SAICAR (BioDeep_00000005666)

 

Secondary id: BioDeep_00001868455

human metabolite Endogenous natural product


代谢物信息卡片


(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

化学式: C13H19N4O12P (454.07370640000005)
中文名称: 琥珀酸S-腺苷甲硫氨酸
谱图信息: 最多检出来源 Homo sapiens(urine) 0.1%

Reviewed

Last reviewed on 2024-08-20.

Cite this Page

SAICAR. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/saicar (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000005666). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C([C@@H](C(=O)O)NC(=O)c1c(N)n(cn1)[C@H]1[C@@H]([C@@H]([C@@H](COP(=O)(O)O)O1)O)O)C(=O)O
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

描述信息

SAICAR, also known as succinylaminoimidazolecarboxamide ribotide or phosphoribosylaminoimidazolesuccinocarboxamide, is a substrate for the multifunctional protein ADE2. SAICAR is an intermediate in purine metabolism. SAICAR is converted from 5-aminoimidazole-4-carboxyribonucleotide (CAIR) via phosphoribosylaminoimidazolesuccinocarboxamide synthetase (EC: 6.3.2.6) or SAICAR synthase. This enzyme catalyzes the eighth step in the biosynthesis of purine nucleotides. SAICAR (a ribotide) can lose its phosphate group leading to the appearance of a riboside known as succinylaminoimidazolecarboxamide riboside (SAICAriboside) in cerebrospinal fluid, in urine, and, to a lesser extent, in plasma. This particular riboside (called SAICAr) is characteristic of a heritable deficiency known as adenylosuccinate lyase deficiency (ADSL). On the other hand, the ribotide (SAICAR) is generally harmless and is an essential intermediate in purine metabolism. When present in sufficiently high levels, SAICAR can act as an oncometabolite. An oncometabolite is a compound that promotes tumour growth and survival. As an oncometabolite, high levels of SAICAR stimulate pyruvate kinase isoform M2 and promote cancer cell survival in glucose-limited conditions such as aerobic glycolysis (PMID: 23086999).
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. [HMDB]. SAICAR is found in many foods, some of which are sweet potato, black chokeberry, common wheat, and globe artichoke.

SAICAR. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=3031-95-6 (retrieved 2024-08-20) (CAS RN: 3031-95-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

同义名列表

40 个代谢物同义名

(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; 1-(5-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole 1-(5-phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole; L-N-[(5-Amino-1-beta-delta-ribofuranosylimidazol-4-yl)carbonyl]-5-(dihydrogen phosphate); N-(5-Amino-1-beta-D-ribofuranosylimidazole-4-carbonyl)-L-aspartic acid 5-phosphate; (2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinic acid; L-N-[(5-Amino-1-b-D-ribofuranosylimidazol-4-yl)carbonyl]-5-(dihydrogen phosphate); (S)-2-(5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinic acid; (2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinic acid; (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; (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-D-ribosyl)imidazole-4-carboxamido]succinic acid; (S)-2-(5-Amino-1-(5-phospho-delta-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-b-D-ribosyl)imidazole-4-carboxamido]succinate; N-(5-Amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5-phosphate; N-[5-Amino-1-(5-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartic acid; (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]succinate; N-[5-Amino-1-(5-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartate; Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphoric acid; 1-(5-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole; 1-(5-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole; Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphate; 5-Phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazole; Succinylaminoimidazolecarboxamide ribose-5-phosphoric acid; 5-Phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole; 5-Phosphoribosyl-4-(N-succinocarbozamide)-5-aminoimidazole; 5-Amino-4-imidazole-N-succinocarboxamide ribonucleotide; Succinylaminoimidazolecarboxamide ribose-5’-phosphate; Succinylaminoimidazolecarboxamide ribose-5-phosphate; Phosphoribosylaminoimidazolesuccinocarboxamide; Succinylaminoimidazole carboxamide ribotide; SAICAR, (D)-isomer; SAICA ribotide; Succino-aicar; SAICAribotide; SCHEMBL73326; SAICAR



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(3)

PlantCyc(0)

代谢反应

74 个相关的代谢反应过程信息。

Reactome(12)

BioCyc(5)

WikiPathways(3)

Plant Reactome(0)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(1)

PathBank(51)

PharmGKB(0)

