3,5-bis(3-amino-3-carboxypropyl)-4-(4-amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)pyridin-1-ium chloride

• ChemBase ID: 155618
• Molecular Formular: C24H40ClN5O8
• Molecular Mass: 562.0561
• Monoisotopic Mass: 561.25654095
• SMILES: c1c(c(c(c[n+]1CCCCC(C(=O)O)N)CCC(C(=O)O)N)CCCC(C(=O)O)N)CCC(C(=O)O)N.[Cl-]
• Canonical SMILES: NC(C(=O)O)CCc1c[n+](CCCCC(C(=O)O)N)cc(c1CCCC(C(=O)O)N)CCC(C(=O)O)N.[Cl-]
• InChI: InChI=1S/C24H39N5O8.ClH/c25-17(21(30)31)5-1-2-11-29-12-14(7-9-19(27)23(34)35)16(4-3-6-18(26)22(32)33)15(13-29)8-10-20(28)24(36)37;/h12-13,17-20H,1-11,25-28H2,(H3-,30,31,32,33,34,35,36,37);1H
• InChIKey: FUPMLZCXPJSGPV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-bis(3-amino-3-carboxypropyl)-4-(4-amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)pyridin-1-ium chloride
• IUPAC Traditional name: desmosine chloride
• Synonyms: Desmosine chloride

Database IDs

• CAS Number: 10019-68-8
• MDL Number: MFCD12910449
• PubChem SID: 162249756
• PubChem CID: 71312174

CALCULATED PROPERTIES

• Acid pKa: 1.0354433
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -13.231828
• LogD (pH = 7.4): -13.243819
• Log P: -13.23201
• Molar Refractivity: 133.5261 cm^3
• Polarizability: 52.80016 Å^3
• Polar Surface Area: 257.16 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 99.5%±0.2%
• Biological Source: from bovine
• Purified By: chromatography (and purified by solvent extraction)
• Empirical Formula (Hill Notation): C24H40ClN5O8

DETAILS

Sigma Aldrich - D9439

Analysis Note
Calibrated by UV and amino acid analysis.
Application
Assays for free or urinary desmosine are often used as markers for disease states characterized by elastin degradation (e.g., emphysema).1 Conversely, excessive levels of incorporated desmosine are indicators of fibrotic conditions (e.g., cirrhosis).2
Desmosine chloride is often used in assays for free or urinary desmosine as markers for disease states characterized by elastin degradation (e.g., emphysema). Elastin degradation has shown strong correlation with vascular calcification, and pretreatment with aluminum ions can inhibit the binding of matrix metalloproteinase (MMP) to elastin.
Biochem/physiol Actions
Desmosine is a polyfunctional amino acid that forms cross-links in mature elastin.3
Caution
Extremely hygroscopic
General description
Each vial contains 1 μmole of purified desmosine.