Moleculium

CID 5957

C10H16N5O13P3

Adenosine triphosphate

  • C 10
  • H 16
  • N 5
  • O 13
  • P 3
Viewer controls

Drag to rotate; pinch or Ctrl + scroll to zoom. Arrow keys rotate, + − zoom, R resets.

47 atoms, 49 bonds.
Ball-and-stick model of adenosine triphosphate: 10 carbon atoms, 16 hydrogen atoms, 5 nitrogen atoms, 13 oxygen atoms and 3 phosphorus atoms, 49 bonds (42 single, 7 double). Carbon is grey, hydrogen white, nitrogen blue, oxygen red, phosphorus orange.
IUPAC name
[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
Molar mass
507.182(44) g/mol
Atoms
47
SMILES
C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)O)N
InChIKey
ZKHQWZAMYRWXGA-KQYNXXCUSA-N
PubChem CID
5957

Made of

C , Carbon, nonmetal H , Hydrogen, nonmetal N , Nitrogen, nonmetal O , Oxygen, nonmetal P , Phosphorus, nonmetal
Structural formula of adenosine triphosphate. Each unlabelled corner is a carbon atom, and the eight hydrogens on carbon are not drawn. Wedges come toward you, hashes go back. It shows which atoms are joined to which, not the shape. The model above shows the shape. Structural formula of adenosine triphosphate, drawn flat from PubChem's 2D record: 10 carbon atoms, 16 hydrogen atoms, 5 nitrogen atoms, 13 oxygen atoms and 3 phosphorus atoms, 49 bonds (42 single, 7 double). Each unlabelled corner is a carbon atom, and the eight hydrogens on carbon are not drawn. Two bonds are drawn as wedges toward the reader and two hashed, away from it. Symbols carry their usual colours: nitrogen blue, oxygen red and phosphorus orange. A structural formula shows how the atoms are joined, not the shape of the molecule.

Inside a working cell, energy released in one place has to be spent in another, and adenosine triphosphate, ATP, is the small molecule that carries it across. ChEBI, a database of biological molecules, describes it as moving chemical energy through metabolic pathways. The US National Cancer Institute’s thesaurus (NCIt) finds it in all living cells.

Its name lists its parts. Adenosine is the base adenine joined to ribose, a five-carbon sugar, and triphosphate is the row of three phosphate groups bonded to that sugar as an ester. In that link an oxygen atom bridges a phosphorus and a carbon of the sugar. The pattern of base, sugar and phosphate makes ATP a nucleotide, the same kind of unit that builds RNA and DNA. The IUPAC name spells the whole thing out atom by atom: “[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate”. The formula C10H16N5O13P3 gives a molar mass of 507.18 g/mol.

Structure and bonding

The readout counts 47 atoms and 49 bonds, joined in one piece that contains three rings. With Labels on, the molecule reads from end to end. Fused rings of six and five atoms form the adenine, with an NH2 group on the larger ring. A ring nitrogen joins it to ribose, a five-membered ring holding one O and two O–H groups. Beyond the sugar runs a chain P–O–P–O–P, three phosphorus atoms bridged by oxygen.

In Ball-and-stick each phosphorus has four oxygen neighbours, one drawn double and three single. Stick view traces six O–H groups, four of them on phosphate oxygens. That is the neutral acid, while ChEBI lists ATP as the conjugate acid of ATP3−, the ion that has lost three of those protons. Since the viewer draws every bond as single or double, the alternating ring bonds and the one P=O per phosphorus are one way of drawing it.

Space-filling merges it into one long body. The O–H and N–H hydrogens sit on its surface. Each can form a hydrogen bond, as Chem1 describes it, with an oxygen or nitrogen on a neighbouring molecule.

Where it turns up

ATP is present wherever cells live. The LOTUS natural-products database reports it in Homo sapiens and in the plant Helianthus tuberosus, among other organisms. Inside cells, mitochondria are the compartments that the US National Human Genome Research Institute (NHGRI) credits with most of the chemical energy used by a cell’s reactions, stored as ATP. Some cells carry more mitochondria than others because they need more energy: muscle, liver and kidney hold many, on NHGRI’s account.

