2.0 2012-08-09 09:16:14 -0600 2015-06-03 17:21:29 -0600 ECMDB21433 M2MDB001828 Adenosine tetraphosphate Adenosine 5' tetraphosphate, Ap4, is a natural nucleotide present in many biological systems. 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). [PMID:9620965] Adenosine 5'-tetraphosphate Adenosine 5'-tetraphosphoric acid Adenosine tetraphosphoric acid Ap4 ATPP P4A C10H17N5O16P4 587.1609 586.962075569 {[({[({[(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 adenosine tetraphosphic acid 58337-43-2 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=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 WWMWAMFHUSTZTA-KQYNXXCUSA-N Solid Cytoplasm logp -0.16 ALOGPS logs -2.09 ALOGPS solubility 4.76e+00 g/l ALOGPS logp -7.2 ChemAxon pka_strongest_acidic 0.59 ChemAxon pka_strongest_basic 5 ChemAxon iupac {[({[({[(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 ChemAxon average_mass 587.1609 ChemAxon mono_mass 586.962075569 ChemAxon 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 ChemAxon formula C10H17N5O16P4 ChemAxon 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 ChemAxon inchikey WWMWAMFHUSTZTA-KQYNXXCUSA-N ChemAxon polar_surface_area 325.66 ChemAxon refractivity 106.69 ChemAxon polarizability 42.12 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 16 ChemAxon donor_count 8 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon D-Glutamine and D-glutamate metabolism L-glutamine is transported into the cytoplasm through a glutamine ABC transporter. Once inside, L-glutamine is metabolized with glutaminase to produce an L-glutamic acid. This process can be reversed through a glutamine synthetase resulting in L-glutamine. L-glutamic acid can also be transported into the cytoplasm through various methods: a glutamate/aspartate:H+ symporter GltP, a glutamate: sodium symporter or a glutamate/aspartate ABC transporter. L-glutamic acid can proceed to L-glutamate metabolism or it can undergo a reversible reaction through a glutamate racemase resulting in D-glutamic acid. This compound can also be obtained from D-glutamine interacting with a glutaminase. D-glutamic acid reacts with UDP-N-acetylmuramoyl-L-alanine through an ATP driven UDP-N-acetylmuramoylalanine-D-glutamate ligase resulting in a UDP-N-acetylmuramoyl-L-alanyl-D-glutamate which is then integrated into the peptidoglycan biosynthesis UDP-N-acetylmuramoyl-L-alanine comes from the amino sugar and nucleotide sugar metabolism product, UDP-N-acetylmuraminate which reacts with L-alanine through an ATP-driven UDP-N-acetylmuramate-L-alanine ligase. PW000769 ec00471 Metabolic Specdb::CMs 17812 Specdb::CMs 38039 Specdb::CMs 282799 Specdb::CMs 411213 Specdb::CMs 411214 Specdb::CMs 411215 Specdb::CMs 411216 Specdb::CMs 411217 Specdb::CMs 411218 Specdb::CMs 411219 Specdb::CMs 411220 Specdb::CMs 411221 Specdb::CMs 411222 Specdb::CMs 411223 Specdb::CMs 411224 Specdb::CMs 411225 Specdb::CMs 411226 Specdb::CMs 411227 Specdb::CMs 411228 Specdb::CMs 411229 Specdb::CMs 411230 Specdb::CMs 411231 Specdb::CMs 411232 Specdb::CMs 411233 Specdb::CMs 411234 Specdb::NmrOneD 87812 Specdb::NmrOneD 87813 Specdb::NmrOneD 87814 Specdb::NmrOneD 87815 Specdb::NmrOneD 87816 Specdb::NmrOneD 87817 Specdb::NmrOneD 87818 Specdb::NmrOneD 87819 Specdb::NmrOneD 87820 Specdb::NmrOneD 87821 Specdb::NmrOneD 87822 Specdb::NmrOneD 87823 Specdb::NmrOneD 87824 Specdb::NmrOneD 87825 Specdb::NmrOneD 87826 Specdb::NmrOneD 87827 Specdb::NmrOneD 87828 Specdb::NmrOneD 87829 Specdb::NmrOneD 87830 Specdb::NmrOneD 87831 Specdb::MsMs 29084 Specdb::MsMs 29085 Specdb::MsMs 29086 Specdb::MsMs 35642 Specdb::MsMs 35643 Specdb::MsMs 35644 Specdb::MsMs 2472180 Specdb::MsMs 2472181 Specdb::MsMs 2472182 Specdb::MsMs 2489673 Specdb::MsMs 2489674 Specdb::MsMs 2489675 HMDB01364 14003 13390 C03483 18334 AQP van der Werf, M. 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Biochimie. 1994;76(5):404-9. 7849106 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. 9027494 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. 11752128 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. 8381042 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. 14600249 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. 8599250 Acetyl-coenzyme A synthetase P27550 ACSA_ECOLI acs http://ecmdb.ca/proteins/P27550.xml