4-Guanidinobutanoic acid (BioDeep_00000001253)
Secondary id: BioDeep_00000265313, BioDeep_00000399960, BioDeep_00000405707, BioDeep_00000896618, BioDeep_00001872945
human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019
代谢物信息卡片
化学式: C5H11N3O2 (145.0851)
中文名称: 4-呱基丁酸, 4-胍基丁酸
谱图信息:
最多检出来源 Homo sapiens(blood) 14.38%
Last reviewed on 2024-09-13.
Cite this Page
4-Guanidinobutanoic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/4-guanidinobutanoic_acid (retrieved
2024-12-22) (BioDeep RN: BioDeep_00000001253). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: C(CC(=O)O)CN=C(N)N
InChI: InChI=1S/C5H11N3O2/c6-5(7)8-3-1-2-4(9)10/h1-3H2,(H,9,10)(H4,6,7,8)
描述信息
4-Guanidinobutanoic acid, also known as gamma-guanidinobutyrate or 4-(carbamimidamido)butanoate, belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. 4-Guanidinobutanoic acid is a normal metabolite present in low concentrations. 4-Guanidinobutanoic acid exists in all eukaryotes, ranging from yeast to humans. Outside of the human body, 4-Guanidinobutanoic acid has been detected, but not quantified in a few different foods, such as apples, french plantains, and loquats. This could make 4-guanidinobutanoic acid a potential biomarker for the consumption of these foods. Patients with hyperargininemia have an arginase deficiency which leads to blockade of the urea cycle in the last step with several clinical symptoms. Owing to the arginase deficiency this patients accumulate arginine which leads eventually to epileptogenic guanidino compounds (PMID 7752905).
4-guanidinobutanoic acid, also known as gamma-guanidinobutyrate or 4-(carbamimidamido)butanoate, belongs to gamma amino acids and derivatives class of compounds. Those are amino acids having a (-NH2) group attached to the gamma carbon atom. 4-guanidinobutanoic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 4-guanidinobutanoic acid can be found in apple, french plantain, and loquat, which makes 4-guanidinobutanoic acid a potential biomarker for the consumption of these food products. 4-guanidinobutanoic acid can be found primarily in blood, cerebrospinal fluid (CSF), and urine, as well as in human prostate tissue. 4-guanidinobutanoic acid exists in all eukaryotes, ranging from yeast to humans. Moreover, 4-guanidinobutanoic acid is found to be associated with cirrhosis.
CONFIDENCE standard compound; ML_ID 15
KEIO_ID G032
4-Guanidinobutanoic acid is a normal metabolite present in low concentrations.
4-Guanidinobutanoic acid is a normal metabolite present in low concentrations.
同义名列表
24 个代谢物同义名
4-[(diaminomethylidene)amino]butanoic acid; gamma-Guanidinobutyrate, monosodium salt; 4-[(Aminoiminomethyl)amino]butanoic acid; 4-[(Aminoiminomethyl)amino]butanoate; 4-(Carbamimidamido)butanoic acid; N-(4-Butanoic acid)guanidine; 4-(Carbamimidamido)butanoate; gamma-Guanidinebutyric acid; gamma-Guanidinobutyric acid; N-(4-Butanoate)guanidine; 4-Guanidinobutanoic acid; Γ-guanidinobutyric acid; Γ-guanidinebutyric acid; gamma-Guanidinebutyrate; gamma-Guanidinobutyrate; 4-Guanidinobutyric acid; g-Guanidinobutyric acid; 4-Guanidinobutanoate; 4-Guanidinobutyrate; Γ-guanidinobutyrate; g-Guanidinobutyrate; Γ-guanidinebutyrate; 4-Guanidinobutanoic acid; 4-Guanidinobutyric acid
数据库引用编号
32 个数据库交叉引用编号
- ChEBI: CHEBI:15728
- ChEBI: CHEBI:86564
- KEGG: C01035
- KEGGdrug: D84250
- PubChem: 500
- HMDB: HMDB0003464
- Metlin: METLIN4155
- ChEMBL: CHEMBL21157
- MetaCyc: CPD-592
- foodb: FDB005408
- chemspider: 486
- CAS: 463-00-3
- MoNA: KO000869
- MoNA: KO000868
- MoNA: KO002961
- MoNA: ML001551
- MoNA: KO002960
- MoNA: KO000870
- MoNA: KO000871
- MoNA: KO002962
- MoNA: KO002963
- MoNA: KO000872
- MoNA: KO002959
- MoNA: ML001501
- PMhub: MS000000209
- PubChem: 4278
- PDB-CCD: ALG
- 3DMET: B00225
- NIKKAJI: J196.182I
- RefMet: 4-Guanidinobutanoic acid
- medchemexpress: HY-113286
- BioNovoGene_Lab2019: BioNovoGene_Lab2019-273
分类词条
相关代谢途径
Reactome(0)
PlantCyc(0)
代谢反应
1 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(1)
- arginine degradation X (arginine monooxygenase pathway):
4-guanidinobutyramide + H2O ⟶ 4-guanidinobutyrate + H+ + ammonia
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
2 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
- S A Majidano, M Y Khuhawar. Gas chromatographic determination of guanidino compounds in uremic patients using glyoxal as derivatizing reagent.
Journal of chromatographic science.
