Showing metabocard for SAICAR (BMDB0000797)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:36:44 UTC
Update Date2020-05-21 16:28:53 UTC
BMDB IDBMDB0000797
Secondary Accession Numbers
  • BMDB00797
Metabolite Identification
Common NameSAICAR
DescriptionSAICAR, also known as saicaribotide or succino-aicar, belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. SAICAR is a strong basic compound (based on its pKa). SAICAR exists in all eukaryotes, ranging from yeast to humans. SAICAR is a potentially toxic compound. SAICAR, with regard to humans, has been linked to several inborn metabolic disorders including fumarase deficiency and atic deficiency.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinic acidChEBI
(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinateChEBI
1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazoleChEBI
1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazoleChEBI
5'-Phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazoleChEBI
Succino-aicarChEBI
Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphateChEBI
Succinylaminoimidazolecarboxamide ribose-5'-phosphateChEBI
(2S)-2-[5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamido]succinateGenerator
(2S)-2-[5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamido]succinic acidGenerator
(2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinateGenerator
(2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinateGenerator
(2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinic acidGenerator
(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinic acidGenerator
Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphoric acidGenerator
Succinylaminoimidazolecarboxamide ribose-5'-phosphoric acidGenerator
(S)-2-(5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinateHMDB
(S)-2-(5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinic acidHMDB
(S)-2-(5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinateHMDB
(S)-2-(5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinic acidHMDB
(S)-2-[5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido]succinateHMDB
1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole' 1-(5'-phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazoleHMDB
5'-Phosphoribosyl-4-(N-succinocarbozamide)-5-aminoimidazoleHMDB
5-Amino-4-imidazole-N-succinocarboxamide ribonucleotideHMDB
L-N-[(5-Amino-1-b-D-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)HMDB
L-N-[(5-Amino-1-beta-delta-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)HMDB
N-(5-Amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-phosphateHMDB
N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartateHMDB
N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartic acidHMDB
PhosphoribosylaminoimidazolesuccinocarboxamideHMDB
N-(5-Amino-1-beta-D-ribofuranosylimidazole-4-carbonyl)-L-aspartic acid 5'-phosphateHMDB
5'-Phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazoleHMDB
SAICAR, (D)-isomerHMDB
SAICAribotideHMDB
Succinylaminoimidazole carboxamide ribotideHMDB
SAICA ribotideHMDB
Succinylaminoimidazolecarboxamide ribose-5’-phosphateHMDB
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 Namesaicar
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
Description belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassImidazole ribonucleosides and ribonucleotides
Sub Class1-ribosyl-imidazolecarboxamides
Direct Parent1-ribosyl-imidazolecarboxamides
Alternative Parents
Substituents
  • 1-ribosyl-imidazolecarboxamide
  • Pentose-5-phosphate
  • Pentose phosphate
  • Aspartic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Alpha-amino acid or derivatives
  • Pentose monosaccharide
  • 2-heteroaryl carboxamide
  • Imidazolyl carboxylic acid derivative
  • Imidazole-4-carbonyl group
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Dicarboxylic acid or derivatives
  • Phosphoric acid ester
  • Aminoimidazole
  • Monosaccharide
  • Imidazole
  • Heteroaromatic compound
  • Azole
  • Vinylogous amide
  • Tetrahydrofuran
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • 1,2-diol
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity90.65 m³·mol⁻¹ChemAxon
Polarizability38.5 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Fibroblasts
  • Intestine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000797
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022251
KNApSAcK IDNot Available
Chemspider ID141175
KEGG Compound IDC04823
BioCyc IDP-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE
BiGG ID44624
Wikipedia LinkPhosphoribosylaminoimidazolesuccinocarboxamide
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 ReferencesNot Available

Enzymes

Enzyme Details
1. Adenylosuccinate lyase
General function:
Nucleotide transport and metabolism
Specific function:
Catalyzes two non-sequential steps in de novo AMP synthesis: converts (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate (SAICAR) to fumarate plus 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide, and thereby also contributes to de novo IMP synthesis, and converts succinyladenosine monophosphate (SAMP) to AMP and fumarate.
Gene Name:
ADSL
Uniprot ID:
A3KN12
Molecular weight:
55484.0
Reactions
SAICAR → Fumaric acid + AICARdetails
Enzyme Details
2. Phosphoribosylaminoimidazole carboxylase, phosphoribosylaminoimidazole succinocarboxamide synthetase
General function:
Not Available
Specific function:
Not Available
Gene Name:
PAICS
Uniprot ID:
Q2HJ26
Molecular weight:
47122.0
Reactions
Adenosine triphosphate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid → ADP + Hydrogen phosphate + SAICARdetails