ChemFOnt: Showing chemical card for QYNAD (CFc000002893)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:53 UTC

Chemfont ID

CFc000002893

Molecule Identification

Common Name

QYNAD

Definition

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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
L-Glutaminyl-L-tyrosyl-L-asparaginyl-L-alanyl-L-aspartic acid	HMDB
Glutaminyl-tyrosyl-asparaginyl-alanyl-aspartate	MeSH, HMDB
Pentapeptide qynad	MeSH, HMDB
GLN-Tyr-asn-ala-asp	MeSH, HMDB
(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxypropylidene]amino}butanedioate	Generator, HMDB

Chemical Formula

C₂₅H₃₅N₇O₁₁

Average Molecular Weight

609.5857

Monoisotopic Molecular Weight

609.239454997

IUPAC Name

(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-carbamoylpropanamido]propanamido]butanedioic acid

Traditional Name

(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-carbamoylpropanamido]propanamido]butanedioic acid

CAS Registry Number

290814-98-1

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

InChI Identifier

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

InChI Key

WKBAPRRMZYHPNB-BXBUPLCLSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Tyrosine or derivatives
Phenylalanine or derivatives
Glutamine or derivatives
Aspartic acid or derivatives
Asparagine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alanine or derivatives
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
Phenol
1-hydroxy-2-unsubstituted benzenoid
N-acyl-amine
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty amide
Secondary carboxylic acid amide
Primary carboxylic acid amide
Carboxamide group
Amino acid
Amino acid or derivatives
Carboxylic acid
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Carbonyl group
Primary amine
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Organic oxygen compound
Primary aliphatic amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Cerebrospinal Fluid (CSF) (PMID: 11293697)
Cerebrospinal fluid (HMDB: HMDB0006730)

Source

Endogenous

Endogenous (HMDB: HMDB0006730)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-7	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.22	ChemAxon
pKa (Strongest Basic)	7.91	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	323.43 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	142.79 m³·mol⁻¹	ChemAxon
Polarizability	57.41 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0006730

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024046

KNApSAcK ID

C00010511

Chemspider ID

8364591

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10189090

PDB ID

Not Available

ChEBI ID

88777

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Brinkmeier, Heinrich; Aulkemeyer, Peter; Wollinsky, Kurt H.; Rodel, Reinhardt. An endogenous pentapeptide acting as a sodium channel blocker in inflammatory autoimmune disorders of the central nervous system. Nature Medicine (New York) (2000), 6(7), 808-811.

Showing chemical card for QYNAD (CFc000002893)

MOL for CFc000002893 (QYNAD)

3D MOL for CFc000002893 (QYNAD)

3D SDF for CFc000002893 (QYNAD)

3D-SDF for CFc000002893 (QYNAD)

PDB for CFc000002893 (QYNAD)

3D PDB for CFc000002893 (QYNAD)

SMILES for CFc000002893 (QYNAD)

INCHI for CFc000002893 (QYNAD)

Structure for CFc000002893 (QYNAD)

3D Structure for CFc000002893 (QYNAD)