Outside living tissue, adenosine triphosphate turns up in cosmetics. The Cosmetic Ingredient Review lists it as an ingredient, and the NORMAN Suspect List Exchange classes its cosmetic function as skin conditioning. The US Environmental Protection Agency (EPA) marks it active in commerce as adenosine 5’-(tetrahydrogen triphosphate). In cancer research, NCIt notes, ATP is synthesised to study whether it can reduce weight loss and improve muscle strength.

Why it matters

Burning a glucose molecule to carbon dioxide and water in one go would do a cell no good. On Chem1’s account the energy would come out as heat, and far too fast to use. Instead the sugar is taken apart in a dozen or more steps. At each one, an ADP (adenosine diphosphate) molecule takes up inorganic phosphate and becomes ATP, catching part of the energy released.

Chem1 puts the free-energy change, the energy available to drive other processes, for ADP and phosphate becoming ATP at +30 kJ per mole. When an ATP molecule reaches a place where work is needed, it loses one phosphate group and that free energy is released. The ADP left over returns to the glucose-processing machinery and is rebuilt into ATP, so the same molecules cycle again and again.

Chem1 counts 38 ATP formed for each glucose fully broken down. That captures 1,140 kJ of the 2,880 kJ the sugar releases per mole, an efficiency of 0.4, or 40 per cent. The remaining 60 per cent leaves as heat rather than driving other processes.

Properties

Properties of adenosine triphosphate Molar mass summed from IUPAC/CIAAW 2024 standard atomic weights; formula, atom and bond counts and PubChem's molecular weight from PubChem CID 5957.
Property Value Unit Source
Molecular formula (Hill order) C10H16N5O13P3
Molar mass 507.182(44)   g/mol g/mol IUPAC/CIAAW 2024
Carbon atoms 10
Hydrogen atoms 16
Nitrogen atoms 5
Oxygen atoms 13
Phosphorus atoms 3
Bonds 49
Single bonds 42
Double bonds 7
PubChem molecular weight 507.18   g/mol g/mol PubChem

Safety

Adenosine triphosphate is essentially harmless in its everyday forms, a normal constituent of every living cell. Both company reports to the European Chemicals Agency (ECHA) leave it Not Classified under the Globally Harmonized System (GHS). Fuller safety data for ATP are in the PubChem Laboratory Chemical Safety Summary.

Questions

What are the three parts of an ATP molecule?

ATP joins a base, a sugar and a phosphate chain, the plan every nucleotide follows. The base is adenine: two fused rings with four nitrogen atoms, and an NH2 group outside them. It links through one ring nitrogen to ribose, a five-membered sugar ring. From the sugar's 5' carbon hangs a row of three phosphate groups, linked through an oxygen. In the 3D model, turning on Labels picks out the three P atoms at the end of that tail.

How does ATP store and release energy?

Joining ADP to inorganic phosphate to give ATP takes about 30 kJ of free energy per mole, according to Chem1; that is the energy ATP carries. Where work is needed, ATP gives up one phosphate group and that free energy is released. The ADP and phosphate left behind travel back to where glucose is broken down and are rebuilt into ATP.

Is ATP an acid?

Yes. ChEBI, a database of biological molecules, lists ATP as the conjugate acid of ATP3−, the ion left when three phosphate O–H protons are lost. The neutral acid in the model carries six O–H hydrogens and no charges, and four of those hydrogens sit on phosphate oxygens. ATP also exists as a disodium salt.

Is ATP a neurotransmitter?

Yes. Besides its work in metabolism, adenosine triphosphate is a neurotransmitter, a chemical messenger between nerve cells, according to MeSH, the US National Library of Medicine's subject vocabulary. The US National Cancer Institute's thesaurus adds that cells also draw on it when they build RNA.

Made of the same elements

Sources

  1. PubChem CID 5957, adenosine triphosphate
  2. IUPAC/CIAAW, Abridged Standard Atomic Weights 2024
  3. PubChem Laboratory Chemical Safety Summary for adenosine triphosphate (CID 5957)
  4. Stephen Lower, Chem1 General Chemistry, §15.7 Some Applications of Entropy and Free Energy (LibreTexts, CC BY 3.0)
  5. Stephen Lower, Chem1 General Chemistry, §7.3 Hydrogen-Bonding and Water (LibreTexts, CC BY 3.0)
  6. National Human Genome Research Institute, Talking Glossary of Genomic and Genetic Terms: Mitochondria
  7. National Human Genome Research Institute, Talking Glossary of Genomic and Genetic Terms: Nucleotide