Kyotorphin (BioDeep_00000005058)

 

Secondary id: BioDeep_00000033516, BioDeep_00001868710

human metabolite Endogenous Volatile Flavor Compounds


代谢物信息卡片


(2S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-5-carbamimidamidopentanoic acid

化学式: C15H23N5O4 (337.17499580000003)
中文名称: TYR-ARG
谱图信息: 最多检出来源 Homo sapiens(feces) 0.14%

分子结构信息

SMILES: C(C[C@@H](C(=O)O)NC(=O)[C@H](Cc1ccc(cc1)O)N)CNC(=N)N
InChI: InChI=1S/C15H23N5O4/c16-11(8-9-3-5-10(21)6-4-9)13(22)20-12(14(23)24)2-1-7-19-15(17)18/h3-6,11-12,21H,1-2,7-8,16H2,(H,20,22)(H,23,24)(H4,17,18,19)

描述信息

Kyotorphin (L-tyrosyl-L-arginine) is a neuroactive dipeptide which plays a role in pain regulation in the brain. It was first isolated from bovine brain by Japanese scientists in 1979. Kyotorphin was named for the site of its discovery, Kyoto, Japan and because of its morphine- (or endorphin-) like analgesic activity. Kyotorphin has an analgesic effect, but it does not interact with the opioid receptors. Instead, it acts by releasing an Met-enkephalin and stabilizing it from degradation. It may also possess properties of neuromediator/neuromodulator. It has been shown that kyotorphin is present in the human cerebrospinal fluid and that it is lower in patients with persistent pain. [HMDB]
Kyotorphin (L-tyrosyl-L-arginine) is a neuroactive dipeptide which plays a role in pain regulation in the brain. It was first isolated from bovine brain by Japanese scientists in 1979. Kyotorphin was named for the site of its discovery, Kyoto, Japan and because of its morphine- (or endorphin-) like analgesic activity. Kyotorphin has an analgesic effect, but it does not interact with the opioid receptors. Instead, it acts by releasing an Met-enkephalin and stabilizing it from degradation. It may also possess properties of neuromediator/neuromodulator. It has been shown that kyotorphin is present in the human cerebrospinal fluid and that it is lower in patients with persistent pain.
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D002491 - Central Nervous System Agents > D000700 - Analgesics
D018377 - Neurotransmitter Agents > D018847 - Opioid Peptides
D018377 - Neurotransmitter Agents > D004723 - Endorphins
Kyotorphin is an endogenou neuroactive dipeptide with analgesic properties. Kyotorphin possesses anti-inflammatory and antimicrobial activity. Kyotorphin levels in cerebro-spinal fluid correlate negatively with the progression of neurodegeneration in Alzheimer's Disease patients[1].

同义名列表

16 个代谢物同义名

(2S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-5-carbamimidamidopentanoic acid; Kyotorphin, 14C-labeled, (L-tyr-L-arg)-isomer; Kyotorphin, 3H-labeled, (L-tyr-D-arg)-isomer; Kyotorphin, 3H-labeled, (L-tyr-L-arg)-isomer; Kyotorphin, (L-tyr-D-arg)-isomer; N(2)-L-Tyrosyl-L-arginine; Kyotorphin acetate salt; (D-Arg(2))-kyotorphin; L-Tyrosyl-L-arginine; L-Tyrosyl-D-arginine; tyrosylarginine; D-Kyotorphin; Kyotorphin; Kiotorphin; Tyr-arg; Kyotorphin



数据库引用编号

18 个数据库交叉引用编号

分类词条

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代谢反应

0 个相关的代谢反应过程信息。

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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

