Beta-Guanidinopropionic acid (BioDeep_00000003082)
Secondary id: BioDeep_00000400271
natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite
描述信息
Beta-Guanidinopropionic acid is analog of creatine and is reported to decrease phosphocreatine and ATP content in animal tissues in vivo.
Acquisition and generation of the data is financially supported in part by CREST/JST.
A human metabolite taken as a putative food compound of mammalian origin [HMDB]
C274 - Antineoplastic Agent > C177430 - Agent Targeting Cancer Metabolism
KEIO_ID G039
同义名列表
27 个代谢物同义名
3-(diaminomethylideneamino)propanoic acid; N-[Amino(imino)methyl]-beta-alanine; N-[Amino(imino)methyl]-β-alanine; N-[Amino(imino)methyl]-b-alanine; 3-carbamimidamidopropanoic acid; beta-Guanidinopropionic acid.; beta-Guanidine propionic acid; Beta-Guanidinopropionic acid; 3-Guanidinopropanoic acid; b-Guanidinopropionic acid; 3-Guanidinopropionic acid; Β-guanidinopropionic acid; beta-Guanidinopropionate; beta-Guanadinopropionate; Guanidinopropionic acid; Β-guanidinopropionate; b-Guanidinopropionate; 3-Guanidinopropanoate; Guanidine propionate; Amidino beta-alanine; Guanidinopropionate; beta-GPA; RGX-202; b-GPA; Β-gpa; 3-Guanidinopropanoate; 3-Guanidinopropionic acid
数据库引用编号
27 个数据库交叉引用编号
- ChEBI: CHEBI:15968
- KEGG: C03065
- PubChem: 67701
- HMDB: HMDB0013222
- Metlin: METLIN44712
- ChEMBL: CHEMBL20489
- Wikipedia: Guanidinopropionic_acid
- foodb: FDB029341
- chemspider: 61020
- CAS: 353-09-3
- MoNA: KO002971
- MoNA: PS038303
- MoNA: PR100630
- MoNA: KO002969
- MoNA: PR100217
- MoNA: KO002972
- MoNA: PS038301
- MoNA: PS038302
- MoNA: PS038305
- MoNA: KO002970
- MoNA: KO002973
- PMhub: MS000008002
- PubChem: 5965
- 3DMET: B00534
- NIKKAJI: J193.824J
- RefMet: 3-Guanidinopropanoic acid
- KNApSAcK: 15968
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 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
- Hisashi Kato, Shinya Masuda, Tomotaka Ohira, Luna Ohira, Hisashi Takakura, Yoshinobu Ohira, Tetsuya Izawa. Differential response of adipose tissue gene and protein expressions to 4- and 8-week administration of β-guanidinopropionic acid in mice.
Physiological reports.
2018 03; 6(5):. doi:
10.14814/phy2.13616. [PMID: 29512301] - Fares A Karamat, Deborah L Horjus, Yentl C Haan, Lisa van der Woude, Marianne C Schaap, Inge Oudman, Gert A van Montfrans, Rienk Nieuwland, Gajja S Salomons, Joseph F Clark, Lizzy M Brewster. The acute effect of beta-guanidinopropionic acid versus creatine or placebo in healthy men (ABC-Trial): A randomized controlled first-in-human trial.
British journal of clinical pharmacology.
2017 12; 83(12):2626-2635. doi:
10.1111/bcp.13390. [PMID: 28795416] - Fares A Karamat, Inge Oudman, Yentl C Haan, Andre B P van Kuilenburg, Rene Leen, Jan A H Danser, Frank P J Leijten, Carrie Ris-Stalpers, Gert A van Montfrans, Joseph F Clark, Lizzy M Brewster. Creatine kinase inhibition lowers systemic arterial blood pressure in spontaneously hypertensive rats: a randomized controlled trial.
Journal of hypertension.
2016 12; 34(12):2418-2426. doi:
10.1097/hjh.0000000000001090. [PMID: 27512977] - Rizwan Ali Zounr, Mumammad Yar Khuhawar, Taj Muhammad Jahangir, Malik Alamgir. Improved Gas Chromatographic Determination of Guanidino Compounds Using Isovaleroylacetone and Ethyl Chloroformate as Derivatizing Reagents.
