Record Information |
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Version |
1.0 |
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Update Date |
1/22/2018 11:54:54 AM |
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Metabolite ID | PAMDB110100 |
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Identification |
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Name: |
5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole |
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Description: | An organophosphate oxoanion that is the tetraanionic form of SAICAR. It is the major species at pH 7.3. |
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Structure |
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Synonyms: | -
(S)-2-[5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate
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1-(5-phosphoribosyl)-4-(N-succino-carboxamide)-5-aminoimidazole
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5'-P-ribosyl-4-(N-succinocarboxamide)-5-aminoimidazole
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5'-p-Ribosyl-4-(N-succinocarboxamide)-5-amino imidazole
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1-(5'-phosphoribosyl)-4-(N-succino-carboxamide)-5-aminoimidazole
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SAICAR
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Chemical Formula: |
C13H15N4O12P
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Average Molecular Weight: |
450.26 |
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Monoisotopic Molecular
Weight: |
454.0737086059 |
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InChI Key: |
NAQGHJTUZRHGAC-LBGUGVGYSA-J |
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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)/p-4/t4?,5-,8-,9-,12-/m1/s1 |
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CAS
number: |
3031-95-6 |
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IUPAC Name: | (2S)-2-[5-amino-1-(5-O-phosphonato-β-D-ribosyl)imidazole-4-carboxamido]succinate |
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Traditional IUPAC Name: |
saicar |
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SMILES: | C(OP([O-])([O-])=O)C2(C(O)C(O)C(N1(C(N)=C(C(=O)NC(C([O-])=O)CC([O-])=O)N=C1))O2) |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of chemical entities 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 |
Chemical entities |
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Super Class | Organic compounds |
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Class |
Nucleosides, nucleotides, and analogues |
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Sub Class | Imidazole ribonucleosides and ribonucleotides |
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Direct Parent |
1-ribosyl-imidazolecarboxamides |
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Alternative Parents |
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Substituents |
- 1-ribosyl-imidazolecarboxamide
- Pentose phosphate
- Pentose-5-phosphate
- Aspartic acid or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Glycosyl compound
- N-glycosyl compound
- Alpha-amino acid or derivatives
- Monosaccharide phosphate
- Pentose monosaccharide
- 2-heteroaryl carboxamide
- Imidazolyl carboxylic acid derivative
- Imidazole-4-carbonyl group
- Monoalkyl phosphate
- Alkyl phosphate
- Organic phosphoric acid derivative
- Primary aromatic amine
- Dicarboxylic acid or derivatives
- Phosphoric acid ester
- N-substituted imidazole
- Aminoimidazole
- Monosaccharide
- Imidazole
- Heteroaromatic compound
- Azole
- Vinylogous amide
- Oxolane
- Amino acid or derivatives
- Carboxamide group
- Amino acid
- Secondary carboxylic acid amide
- Secondary alcohol
- 1,2-diol
- 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: | -4 |
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Melting point: |
Not Available |
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Experimental Properties: |
Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties |
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Biological Properties |
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Cellular Locations: |
Not Available |
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Reactions: | |
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Pathways: |
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Spectra |
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Spectra: |
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References |
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References: |
- Keller KE, Tan IS, Lee YS (2012)SAICAR stimulates pyruvate kinase isoform M2 and promotes cancer cell survival in glucose-limited conditions. Science (New York, N.Y.) 338, Pubmed: 23086999
- Keller KE, Doctor ZM, Dwyer ZW, Lee YS (2014)SAICAR induces protein kinase activity of PKM2 that is necessary for sustained proliferative signaling of cancer cells. Molecular cell 53, Pubmed: 24606918
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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 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. |
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Material Safety Data Sheet (MSDS) |
Not Available |
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Links |
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External Links: |
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