desmosine

Desmosine is an amino acid found uniquely in elastin, a protein found in connective tissue such as skin, lungs, and elastic arteries.

Chemical data

Formula: C24H40N5O8+
Molecular weight: 526.6 g/mol
IUPAC name: (2S)-2-amino-6-[4-[(4S)-4-amino-4-carboxybutyl]-3,5-bis[(3S)-3-amino-3-carboxypropyl]pyridin-1-ium-1-yl]hexanoic acid
SMILES: C1=C(C(=C(C=[N+]1CCCC[C@@H](C(=O)O)N)CC[C@@H](C(=O)O)N)CCC[C@@H](C(=O)O)N)CC[C@@H](C(=O)O)N
InChIKey: VEVRNHHLCPGNDU-MUGJNUQGSA-O
XLogP: -10.2
Polar surface area: 257 Å²
H-bond donors: 8
H-bond acceptors: 12
Formal charge: 1

via PubChem

Research

721 papers

Desmosine in Aortic Disease: Biology, Measurement, and Clinical Applications in Aortic Pathologies.Journal of clinical medicine · 2026
Desmosine as a biomarker for the emergent properties of pulmonary emphysema.Frontiers in medicine · 2023
Plasma Desmosine and Abdominal Aortic Aneurysm Disease.Journal of the American Heart Association · 2019
Fingerprinting desmosine-containing elastin peptides.Journal of the American Society for Mass Spectrometry · 2015
Plasma desmosine for prediction of outcomes after acute myocardial infarction.Frontiers in cardiovascular medicine · 2022

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 526.28713966009

Show 4 more facts

chemical formula: C₂₄H₄₀N₅O₈
canonical SMILES: C1=C(C(=C(C=[N+]1CCCCC(C(=O)O)N)CCC(C(=O)O)N)CCCC(C(=O)O)N)CCC(C(=O)O)N
Commons category: Desmosine
isomeric SMILES: C1=C(C(=C(C=[N+]1CCCC[C@@H](C(=O)O)N)CC[C@@H](C(=O)O)N)CCC[C@@H](C(=O)O)N)CC[C@@H](C(=O)O)N

Sources (3)

via Wikidata · CC0

~11 min read

Encyclopedic overview

11 sections

Contents

Structure
Synthesis
Biosynthesis
Lab Synthesis
Bonding
Bonding in elastin/collagen
Function
Material properties
Current usage in medicine
Application of desmosine
References

{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 441687359 | ImageFile = Desmosine Structural Formulae V.1.svg | ImageSize = 300px | IUPACName = 6-{4-[(4S)-4-Amino-4-carboxybutyl]-3,5-bis[(3S)-3-amino-3-carboxypropyl]-1-pyridiniumyl}-L-norleucine | OtherNames = |Section1= |Section2= |Section3= }}

Desmosine is an amino acid found uniquely in elastin, a protein found in connective tissue such as skin, lungs, and elastic arteries.

Excerpted from Wikipedia’s “desmosine” article, available under the CC BY-SA 4.0 licence.