1.02011-09-21 00:39:00 UTC2015-07-21 06:57:59 UTCFDB024046QYNADQYNAD is an endogenous pentapeptide with the sequence Gln-Tyr-Asn-Ala-Asp (QYNAD in the international one letter code of amino acids), isolated from the cerebrospinal fluid (CSF) of patients with multiple sclerosis (MS) and Guillain-Barre syndrome (GBS). Immune mediated inflammatory neurological disorders like MS and GBS are characterized by demyelination and axonal damage. QYNAD can reversibly block voltage-gated sodium channels in a concentration-dependent manner. The blocking mechanism is a shift of the steady state inactivation curve of the sodium channels to more negative potentials, as with many local anaesthetics. QYNAD was found to reach concentrations in the CSF of MS or GBS that could subsantially block neuronal sodium channels. (PMID: 11750990) [HMDB]L-glutaminyl-L-tyrosyl-L-asparaginyl-L-alanyl-L-Aspartic acidC25H35N7O11609.5857609.239454997(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-carbamoylpropanamido]propanamido]butanedioic acid(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-carbamoylpropanamido]propanamido]butanedioic acid290814-98-1C[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@@H](N)CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(O)=OInChI=1S/C25H35N7O11/c1-11(21(38)32-17(25(42)43)10-20(36)37)29-23(40)16(9-19(28)35)31-24(41)15(8-12-2-4-13(33)5-3-12)30-22(39)14(26)6-7-18(27)34/h2-5,11,14-17,33H,6-10,26H2,1H3,(H2,27,34)(H2,28,35)(H,29,40)(H,30,39)(H,31,41)(H,32,38)(H,36,37)(H,42,43)/t11-,14-,15-,16-,17-/m0/s1WKBAPRRMZYHPNB-BXBUPLCLSA-N belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.OligopeptidesOrganic compoundsOrganic acids and derivativesCarboxylic acids and derivativesAmino acids, peptides, and analoguesAromatic homomonocyclic compounds1-hydroxy-2-unsubstituted benzenoidsAlanine and derivativesAlpha amino acid amidesAmino acidsAmphetamines and derivativesAsparagine and derivativesAspartic acid and derivativesCarbonyl compoundsCarboxylic acidsDicarboxylic acids and derivativesGlutamine and derivativesHydrocarbon derivativesMonoalkylaminesN-acyl aminesN-acyl-L-alpha-amino acidsOrganic oxidesOrganopnictogen compoundsPhenylalanine and derivativesPrimary carboxylic acid amidesSecondary carboxylic acid amidesTyrosine and derivatives1-hydroxy-2-unsubstituted benzenoidAlanine or derivativesAlpha-amino acid amideAlpha-amino acid or derivativesAlpha-oligopeptideAmineAmino acidAmino acid or derivativesAmphetamine or derivativesAromatic homomonocyclic compoundAsparagine or derivativesAspartic acid or derivativesBenzenoidCarbonyl groupCarboxamide groupCarboxylic acidDicarboxylic acid or derivativesFatty acylFatty amideGlutamine or derivativesHydrocarbon derivativeMonocyclic benzene moietyN-acyl-alpha amino acid or derivativesN-acyl-alpha-amino acidN-acyl-amineN-acyl-l-alpha-amino acidN-substituted-alpha-amino acidOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPhenolPhenylalanine or derivativesPrimary aliphatic aminePrimary aminePrimary carboxylic acid amideSecondary carboxylic acid amideTyrosine or derivativesSolidlogp-2.58logs-3.60solubility1.53e-01 g/llogp-7pka_strongest_acidic3.22pka_strongest_basic7.91iupac(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-carbamoylpropanamido]propanamido]butanedioic acidaverage_mass609.5857mono_mass609.239454997smilesC[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@@H](N)CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(O)=OformulaC25H35N7O11inchiInChI=1S/C25H35N7O11/c1-11(21(38)32-17(25(42)43)10-20(36)37)29-23(40)16(9-19(28)35)31-24(41)15(8-12-2-4-13(33)5-3-12)30-22(39)14(26)6-7-18(27)34/h2-5,11,14-17,33H,6-10,26H2,1H3,(H2,27,34)(H2,28,35)(H,29,40)(H,30,39)(H,31,41)(H,32,38)(H,36,37)(H,42,43)/t11-,14-,15-,16-,17-/m0/s1inchikeyWKBAPRRMZYHPNB-BXBUPLCLSA-Npolar_surface_area323.43refractivity142.79polarizability57.41rotatable_bond_count18acceptor_count12donor_count10physiological_charge-1formal_charge0Specdb::NmrOneD150480Specdb::NmrOneD150481Specdb::NmrOneD150482Specdb::NmrOneD150483Specdb::NmrOneD150484Specdb::NmrOneD150485Specdb::NmrOneD150486Specdb::NmrOneD150487Specdb::NmrOneD150488Specdb::NmrOneD150489Specdb::NmrOneD150490Specdb::NmrOneD150491Specdb::NmrOneD150492Specdb::NmrOneD150493Specdb::NmrOneD150494Specdb::NmrOneD150495Specdb::NmrOneD150496Specdb::NmrOneD150497Specdb::NmrOneD150498Specdb::NmrOneD150499Specdb::CMs13938Specdb::CMs39065Specdb::CMs497524Specdb::CMs497525Specdb::CMs497526Specdb::CMs497527Specdb::CMs497528Specdb::CMs497529Specdb::CMs497530Specdb::CMs497531Specdb::CMs497532Specdb::CMs497533Specdb::CMs497534Specdb::CMs497535Specdb::CMs497536Specdb::CMs497537Specdb::CMs497538Specdb::CMs497539Specdb::CMs497540Specdb::CMs497541Specdb::CMs497542Specdb::CMs497543Specdb::CMs497544Specdb::CMs497545Specdb::CMs497546Specdb::MsMs296743Specdb::MsMs296744Specdb::MsMs296745Specdb::MsMs338107Specdb::MsMs338108Specdb::MsMs338109Specdb::MsMs2330604Specdb::MsMs2330605Specdb::MsMs2330606Specdb::MsMs2635783Specdb::MsMs2635784Specdb::MsMs2635785HMDB06730#<Reference:0x0000555674ef3ba0>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