2012 May; 50(5):380-6. doi:
10.1093/chromsci/bms013. [PMID: 22392369] - Eva Schepers, Griet Glorieux, Laetitia Dou, Claire Cerini, Nathalie Gayrard, Loïc Louvet, Charlotte Maugard, Pierre Preus, Maria Rodriguez-Ortiz, Angel Argiles, Philippe Brunet, Gerald Cohen, Joachim Jankowski, Vera Jankowski, Ziad Massy, Mariano Rodriguez, Raymond Vanholder. Guanidino compounds as cause of cardiovascular damage in chronic kidney disease: an in vitro evaluation.
Blood purification.
2010; 30(4):277-87. doi:
10.1159/000320765. [PMID: 21079396] - Linda Metzner, Madlen Dorn, Fritz Markwardt, Matthias Brandsch. The orally active antihyperglycemic drug beta-guanidinopropionic acid is transported by the human proton-coupled amino acid transporter hPAT1.
Molecular pharmaceutics.
2009 May; 6(3):1006-11. doi:
10.1021/mp9000684. [PMID: 19358571] - R Gatti, M G Gioia. Anisoin: a useful pre-chromatographic derivatization fluorogenic reagent for LC analysis of guanidino compounds.
Journal of pharmaceutical and biomedical analysis.
2006 Sep; 42(1):11-6. doi:
10.1016/j.jpba.2005.12.035. [PMID: 16460903] - Erwin E W Jansen, Nanda M Verhoeven, Cornelis Jakobs, Andreas Schulze, Henry Senephansiri, Maneesh Gupta, O Carter Snead, K Michael Gibson. Increased guanidino species in murine and human succinate semialdehyde dehydrogenase (SSADH) deficiency.
Biochimica et biophysica acta.
2006 Apr; 1762(4):494-8. doi:
10.1016/j.bbadis.2006.01.006. [PMID: 16504488] - Olivier Levillain, Bart Marescau, Ilse Possemiers, Paul De Deyn. Dehydration modifies guanidino compound concentrations in the different zones of the rat kidney.
Pflugers Archiv : European journal of physiology.
2002 May; 444(1-2):143-52. doi:
10.1007/s00424-002-0787-z. [PMID: 11976926] - M Al Banchaabouchi, B Marescau, R D'Hooge, P P De Deyn. The effect of high protein diet on urea and guanidino compound levels in renal insufficient mice.
Amino acids.
2001 Dec; 21(4):401-15. doi:
10.1007/s007260170005. [PMID: 11858699] - M Al Banchaabouchi, B Marescau, E Van Marck, R D'hooge, P P De Deyn. Long-term effect of partial nephrectomy on biological parameters, kidney histology, and guanidino compound levels in mice.
Metabolism: clinical and experimental.
2001 Dec; 50(12):1418-25. doi:
10.1053/meta.2001.26763. [PMID: 11735086] - O Levillain, B Marescau, I Possemiers, M Al Banchaabouchi, P P De Deyn. Influence of 72\% injury in one kidney on several organs involved in guanidino compound metabolism: a time course study.
Pflugers Archiv : European journal of physiology.
2001 Jul; 442(4):558-69. doi:
10.1007/s004240100581. [PMID: 11510889] - A Schulze, E Mayatepek, S Frank, B Marescau, P P De Deyn, P Bachert. Disturbed metabolism of guanidino compounds characterized by elevated excretion of beta-guanidinopropionic acid and gamma-guanidinobutyric acid--an effect of vigabatrin treatment?.
Journal of inherited metabolic disease.
1998 Jun; 21(3):268-71. doi:
10.1023/a:1005376307471. [PMID: 9686372] - M Al Banchaabouchi, B Marescau, R D'Hooge, E Van Marck, A Van Daele, O Levillain, P P De Deyn. Biochemical and histopathological changes in nephrectomized mice.
Metabolism: clinical and experimental.
1998 Mar; 47(3):355-61. doi:
10.1016/s0026-0495(98)90271-2. [PMID: 9500577] - B Marescau, P P De Deyn, J Holvoet, I Possemiers, G Nagels, V Saxena, C Mahler. Guanidino compounds in serum and urine of cirrhotic patients.
Metabolism: clinical and experimental.
1995 May; 44(5):584-8. doi:
10.1016/0026-0495(95)90114-0. [PMID: 7752905] - S Shindo, Y Watanabe, A Mori. Effects of starvation on guanidino compound metabolism in mice.
Research communications in chemical pathology and pharmacology.
1986 Oct; 54(1):73-85. doi:
. [PMID: 3797807] - B Marescau, A Lowenthal, H G Terheggen, E Esmans, F Alderweireldt. Guanidino compounds in hyperargininemia.
Advances in experimental medicine and biology.
1982; 153(?):427-34. doi:
10.1007/978-1-4757-6903-6_52. [PMID: 7164915] - N M Pattnaik, F J Kézdy, A M Scanu. Kinetic study of the action of snake venom phospholipase A2 on human serum high density lipoprotein 3.
The Journal of biological chemistry.
1976 Apr; 251(7):1984-90. doi:
NULL. [PMID: 5436] - P BOULANGER, E SACQUET, R OSTEUX, H CHARLIER. [FORMATION OF GAMMA-GUANIDINOBUTYRIC ACID FROM ARGININE IN THE WHITE RAT].
Comptes rendus hebdomadaires des seances de l'Academie des sciences.
1964 Apr; 258(?):4159-61. doi:
. [PMID: 14146810] - R L BARNES. Formation of gamma-guanidinobutyric acid in pine tissue.
Nature.
1962 Feb; 193(?):781. doi:
10.1038/193781a0. [PMID: 13865107]
