Adenylosuccinate

Adenylosuccinate
Names

IUPAC name (2S)-2-[[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid
Identifiers
CAS Registry Number	19046-78-7^Y
ChEBI	CHEBI:15919^Y
ChemSpider	389122^Y
InChI InChI=1S/C14H18N5O11P/c20-7(21)1-5(14(24)25)18-11-8-12(16-3-15-11)19(4-17-8)13-10(23)9(22)6(30-13)2-29-31(26,27)28/h3-6,9-10,13,22-23H,1-2H2,(H,20,21)(H,24,25)(H,15,16,18)(H2,26,27,28)/t5?,6-,9-,10-,13-/m1/s1^Y Key: OFBHPPMPBOJXRT-DPXQIYNJSA-N^Y InChI=1/C14H18N5O11P/c20-7(21)1-5(14(24)25)18-11-8-12(16-3-15-11)19(4-17-8)13-10(23)9(22)6(30-13)2-29-31(26,27)28/h3-6,9-10,13,22-23H,1-2H2,(H,20,21)(H,24,25)(H,15,16,18)(H2,26,27,28)/t5?,6-,9-,10-,13-/m1/s1 Key: OFBHPPMPBOJXRT-DPXQIYNJBG
Jmol-3D images	Image
MeSH	Adenylosuccinate
PubChem	447145
SMILES C1=NC2=C(C(=N1)N[C@@H](CC(=O)O)C(=O)O)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O
Properties
Chemical formula	C₁₄H₁₈N₅O₁₁P
Molar mass	463.294 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
Infobox references

Adenylosuccinate is an intermediate in the interconversion of purine nucleotides inosine monophosphate (IMP) and adenosine monophosphate (AMP). The enzyme adenylosuccinate synthase carries out the reaction by the addition of aspartate to IMP and requires the input of energy from a phosphoanhydride bond in the form of guanosine triphosphate (GTP).^[1] GTP is used instead of adenosine triphosphate (ATP), so the reaction is not dependent on its products.

References

↑ Figures 20.4 and 20.7 in Textbook of Biochemistry, with clinical correlations, Sixth Edition, Thomas M. Devlin, Ed., Wiley-Liss, Inc., New York, NY, 2006

Nucleotide metabolic intermediates

Purine metabolism

Anabolism

R5P→IMP:	R5P PRPP PRA GAR FGAR FGAM AIR CAIR SAICAR AICAR FAICAR

IMP→AMP:	Adenylosuccinate

IMP→GMP:	Xanthosine monophosphate

Catabolism

Pyrimidine metabolism

Anabolism

Catabolism

uracil:	Dihydrouracil 3-Ureidopropionic acid β-Alanine

thymine:	Dihydrothymine β-Ureidoisobutyric acid 3-Aminoisobutyric acid

Index of inborn errors of metabolism

Description	Metabolism Enzymes and pathways: citric acid cycle enzymes pentose phosphate intermediates glycoproteins enzymes glycosaminoglycans proteoglycan enzymes phospholipid metabolism cholesterol and steroid intermediates sphingolipids enzymes eicosanoids enzymes amino acid intermediates urea cycle enzymes nucleotide intermediates

Disorders	Citric acid cycle and electron transport chain Glycoprotein Proteoglycan Fatty-acid Phospholipid Cholesterol and steroid Eicosanoid Amino acid Purine-pyrimidine Heme metabolism Symptoms and signs

Treatment	Drugs other

Index of biochemical families

Carbohydrates	Alcohols Glycoproteins Glycosides

Lipids	Eicosanoids Fatty acids intermediates Glycerides Phospholipids Sphingolipids Steroids

Nucleic acids	Constituents intermediates

Proteins	Amino acids intermediates

Other	Tetrapyrroles intermediates

Adenylosuccinate

See also

References