1.0 2010-04-08 22:04:36 UTC 2025-11-18 22:19:10 UTC FDB000516 Desmosine 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. 4-(4-amino-4-Carboxybutyl)-1-(5-amino-5-carboxypentyl)-3,5-bis(3-amino-3-carboxypropyl)pyridinium 4-(4-Amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)-3,5-bis(3-amino-3-carboxypropyl)pyridinium, 9CI C24H40N5O8 526.6031 526.287688281 3,5-bis(3-amino-3-carboxypropyl)-4-(4-amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)pyridin-1-ium desmosine 11003-57-9 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 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 VEVRNHHLCPGNDU-UHFFFAOYSA-O belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Tetracarboxylic acids and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Tetracarboxylic acids and derivatives Aromatic heteromonocyclic compounds Alpha amino acids Amino acids Aralkylamines Azacyclic compounds Carbonyl compounds Carboxylic acids Heteroaromatic compounds Hydrocarbon derivatives Monoalkylamines Organic cations Organic oxides Organopnictogen compounds Pyridinium derivatives Alpha-amino acid Alpha-amino acid or derivatives Amine Amino acid Amino acid or derivatives Aralkylamine Aromatic heteromonocyclic compound Azacycle Carbonyl group Carboxylic acid Heteroaromatic compound Hydrocarbon derivative Organic cation Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Pyridine Pyridinium Tetracarboxylic acid or derivatives Solid logp -4.54 ALOGPS logs -4.69 ALOGPS solubility 1.15e-02 g/l ALOGPS logp -13 ChemAxon pka_strongest_acidic 1.04 ChemAxon pka_strongest_basic 10.12 ChemAxon iupac 3,5-bis(3-amino-3-carboxypropyl)-4-(4-amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)pyridin-1-ium ChemAxon average_mass 526.6031 ChemAxon mono_mass 526.287688281 ChemAxon 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 ChemAxon formula C24H40N5O8 ChemAxon inchi 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 ChemAxon inchikey VEVRNHHLCPGNDU-UHFFFAOYSA-O ChemAxon polar_surface_area 257.16 ChemAxon refractivity 133.53 ChemAxon polarizability 56.68 ChemAxon rotatable_bond_count 19 ChemAxon acceptor_count 12 ChemAxon donor_count 8 ChemAxon physiological_charge 1 ChemAxon formal_charge 1 ChemAxon HMDB00572 37628 #<Reference:0x00007f093c1a6138> #<Reference:0x00007f093c1a5eb8> #<Reference:0x00007f093c1a5d00> #<Reference:0x00007f093c1a5a80> #<Reference:0x00007f093c1a58c8> #<Reference:0x00007f093c1a5648> #<Reference:0x00007f093c1a5490> #<Reference:0x00007f093c1a5210> #<Reference:0x00007f093c1a5058> #<Reference:0x00007f093c1a4ea0> #<Reference:0x00007f093c1a4b08> #<Reference:0x00007f093c1a48d8> #<Reference:0x00007f093c1a4658> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823