Basic information
- 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
- 506.99574546
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
Show more names
Database identifiers
- CAS
56-65-5- PubChem CID
- 5957
- DTXSID
DTXSID6022559- ChEMBL
CHEMBL14249- ChEBI
CHEBI:15422- UNII
- 8L70Q75FXE
- EC Number
- 200-283-2
- Nikkaji
- J10.680A
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
Cosmetics
Cosmetic ingredients (Adenosine Triphosphate) -> CIR (Cosmetic Ingredient Review)
Skin conditioning
Collision Cross Section
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)]
196.6 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
204.2 Ų [M+Na]+
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
- 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
- Toxicity
- 10 mmol/L · dni-hmn:lym 10 mmol/L CNREA8 42,2092,82
Safety & regulation
GHS classification
GHS Classification
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
Chemical: Adenosine 5'-(tetrahydrogen triphosphate)
Adenosine triphosphate: Does not have an individual approval but may be used under an appropriate group standard
Toxicology
Toxicity Summary
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.
Safety data
- wgk
- 3
- tsca
- TSCA listed
- Toxicity
- dni-hmn:lym 10 mmol/L CNREA8 42,2092,82
- safety_code
- 22-24/25
Chemistry & industry
Pharmacology
Pharmacodynamics
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
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
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.
Uses & manufacturing
Uses
CIR ingredient: Adenosine Triphosphate
For nutritional supplementation, also for treating dietary shortage or imbalance
Applications
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
Downstream products
Suppliers50 total
Additional notes
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.
Related reactions
Linked notes
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