 1988 Feb;49(2):322-7. [3338588 ]
  • Mahmoud AM, Comhaire FH, Vermeulen L, Andreou E: Comparison of the resazurin test, adenosine triphosphate in semen, and various sperm parameters. Hum Reprod. 1994 Sep;9(9):1688-93. [7836519 ]
  • Kadmon M, Klunemann C, Bohme M, Ishikawa T, Gorgas K, Otto G, Herfarth C, Keppler D: Inhibition by cyclosporin A of adenosine triphosphate-dependent transport from the hepatocyte into bile. Gastroenterology. 1993 May;104(5):1507-14. [7683296 ]
  • Sun Y, MaLossi J, Jacobs SC, Chai TC: Effect of doxazosin on stretch-activated adenosine triphosphate release in bladder urothelial cells from patients with benign prostatic hyperplasia. Urology. 2002 Aug;60(2):351-6. [12137852 ]
  • Ryan LM, Rachow JW, McCarty BA, McCarty DJ: Adenosine triphosphate levels in human plasma. J Rheumatol. 1996 Feb;23(2):214-9. [8882021 ]
  • Yoshida M, Miyamae K, Iwashita H, Otani M, Inadome A: Management of detrusor dysfunction in the elderly: changes in acetylcholine and adenosine triphosphate release during aging. Urology. 2004 Mar;63(3 Suppl 1):17-23. [15013648 ]
  • Bar-Meir M, Elpeleg ON, Saada A: Effect of various agents on adenosine triphosphate synthesis in mitochondrial complex I deficiency. J Pediatr. 2001 Dec;139(6):868-70. [11743516 ]
  • Mannucci L, Pastore A, Rizzo C, Piemonte F, Rizzoni G, Emma F: Impaired activity of the gamma-glutamyl cycle in nephropathic cystinosis fibroblasts. Pediatr Res. 2006 Feb;59(2):332-5. [16439602 ]
  • Livingston JH, Brown JK, Harkness RA, McCreanor GM: Cerebrospinal fluid nucleotide metabolites following non-convulsive status epilepticus. Dev Med Child Neurol. 1989 Apr;31(2):168-73. [2737369 ]
  • Rutkowski B, Swierczynski J, Slominska E, Szolkiewicz M, Smolenski RT, Marlewski M, Butto B, Rutkowski P: Disturbances of purine nucleotide metabolism in uremia. Semin Nephrol. 2004 Sep;24(5):479-83. [15490415 ]
  • Holzer AM, Granstein RD: Role of extracellular adenosine triphosphate in human skin. J Cutan Med Surg. 2004 Mar-Apr;8(2):90-6. Epub 2004 May 3. [15129319 ]
  • Myburgh KH: Can any metabolites partially alleviate fatigue manifestations at the cross-bridge? Med Sci Sports Exerc. 2004 Jan;36(1):20-7. [14707763 ]
  • Gartland A, Buckley KA, Hipskind RA, Bowler WB, Gallagher JA: P2 receptors in bone--modulation of osteoclast formation and activity via P2X7 activation. Crit Rev Eukaryot Gene Expr. 2003;13(2-4):237-42. [14696970 ]
  • Di Virgilio F, Chiozzi P, Ferrari D, Falzoni S, Sanz JM, Morelli A, Torboli M, Bolognesi G, Baricordi OR: Nucleotide receptors: an emerging family of regulatory molecules in blood cells. Blood. 2001 Feb 1;97(3):587-600. [11157473 ]
Synthesis Reference: Clark, V. M.; Kirby, G. W.; Todd, Alexander. Phosphorylation. XV. Use of phosphoramidic esters in acylation-new preparation of adenosine 5'-pyrophosphate and adenosine 5'-triphosphate. Journal of the Chemical Society (1957), 1497-1501.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CAS56-65-5
ChEBI30616
ChemSpider4574455
HMDBHMDB00538
IAF126033477
KEGGC00002
MetaboLightsMTBLC30616
PubChem5461108