<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4335</id>
  <title>T3D4281</title>
  <common-name>SAICAR</common-name>
  <description>SAICAR (or (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate) is a substrate for the multifunctional protein ADE2. SAICAR is an intermediate in purine metabolism. (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate is converted from 5-Amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate via phosphoribosylaminoimidazole-succinocarboxamide synthase [EC: 6.3.2.6] or SAICAR synthase. This enzyme catalyses the seventh step out of ten in the biosynthesis of purine nucleotides. The appearance of succinylaminoimidazolecarboxamide riboside (SAICAriboside) and succinyladenosine (S-Ado) in cerebrospinal fluid, urine, and to a lesser extent in plasma is characteristic of a heritable deficiency Adenylosuccinate lyase deficiency. .</description>
  <cas>3031-95-6</cas>
  <pubchem-id>160666</pubchem-id>
  <chemical-formula>C13H19N4O12P</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity nil="true"/>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Chronically high levels of SAICAR are associated with Adenylosuccinate Lyase Deficiency.</health-effects>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T06:13:39Z</created-at>
  <updated-at type="dateTime">2026-04-06T12:24:34Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C04823</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>18319</chebi-id>
  <biocyc-id>P-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(=O)N[C@@H](CC(O)=O)C(O)=O</moldb-smiles>
  <moldb-formula>C13H19N4O12P</moldb-formula>
  <moldb-inchi>InChI=1S/C13H19N4O12P/c14-10-7(11(22)16-4(13(23)24)1-6(18)19)15-3-17(10)12-9(21)8(20)5(29-12)2-28-30(25,26)27/h3-5,8-9,12,20-21H,1-2,14H2,(H,16,22)(H,18,19)(H,23,24)(H2,25,26,27)/t4-,5+,8+,9+,12+/m0/s1</moldb-inchi>
  <moldb-inchikey>NAQGHJTUZRHGAC-ZZZDFHIKSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">454.2833</moldb-average-mass>
  <moldb-mono-mass type="decimal">454.073708604</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB00797</hmdb-id>
  <chembl-id nil="true"/>
  <chemspider-id>141175</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>Shaw, Gordon; Thomas, Peter S.; Patey, Carole A. H.; Thomas, Susan E.  Purines, pyrimidines and imidazoles.  Part 50.  Inhibition of adenylosuccinate AMP-lyase no. 4.3.2.2. by derivatives of N-(5-amino-1-b-D-ribofuranosylimidazole-4-carbonyl)-L-aspartic acid 5'-phosphate (SAICAR) and virazole 5'-phosphate.    Journal of the Chemical Society, Perkin Transactions 1:  Organic and Bio-Organic Chemistry (1972-1999)  (1979),   (6),  1415-24. </synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003241</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00123667</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>263.98999999999995</moldb-polar-surface-area>
  <moldb-refractivity>90.65269999999998</moldb-refractivity>
  <moldb-polarizability>38.50191613972262</moldb-polarizability>
  <moldb-rotatable-bond-count>9</moldb-rotatable-bond-count>
  <moldb-acceptor-count>13</moldb-acceptor-count>
  <moldb-donor-count>8</moldb-donor-count>
  <moldb-pka-strongest-acidic>1.2173138245476895</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>4.543300932982183</moldb-pka-strongest-basic>
  <moldb-physiological-charge>-4</moldb-physiological-charge>
  <moldb-number-of-rings>2</moldb-number-of-rings>
  <moldb-alogps-logp>-1.82</moldb-alogps-logp>
  <moldb-alogps-logs>-2.42</moldb-alogps-logs>
  <moldb-alogps-solubility>1.73e+00 g/l</moldb-alogps-solubility>
</compound>