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.
2016; 32(2):141-6. doi:
10.2116/analsci.32.141. [PMID: 26860556] - Fares A Karamat, Deborah L Horjus, Yentl C Haan, Lisa van der Woude, Inge Oudman, Gert A van Montfrans, Joseph F Clark, Lizzy M Brewster. The acute effect of beta-guanidinopropionic acid versus creatine or placebo in healthy men (ABC Trial): study protocol for a randomized controlled trial.
Trials.
2015 Feb; 16(?):56. doi:
10.1186/s13063-015-0581-9. [PMID: 25888414] - Laetitia Van Noolen, Denis Monneret, Véronique Ducros, Christelle Corne, Joël Lunardi, Patrice Faure. [Simultaneous determination of guanidinoacetate, creatine and creatinine by liquid chromatography-tandem mass spectrometry: a diagnostic tool for creatine deficiency syndromes in body fluids and a perspective use on cultured fibroblasts].
Annales de biologie clinique.
2013 Jul; 71(4):429-37. doi:
10.1684/abc.2013.0871. [PMID: 23906570] - 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] - David T Thwaites, Catriona M H Anderson. The SLC36 family of proton-coupled amino acid transporters and their potential role in drug transport.
British journal of pharmacology.
2011 Dec; 164(7):1802-16. doi:
10.1111/j.1476-5381.2011.01438.x. [PMID: 21501141] - 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] - Kristin E Pandke, Kerry L Mullen, Laelie A Snook, Arend Bonen, David J Dyck. Decreasing intramuscular phosphagen content simultaneously increases plasma membrane FAT/CD36 and GLUT4 transporter abundance.
American journal of physiology. Regulatory, integrative and comparative physiology.
2008 Sep; 295(3):R806-13. doi:
10.1152/ajpregu.90540.2008. [PMID: 18650314] - Olivier Levillain, Bart Marescau, Ilse Possemiers, Peter Paul De Deyn. Accumulation of methylguanidine and changes in guanidino compound levels in plasma, urine, and kidneys of furosemide-treated rats.
Metabolism: clinical and experimental.
2008 Jun; 57(6):802-10. doi:
10.1016/j.metabol.2008.01.025. [PMID: 18502263] - Malin Lindbom, Truls Ramunddal, German Camejo, Finn Waagstein, Elmir Omerovic. In vivo effects of myocardial creatine depletion on left ventricular function morphology and lipid metabolism: study in a mouse model.
Journal of cardiac failure.
2008 Mar; 14(2):161-6. doi:
10.1016/j.cardfail.2007.10.020. [PMID: 18325464] - M García-Delgado, P García-Miranda, M J Peral, M L Calonge, A A Ilundáin. Ontogeny up-regulates renal Na(+)/Cl(-)/creatine transporter in rat.
Biochimica et biophysica acta.
2007 Nov; 1768(11):2841-8. doi:
10.1016/j.bbamem.2007.07.022. [PMID: 17916324] - Malin Lorentzon, Truls Råmunddal, Entela Bollano, Bassam Soussi, Finn Waagstein, Elmir Omerovic. In vivo effects of myocardial creatine depletion on left ventricular function, morphology, and energy metabolism--consequences in acute myocardial infarction.
Journal of cardiac failure.
2007 Apr; 13(3):230-7. doi:
10.1016/j.cardfail.2006.11.012. [PMID: 17448422] - Richard M Reznick, Haihong Zong, Ji Li, Katsutaro Morino, Irene K Moore, Hannah J Yu, Zhen-Xiang Liu, Jianying Dong, Kirsty J Mustard, Simon A Hawley, Douglas Befroy, Marc Pypaert, D Grahame Hardie, Lawrence H Young, Gerald I Shulman. Aging-associated reductions in AMP-activated protein kinase activity and mitochondrial biogenesis.
Cell metabolism.
