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Record Information
Version1.0
Creation Date2016-09-30 22:32:23 UTC
Update Date2020-06-04 20:34:03 UTC
MCDB ID BMDB0000538
Secondary Accession Numbers
  • BMDB00538
Metabolite Identification
Common NameAdenosine triphosphate
DescriptionAdenosine triphosphate, also known as ATP or atriphos, belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety. Adenosine triphosphate is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Adenosine triphosphate is possibly soluble (in water) and a strong basic compound (based on its pKa). Adenosine triphosphate exists in all living species, ranging from bacteria to humans. Adenosine triphosphate is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
Adenosine 5'-triphosphateChEBI
Adenosine-5'-triphosphateChEBI
AdephosChEBI
AdetolChEBI
AdynolChEBI
AtipiChEBI
AtriphosChEBI
CardenosineChEBI
FosfobionChEBI
GlucobasinChEBI
H4ATPChEBI
MyotriphosChEBI
TriadenylChEBI
TriphosphadenChEBI
Adenosine 5'-triphosphoric acidGenerator
Adenosine triphosphoric acidGenerator
ADENOSINE-5'-triphosphoric acidGenerator
5'-(Tetrahydrogen triphosphate) adenosineHMDB
5'-ATPHMDB
Adenosine 5'-triphosphorateHMDB
AdenylpyrophosphorateHMDB
Adenylpyrophosphoric acidHMDB
ATPHMDB, KEGG
PhosphobionHMDB
StriadyneHMDB, MeSH
Triphosphoric acid adenosine esterHMDB
AdenylpyrophosphateMeSH, HMDB
5’-ATPHMDB
Adenosine 5’-triphosphateHMDB
Adenosine 5’-triphosphoric acidHMDB
Adenosine triphosphateHMDB
Adenosine-5’-triphosphateHMDB
Chemical FormulaC10H16N5O13P3
Average Molecular Weight507.181
Monoisotopic Molecular Weight506.995745159
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
Traditional Nameadenosine triphosphate
CAS Registry Number56-65-5
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
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
InChI KeyZKHQWZAMYRWXGA-KQYNXXCUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine 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
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Azole
  • Tetrahydrofuran
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Primary amine
  • Organic oxygen compound
  • Alcohol
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL; 862 mg/mL (magnesium salt)MERCK INDEX (1996); Human Metabolome Project (salt)
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.84ALOGPS
logP-5.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)0.9ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area279.13 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity95.81 m³·mol⁻¹ChemAxon
Polarizability38.92 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-9785600000-9d385d54b8bf3d01c79a2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0f7a-2129514000-9059f6c87291f92b0cb52017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_17) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientific ) , Negativesplash10-0a4i-0131190000-316dbdca27f38ad8ee572012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientific ) , Negativesplash10-004i-0000900000-f5ffc4694dfd302fd52d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientific ) , Negativesplash10-0a4i-0000900000-e9a09b9360491c3102802012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0000900000-f5ffc4694dfd302fd52d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0000900000-e9a09b9360491c3102802017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 35V, positivesplash10-03di-0003900000-82c389314f7350fab8752020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-0a4i-0100190000-922e5f751812c8bd89bc2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, positivesplash10-000i-0901420000-44d898eb6218dc6e081f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-000i-0900100000-b93a7d45ee103ceb59b62020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 40V, positivesplash10-000i-0900000000-296ded2a98ed98f224502020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 50V, positivesplash10-000i-0900000000-9349def51790b33b63232020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 66V, positivesplash10-000i-1900000000-049985fb880827a0d9a42020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 82V, positivesplash10-000i-1900000000-1d79fc72baa703a816cf2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 97V, positivesplash10-000i-2900000000-136ea397740616434de72020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 112V, positivesplash10-014r-4900000000-e53bae9d9851c94179c82020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 133V, positivesplash10-014i-9700000000-76dacfdda05972956c702020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 154V, positivesplash10-014i-9200000000-4ca00afb7e2831eedaa22020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 184V, positivesplash10-014i-9000000000-7208de8d2446aa0799e22020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 35V, positivesplash10-03di-0002900000-39bf04fe36582d1915612020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0911310000-f883981fb555288ec8582016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-8ed3fe63c389ec26b73f2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-96bc47060403ae952c302016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-0830290000-0774525fed54afda165a2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3930000000-a285e09b97437217cb032016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9300000000-7648d24e56aa73a5feb02016-09-12View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Not Available2021-10-10View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.21 - 0.24 uM details
Detected and Quantified0.21 - 0.24 uM details
Detected and Quantified0.22 - 0.28 uM details
HMDB IDHMDB0000538
DrugBank IDDB00171
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030683
KNApSAcK IDC00001491
Chemspider ID5742
KEGG Compound IDC00002
BioCyc IDATP
BiGG ID33477
Wikipedia LinkAdenosine_triphosphate
METLIN ID5523
PubChem Compound5957
PDB IDNot Available
ChEBI ID15422
References
Synthesis ReferenceClark, 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
General References
  1. Richardson T, McGann TC, Kearney RD: Levels and location of adenosine 5'-triphosphate in bovine milk. J Dairy Res. 1980 Feb;47(1):91-6. [PubMed:7372888 ]