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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-12-19 16:55:37 UTC
Update Date2021-09-14 15:37:04 UTC
HMDB IDHMDB0005768
Secondary Accession Numbers
  • HMDB05768
Metabolite Identification
Common NameKyotorphin
DescriptionKyotorphin (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.
Structure
Data?1582752363
Synonyms
ValueSource
L-Tyrosyl-L-arginineChEBI
N(2)-L-Tyrosyl-L-arginineChEBI
(D-Arg(2))-kyotorphinMeSH
D-KyotorphinMeSH
L-Tyrosyl-D-arginineMeSH
Tyr-argMeSH
Kyotorphin, (L-tyr-D-arg)-isomerMeSH
Kyotorphin, 14C-labeled, (L-tyr-L-arg)-isomerMeSH
Kyotorphin, 3H-labeled, (L-tyr-D-arg)-isomerMeSH
Kyotorphin, 3H-labeled, (L-tyr-L-arg)-isomerMeSH
KyotorphinChEBI
Chemical FormulaC15H23N5O4
Average Molecular Weight337.3742
Monoisotopic Molecular Weight337.175004249
IUPAC Name(2S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-5-carbamimidamidopentanoic acid
Traditional Nametyr-arg
CAS Registry Number70904-56-2
SMILES
N[C@@H](CC1=CC=C(O)C=C1)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O
InChI Identifier
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)/t11-,12-/m0/s1
InChI KeyJXNRXNCCROJZFB-RYUDHWBXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • Arginine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid or derivatives
  • Amino acid
  • Guanidine
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Primary aliphatic amine
  • Imine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.00119 +/- 0.00051 uMNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.00024 +/- 0.00004 uMNot SpecifiedNot Specifiedpersistent pain details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023758
KNApSAcK IDNot Available
Chemspider ID110353
KEGG Compound IDC02993
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkKyotorphin
METLIN IDNot Available
PubChem Compound123804
PDB IDNot Available
ChEBI ID17537
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBergmann, Max; Zervas, Leonidas; du Vigneaud, Vincent. Rearrangements of peptide-like substances. XXVIII. Synthesis of peptides containing arginine: d-tyrosyl-d-arginine. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1929), 62B 1905-9.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kee AJ, Smith RC: Addition of tyrosyl-arginine to parenteral nutrition is anabolic in unstressed rats. Nutrition. 2000 May;16(5):361-7. [PubMed:10793305 ]
  2. Schwarz A, Wandrey C, Steinke D, Kula MR: A two-step enzymatic synthesis of dipeptides. Biotechnol Bioeng. 1992 Jan 20;39(2):132-40. [PubMed:18600923 ]
  3. Kee AJ, Smith RC, Gross AS, Madsen DC, Rowe B: The effect of dipeptide structure on dipeptide and amino acid clearance in rats. Metabolism. 1994 Nov;43(11):1373-8. [PubMed:7968592 ]
  4. Kee AJ, Smith RC: Organ clearance of tyrosyl-arginine and its effect on amino acid metabolism in young sheep. Metabolism. 1993 Aug;42(8):958-66. [PubMed:8345819 ]