2007 Feb; 5(2):151-6. doi:
10.1016/j.cmet.2007.01.008. [PMID: 17276357] - G Lunardi, A Parodi, L Perasso, A V Pohvozcheva, S Scarrone, E Adriano, T Florio, C Gandolfo, A Cupello, S V Burov, M Balestrino. The creatine transporter mediates the uptake of creatine by brain tissue, but not the uptake of two creatine-derived compounds.
Neuroscience.
2006 Nov; 142(4):991-7. doi:
10.1016/j.neuroscience.2006.06.058. [PMID: 16949212] - 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] - Efraim H Rosenberg, Cristina Martínez Muñoz, Ton J Degrauw, Cor nelis Jakobs, Gajja S Salomons. Overexpression of wild-type creatine transporter (SLC6A8) restores creatine uptake in primary SLC6A8-deficient fibroblasts.
Journal of inherited metabolic disease.
2006 Apr; 29(2-3):345-6. doi:
10.1007/s10545-006-0271-6. [PMID: 16763899] - Andrea Kragler, Georg Höfner, Klaus T Wanner. Novel parent structures for inhibitors of the murine GABA transporters mGAT3 and mGAT4.
European journal of pharmacology.
2005 Sep; 519(1-2):43-7. doi:
10.1016/j.ejphar.2005.06.053. [PMID: 16111674] - Alessandra F Perna, Diego Ingrosso, Ersilia Satta, Cinzia Lombardi, Patrizia Galletti, Antimo D'Aniello, Natale G De Santo. Plasma protein aspartyl damage is increased in hemodialysis patients: studies on causes and consequences.
Journal of the American Society of Nephrology : JASN.
2004 Oct; 15(10):2747-54. doi:
10.1097/01.asn.0000141041.71717.11. [PMID: 15466280] - Ernest Boehm, Sharon Chan, Mina Monfared, Theo Wallimann, Kieran Clarke, Stefan Neubauer. Creatine transporter activity and content in the rat heart supplemented by and depleted of creatine.
American journal of physiology. Endocrinology and metabolism.
2003 Feb; 284(2):E399-406. doi:
10.1152/ajpendo.00259.2002. [PMID: 12531746] - 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] - Marta García-Delgado, María J Peral, Mercedes Cano, María L Calonge, Anunciación A Ilundáin. Creatine transport in brush-border membrane vesicles isolated from rat kidney cortex.
Journal of the American Society of Nephrology : JASN.
2001 Sep; 12(9):1819-1825. doi:
10.1681/asn.v1291819. [PMID: 11518774] - 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] - V A Vaillancourt, S D Larsen, S P Tanis, J E Burr, M A Connell, M M Cudahy, B R Evans, P V Fisher, P D May, M D Meglasson, D D Robinson, F C Stevens, J A Tucker, T J Vidmar, J H Yu. Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid.
Journal of medicinal chemistry.
2001 Apr; 44(8):1231-48. doi:
10.1021/jm000094n. [PMID: 11312923] - C A Willott, M E Young, B Leighton, G J Kemp, E A Boehm, G K Radda, K Clarke. Creatine uptake in isolated soleus muscle: kinetics and dependence on sodium, but not on insulin.
Acta physiologica Scandinavica.
1999 Jun; 166(2):99-104. doi:
10.1046/j.1365-201x.1999.00539.x. [PMID: 10383488] - 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] - G Ara, L M Gravelin, R Kaddurah-Daouk, B A Teicher. Antitumor activity of creatine analogs produced by alterations in pancreatic hormones and glucose metabolism.
In vivo (Athens, Greece).
1998 Mar; 12(2):223-31. doi:
. [PMID: 9627806] - O Levillain, B Marescau, P P De Deyn. Renal handling of guanidino compounds in rat and rabbit.
The Journal of physiology.
1997 Mar; 499 ( Pt 2)(?):561-70. doi:
10.1113/jphysiol.1997.sp021949. [PMID: 9080382] - V Pelouch, F Kolár, Z A Khuchua, G V Elizarova, M Milerová, B Ost'ádal, V A Saks. Cardiac phosphocreatine deficiency induced by GPA during postnatal development in rat.
Molecular and cellular biochemistry.
