ChemFOnt: Showing chemical card for Gliadorphin (CFc000040257)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:41:39 UTC

Chemfont ID

CFc000040257

Molecule Identification

Common Name

Gliadorphin

Definition

Gliadorphin (or gluteomorphin) is a 7-residue opioid peptide (Tyr-Pro-Gln-Pro-Gln-Pro-Phe) derived from the wheat protein gluten. Other related grains such as rye, barley and oats also contain the same sequence of amino acids found in gluten. Gliadorphin is very similar to casomorphin (a casein-derived peptide). Gliadorphin has been verified by mass spectrometry techniques to be present in urine samples of children with autism.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₄₃H₅₇N₉O₁₁

Average Molecular Weight

875.9664

Monoisotopic Molecular Weight

875.417753711

IUPAC Name

(2R)-2-({[(2R)-1-[(2S)-2-({[(2S)-1-[(2R)-2-({[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-4-(C-hydroxycarbonimidoyl)butanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-4-(C-hydroxycarbonimidoyl)butanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-phenylpropanoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CC1=CC=C(O)C=C1)C(=O)N1CCC[C@@]1([H])C(O)=N[C@]([H])(CCC(O)=N)C(=O)N1CCC[C@@]1([H])C(O)=N[C@@]([H])(CCC(O)=N)C(=O)N1CCC[C@]1([H])C(O)=N[C@]([H])(CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C43H57N9O11/c44-28(23-26-12-14-27(53)15-13-26)40(59)50-20-4-9-32(50)37(56)47-29(16-18-35(45)54)41(60)51-21-5-10-33(51)38(57)48-30(17-19-36(46)55)42(61)52-22-6-11-34(52)39(58)49-31(43(62)63)24-25-7-2-1-3-8-25/h1-3,7-8,12-15,28-34,53H,4-6,9-11,16-24,44H2,(H2,45,54)(H2,46,55)(H,47,56)(H,48,57)(H,49,58)(H,62,63)/t28-,29+,30-,31+,32-,33-,34+/m0/s1

InChI Key

QGFISQMZJLWFEE-HMJDZOACSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
Phenylalanine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
3-phenylpropanoic-acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
N-acylpyrrolidine
Phenol
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Monocyclic benzene moiety
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid
Carboxamide group
Amino acid or derivatives
Carboximidic acid
Carboximidic acid derivative
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organopnictogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Primary aliphatic amine
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0059786)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.084 g/L	ALOGPS
logP	-0.33	ALOGPS
logP	-2.1	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.54	ChemAxon
pKa (Strongest Basic)	8.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	330.41 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	247.23 m³·mol⁻¹	ChemAxon
Polarizability	88.68 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0059786

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gliadorphin

METLIN ID

Not Available

PubChem Compound

75358284

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Gliadorphin (CFc000040257)

MOL for CFc000040257 (Gliadorphin)

3D MOL for CFc000040257 (Gliadorphin)

3D SDF for CFc000040257 (Gliadorphin)

3D-SDF for CFc000040257 (Gliadorphin)

PDB for CFc000040257 (Gliadorphin)

3D PDB for CFc000040257 (Gliadorphin)

SMILES for CFc000040257 (Gliadorphin)

INCHI for CFc000040257 (Gliadorphin)

Structure for CFc000040257 (Gliadorphin)

3D Structure for CFc000040257 (Gliadorphin)