Structure via PubChem · Public domain (PubChem)
kyotorphin
Sign in to saveAlso known as Tyr-Arg, N(2)-L-tyrosyl-L-arginine, L-Tyrosyl-L-arginine, Kiotorphin, (2S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-5-carbamimidamidopentanoic acid
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 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 Vinony graph
Vinony's link graph records 694 inbound references to kyotorphin, and connects out to opioid receptor, (+)-catechin and butorphanol.
It is catalogued under topics including Chembox image size set and Dipeptides.
Vinony links it to 10 Wikipedia language editions.
Chemical data
- Formula
- C15H23N5O4
- Molecular weight
- 337.37 g/mol
- IUPAC name
- (2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid
- SMILES
- C1=CC(=CC=C1C[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)N)O
- InChIKey
- JXNRXNCCROJZFB-RYUDHWBXSA-N
- XLogP
- -4.3
- Polar surface area
- 177 Ų
- H-bond donors
- 6
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
255 papers- Review of Kyotorphin Research: A Mysterious Opioid Analgesic Dipeptide and Its Molecular, Physiological, and Pharmacological Characteristics.Frontiers in medical technology · 2021
- Pharmacological Potential of the Endogenous Dipeptide Kyotorphin and Selected Derivatives.Frontiers in pharmacology · 2016
- Impact of arginine therapy on kyotorphin in children with sickle cell disease and vaso-occlusive pain.Blood advances · 2024
- Continuous production of kyotorphin.Biotechnology and bioengineering · 1989
- [Kyotorphin as an enkephalin releasing factor (author's transl)].Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme · 1981
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 337.175004
Show 4 more facts
- chemical formula
- C₁₅H₂₃N₅O₄
- isomeric SMILES
- C1=CC(=CC=C1C[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)N)O
- canonical SMILES
- C1=CC(=CC=C1CC(C(=O)NC(CCCN=C(N)N)C(=O)O)N)O
- subject has role
- analgesic
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
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 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 its concentration is lower in patients with persistent pain.
==References==
Excerpted from Wikipedia’s “kyotorphin” article, available under the CC BY-SA 4.0 licence.