  • Tiago N Figueira, João M Freire, Catarina Cunha-Santos, Montserrat Heras, João Gonçalves, Anne Moscona, Matteo Porotto, Ana Salomé Veiga, Miguel A R B Castanho. Quantitative analysis of molecular partition towards lipid membranes using surface plasmon resonance. Scientific reports. 2017 03; 7(?):45647. doi: 10.1038/srep45647. [PMID: 28358389]
  • Katia Conceição, Pedro R Magalhães, Sara R R Campos, Marco M Domingues, Vasanthakumar G Ramu, Matthias Michalek, Philippe Bertani, António M Baptista, Montserrat Heras, Eduard R Bardaji, Burkhard Bechinger, Mônica Lopes Ferreira, Miguel A R B Castanho. The anti-inflammatory action of the analgesic kyotorphin neuropeptide derivatives: insights of a lipid-mediated mechanism. Amino acids. 2016 Jan; 48(1):307-18. doi: 10.1007/s00726-015-2088-9. [PMID: 26347373]
  • Pedro R Magalhães, Miguel Machuqueiro, António M Baptista. Constant-pH Molecular Dynamics Study of Kyotorphin in an Explicit Bilayer. Biophysical journal. 2015 May; 108(9):2282-90. doi: 10.1016/j.bpj.2015.03.052. [PMID: 25954885]
  • Isa D Serrano, Vasanthakumar G Ramu, Antónia R T Pinto, João M Freire, Isaura Tavares, Montserrat Heras, Eduard R Bardaji, Miguel A R B Castanho. Correlation between membrane translocation and analgesic efficacy in kyotorphin derivatives. Biopolymers. 2015 Jan; 104(1):1-10. doi: 10.1002/bip.22580. [PMID: 25363470]
  • Marta M B Ribeiro, Henri G Franquelim, Inês M Torcato, Vasanthakumar G Ramu, Montserrat Heras, Eduard R Bardaji, Miguel A R B Castanho. Antimicrobial properties of analgesic kyotorphin peptides unraveled through atomic force microscopy. Biochemical and biophysical research communications. 2012 Apr; 420(3):676-9. doi: 10.1016/j.bbrc.2012.03.065. [PMID: 22450328]
  • Joakim E Swedberg, Jonathan M Harris. Plasmin substrate binding site cooperativity guides the design of potent peptide aldehyde inhibitors. Biochemistry. 2011 Oct; 50(39):8454-62. doi: 10.1021/bi201203y. [PMID: 21877690]
  • Marta M B Ribeiro, Antónia R T Pinto, Marco M Domingues, Isa Serrano, Montserrat Heras, Eduard R Bardaji, Isaura Tavares, Miguel A Castanho. Chemical conjugation of the neuropeptide kyotorphin and ibuprofen enhances brain targeting and analgesia. Molecular pharmaceutics. 2011 Oct; 8(5):1929-40. doi: 10.1021/mp2003016. [PMID: 21830793]
  • Gyöngyi Horváth, László Mécs. Antinociception by endogenous ligands at peripheral level. Ideggyogyaszati szemle. 2011 Mar; 64(5-6):193-207. doi: ". [PMID: 21688721]
  • Miguel Machuqueiro, Sara R R Campos, Cláudio M Soares, António M Baptista. Membrane-induced conformational changes of kyotorphin revealed by molecular dynamics simulations. The journal of physical chemistry. B. 2010 Sep; 114(35):11659-67. doi: 10.1021/jp104418g. [PMID: 20707376]
  • Ying Huang, Xiuyan Jiang, Wei Wang, Jianping Duan, Guonan Chen. Separation and determination of l-tyrosine and its metabolites by capillary zone electrophoresis with a wall-jet amperometric detection. Talanta. 2006 Dec; 70(5):1157-63. doi: 10.1016/j.talanta.2006.03.009. [PMID: 18970894]
  • Sílvia C D N Lopes, Alexandre Fedorov, Miguel A R B Castanho. Chiral recognition of D-kyotorphin by lipidic membranes: relevance toward improved analgesic efficiency. ChemMedChem. 2006 Jul; 1(7):723-8. doi: 10.1002/cmdc.200600096. [PMID: 16902926]
  • Sílvia C D N Lopes, Cláudio M Soares, António M Baptista, Erik Goormaghtigh, Benedito J Costa Cabral, Miguel A R B Castanho. Conformational and orientational guidance of the analgesic dipeptide kyotorphin induced by lipidic membranes: putative correlation toward receptor docking. The journal of physical chemistry. B. 2006 Feb; 110(7):3385-94. doi: 10.1021/jp053651w. [PMID: 16494353]
  • Silvina A Bravo, Carsten Uhd Nielsen, Sven Frokjaer, Birger Brodin. Characterization of rPEPT2-mediated Gly-Sar transport parameters in the rat kidney proximal tubule cell line SKPT-0193 cl.2 cultured in basic growth media. Molecular pharmaceutics. 2005 Mar; 2(2):98-108. doi: 10.1021/mp049892q. [PMID: 15804184]
