Structure via PubChem · Public domain (PubChem)
isodesmosine
Sign in to saveAlso known as 2-amino-6-[3,5-bis(3-amino-4-hydroxy-4-oxobutyl)-2-(4-amino-5-hydroxy-5-oxopentyl)pyridin-1-ium-1-yl]hexanoic acid, Ide, 2-(4-amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)-3,5-bis(3-amino-3-carboxypropyl)pyridinium, Iso-desmosin, 3,5-bis(3-amino-3-carboxypropyl)-2-(4-amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)pyridin-1-ium, 2-(4-Amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)-3,5-bis(3-amino-3-carboxypropyl)-Pyridinium
Isodesmosine is a lysine derivative found in elastin. Isodesmosine is an isomeric pyridinium-based amino acid resulting from the condensation of four lysine residues between elastin proteins by lysyl-oxidase. These represent ideal biomarkers for monitoring elastin turnover because these special cross-links are only found in mature elastin in mammals.
Chemical data
- Formula
- C24H40N5O8+
- Molecular weight
- 526.6 g/mol
- IUPAC name
- 2-amino-6-[2-(4-amino-4-carboxybutyl)-3,5-bis(3-amino-3-carboxypropyl)pyridin-1-ium-1-yl]hexanoic acid
- SMILES
- C1=C(C=[N+](C(=C1CCC(C(=O)O)N)CCCC(C(=O)O)N)CCCCC(C(=O)O)N)CCC(C(=O)O)N
- InChIKey
- RGXCTRIQQODGIZ-UHFFFAOYSA-O
- XLogP
- -10.1
- Polar surface area
- 257 Ų
- H-bond donors
- 8
- H-bond acceptors
- 12
- Formal charge
- 1
via PubChem
Research
291 papers- Preparation of isodesmosine-KLH conjugate for ELISA system.Chirality · 2020
- Progress in the methodological strategies for the detection in real samples of desmosine and isodesmosine, two biological markers of elastin degradation.Journal of separation science · 2007
- [(13)C3,(15)N1]-labeled isodesmosine: A potential internal standard for LC-MS/MS analysis of desmosines in elastin degradation.Bioorganic & medicinal chemistry letters · 2015
- IsoChichibabin desmosine-(13)C(3),(15)N(1) synthesis and quantitative LC-MS/MS analysis of desmosine and isodesmosine in human skin.Bioorganic & medicinal chemistry · 2021
- Isotope-dilution LC-MS/MS analysis of the elastin crosslinkers desmosine and isodesmosine in acute cerebral stroke patients.RSC advances · 2022
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 526.288
Show 2 more facts
- canonical SMILES
- C1=C(C=[N+](C(=C1CCC(C(=O)O)N)CCCC(C(=O)O)N)CCCCC(C(=O)O)N)CCC(C(=O)O)N
- chemical formula
- C₂₄H₄₀N₅O₈⁺
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Isodesmosine is a lysine derivative found in elastin. Isodesmosine is an isomeric pyridinium-based amino acid resulting from the condensation of four lysine residues between elastin proteins by lysyl-oxidase. These represent ideal biomarkers for monitoring elastin turnover because these special cross-links are only found in mature elastin in mammals.
==See also== Desmosine
Excerpted from Wikipedia’s “isodesmosine” article, available under the CC BY-SA 4.0 licence.