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Identification |
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YMDB ID | YMDB00350 |
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Name | SAICAR |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | SAICAR, 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. |
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Structure | |
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Synonyms | - (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate
- (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinic acid
- (S)-2-(5-amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinate
- (S)-2-(5-amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinic acid
- (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate
- (S)-2-[5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido]succinate
- 1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole
- 1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole
- 1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole' 1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole
- 5-Amino-4-imidazole-N-succinocarboxamide ribonucleotide
- 5'-Phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole
- 5'-Phosphoribosyl-4-(N-succinocarbozamide)-5-aminoimidazole
- L-N-[(5-amino-1-b-D-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)
- L-N-[(5-amino-1-beta-delta-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)
- N-(5-Amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-phosphate
- N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartate
- N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartic acid
- Phosphoribosylaminoimidazolesuccinocarboxamide
- SAICAR
- SAICAriboside
- Succino-AICAR
- Succinylaminoimidazole carboxamide riboside
- (2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinic acid
- Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphate
- Succinylaminoimidazolecarboxamide ribose-5'-phosphate
- (2S)-2-[5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamido]succinate
- (2S)-2-[5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamido]succinic acid
- (2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinate
- (2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinate
- (2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinic acid
- (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinic acid
- Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphoric acid
- Succinylaminoimidazolecarboxamide ribose-5'-phosphoric acid
- N-(5-Amino-1-beta-D-ribofuranosylimidazole-4-carbonyl)-L-aspartic acid 5'-phosphate
- 5'-Phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazole
- SAICAR, (D)-isomer
- SAICAribotide
- Succinylaminoimidazole carboxamide ribotide
- SAICA ribotide
- Succinylaminoimidazolecarboxamide ribose-5’-phosphate
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CAS number | 3031-95-6 |
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Weight | Average: 454.2833 Monoisotopic: 454.073708604 |
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InChI Key | NAQGHJTUZRHGAC-ZZZDFHIKSA-N |
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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 |
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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 |
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Traditional IUPAC Name | saicar |
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Chemical Formula | C13H19N4O12P |
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SMILES | [H]OC(=O)C([H])([H])[C@]([H])(N([H])C(=O)C1=C(N([H])[H])N(C([H])=N1)[C@]1([H])O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]([H])(O[H])[C@@]1([H])O[H])C(=O)O[H] |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Imidazole ribonucleosides and ribonucleotides |
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Sub Class | 1-ribosyl-imidazolecarboxamides |
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Direct Parent | 1-ribosyl-imidazolecarboxamides |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | Not Available |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | Not Available | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | purine nucleotides de novo biosynthesis | PW002478 |    |
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KEGG Pathways | |
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SMPDB Reactions | |
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KEGG Reactions | |
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Concentrations |
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Intracellular Concentrations | Not Available |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-05n1-9732500000-f3a7f13b1dee5f81c7a8 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-05ot-9600116000-74a62efcb34072bbe352 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-055o-1592600000-05db249dfb0f14143f9f | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-3950000000-6ebf6a64483dd1392782 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001l-5940000000-e218e278f5195eb90341 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0ug3-6381900000-4fec69ff813fe652ea7d | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004j-9350000000-e4e387627fbca1ef1201 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9100000000-95f6153e96335a5d2b32 | JSpectraViewer |
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References |
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References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
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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 a |
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External Links: | |
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