  • G Baggerman, J Huybrechts, E Clynen, K Hens, L Harthoorn, D Van der Horst, C Poulos, A De Loof, L Schoofs. New insights in Adipokinetic Hormone (AKH) precursor processing in Locusta migratoria obtained by capillary liquid chromatography-tandem mass spectrometry. Peptides. 2002 Apr; 23(4):635-44. doi: 10.1016/s0196-9781(01)00657-x. [PMID: 11897382]
  • T Sakaeda, Y Tada, T Sugawara, T Ryu, F Hirose, T Yoshikawa, K Hirano, L Kupczyk-Subotkowska, T J Siahaan, K L Audus, V J Stella. Conjugation with L-Glutamate for in vivo brain drug delivery. Journal of drug targeting. 2001; 9(1):23-37. doi: 10.3109/10611860108995630. [PMID: 11378521]
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  • T Mizuma, A Koyanagi, S Awazu. Intestinal transport and metabolism of glucose-conjugated kyotorphin and cyclic kyotorphin: metabolic degradation is crucial to intestinal absorption of peptide drugs. Biochimica et biophysica acta. 2000 Jun; 1475(1):90-8. doi: 10.1016/s0304-4165(00)00051-9. [PMID: 10806343]
  • H Ueda, M Inoue. In vivo signal transduction of nociceptive response by kyotorphin (tyrosine-arginine) through Galpha(i)- and inositol trisphosphate-mediated Ca(2+) influx. Molecular pharmacology. 2000 Jan; 57(1):108-15. doi: . [PMID: 10617685]
  • T Fujita, T Kishida, N Okada, V Ganapathy, F H Leibach, A Yamamoto. Interaction of kyotorphin and brain peptide transporter in synaptosomes prepared from rat cerebellum: implication of high affinity type H+/peptide transporter PEPT2 mediated transport system. Neuroscience letters. 1999 Aug; 271(2):117-20. doi: 10.1016/s0304-3940(99)00540-6. [PMID: 10477116]
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  • J Y Summy-Long, V Bui, S Gestl, E Koehler-Stec, H Liu, M L Terrell, M Kadekaro. Effects of central injection of kyotorphin and L-arginine on oxytocin and vasopressin release and blood pressure in conscious rats. Brain research bulletin. 1998; 45(4):395-403. doi: 10.1016/s0361-9230(97)00341-9. [PMID: 9527014]
  • S Haseto, T Mizuma, H Ouchi, T Isoda, M Hayashi, S Awazu. Preference of Peyer's patches to jejunal epithelium for intestinal absorption of oligopeptides, tyrosylglycylglycine and D-kyotorphin. Biological & pharmaceutical bulletin. 1997 Sep; 20(9):1024-5. doi: 10.1248/bpb.20.1024. [PMID: 9331991]
  • G Bronnikov, L Dolgacheva, S J Zhang, E Galitovskaya, L Kramarova, V Zinchenko. The effect of neuropeptides kyotorphin and neokyotorphin on proliferation of cultured brown preadipocytes. FEBS letters. 1997 Apr; 407(1):73-7. doi: 10.1016/s0014-5793(97)00298-6. [PMID: 9141484]
  • H Ueda, S Tamura, N Fukushima, T Katada, M Ui, M Satoh. Inositol 1,4,5-trisphosphate-gated calcium transport through plasma membranes in nerve terminals. The Journal of neuroscience : the official journal of the Society for Neuroscience. 1996 May; 16(9):2891-900. doi: NULL. [PMID: 8622120]
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  • A Kawabata, S Manabe, H Takagi. Comparison of antinociception induced by supraspinally administered L-arginine and kyotorphin. British journal of pharmacology. 1994 Jul; 112(3):817-22. doi: 10.1111/j.1476-5381.1994.tb13152.x. [PMID: 7921607]
  • S Haseto, H Ouchi, T Isoda, T Mizuma, M Hayashi, S Awazu. Transport of low and high molecular peptides across rabbit Peyer's patches. Pharmaceutical research. 1994 Mar; 11(3):361-4. doi: 10.1023/a:1018948617587. [PMID: 8008699]
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  • P Tengamnuay, A K Mitra. Bile salt-fatty acid mixed micelles as nasal absorption promoters of peptides. I. Effects of ionic strength, adjuvant composition, and lipid structure on the nasal absorption of [D-Arg2]kyotorphin. Pharmaceutical research. 1990 Feb; 7(2):127-33. doi: 10.1023/a:1015868516602. [PMID: 2308892]
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