Livestock Metabolome Database: Showing metabocard for Adenosine triphosphate (LMDB00177)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:44:03 UTC

Update Date

2016-09-23 18:44:52 UTC

Lmdb

LMDB00177

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Adenosine triphosphate

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 animal 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. (PMID: 15490415 , 15129319 , 14707763 , 14696970 , 11157473 ).

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 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Brain
Colostrum
Meat

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Brain	Detected but not Quantified	Not Applicable	Not Available	Ovine	25959287	details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	0.73+/-0.04 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	1.12+/-0.02 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	1.83+/-0.02 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	2.31+/-0.03 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details

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

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Rutkowski B, Swierczynski J, Slominska E, Szolkiewicz M, Smolenski RT, Marlewski M, Butto B, Rutkowski P: Disturbances of purine nucleotide metabolism in uremia. Semin Nephrol. 2004 Sep;24(5):479-83. [15490415 ]
Holzer AM, Granstein RD: Role of extracellular adenosine triphosphate in human skin. J Cutan Med Surg. 2004 Mar-Apr;8(2):90-6. Epub 2004 May 3. [15129319 ]
Myburgh KH: Can any metabolites partially alleviate fatigue manifestations at the cross-bridge? Med Sci Sports Exerc. 2004 Jan;36(1):20-7. [14707763 ]
Gartland A, Buckley KA, Hipskind RA, Bowler WB, Gallagher JA: P2 receptors in bone--modulation of osteoclast formation and activity via P2X7 activation. Crit Rev Eukaryot Gene Expr. 2003;13(2-4):237-42. [14696970 ]
Di Virgilio F, Chiozzi P, Ferrari D, Falzoni S, Sanz JM, Morelli A, Torboli M, Bolognesi G, Baricordi OR: Nucleotide receptors: an emerging family of regulatory molecules in blood cells. Blood. 2001 Feb 1;97(3):587-600. [11157473 ]

Showing metabocard for Adenosine triphosphate (LMDB00177)

Structure for LMDB00177 (Adenosine triphosphate)