ContaminantDB: Adenosine triphosphate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (46)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:12:10 UTC

Update Date

2026-05-14 16:24:27 UTC

Accession Number

CHEM003236

Identification

Common Name

Adenosine triphosphate

Class

Small Molecule

Description

Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (1, 2, 3, 4, 5).

Contaminant Sources

FooDB Chemicals
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Animal Toxin
Dietary Supplement
Drug
Ether
Food Toxin
Metabolite
Micronutrient
Natural Compound
Nutraceutical
Organic Compound
Supplement

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Adenosine 5'-triphosphate	ChEBI
Adenosine-5'-triphosphate	ChEBI
Adephos	ChEBI
Adetol	ChEBI
Adynol	ChEBI
Atipi	ChEBI
Atriphos	ChEBI
Cardenosine	ChEBI
Fosfobion	ChEBI
Glucobasin	ChEBI
H4ATP	ChEBI
Myotriphos	ChEBI
Triadenyl	ChEBI
Triphosphaden	ChEBI
Adenosine 5'-triphosphoric acid	Generator
Adenosine triphosphoric acid	Generator
ADENOSINE-5'-triphosphoric acid	Generator
5'-(Tetrahydrogen triphosphate) adenosine	HMDB
5'-ATP	HMDB
Adenosine 5'-triphosphorate	HMDB
Adenylpyrophosphorate	HMDB
Adenylpyrophosphoric acid	HMDB
ATP	HMDB, KEGG
Phosphobion	HMDB
Striadyne	HMDB, MeSH
Triphosphoric acid adenosine ester	HMDB
Adenylpyrophosphate	MeSH, HMDB
5’-ATP	HMDB
Adenosine 5’-triphosphate	HMDB
Adenosine 5’-triphosphoric acid	HMDB
Adenosine triphosphate	HMDB
Adenosine-5’-triphosphate	HMDB

Chemical Formula

C₁₀H₁₆N₅O₁₃P₃

Average Molecular Mass

507.181 g/mol

Monoisotopic Mass

506.996 g/mol

CAS Registry Number

56-65-5

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 Name

adenosine triphosphate

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 Key

ZKHQWZAMYRWXGA-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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

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
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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

adenosine 5'-phosphate (CHEBI:15422 )
purine ribonucleoside 5'-triphosphate (CHEBI:15422 )
Ribonucleotides (C00002 )
Coenzymes (C00002 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane
Mitochondria
Nucleus
Peroxisome

Biofluid Locations

Not Available

Tissue Locations

Adipose Tissue
Bladder
Fibroblasts
Intestine
Kidney
Muscle
Myelin
Nerve Cells
Neuron
Pancreas
Platelet
Skeletal Muscle

Pathways

Name	SMPDB Link	KEGG Link
Amino Sugar Metabolism	SMP00045	map00520
Ammonia Recycling	SMP00009	map00910
Citric Acid Cycle	SMP00057	map00020
DNA Replication Fork	SMP00477	Not Available
Ethanol Degradation	SMP00449	Not Available
Folate Metabolism	SMP00053	map00670
Gluconeogenesis	SMP00128	Not Available
Glycerolipid Metabolism	SMP00039	map00561
Glycine and Serine Metabolism	SMP00004	map00260
Glycolysis	SMP00040	Not Available
Histidine Metabolism	SMP00044	map00340
Inositol Phosphate Metabolism	SMP00462	map00562
Lactose Degradation	SMP00457	Not Available
Lactose Synthesis	SMP00444	Not Available
Methionine Metabolism	SMP00033	map00270
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids	SMP00482	Not Available
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids	SMP00481	Not Available
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids	SMP00480	Not Available
Mitochondrial Electron Transport Chain	SMP00355	map00190
Phosphatidylinositol Phosphate Metabolism	SMP00463	map00562
Phytanic Acid Peroxisomal Oxidation	SMP00450	Not Available
Purine Metabolism	SMP00050	map00230
Spermidine and Spermine Biosynthesis	SMP00445	Not Available
Threonine and 2-Oxobutanoate Degradation	SMP00452	Not Available
Transcription/Translation	SMP00019	Not Available
Transfer of Acetyl Groups into Mitochondria	SMP00466	Not Available
Trehalose Degradation	SMP00467	Not Available
Urea Cycle	SMP00059	Not Available
Adenosine Deaminase Deficiency	SMP00144	Not Available

Applications

nutraceutical

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	176°C
Boiling Point	Not Available
Solubility	1E+006 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	4.49 g/L	ALOGPS
logP	-0.84	ALOGPS
logP	-5.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	0.9	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	279.13 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	95.81 m³·mol⁻¹	ChemAxon
Polarizability	38.92 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-9785600000-9d385d54b8bf3d01c79a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0f7a-2129514000-9059f6c87291f92b0cb5	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_17) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientific ) , Negative	splash10-0a4i-0131190000-316dbdca27f38ad8ee57	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientific ) , Negative	splash10-004i-0000900000-f5ffc4694dfd302fd52d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientific ) , Negative	splash10-0a4i-0000900000-e9a09b9360491c310280	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0000900000-f5ffc4694dfd302fd52d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0000900000-e9a09b9360491c310280	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 35V, positive	splash10-03di-0003900000-82c389314f7350fab875	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-0a4i-0100190000-922e5f751812c8bd89bc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 20V, positive	splash10-000i-0901420000-44d898eb6218dc6e081f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 30V, positive	splash10-000i-0900100000-b93a7d45ee103ceb59b6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 40V, positive	splash10-000i-0900000000-296ded2a98ed98f22450	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 50V, positive	splash10-000i-0900000000-9349def51790b33b6323	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 66V, positive	splash10-000i-1900000000-049985fb880827a0d9a4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 82V, positive	splash10-000i-1900000000-1d79fc72baa703a816cf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 97V, positive	splash10-000i-2900000000-136ea397740616434de7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 112V, positive	splash10-014r-4900000000-e53bae9d9851c94179c8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 133V, positive	splash10-014i-9700000000-76dacfdda05972956c70	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 154V, positive	splash10-014i-9200000000-4ca00afb7e2831eedaa2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 184V, positive	splash10-014i-9000000000-7208de8d2446aa0799e2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 35V, positive	splash10-03di-0002900000-39bf04fe36582d191561	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0911310000-f883981fb555288ec858	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-8ed3fe63c389ec26b73f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-96bc47060403ae952c30	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a59-0830290000-0774525fed54afda165a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3930000000-a285e09b97437217cb03	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9300000000-7648d24e56aa73a5feb0	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

ATP is able to store and transport chemical energy within cells. ATP also plays an important role in the synthesis of nucleic acids. ATP can be produced by various cellular processes, most typically in mitochondria by oxidative phosphorylation under the catalytic influence of ATP synthase. 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.

Metabolism

Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.

Toxicity Values

Oral LD₅₀ in rats is > 2 g/kg.

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For nutritional supplementation, also for treating dietary shortage or imbalance

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00171

HMDB ID

HMDB0000538

FooDB ID

FDB030683

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Adenosine_triphosphate

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

George M. Whitesides, Patricia E. Garrett, Merrell G. Siegel, “Method for preparing adenosine triphosphate.” U.S. Patent US4164444, issued April, 1975.

MSDS

Link

General References

1. 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.

2. 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.

3. 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.

4. 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.

5. 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.

6. 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.

7. 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.

8. Ryan LM, Rachow JW, McCarty BA, McCarty DJ: Adenosine triphosphate levels in human plasma. J Rheumatol. 1996 Feb;23(2):214-9.

9. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18.