ChemFOnt: Showing chemical card for Indolylacryloylglycine (CFc000002615)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:32 UTC

Chemfont ID

CFc000002615

Molecule Identification

Common Name

Indolylacryloylglycine

Definition

Indolylacryloylglycine, also known as Indolyl-3-acrylogylglycine or IAG, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Indolylacryloylglycine is synthesized from tryptophan via indoleacrylic acid (IAcrA) through the conjugation of glycine to IAcrA via endogenous enzymes such as glycine N-acyltransferase (PMID: 10707769 ). The IAcrA must be first conjugated to CoA for this reaction to occur. The indoleacrylic acid is typically produced via microbially derived commensal Peptostreptococcus species (PMID: 28704649 ). IAG is also directly produced by L-tryptophan via certain mammalian gut microbes containing the enzyme tryptophan ammonia lyase (PMID: 25961404 ). Tryptophan ammonia lyase (EC 4.3.1.31) catalyzes the reaction of L-tryptophan to directly produce indole-3-acrylic acid and ammonia. This enzyme was initially characterized from the bacterium Rubrivivax benzoatilyticus JA2 (PMID: 25961404 ). It requires no cofactors and acts on L-phenylalanine and L-glutamate with about 60% of the activity of L-tryptophan, and on L-tyrosine, glycine, and L-alanine with about 30% of the activity (PMID: 25961404 ). Overall, IAG is both a microbial-host co-metabolite and a pure microbial metabolite. IAG may be a biomarker for autism spectrum disorders (PMID: 11858215 , PMID: 14523330 , PMID: 19697973 ). It has been reported that urinary levels of IAG are much higher in autistic children than in controls. However, these findings are controversial and have not been reproduced consistently (PMID: 27569540 , PMID: 27879968 ). Elevated urinary Indolylacryloylglycine may also be a marker for gastroinstestinal dysfunction (PMID: 19697973 ). Urinary Indolylacryloylglycine has also been reported as a potential biomarker to distinguish high-grade bladder cancer from low-grade bladder cancer (PMID: 29451296 ). Indolylacryloylglycine has been detected, but not quantified in, several different foods, such as chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and milk (cow). This could make indolylacryloylglycine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
IAG	HMDB
Indole-3-acryloyl-glycine	HMDB
Indoleacrylic glycine	HMDB
Indolyl acryloylglycine	HMDB
N-(3-(1-indol-3-yl)-1-oxo-2-Propenyl)glycine	HMDB
Indolylacryloylglycine, (e)-isomer	MeSH, HMDB
Indolyl-3-acryloylglycine	MeSH, HMDB
2-{[(2E)-1-hydroxy-3-(1H-indol-3-yl)prop-2-en-1-ylidene]amino}acetate	Generator, HMDB
Indolylacryloylglycine	MeSH

Chemical Formula

C₁₃H₁₂N₂O₃

Average Molecular Weight

244.246

Monoisotopic Molecular Weight

244.08479226

IUPAC Name

2-{[(2E)-1-hydroxy-3-(1H-indol-3-yl)prop-2-en-1-ylidene]amino}acetic acid

Traditional Name

{[(2E)-1-hydroxy-3-(1H-indol-3-yl)prop-2-en-1-ylidene]amino}acetic acid

CAS Registry Number

3475-68-1

SMILES

[H]\C(=C(\[H])C1=CNC2=CC=CC=C12)C(O)=NCC(O)=O

InChI Identifier

InChI=1S/C13H12N2O3/c16-12(15-8-13(17)18)6-5-9-7-14-11-4-2-1-3-10(9)11/h1-7,14H,8H2,(H,15,16)(H,17,18)/b6-5+

InChI Key

DUIFVCFSAWHIOD-AATRIKPKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Indole
Indole or derivatives
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Secondary carboxylic acid amide
Carboxamide group
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0006005)

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)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	1.75	ALOGPS
logP	1.8	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.03	ChemAxon
pKa (Strongest Basic)	2.37	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	85.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	67.47 m³·mol⁻¹	ChemAxon
Polarizability	25.58 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0006005

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023799

KNApSAcK ID

Not Available

Chemspider ID

4521424

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5370648

PDB ID

Not Available

ChEBI ID

145761

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Indolylacryloylglycine (CFc000002615)

MOL for CFc000002615 (Indolylacryloylglycine)

3D MOL for CFc000002615 (Indolylacryloylglycine)

3D SDF for CFc000002615 (Indolylacryloylglycine)

3D-SDF for CFc000002615 (Indolylacryloylglycine)

PDB for CFc000002615 (Indolylacryloylglycine)

3D PDB for CFc000002615 (Indolylacryloylglycine)

SMILES for CFc000002615 (Indolylacryloylglycine)

INCHI for CFc000002615 (Indolylacryloylglycine)

Structure for CFc000002615 (Indolylacryloylglycine)

3D Structure for CFc000002615 (Indolylacryloylglycine)