Human Metabolome Database Version 3.5

Showing metabocard for SAICAR (HMDB00797)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:21 -0700
HMDB ID HMDB00797
Secondary Accession Numbers
  • HMDB06274
Metabolite Identification
Common Name SAICAR
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. (Wikipedia).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate
  2. (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinic acid
  3. (S)-2-(5-amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinate
  4. (S)-2-(5-amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinic acid
  5. (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate
  6. (S)-2-[5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido]succinate
  7. 1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole
  8. 1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole
  9. 1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole' 1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole
  10. 5'-Phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole
  11. 5'-Phosphoribosyl-4-(N-succinocarbozamide)-5-aminoimidazole
  12. 5-Amino-4-imidazole-N-succinocarboxamide ribonucleotide
  13. L-N-[(5-Amino-1-b-D-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)
  14. L-N-[(5-Amino-1-beta-delta-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)
  15. N-(5-Amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-phosphate
  16. N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartate
  17. N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartic acid
  18. Phosphoribosylaminoimidazolesuccinocarboxamide
  19. SAICAR
  20. SAICAriboside
  21. Succino-AICAR
  22. Succinylaminoimidazole carboxamide riboside
Chemical Formula C13H19N4O12P
Average Molecular Weight 454.2833
Monoisotopic Molecular Weight 454.073708604
IUPAC Name (2S)-2-({5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-4-yl}formamido)butanedioic acid
Traditional IUPAC Name (2S)-2-({5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazol-4-yl}formamido)butanedioic acid
CAS Registry Number 3031-95-6
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
InChI Identifier 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
InChI Key NAQGHJTUZRHGAC-ZZZDFHIKSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Glycoamino Acids and Derivatives
Other Descriptors
  • 1-Phosphoribosyl-imidazoles
  • Aromatic Heteropolycyclic Compounds
  • N-acyl-alpha Amino Acids and Derivatives
Substituents
  • 1,2 Diol
  • 1,3 Aminoalcohol
  • 1 Ribosyl Imidazolecarboxamide
  • Alpha Amino Acid Or Derivative
  • Aminoimidazole
  • Carboxamide Group
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Glycosyl Compound
  • Imidazole
  • Imidazolyl Carboxylic Acid Derivative
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • N Substituted Alpha Amino Acid
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Succinic Acid
Direct Parent Glycoamino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.73 g/L ALOGPS
LogP -1.82 ALOGPS
LogP -4.8 ChemAxon
LogS -2.42 ALOGPS
pKa (strongest acidic) 1.22 ChemAxon
pKa (strongest basic) 4.54 ChemAxon
Hydrogen Acceptor Count 13 ChemAxon
Hydrogen Donor Count 8 ChemAxon
Polar Surface Area 263.99 A2 ChemAxon
Rotatable Bond Count 9 ChemAxon
Refractivity 90.65 ChemAxon
Polarizability 38.5 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
Pathways
Name SMPDB Link KEGG Link
Purine Metabolism SMP00050 map00230 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 921.0 (0.0-1842.0) uM Adult (>18 years old) Not Specified Adenylosuccinate lyase (ASDL) deficiency
Urine Detected and Quantified 214 umol/mmol creatinine Adult (>18 years old) Both Adenylosuccinate lyase deficiency
Associated Disorders and Diseases
Disease References
Adenylosuccinate lyase deficiency
  • Marinaki AM, Champion M, Kurian MA, Simmonds HA, Marie S, Vincent MF, van den Berghe G, Duley JA, Fairbanks LD: Adenylosuccinate lyase deficiency--first British case. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1231-3. Pubmed: 15571235 Link_out
  • Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. Pubmed: 10102915 Link_out
      Associated OMIM IDs
      • 103050 Link_out (Adenylosuccinate lyase deficiency)
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB022251
      KNApSAcK ID Not Available
      Chemspider ID 141175 Link_out
      KEGG Compound ID C04823 Link_out
      BioCyc ID P-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE Link_out
      BiGG ID 44624 Link_out
      Wikipedia Link Not Available
      NuGOwiki Link HMDB00797 Link_out
      Metagene Link HMDB00797 Link_out
      METLIN ID 5762 Link_out
      PubChem Compound 160666 Link_out
      PDB ID Not Available
      ChEBI ID 18319 Link_out
      References
      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.
      Material Safety Data Sheet (MSDS) Not Available
      General References
      1. Marinaki AM, Champion M, Kurian MA, Simmonds HA, Marie S, Vincent MF, van den Berghe G, Duley JA, Fairbanks LD: Adenylosuccinate lyase deficiency--first British case. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1231-3. Pubmed: 15571235 Link_out
      2. Laikind PK, Seegmiller JE, Gruber HE: Detection of 5'-phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazole in urine by use of the Bratton-Marshall reaction: identification of patients deficient in adenylosuccinate lyase activity. Anal Biochem. 1986 Jul;156(1):81-90. Pubmed: 3740420 Link_out
      3. Race V, Marie S, Vincent MF, Van den Berghe G: Clinical, biochemical and molecular genetic correlations in adenylosuccinate lyase deficiency. Hum Mol Genet. 2000 Sep 1;9(14):2159-65. Pubmed: 10958654 Link_out
      4. Zikanova M, Krijt J, Hartmannova H, Kmoch S: Preparation of 5-amino-4-imidazole-N-succinocarboxamide ribotide, 5-amino-4-imidazole-N-succinocarboxamide riboside and succinyladenosine, compounds usable in diagnosis and research of adenylosuccinate lyase deficiency. J Inherit Metab Dis. 2005;28(4):493-9. Pubmed: 15902552 Link_out
      5. Kmoch S, Hartmannova H, Stiburkova B, Krijt J, Zikanova M, Sebesta I: Human adenylosuccinate lyase (ADSL), cloning and characterization of full-length cDNA and its isoform, gene structure and molecular basis for ADSL deficiency in six patients. Hum Mol Genet. 2000 Jun 12;9(10):1501-13. Pubmed: 10888601 Link_out
      6. Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. Pubmed: 10102915 Link_out

      Enzymes
      Name: Adenylosuccinate lyase
      Reactions:
      SAICAR unknown Fumaric acid + AICAR details
      SAICAR unknown Fumaric acid + AICAR details
      Gene Name: ADSL
      Uniprot ID: P30566 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Multifunctional protein ADE2
      Reactions:
      Adenosine triphosphate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid unknown ADP + Phosphoric acid + SAICAR details
      Adenosine triphosphate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid unknown ADP + Phosphoric acid + SAICAR details
      Gene Name: PAICS
      Uniprot ID: P22234 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA