Milk Composition Database: Showing metabocard for Adenosine triphosphate (BMDB0000538)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:32:23 UTC

Update Date

2020-06-04 20:34:03 UTC

MCDB ID

BMDB0000538

Secondary Accession Numbers

BMDB00538

Metabolite Identification

Common Name

Adenosine triphosphate

Description

Adenosine 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

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 Weight

507.181

Monoisotopic Molecular Weight

506.995745159

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 Name

adenosine triphosphate

CAS Registry Number

56-65-5

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 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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000 mg/mL; 862 mg/mL (magnesium salt)	MERCK INDEX (1996); Human Metabolome Project (salt)
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-9785600000-9d385d54b8bf3d01c79a	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0f7a-2129514000-9059f6c87291f92b0cb5	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_17) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientific ) , Negative	splash10-0a4i-0131190000-316dbdca27f38ad8ee57	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientific ) , Negative	splash10-004i-0000900000-f5ffc4694dfd302fd52d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientific ) , Negative	splash10-0a4i-0000900000-e9a09b9360491c310280	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0000900000-f5ffc4694dfd302fd52d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0000900000-e9a09b9360491c310280	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 35V, positive	splash10-03di-0003900000-82c389314f7350fab875	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-0a4i-0100190000-922e5f751812c8bd89bc	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 20V, positive	splash10-000i-0901420000-44d898eb6218dc6e081f	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 30V, positive	splash10-000i-0900100000-b93a7d45ee103ceb59b6	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 40V, positive	splash10-000i-0900000000-296ded2a98ed98f22450	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 50V, positive	splash10-000i-0900000000-9349def51790b33b6323	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 66V, positive	splash10-000i-1900000000-049985fb880827a0d9a4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 82V, positive	splash10-000i-1900000000-1d79fc72baa703a816cf	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 97V, positive	splash10-000i-2900000000-136ea397740616434de7	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 112V, positive	splash10-014r-4900000000-e53bae9d9851c94179c8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 133V, positive	splash10-014i-9700000000-76dacfdda05972956c70	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 154V, positive	splash10-014i-9200000000-4ca00afb7e2831eedaa2	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 184V, positive	splash10-014i-9000000000-7208de8d2446aa0799e2	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 35V, positive	splash10-03di-0002900000-39bf04fe36582d191561	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0911310000-f883981fb555288ec858	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-8ed3fe63c389ec26b73f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-96bc47060403ae952c30	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a59-0830290000-0774525fed54afda165a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3930000000-a285e09b97437217cb03	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9300000000-7648d24e56aa73a5feb0	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.21 - 0.24 uM	PMID: 7372888	details
Detected and Quantified	0.21 - 0.24 uM	PMID: 7372888	details
Detected and Quantified	0.22 - 0.28 uM	PMID: 7372888	details

External Links

HMDB ID

HMDB0000538

DrugBank ID

DB00171

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Adenosine_triphosphate

METLIN ID

5523

PubChem Compound

5957

PDB ID

Not Available

ChEBI ID

15422

References

Synthesis Reference

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for Adenosine triphosphate (BMDB0000538)

Structure for BMDB0000538 (Adenosine triphosphate)