P. aeruginosa Metabolome Database: Dehydroglycine (PAMDB001730)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB001730

Identification

Name:

Dehydroglycine

Description:

Dehydroglycine is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).Dehydroglycine is catalyzed by ThiH. ThiH is a tyrosine lyase that cleaves the C alpha-C beta bond of tyrosine, generating p-cresol as a by-product, to form dehydroglycine. (PMID 19923213)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

2-Iminoacetate
2-Iminoacetic acid
Dehydroglycine
Iminoacetate
Iminoacetic acid

Chemical Formula:

C₂H₂NO₂

Average Molecular Weight:

72.0428

Monoisotopic Molecular Weight:

72.008553313

InChI Key:

TVMUHOAONWHJBV-UHFFFAOYSA-M

InChI:

InChI=1S/C2H3NO2/c3-1-2(4)5/h1,3H,(H,4,5)/p-1

CAS number:

Not Available

IUPAC Name:

2-iminoacetate

Traditional IUPAC Name:

2-iminoacetate

SMILES:

[O-]C(=O)C=N

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as carboxylic acid salts. These are ionic derivatives of carboxylic acid.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid salts

Alternative Parents

Substituents

Carboxylic acid salt
Aldimine
Primary aldimine
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxylic acid anion (CHEBI:53664 )
a small molecule (CPD-12279 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	9.41 mg/mL	ALOGPS
logP	-0.94	ALOGPS
logP	-0.77	ChemAxon
logS	-0.98	ALOGPS
pKa (Strongest Acidic)	3.93	ChemAxon
pKa (Strongest Basic)	3.27	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.98 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.81 m³·mol^-1	ChemAxon
Polarizability	5.49 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Adenosine triphosphate + Dehydroglycine + 1-Deoxy-D-xylulose 5-phosphate + Hydrogen ion + IscS with bound sulfur + NADPH > 4-Methyl-5-(2-phosphoethyl)-thiazole + Adenosine monophosphate + Carbon dioxide +2 Water + IscS sulfur acceptor protein + NADP + Pyrophosphate
S-Adenosylmethionine + NADPH + L-Tyrosine > p-Cresol + 5'-Deoxyadenosine + Dehydroglycine + Hydrogen ion + L-Methionine + NADP
Dehydroglycine + Water > Glyoxylic acid + Ammonia
L-Tyrosine + S-Adenosylmethionine + a reduced electron acceptor > Dehydroglycine + p-Cresol + 5'-Deoxyadenosine + L-Methionine + an oxidized electron acceptor + Hydrogen ion

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-7f7accee9d40e6bcea83	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-0266621f8a393599804c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-9000000000-1ab9d2576000afcc6a2f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-a0b230949457ea313c0a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-7c54e28c865a42d485a3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-9000000000-152493d50467ffb1c8bf	View in MoNA

References

References:

Challand, M. R., Martins, F. T., Roach, P. L. (2010). "Catalytic activity of the anaerobic tyrosine lyase required for thiamine biosynthesis in Escherichia coli." J Biol Chem 285:5240-5248. Pubmed: 19923213
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	53664
HMDB ID	Not Available
Pubchem Compound ID	23347814
Kegg ID	Not Available
ChemSpider ID	15272272
Wikipedia ID	Not Available
BioCyc ID	CPD-12279
EcoCyc ID	CPD-12279

Dehydroglycine (PAMDB001730)

Structure for Dehydroglycine (PAMDB001730)