MiMeDB: Showing metabocard for N-ethylglycine (MMDBc0054585)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:19:25 UTC

Update Date

2024-04-30 20:54:27 UTC

Metabolite ID

MMDBc0054585

Metabolite Identification

Common Name

N-ethylglycine

Description

N-Ethylglycine, also known as EG, belongs to the family of compounds 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). N-ethylglyicne is a known metabolite of the anesthesia drug lidocaine (PMID: 25932687 ). N-ethylglyicne is also an endogenously produced metabolite and appears in normal subjects’ urine in small amounts, but its presence is significantly higher in patients with metastatic bone disease (PMID: 16962088 ). Research has shown that it is lidocaine’s metabolites, n-ethylglycine and monoethylglycinexylidide inhibit GlyT1-mediated uptake of glycine. N-ethylglycine acts as a substrate for the glycine transporter GlyT1 (PMID: 22133759 , 25932687 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
EtGly	ChEBI
2-Ethylaminoacetic acid	HMDB

Molecular Formula

C₄H₉NO₂

Average Mass

103.1198

Monoisotopic Mass

103.063328537

IUPAC Name

2-(ethylamino)acetic acid

Traditional Name

N-ethylglycine

CAS Registry Number

Not Available

SMILES

CCNCC(O)=O

InChI Identifier

InChI=1S/C4H9NO2/c1-2-5-3-4(6)7/h5H,2-3H2,1H3,(H,6,7)

InChI Key

YPIGGYHFMKJNKV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Amino acid
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-alkylglycine (CHEBI:15620 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	263 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-2.8	ChemAxon
logS	0.41	ALOGPS
pKa (Strongest Acidic)	2.2	ChemAxon
pKa (Strongest Basic)	10.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	25.53 m³·mol⁻¹	ChemAxon
Polarizability	10.65 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-008a-0910000000-db6dc229f7ca12407db5	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001i-0900000000-f9f61c44b73aa9770901	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-008a-0910000000-db6dc229f7ca12407db5	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001i-0900000000-f9f61c44b73aa9770901	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9000000000-cb0320b1cbc01c10a830	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9100000000-fb5c379e456a390a144d	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zfr-9700000000-d390c9cee5c2046e400d	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9100000000-d8102bae4c29ac62b12a	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6u-9000000000-e0cddad6a53d4b2b97d7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3900000000-fd3c7dd4afd6e6d27609	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-6900000000-08351f25a42addb8e6bb	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abc-9000000000-21da41b0e896a34f7538	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-7900000000-b440649bfd24bee54888	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-9de545e1bbd717216162	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-214368c7b616c9196bd4	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-1900000000-9a46b26bf3138de0b565	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-1785c2eff225a46f27cb	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-0c602ba2e23e7a22f3d7	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0013123	Water	ethylamine	Glycine oxidase	Oxidation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	3	Human feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0041945

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alpha-Aminobutyric acid

METLIN ID

Not Available

PubChem Compound

6992079

PDB ID

Not Available

ChEBI ID

15620

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Tsuruta Y, Matsumoto M, Inoue H, Munemura S, Ishizu T, Yamano S, Iguchi H: Identification of N-ethylglycine in urine of cancer patients with metastatic bone disease. Clin Chim Acta. 2007 Feb;376(1-2):226-8. doi: 10.1016/j.cca.2006.07.023. Epub 2006 Jul 28. [PubMed:16962088 ]
Werdehausen R, Kremer D, Brandenburger T, Schlosser L, Jadasz J, Kury P, Bauer I, Aragon C, Eulenburg V, Hermanns H: Lidocaine metabolites inhibit glycine transporter 1: a novel mechanism for the analgesic action of systemic lidocaine? Anesthesiology. 2012 Jan;116(1):147-58. doi: 10.1097/ALN.0b013e31823cf233. [PubMed:22133759 ]
Werdehausen R, Mittnacht S, Bee LA, Minett MS, Armbruster A, Bauer I, Wood JN, Hermanns H, Eulenburg V: The lidocaine metabolite N-ethylglycine has antinociceptive effects in experimental inflammatory and neuropathic pain. Pain. 2015 Sep;156(9):1647-1659. doi: 10.1097/j.pain.0000000000000206. [PubMed:25932687 ]

Showing metabocard for N-ethylglycine (MMDBc0054585)

MOL for #<Metabolite:0x00007fa4ae432038>

3D MOL for #<Metabolite:0x00007fa4ae432038>

3D SDF for #<Metabolite:0x00007fa4ae432038>

3D-SDF for #<Metabolite:0x00007fa4ae432038>

PDB for #<Metabolite:0x00007fa4ae432038>

3D PDB for #<Metabolite:0x00007fa4ae432038>

SMILES for #<Metabolite:0x00007fa4ae432038>

INCHI for #<Metabolite:0x00007fa4ae432038>

Structure for #<Metabolite:0x00007fa4ae432038>

3D Structure for #<Metabolite:0x00007fa4ae432038>