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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:21 UTC
HMDB IDHMDB00797
Secondary Accession Numbers
  • HMDB06274
Metabolite Identification
Common NameSAICAR
DescriptionSAICAR (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
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 FormulaC13H19N4O12P
Average Molecular Weight454.2833
Monoisotopic Molecular Weight454.073708604
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 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 Number3031-95-6
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 KeyNAQGHJTUZRHGAC-ZZZDFHIKSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassGlycoamino 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 ParentGlycoamino Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.73ALOGPS
logP-1.8ALOGPS
logP-4.8ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)4.54ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area263.99 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity90.65 m3·mol-1ChemAxon
Polarizability38.5 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050map00230
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified921.0 (0.0-1842.0) uMAdult (>18 years old)Not SpecifiedAdenylosuccinate lyase (ASDL) deficiency details
UrineDetected and Quantified214 umol/mmol creatinineAdult (>18 years old)BothAdenylosuccinate lyase (ASDL) deficiency details
Associated Disorders and Diseases
Disease References
Adenylosuccinate lyase deficiency
  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
  2. 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
Associated OMIM IDs
  • 103050 (Adenylosuccinate lyase deficiency)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022251
KNApSAcK IDNot Available
Chemspider ID141175
KEGG Compound IDC04823
BioCyc IDP-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE
BiGG ID44624
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00797
Metagene LinkHMDB00797
METLIN ID5762
PubChem Compound160666
PDB IDNot Available
ChEBI ID18319
References
Synthesis ReferenceShaw, 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. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ADSL
Uniprot ID:
P30566
Molecular weight:
54888.735
Reactions
SAICAR → Fumaric acid + AICARdetails
SAICAR → Fumaric acid + AICARdetails
General function:
Involved in phosphoribosylaminoimidazole carboxylase activity
Specific function:
Not Available
Gene Name:
PAICS
Uniprot ID:
P22234
Molecular weight:
47078.82
Reactions
Adenosine triphosphate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid → ADP + Phosphoric acid + SAICARdetails
Adenosine triphosphate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid → ADP + Phosphoric acid + SAICARdetails