Adenosine 5'-tetraphosphate

Adenosine 5'-tetraphosphate
Names
	IUPAC name Adenosine 5′-(pentahydrogen tetraphosphate)
	Preferred IUPAC name O1-{[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl} pentahydrogen tetraphosphate
	Other names Adenosine tetraphosphate
Identifiers
CAS Number	1062-98-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18334;
ChEMBL	ChEMBL490984;
ChemSpider	13390;
KEGG	C03483;
PubChem CID	14003;
UNII	DBK98M4ZT7 ;
CompTox Dashboard (EPA)	DTXSID901261206 ;
	InChI 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 Key: WWMWAMFHUSTZTA-KQYNXXCUSA-N;
	SMILES Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O;
Properties
Chemical formula	C10H17N5O16P4
Molar mass	587.160 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Adenosine 5′-tetraphosphate, Ap4 or ATPP is a nucleotide. It is produced from ATP and triphosphate (P₃) through the action of acetyl—CoA synthetase.^[1] Acetyl—CoA synthetase also produces adenosine 5'-pentaphosphate through the reaction of ADP and tetraphosphate (P₄).

Functions

ATPP has been found to play physiological roles in some mammals.

Rabbits

ATPP is a constituent of aqueous humor in rabbits, where it was found to reduce the intraocular pressure.^[2]

Rats

ATPP has been suggested to play a regulatory role in rat aorta.

References

^ Guranowski, A.; Günther Sillero, M.A.; Sillero, A. (1994). "Adenosine 5′-tetraphosphate and adenosine 5′-pentaphosphate are synthesized by yeast acetyl coenzyme A synthetase". J Bacteriol. 176 (10): 2986–90. doi:10.1128/jb.176.10.2986-2990.1994. PMC 205455. PMID 7910605.
^ Pintor, Jesús; Peláez, Teresa; Peral, Assumpta (February 2004). "Adenosine tetraphosphate, Ap4, a physiological regulator of intraocular pressure in normotensive rabbit eyes". The Journal of Pharmacology and Experimental Therapeutics. 308 (2): 468–473. doi:10.1124/jpet.103.058669. ISSN 0022-3565. PMID 14600249. S2CID 27129583.

[1] Guranowski, A.; Günther Sillero, M.A.; Sillero, A. (1994). "Adenosine 5′-tetraphosphate and adenosine 5′-pentaphosphate are synthesized by yeast acetyl coenzyme A synthetase". J Bacteriol. 176 (10): 2986–90. doi:10.1128/jb.176.10.2986-2990.1994. PMC 205455. PMID 7910605.

[2] Pintor, Jesús; Peláez, Teresa; Peral, Assumpta (February 2004). "Adenosine tetraphosphate, Ap4, a physiological regulator of intraocular pressure in normotensive rabbit eyes". The Journal of Pharmacology and Experimental Therapeutics. 308 (2): 468–473. doi:10.1124/jpet.103.058669. ISSN 0022-3565. PMID 14600249. S2CID 27129583.

[1]

Names

IUPAC name Adenosine 5′-(pentahydrogen tetraphosphate)
Preferred IUPAC name O¹-{[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl} pentahydrogen tetraphosphate
Other names Adenosine tetraphosphate
Identifiers
CAS Number	1062-98-2^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18334
ChEMBL	ChEMBL490984
ChemSpider	13390
KEGG	C03483
PubChem CID	14003
UNII	DBK98M4ZT7^Y
CompTox Dashboard (EPA)	DTXSID901261206
InChI 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 Key: WWMWAMFHUSTZTA-KQYNXXCUSA-N
SMILES Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O
Properties
Chemical formula	C₁₀H₁₇N₅O₁₆P₄
Molar mass	587.160 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references