1996 Oct; 163-164(?):67-76. doi:
10.1007/bf00408642. [PMID: 8974041] - Y Ohira, N Inoue. Effects of creatine and beta-guanidinopropionic acid on the growth of Ehrlich ascites tumor cells: i.p. injection and culture study.
Biochimica et biophysica acta.
1995 Apr; 1243(3):367-72. doi:
10.1016/0304-4165(94)00161-p. [PMID: 7727511] - O Levillain, B Marescau, P P de Deyn. Guanidino compound metabolism in rats subjected to 20\% to 90\% nephrectomy.
Kidney international.
1995 Feb; 47(2):464-72. doi:
10.1038/ki.1995.59. [PMID: 7536856] - P Schloss, W Mayser, H Betz. The putative rat choline transporter CHOT1 transports creatine and is highly expressed in neural and muscle-rich tissues.
Biochemical and biophysical research communications.
1994 Jan; 198(2):637-45. doi:
10.1006/bbrc.1994.1093. [PMID: 8297374] - Y Ohira, S Ishine, I Tabata, H Kurata, T Wakatsuki, S Sugawara, W Yasui, H Tanaka, Y Kuroda. Non-insulin and non-exercise related increase of glucose utilization in rats and mice.
The Japanese journal of physiology.
1994; 44(4):391-402. doi:
10.2170/jjphysiol.44.391. [PMID: 7869601] - M D Meglasson, J M Wilson, J H Yu, D D Robinson, B M Wyse, C J de Souza. Antihyperglycemic action of guanidinoalkanoic acids: 3-guanidinopropionic acid ameliorates hyperglycemia in diabetic KKAy and C57BL6Job/ob mice and increases glucose disappearance in rhesus monkeys.
The Journal of pharmacology and experimental therapeutics.
1993 Sep; 266(3):1454-62. doi:
. [PMID: 8371149] - Y Ohira, S Ishine, N Inoue, K Yunoki. Reduced growth of Ehrlich ascites tumor cells in creatine depleted mice fed beta-guanidinopropionic acid.
Biochimica et biophysica acta.
1991 Sep; 1097(2):117-22. doi:
10.1016/0925-4439(91)90094-p. [PMID: 1911884] - T S Moerland, N G Wolf, M J Kushmerick. Administration of a creatine analogue induces isomyosin transitions in muscle.
The American journal of physiology.
1989 Oct; 257(4 Pt 1):C810-6. doi:
10.1152/ajpcell.1989.257.4.c810. [PMID: 2801930] - H Muramoto. [Metabolism of guanidinoacetic acid and creatine in uremia].
Nihon Jinzo Gakkai shi.
1988 Feb; 30(2):117-28. doi:
NULL. [PMID: 3386016] - R Shainkin-Kestenbaum, Y Winikoff, A Dvilansky, C Chaimovitz, I Nathan. Effect of guanidino-propionic acid on lymphocyte proliferation.
Nephron.
1986; 44(4):295-8. doi:
10.1159/000184009. [PMID: 3796772] - M Boroujerdi, A M Mattocks. Metabolism of creatinine in vivo.
Clinical chemistry.
1983 Jul; 29(7):1363-6. doi:
. [PMID: 6861341] - R Shainkin-Kestenbaum, Y Giat, G M Berlyne. The toxicity of guanidino compounds in the red blood cell in uremia and the effects of hemodialysis.
Nephron.
1982; 31(1):20-3. doi:
10.1159/000182603. [PMID: 7110471] - P P Kamoun, J J Zingraff, G Turlin, P Lebreton. Ascorbate-cyanide test on red blood cells in uremia: effect of guanidinopropionic acid.
Nephron.
1981; 28(1):26-9. doi:
10.1159/000182089. [PMID: 7266724] - B M Davis, R K Miller, R L Brent, T R Koszalka. Materno-fetal transport of creatine in the rat.
Biology of the neonate.
1978; 33(1-2):43-54. doi:
10.1159/000241050. [PMID: 656521] - R P Shields, C K Whitehair. Muscle creatine: in vivo depletion by feeding beta-guanidinopropionic acid.
Canadian journal of biochemistry.
1973 Jul; 51(7):1046-9. doi:
10.1139/o73-136. [PMID: 4725354]
