1.0 2011-09-21 00:39:00 UTC 2015-07-21 06:57:59 UTC FDB024046 QYNAD QYNAD 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 acid C25H35N7O11 609.5857 609.239454997 (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 acid 290814-98-1 C[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)=O InChI=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/s1 WKBAPRRMZYHPNB-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. Oligopeptides Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alanine and derivatives Alpha amino acid amides Amino acids Amphetamines and derivatives Asparagine and derivatives Aspartic acid and derivatives Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Glutamine and derivatives Hydrocarbon derivatives Monoalkylamines N-acyl amines N-acyl-L-alpha-amino acids Organic oxides Organopnictogen compounds Phenylalanine and derivatives Primary carboxylic acid amides Secondary carboxylic acid amides Tyrosine and derivatives 1-hydroxy-2-unsubstituted benzenoid Alanine or derivatives Alpha-amino acid amide Alpha-amino acid or derivatives Alpha-oligopeptide Amine Amino acid Amino acid or derivatives Amphetamine or derivatives Aromatic homomonocyclic compound Asparagine or derivatives Aspartic acid or derivatives Benzenoid Carbonyl group Carboxamide group Carboxylic acid Dicarboxylic acid or derivatives Fatty acyl Fatty amide Glutamine or derivatives Hydrocarbon derivative Monocyclic benzene moiety N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-amine N-acyl-l-alpha-amino acid N-substituted-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol Phenylalanine or derivatives Primary aliphatic amine Primary amine Primary carboxylic acid amide Secondary carboxylic acid amide Tyrosine or derivatives Solid logp -2.58 ALOGPS logs -3.60 ALOGPS solubility 1.53e-01 g/l ALOGPS logp -7 ChemAxon pka_strongest_acidic 3.22 ChemAxon pka_strongest_basic 7.91 ChemAxon iupac (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-carbamoylpropanamido]propanamido]butanedioic acid ChemAxon average_mass 609.5857 ChemAxon mono_mass 609.239454997 ChemAxon smiles C[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)=O ChemAxon formula C25H35N7O11 ChemAxon inchi InChI=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/s1 ChemAxon inchikey WKBAPRRMZYHPNB-BXBUPLCLSA-N ChemAxon polar_surface_area 323.43 ChemAxon refractivity 142.79 ChemAxon polarizability 57.41 ChemAxon rotatable_bond_count 18 ChemAxon acceptor_count 12 ChemAxon donor_count 10 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 150480 Specdb::NmrOneD 150481 Specdb::NmrOneD 150482 Specdb::NmrOneD 150483 Specdb::NmrOneD 150484 Specdb::NmrOneD 150485 Specdb::NmrOneD 150486 Specdb::NmrOneD 150487 Specdb::NmrOneD 150488 Specdb::NmrOneD 150489 Specdb::NmrOneD 150490 Specdb::NmrOneD 150491 Specdb::NmrOneD 150492 Specdb::NmrOneD 150493 Specdb::NmrOneD 150494 Specdb::NmrOneD 150495 Specdb::NmrOneD 150496 Specdb::NmrOneD 150497 Specdb::NmrOneD 150498 Specdb::NmrOneD 150499 Specdb::MsMs 296743 Specdb::MsMs 296744 Specdb::MsMs 296745 Specdb::MsMs 338107 Specdb::MsMs 338108 Specdb::MsMs 338109 Specdb::MsMs 2330604 Specdb::MsMs 2330605 Specdb::MsMs 2330606 Specdb::MsMs 2635783 Specdb::MsMs 2635784 Specdb::MsMs 2635785 Specdb::CMs 13938 Specdb::CMs 39065 Specdb::CMs 497524 Specdb::CMs 497525 Specdb::CMs 497526 Specdb::CMs 497527 Specdb::CMs 497528 Specdb::CMs 497529 Specdb::CMs 497530 Specdb::CMs 497531 Specdb::CMs 497532 Specdb::CMs 497533 Specdb::CMs 497534 Specdb::CMs 497535 Specdb::CMs 497536 Specdb::CMs 497537 Specdb::CMs 497538 Specdb::CMs 497539 Specdb::CMs 497540 Specdb::CMs 497541 Specdb::CMs 497542 Specdb::CMs 497543 Specdb::CMs 497544 Specdb::CMs 497545 Specdb::CMs 497546 HMDB06730 #<Reference:0x000055ce30731370> 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