19046-78-7, 腺苷酸基琥珀酸,
Adenylsuccinic acid,
CAS:19046-78-7
C14H18N5O11P / 463.29
Adenylsuccinic acid, also known as adenylosuccinate or aspartyl adenylate, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Adenylsuccinic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, adenylsuccinic acid is primarily located in the cytoplasm and mitochondria. Adenylsuccinic acid exists in all eukaryotes, ranging from yeast to humans. Adenylsuccinic acid participates in a number of enzymatic reactions. In particular, Adenylsuccinic acid can be biosynthesized from inosinic acid and L-aspartic acid; which is catalyzed by the enzyme adenylosuccinate synthetase isozyme 2. In addition, Adenylsuccinic acid can be converted into fumaric acid and adenosine monophosphate through the action of the enzyme adenylosuccinate lyase. In humans, adenylsuccinic acid is involved in the aspartate metabolism pathway, the mercaptopurine action pathway, the azathioprine action pathway, and the purine metabolism pathway. Adenylsuccinic acid is also involved in several metabolic disorders, some of which include adenylosuccinate lyase deficiency, the hypoacetylaspartia pathway, the gout or kelley-seegmiller syndrome pathway, and myoadenylate deaminase deficiency.
N(6)-(1,2-dicarboxyethyl)-AMP is the N(6)-(1,2-dicarboxyethyl) derivative of adenosine 5'-monophosphate. It has a role as a fundamental metabolite. It derives from a succinic acid and an adenosine 5'-monophosphate. It is a conjugate acid of a N(6)-(1,2-dicarboxylatoethyl)-AMP(4-).
Adenylosuccinic acid is an organic acid that is synthesized through the deamination of adenosine monophosphate. It is used in transfection experiments to inhibit polymerase chain reaction (PCR) and reverse transcriptase. Adenylosuccinic acid inhibits DNA synthesis by targeting enzymes such as the ribonucleotide reductase and the DNA polymerase β-subunit. Adenylosuccinic acid also inhibits protein synthesis, which may be due to its ability to inhibit energy metabolism, leading to cellular death. This drug has been shown to have a wide range of pharmacological effects, including anti-inflammatory, analgesic, and antifungal activity.
CAS Number | 19046-78-7 |
Product Name | Adenylosuccinic acid |
IUPAC Name | (2S)-2-[[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]purin-6-yl]amino]butanedioic acid |
Molecular Formula | C14H18N5O11P |
Molecular Weight | 463.29 g/mol |
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+/m0/s1 |
InChI Key | OFBHPPMPBOJXRT-VWJPMABRSA-N |
SMILES | C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)O)O)O)NC(CC(=O)O)C(=O)O |
Solubility | Soluble in DMSO |
Synonyms | adenylosuccinate, adenylosuccinic acid |
Canonical SMILES | C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)O)O)O)NC(CC(=O)O)C(=O)O |
Isomeric SMILES | C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N[C@@H](CC(=O)O)C(=O)O |
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