A purine nucleotide
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Alternative(s)
29696Adenylosuccinic Acid
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Adenylosuccinic Acid (ammonium salt)

Item No. 34334

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[9-(5-O-phosphono-β-D-ribofuranosyl)-9H-purin-6-yl]-L-aspartic acid, tetraammonium salt
Synonyms
  • Aspartyl Adenylate
  • Succinyl AMP
  • Succinyladenosine monophosphoric Acid
Molecular Formula
C14H14N5O11P • 4NH4
Formula Weight
531.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
λmax
214, 268 nm
SMILES
[O-]P(OC[C@H]([C@@H](O)[C@H]1O)O[C@@]1([H])N2C=NC3=C(N[C@@H](CC([O-])=O)C([O-])=O)N=CN=C32)([O-])=O.[NH4+].[NH4+].[NH4+].[NH4+]
InChi Code
InChI=1S/C14H18N5O11P.4H3N/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);4*1H3/t5-,6+,9+,10+,13+;;;;/m0..../s1
InChi Key
XCLZBEXZAOLWGA-BFHDGDRYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

    $76

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    10 mg

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    25 mg

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    50 mg

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Adenylosuccinic acid is a purine nucleotide and an intermediate in the purine nucleotide cycle.1 It is converted into AMP (Item No. 21094) and fumarate by adenylosuccinate lyase (ADSL) in the cytosol. Adenylosuccinic acid (10 µM) inhibits calcium-induced activation of non-selective cation channels in isolated rat brown adipocytes in a patch-clamp assay.2 It induces contractions in isolated guinea pig uterus strips, which express adenosine receptors, when used at a concentration of 100 µM.3 Adenylosuccinic acid (10 µM) increases glucose-induced insulin exocytosis in INS-1 832/13 insulinoma cells.4 In vivo, adenylosuccinic acid (3,000 µg/ml in the drinking water) decreases muscle damage and pseudohypertrophy in a dystrophin-deficient mdx mouse model of Duchenne muscular dystrophy (DMD).5 Urine levels of adenylosuccinic acid are increased in patients with ADSL deficiency, an inborn error of metabolism characterized by various neurological symptoms, including intellectual disability and seizures, as well as respiratory failure.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Waarde, A. Operation of the purine nucleotide cycle in animal tissues. Biol. Rev. Camb. Philos. Soc. 63(2), 259-298 (1988).

    2. Halonen, J., and Nedergaard, J. Adenosine 5'-monophosphate is a selective inhibitor of the brown adipocyte nonselective cation channel. J. Membr. Biol. 188(1), 183-197 (2002).

    3. Nishida, Y., and Miyamoto, T. Contractile effect of succinylpurines on guinea pig uterus. Gen. Pharmacol. 19(2), 277-279 (1988).

    4. Gooding, J.R., Jensen, M.W., Dai, X., et al. Adenylosuccinate is an insulin secretagogue derived from glucose-induced purine metabolism. Cell Rep. 13(1), 157-167 (2015).

    5. Timpani, C.A., Goodman, C.A., Stathis, C.G., et al. Adenylosuccinic acid therapy ameliorates murine Duchenne Muscular Dystrophy. Sci. Rep. 10(1), 1125 (2020).

    6. Jin, X., Dimitriadis, E.K., Liu, Y., et al. Macrophages shed excess cholesterol in unique extracellular structures containing cholesterol microdomains. Arterioscler. Thromb. Vasc. Biol. 38(7), 1504-1518 (2018).