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 Number	19046-78-7^N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:15919^Y
ChemSpider	389122^Y
MeSH	Adenylosuccinate
PubChem	447145
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
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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
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

Anabolism

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

IMP→AMP:	Adenylosuccinate

IMP→GMP:	Xanthosine monophosphate

Catabolism

Anabolism

Catabolism

uracil:	Dihydrouracil 3-Ureidopropionic acid β-Alanine

thymine:	Dihydrothymine β-Ureidoisobutyric acid 3-Aminoisobutyric acid

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