7 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Péter Monostori, Glynis Klinke, Jana Hauke, Sylvia Richter, Jörgen Bierau, Sven F Garbade, Georg F Hoffmann, Claus-Dieter Langhans, Dorothea Haas, Jürgen G Okun. Extended diagnosis of purine and pyrimidine disorders from urine: LC MS/MS assay development and clinical validation. PloS one. 2019; 14(2):e0212458. doi: 10.1371/journal.pone.0212458. [PMID: 30817767]
  • Belén Pérez-Dueñas, Angela Sempere, Jaume Campistol, Itziar Alonso-Colmenero, María Díez, Verónica González, Begoña Merinero, Lourdes R Desviat, Rafael Artuch. Novel features in the evolution of adenylosuccinate lyase deficiency. European journal of paediatric neurology : EJPN : official journal of the European Paediatric Neurology Society. 2012 Jul; 16(4):343-8. doi: 10.1016/j.ejpn.2011.08.008. [PMID: 21903433]
  • K V Lobanov, L Errais Lopes, N V Korol'kova, B V Tyaglov, A V Glazunov, R S Shakulov, A S Mironov. Reconstruction of Purine Metabolism in Bacillus subtilis to Obtain the Strain Producer of AICAR: A New Drug with a Wide Range of Therapeutic Applications. Acta naturae. 2011 Apr; 3(2):79-89. doi: . [PMID: 22649686]
  • M Henneke, S Dreha-Kulaczewski, K Brockmann, M van der Graaf, M A A P Willemsen, U Engelke, P Dechent, A Heerschap, G Helms, R A Wevers, J Gärtner. In vivo proton MR spectroscopy findings specific for adenylosuccinate lyase deficiency. NMR in biomedicine. 2010 Jun; 23(5):441-5. doi: 10.1002/nbm.1480. [PMID: 20175147]
  • S Samuel Yang, Oswaldo Valdés-López, Wayne W Xu, Bruna Bucciarelli, John W Gronwald, Georgina Hernández, Carroll P Vance. Transcript profiling of common bean (Phaseolus vulgaris L.) using the GeneChip Soybean Genome Array: optimizing analysis by masking biased probes. BMC plant biology. 2010 May; 10(?):85. doi: 10.1186/1471-2229-10-85. [PMID: 20459672]
  • Cyril Gitiaux, Irène Ceballos-Picot, Sandrine Marie, Vassili Valayannopoulos, Marlène Rio, Séverine Verrieres, Jean François Benoist, Marie Françoise Vincent, Isabelle Desguerre, Nadia Bahi-Buisson. Misleading behavioural phenotype with adenylosuccinate lyase deficiency. European journal of human genetics : EJHG. 2009 Jan; 17(1):133-6. doi: 10.1038/ejhg.2008.174. [PMID: 18830228]
  • Renata Usaite, Michael C Jewett, Ana Paula Oliveira, John R Yates, Lisbeth Olsson, Jens Nielsen. Reconstruction of the yeast Snf1 kinase regulatory network reveals its role as a global energy regulator. Molecular systems biology. 2009; 5(?):319. doi: 10.1038/msb.2009.67. [PMID: 19888214]
  • A M Marinaki, M Champion, M A Kurian, H A Simmonds, S Marie, M F Vincent, G van den Berghe, J A Duley, L D Fairbanks. Adenylosuccinate lyase deficiency--first British case. Nucleosides, nucleotides & nucleic acids. 2004 Oct; 23(8-9):1231-3. doi: 10.1081/ncn-200027494. [PMID: 15571235]
  • M Castro, C Pérez-Cerdá, B Merinero, M J García, J Bernar, A Gil Nagel, J Torres, M Bermúdez, P Garavito, S Marie, F Vincent, G Van den Berghe, M Ugarte. Screening for adenylosuccinate lyase deficiency: clinical, biochemical and molecular findings in four patients. Neuropediatrics. 2002 Aug; 33(4):186-9. doi: 10.1055/s-2002-34493. [PMID: 12368987]
  • F A van den Bergh, A N Bosschaart, G Hageman, M Duran, B Tien Poll-The. Adenylosuccinase deficiency with neonatal onset severe epileptic seizures and sudden death. Neuropediatrics. 1998 Feb; 29(1):51-3. doi: 10.1055/s-2007-973536. [PMID: 9553952]
  • J Krijt, I Sebesta, A Svehlakova, A Zumrova, J Zeman. Adenylosuccinate lyase deficiency in a Czech girl and two siblings. Advances in experimental medicine and biology. 1994; 370(?):367-70. doi: 10.1007/978-1-4615-2584-4_79. [PMID: 7660930]
  • C Salerno, C Crifò, E Capuozzo, O Giardini. Anomalous response to intravenous fructose tolerance test in a case of deficit of adenylosuccinate lyase. Advances in experimental medicine and biology. 1994; 370(?):371-4. doi: 10.1007/978-1-4615-2584-4_80. [PMID: 7660931]
  • P K Laikind, J E Seegmiller, H E Gruber. 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. Analytical biochemistry. 1986 Jul; 156(1):81-90. doi: 10.1016/0003-2697(86)90158-2. [PMID: 3740420]