You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-01-11 19:15:53 UTC
HMDB IDHMDB0001364
Secondary Accession Numbers
  • HMDB01364
Metabolite Identification
Common NameAdenosine tetraphosphate
DescriptionAdenosine 5' tetraphosphate, Ap4, is a natural nucleotide present in many biological systems. This nucleotide has been found as a constituent of the nucleotide pool present in the aqueous humor of a number of mammals and appears to act as a regulator of intraocular pressure (PMID: 14600249 ). AP4 may also play a significant role in the physiological regulation of vascular tone (PMID: 8599250 ). The plasma concentration of AP4 is in the nanomolar range. Technically adenosine tetraphosphate is condensation product of adenosine with tetraphosphoric acid at the 5' position. Acetyl coenzyme A (CoA) synthetase (EC 6.2.1.1) catalyzes the synthesis of adenosine 5'-tetraphosphate (P4A) and adenosine 5'-pentaphosphate (p5A) from ATP and tri- or tetrapolyphosphate (P3 or P4).
Structure
Data?1547234153
Synonyms
ValueSource
Adenosine 5'-tetraphosphateChEBI
Adenosine 5'-tetraphosphoric acidGenerator
Adenosine tetraphosphoric acidGenerator
Ap4HMDB
ATPPHMDB
P4AHMDB
Chemical FormulaC10H17N5O16P4
Average Molecular Weight587.1609
Monoisotopic Molecular Weight586.962075569
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)(hydroxy)phosphoryl]oxy}phosphonic acid
Traditional Nameadenosine tetraphosphic acid
CAS Registry Number58337-43-2
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C10H17N5O16P4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(28-10)1-27-33(21,22)30-35(25,26)31-34(23,24)29-32(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H,25,26)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
InChI KeyWWMWAMFHUSTZTA-KQYNXXCUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-chain fatty acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Diterpenoid
  • Pentose phosphate
  • Ribonucleoside 3'-phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Monosaccharide
  • Fatty amide
  • N-substituted imidazole
  • N-acyl-amine
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Thiocarboxylic acid ester
  • Amino acid or derivatives
  • Carbothioic s-ester
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Alcohol
  • Amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.76 g/LALOGPS
logP-0.16ALOGPS
logP-7.2ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.59ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area325.66 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity106.69 m³·mol⁻¹ChemAxon
Polarizability42.12 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6s-4549340000-210817169cf3b8699238JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0095-5113911000-82bc4c92b9337df7306aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0911130000-19506c43ebd0f8ebe636JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-e1087671984c86d697c4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-7e71a7b8bff220f033ffJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-0602090000-68b493a20b226427e5a8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4912000000-72b850c30b2812dec13bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-7941000000-5f2cee78204735692a65JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Adrenal Medulla
  • Placenta
  • Spleen
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022579
KNApSAcK IDNot Available
Chemspider ID13390
KEGG Compound IDC03483
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAdenosine 5'-tetraphosphate
METLIN ID6191
PubChem Compound14003
PDB IDNot Available
ChEBI ID18334
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Luthje J, Baringer J, Ogilvie A: Effects of diadenosine triphosphate (Ap3A) and diadenosine tetraphosphate (Ap4A) on platelet aggregation in unfractionated human blood. Blut. 1985 Dec;51(6):405-13. [PubMed:3852686 ]
  2. Sillero MA, Del Valle M, Zaera E, Michelena P, Garcia AG, Sillero A: Diadenosine 5',5"-P1,P4-tetraphosphate (Ap4A), ATP and catecholamine content in bovine adrenal medulla, chromaffin granules and chromaffin cells. Biochimie. 1994;76(5):404-9. [PubMed:7849106 ]
  3. Liu Q, Dumont DJ: Molecular cloning and chromosomal localization in human and mouse of the SH2-containing inositol phosphatase, INPP5D (SHIP). Amgen EST Program. Genomics. 1997 Jan 1;39(1):109-12. [PubMed:9027494 ]
  4. Pintor J, Peral A, Hoyle CH, Redick C, Douglass J, Sims I, Yerxa B: Effects of diadenosine polyphosphates on tear secretion in New Zealand white rabbits. J Pharmacol Exp Ther. 2002 Jan;300(1):291-7. [PubMed:11752128 ]
  5. Pintor J, Carracedo G, Alonso MC, Bautista A, Peral A: Presence of diadenosine polyphosphates in human tears. Pflugers Arch. 2002 Jan;443(3):432-6. Epub 2001 Aug 23. [PubMed:11810214 ]
  6. Lazewska D, Starzynska E, Guranowski A: Human placental (Asymmetrical) diadenosine 5',5'''-P1,P4-tetraphosphate hydrolase: purification to homogeneity and some properties. Protein Expr Purif. 1993 Feb;4(1):45-51. [PubMed:8381042 ]
  7. Pintor J, Pelaez T, Peral A: Adenosine tetraphosphate, Ap4, a physiological regulator of intraocular pressure in normotensive rabbit eyes. J Pharmacol Exp Ther. 2004 Feb;308(2):468-73. Epub 2003 Nov 4. [PubMed:14600249 ]
  8. Lee JW, Kong ID, Park KS, Jeong SW: Effects of adenosine tetraphosphate (ATPP) on vascular tone in the isolated rat aorta. Yonsei Med J. 1995 Dec;36(6):487-96. [PubMed:8599250 ]

Enzymes

General function:
Involved in acetate-CoA ligase activity
Specific function:
Important for maintaining normal body temperature during fasting and for energy homeostasis. Essential for energy expenditure under ketogenic conditions (By similarity). Converts acetate to acetyl-CoA so that it can be used for oxidation through the tricarboxylic cycle to produce ATP and CO(2).
Gene Name:
ACSS1
Uniprot ID:
Q9NUB1
Molecular weight:
74625.88
General function:
Involved in hydrolase activity
Specific function:
Cleaves a beta-phosphate from the diphosphate groups in PP-InsP5 (diphosphoinositol pentakisphosphate), suggesting that it may play a role in signal transduction. Also able to catalyze the hydrolysis of dinucleoside oligophosphates, with Ap6A and Ap5A being the preferred substrates. The major reaction products are ADP and p4a from Ap6A and ADP and ATP from Ap5A. Also able to hydrolyze 5-phosphoribose 1-diphosphate.
Gene Name:
NUDT10
Uniprot ID:
Q8NFP7
Molecular weight:
18499.765
Reactions
P(1),P(5)-bis(5'-adenosyl)pentaphosphate + Water → Adenosine tetraphosphate + Adenosine monophosphatedetails
General function:
Involved in hydrolase activity
Specific function:
Cleaves a beta-phosphate from the diphosphate groups in PP-InsP5 (diphosphoinositol pentakisphosphate), suggesting that it may play a role in signal transduction. Also able to catalyze the hydrolysis of dinucleoside oligophosphates, with Ap6A and Ap5A being the preferred substrates. The major reaction products are ADP and p4a from Ap6A and ADP and ATP from Ap5A. Also able to hydrolyze 5-phosphoribose 1-diphosphate.
Gene Name:
NUDT11
Uniprot ID:
Q96G61
Molecular weight:
18558.835
Reactions
P(1),P(5)-bis(5'-adenosyl)pentaphosphate + Water → Adenosine tetraphosphate + Adenosine monophosphatedetails