1.02010-04-08 22:04:36 UTC2019-11-26 02:54:55 UTCFDB000516DesmosineDegradation 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)pyridinium4-(4-Amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)-3,5-bis(3-amino-3-carboxypropyl)pyridinium, 9CIC24H40N5O8526.6031526.2876882813,5-bis(3-amino-3-carboxypropyl)-4-(4-amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)pyridin-1-iumdesmosine11003-57-9NC(CCCC[N+]1=CC(CCC(N)C(O)=O)=C(CCCC(N)C(O)=O)C(CCC(N)C(O)=O)=C1)C(O)=OInChI=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+1VEVRNHHLCPGNDU-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 derivativesOrganic compoundsOrganic acids and derivativesCarboxylic acids and derivativesTetracarboxylic acids and derivativesAromatic heteromonocyclic compoundsAlpha amino acidsAmino acidsAralkylaminesAzacyclic compoundsCarbonyl compoundsCarboxylic acidsHeteroaromatic compoundsHydrocarbon derivativesMonoalkylaminesOrganic cationsOrganic oxidesOrganopnictogen compoundsPyridinium derivativesAlpha-amino acidAlpha-amino acid or derivativesAmineAmino acidAmino acid or derivativesAralkylamineAromatic heteromonocyclic compoundAzacycleCarbonyl groupCarboxylic acidHeteroaromatic compoundHydrocarbon derivativeOrganic cationOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPrimary aliphatic aminePrimary aminePyridinePyridiniumTetracarboxylic acid or derivativesSolidlogp-4.54logs-4.69solubility1.15e-02 g/llogp-13pka_strongest_acidic1.04pka_strongest_basic10.12iupac3,5-bis(3-amino-3-carboxypropyl)-4-(4-amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)pyridin-1-iumaverage_mass526.6031mono_mass526.287688281smilesNC(CCCC[N+]1=CC(CCC(N)C(O)=O)=C(CCCC(N)C(O)=O)C(CCC(N)C(O)=O)=C1)C(O)=OformulaC24H40N5O8inchiInChI=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+1inchikeyVEVRNHHLCPGNDU-UHFFFAOYSA-Opolar_surface_area257.16refractivity133.53polarizability56.68rotatable_bond_count19acceptor_count12donor_count8physiological_charge1formal_charge1HMDB0057237628#<Reference:0x0000555675b2c048>#<Reference:0x0000555675b2ba30>#<Reference:0x0000555675b2b828>#<Reference:0x0000555675b2b670>#<Reference:0x0000555675b2b3f0>#<Reference:0x0000555675b2b0d0>#<Reference:0x0000555675b2aec8>#<Reference:0x0000555675b2a9c8>#<Reference:0x0000555675b2a6a8>#<Reference:0x0000555675b2a3d8>#<Reference:0x0000555675b2a1f8>#<Reference:0x0000555675b29de8>#<Reference:0x0000555675b29aa0>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823