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5'-Atp

HCID 5957
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Basic information

CAS
56-65-5
Standard SMILES
Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O
InChIKey
ZKHQWZAMYRWXGA-KQYNXXCUSA-N
Molecular formula
C10H16N5O13P3
Average molar mass
507.18 g/mol
Monoisotopic mass
506.99574658

Overview

ATP is an adenosine 5'-phosphate in which the 5'-phosphate is a triphosphate group. It is involved in the transportation of chemical energy during metabolic pathways. It has a role as a cofactor, a micronutrient, a nutraceutical and a fundamental metabolite. It is a purine ribonucleoside 5'-triphosphate and an adenosine 5'-phosphate. It is a conjugate acid of an ATP(3-).

Names & identifiers

Preferred name
5'-Atp
IUPAC
[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
English name
Adenosine triphosphate
Molecular formula
C10H16N5O13P3
Molecular weight
507.18

Names & synonyms

Adenosine triphosphate56-65-5TriphosphadenMyotriphosTriadenylGlucobasinAdetolAdynolAtipiAdephosAdenosine 5'-(tetrahydrogen triphosphate)Adenylpyrophosphoric acid
Show more names
ADENOSINE 5'-TRIPHOSPHATEATP-H((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl tetrahydrogen triphosphateATP Sodium5’-atpATP.H2
5'-AtpAdenosine 5'-triphosphoric acidTriphosphoric acid adenosine esterDTXSID6022559adenosine 5' triphosphateadenylpyrophosphate8L70Q75FXECHEBI:15422

Database identifiers

CAS
56-65-5
PubChem CID
5957
DTXSID
DTXSID6022559
ChEMBL
CHEMBL14249

Properties

Computed structural properties

XLogP
-5.7
Topological polar surface area
279 Ų
Hydrogen bond donors
7
Hydrogen bond acceptors
17
Rotatable bonds
8
Heavy atoms
31
Formal charge
0
Complexity
800

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics · 2 items

Cosmetic ingredients (Adenosine Triphosphate) -> CIR (Cosmetic Ingredient Review)

Skin conditioning

Solubility1000.0 mg/mL; 862 mg/mL (magnesium salt)
Physical DescriptionSolid
Collision Cross Section · 4 items

198.86 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

185.74 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

196.9 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

188.3 Ų [M-H]-

Physicochemical properties

Melting point
144 °C · 144°C (rough estimate)
Boiling point
951.4 · 951.4±75.0 °C(Predicted)
alpha
22 · D22 -26.7° (c = 3.095)
Density

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.

Not Classified

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 2 items

Chemical: Adenosine 5'-(tetrahydrogen triphosphate)

Adenosine triphosphate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Adenosine 5'-(tetrahydrogen triphosphate): Environment tier I assessment
Hazard Classes and CategoriesNot Classified

Toxicology

Toxicity Summary · 2 items

Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org

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.

Carcinogen Classification

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

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.

Mechanism of Action · 1 item

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/Metabolites · 1 item

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.

Tissue LocationsAdipose Tissue

Related reactions

131 records
New reaction record
HRID 19449 reaction equation
HRID 19449As reactantuspto-grants-2010_06
HRID 23844 reaction equation
HRID 23844As reactantuspto-grants-2005_02
HRID 67943 reaction equation
HRID 67943As productuspto-grants-1982_08
HRID 227216 reaction equation
HRID 227216As reactantuspto-grants-2009_07
HRID 233545 reaction equation
HRID 233545As reactantuspto-grants-1997_01
HRID 234735 reaction equation
HRID 234735As reactantuspto-grants-1997_01
HRID 246815 reaction equation
HRID 246815As productuspto-grants-1987_11
HRID 249287 reaction equation
HRID 249287As reactantuspto-grants-1993_05
Page 1 of 17

