| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:04:36 UTC |
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| Update date | 2019-11-26 02:54:55 UTC |
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| Primary ID | FDB000516 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Desmosine |
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| Description | Degradation production of Elastin
Desmosine is formed by condensation of four molecules of lysine into a pyridinium ring.; Elastin molecules aggregate in the extracellular space where they are crosslinked by stable desmosine bridges. The resulting polymer is structurally organized as branched fibers and lamellae, which, in skin, are wider (a few microns) in the deep dermis and become progressively thinner (fraction of a micron) towards the papillary dermis. Several general and local factors seem to regulate elastin gene expression, deposition and degradation. (PMID: 9297692); Desmosines are crosslinking amino acids unique to mature elastin in humans. Owing to this unicity, they have been discussed as potentially indicators of connective tissue disorders whose clinical manifestations are mostly the result of elastin degradation. (PMID: 17390614); Emphysema (Pulmonary emphysema is a devastating disease for which there is no effective treatment) is associated with degradation of elastic fibers (PMID: 14704646); It has been shown that the urinary concentration of elastin specific crosslinks, desmosine correlates well with liver fibrosis score in biopsy specimens from patients with liver disease secondary to hepatitis C virus and alcohol. (PMID: 10996125). Desmosine is found in animal foods. |
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| CAS Number | 11003-57-9 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | |
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| Chemical Formula | C24H40N5O8 |
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| IUPAC name | 3,5-bis(3-amino-3-carboxypropyl)-4-(4-amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)pyridin-1-ium |
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| InChI Identifier | InChI=1S/C24H39N5O8/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)/p+1 |
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| InChI Key | VEVRNHHLCPGNDU-UHFFFAOYSA-O |
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| Isomeric SMILES | NC(CCCC[N+]1=CC(CCC(N)C(O)=O)=C(CCCC(N)C(O)=O)C(CCC(N)C(O)=O)=C1)C(O)=O |
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| Average Molecular Weight | 526.6031 |
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| Monoisotopic Molecular Weight | 526.287688281 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Tetracarboxylic acids and derivatives |
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| Direct Parent | Tetracarboxylic acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Tetracarboxylic acid or derivatives
- Alpha-amino acid
- Alpha-amino acid or derivatives
- Aralkylamine
- Pyridine
- Pyridinium
- Heteroaromatic compound
- Amino acid or derivatives
- Amino acid
- Azacycle
- Organoheterocyclic compound
- Carboxylic acid
- Organic nitrogen compound
- Organic oxygen compound
- Organic oxide
- Organopnictogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Hydrocarbon derivative
- Amine
- Organic cation
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Solid | |
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| Physical Description | Not Available | |
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| Mass Composition | C 54.74%; H 7.66%; N 13.30%; O 24.31% | DFC |
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| Melting Point | Not Available | |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | Not Available | |
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| Spectroscopic UV Data | Not Available | |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | Not Available |
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| External Links |
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| ChemSpider ID | Not Available |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | 53477704 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 37628 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB00572 |
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| CRC / DFC (Dictionary of Food Compounds) ID | BDC57-J:BDC57-J |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | Not Available |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Desmosine |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | |
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