ContaminantDB: Indolylacryloylglycine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 07:09:30 UTC

Update Date

2016-11-09 01:21:25 UTC

Accession Number

CHEM036014

Identification

Common Name

Indolylacryloylglycine

Class

Small Molecule

Description

Indolylacryloylglycine, also known as IAG or indoleacrylic glycine, 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 possibly soluble (in water) and a moderately basic compound (based on its pKa).

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical 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 Mass

244.246 g/mol

Monoisotopic Mass

244.085 g/mol

CAS Registry Number

3475-68-1

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

SMILES

OC(=O)CNC(=O)\C=C\C1=CNC2=CC=CC=C12

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

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1910000000-af9421f979b84f7c1d21	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-5920000000-34a6af95e2fa1e07e867	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-4590000000-bfd50d5180c6bd14c6cd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-9710000000-8b4ac64ee5199a960b5e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056u-7900000000-12988d991d4fb8d3f60c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0190000000-4a969f2be20f7b81f7fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-6890000000-d7bb4b025f6e9caddfc7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fu-9400000000-0ac0d883ab78f58631e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-006x-0960000000-27152d1fd1bb75d52117	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-2920000000-95b20ae472699500646a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0900000000-e1ada5cb92852f044560	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0190000000-d2eeedccf34de3bbcbb5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-0910000000-19365eb3817e6e25ff6f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0900000000-e7f97c6d0f9554f2ee7a	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0006005

FooDB ID

FDB023799

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

4521424

ChEBI ID

145761

PubChem Compound ID

5370648

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.

2. Bull G, Shattock P, Whiteley P, Anderson R, Groundwater PW, Lough JW, Lees G: Indolyl-3-acryloylglycine (IAG) is a putative diagnostic urinary marker for autism spectrum disorders. Med Sci Monit. 2003 Oct;9(10):CR422-5.

3. Wright B, Brzozowski AM, Calvert E, Farnworth H, Goodall DM, Holbrook I, Imrie G, Jordan J, Kelly A, Miles J, Smith R, Town J: Is the presence of urinary indolyl-3-acryloylglycine associated with autism spectrum disorder? Dev Med Child Neurol. 2005 Mar;47(3):190-2.

4. Anderson RJ, Bendell DJ, Garnett I, Groundwater PW, Lough WJ, Mills MJ, Savery D, Shattock PE: Identification of indolyl-3-acryloylglycine in the urine of people with autism. J Pharm Pharmacol. 2002 Feb;54(2):295-8.

Indolylacryloylglycine (CHEM036014)

Structure for CHEM036014: Indolylacryloylglycine