Compound notes

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ChEBI
CHEBI:15422
UNII
8L70Q75FXE
EC Number
200-283-2
Nikkaji
J10.680A
1 g/mL · 1.0 g/mL at 20 °C
storage temp.
-20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility
Soluble (water), Na and K salts are easily soluble in water, Ba salts are insoluble in water
form
lyophilized powder
pka
2 · pK2: 4.00(-1);pK3: 6.48(-2) (25°C)
color
White to off-white
PH
7 · 7.0 ± 0.1
Water Solubility
100 mg/mL · Water : ≥ 100 mg/mL (197.17 mM)
Cosmetics Ingredients Functions
SKIN CONDITIONING
Cosmetic Ingredient Review (CIR)
Adenosine triphosphate (56-65-5)
InChIKey
ZKHQWZAMYRWXGA-KQYNXXCUSA-N
SMILES
C(OP(=O)(O)OP(O)(=O)OP(O)(O)=O)[C@H]1O[C@@H](N2C3C(=C(N=CN=3)N)N=C2)[C@H](O)[C@@H]1O
LogP
-4.18 · -4.180 (est)
CAS DataBase Reference
56 · 56-65-5(CAS DataBase Reference)
EWG's Food Scores
1 · 1
NCI Dictionary of Cancer Terms
adenosine triphosphate
FDA UNII
8 L70Q75FXE · 8L70Q75FXE
EPA Substance Registry System
Adenosine triphosphate (56-65-5)
UNSPSC Code
41106305 · 41106305
NACRES
51 · NA.51
Safety Statements
22 · 22-24/25
WGK Germany
3 · 3
TSCA
TSCA listed
HS Code
2938909090 · 2938909090
Toxicity
10 mmol/L · dni-hmn:lym 10 mmol/L CNREA8 42,2092,82
No indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataOral LD<sub>50</sub> in rats is > 2 g/kg.

Safety data

wgk
3
tsca
TSCA listed
hs_code
2938909090
Toxicity
dni-hmn:lym 10 mmol/L CNREA8 42,2092,82
safety_code
22-24/25
Cellular LocationsCytoplasm
Metabolite Pathways2-Hydroxyglutric Aciduria (D And L Form)

Uses & manufacturing

Uses · 2 items

CIR ingredient: Adenosine Triphosphate

For nutritional supplementation, also for treating dietary shortage or imbalance

Use ClassificationCosmetics -> Skin conditioning
General Manufacturing InformationAdenosine 5'-(tetrahydrogen triphosphate): ACTIVE
Applications · 3 items

DescriptionAdenosine triphosphate, also known as ATP, is a molecule that carries energy within cells. It is one of the most important biological compounds because of its role in supplying energy for life. ATP is the universal energy carrier used by all organisms to supply energy for biological functions. It is often referred to as the energy currency of cells.ATP also functions as a neurotransmitter that is stored and secreted with other neurotransmitters from the pancreas. ATP is a nucleotide consisting of the nucleoside adenosine with three attached phosphate groups (see Adenine). Like other nucleotides, ATP consists of three parts: a sugar, an amine base, and a phosphate group. The central part of the molecule in ATP is the sugar ribose. The amine base adenine is attached to the ribose, forming adenosine. Opposite the adenine on the ribose is attached a chain of three phosphate groups.

HistoryATP was first isolated by the German chemist Karl Lohmann (1898–1978) from muscle tissue extracts in 1929. Alexander Todd’s (1907–1997) research helped to clarify ATP’s structure, and it was first synthesized by Todd in 1948.

UsesAdenosine triphosphate (ATP) plays a critical role in the transport of macromolecules such as proteins and lipids into and out of the cell. The hydrolysis of ATP provides the required energy for active transport mechanisms to carry such molecules across a concentration gradient.

Upstream & downstream products

Upstream raw materials

ATPαS2',3'-DI-O-ACETYLADENOSINE5'-Tosyladenosine

Downstream products

UTPguanosine 5'-(tetrahydrogen triphosphate)6-amino-9-[3-hydroxy-5-[(hydroxy-sulfooxy-phosphoryl)oxymethyl]-4-phosphonooxy-oxolan-2-yl]-purineADPNADPH5'-Deoxy-S-adenosyl-L-homocysteine[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] 5-[(6S)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-6-yl]pentanoate
Additional notes · 1 item

DefinitionAdenosine triphosphate (ATP) is the source of energy for use and storage at the cellular level. It is an adenosine 5'-phosphate in which the 5'-phosphate is a triphosphate group. It is involved in the transportation of chemical energy during metabolic pathways.