MiMeDB: Showing metabocard for Propionylglycine (MMDBc0000545)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:40:12 UTC

Update Date

2024-04-30 19:32:57 UTC

Metabolite ID

MMDBc0000545

Metabolite Identification

Common Name

Propionylglycine

Description

Propionylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:acyl-CoA + glycine < -- > CoA + N-acylglycineThe level of propionylglycine is elevated in patients with propionic acidemia, which is an inherited deficiency of propionyl-CoA carboxylase. (Disorders of propionate and methylmalonate metabolism. In The Metabolic and Molecular Bases of Inherited Disease).

Structure

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

Synonyms

Value	Source
2-Propanamidoacetic acid	ChEBI
N-Propionyl-glycine	ChEBI
N-Propionylglycine	ChEBI
Propanamidoacetic acid	ChEBI
Propanoylglycine	ChEBI
Propionylaminoacetic acid	ChEBI
2-Propanamidoacetate	Generator
Propanamidoacetate	Generator
Propionylaminoacetate	Generator

Molecular Formula

C₅H₉NO₃

Average Mass

131.1299

Monoisotopic Mass

131.058243159

IUPAC Name

2-propanamidoacetic acid

Traditional Name

propionylglycine

CAS Registry Number

Not Available

SMILES

CCC(=O)NCC(O)=O

InChI Identifier

InChI=1S/C5H9NO3/c1-2-4(7)6-3-5(8)9/h2-3H2,1H3,(H,6,7)(H,8,9)

InChI Key

WOMAZEJKVZLLFE-UHFFFAOYSA-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
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	33.4 g/L	ALOGPS
logP	-0.44	ALOGPS
logP	-0.63	ChemAxon
logS	-0.59	ALOGPS
pKa (Strongest Acidic)	3.93	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	30.07 m³·mol⁻¹	ChemAxon
Polarizability	12.6 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-acef9a740ced48fb00e5	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9200000000-3c7887407ce148e2cf1f	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 (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-9000000000-b5e80be4de97e1de4998	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-be56348c0dca03c02203	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9000000000-39baca715a0a4ac09f6d	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-a542f238b72f94710754	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0a4i-9000000000-f003324aa699706d4194	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-41c8ac7e6950711c9df3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-9000000000-b0a4f15698d2fadefea4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-9000000000-c7b66f7421e9853fc994	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-053r-8900000000-60899826a66d302aa237	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9000000000-a71e372fed182c0edcd0	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-680ef8911029bf2b3421	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2900000000-15bf873be2a495ed8e12	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0089-9800000000-e11bb20c11f7905d489f	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-9000000000-5714cacb51d7e4829db2	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-f90d0d3f7ca3b7f6fcac	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a70-9000000000-b2276b1a1287ab61619d	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-25bcb7a92417ed5e9938	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9100000000-0976ec7bea067ea09d0e	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-9000000000-da3ce82cba870fdddfb2	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-9000000000-fa643a49d9a9e8d5e94a	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Urine

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
MMDBp0194143	Glycine N-acyltransferase	Enzyme	Q6IB77	Homo sapiens
MMDBp0194144	Glycine N-acyltransferase-like protein 1	Enzyme	Q969I3	Homo sapiens
MMDBp0194145	Glycine N-acyltransferase-like protein 2	Enzyme	Q8WU03	Homo sapiens
MMDBp0194146	Glycine N-acyltransferase-like protein 3	Enzyme	Q5SZD4	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0008599	Glycine	Coenzyme A	Glycine-n-acyltransferase	VMH	30371894
MMDBr0008600	Propionylglycine	Propionylglycine	Not Available	VMH	30371894
MMDBr0008601	Propionylglycine	Propionylglycine	Not Available	VMH	30371894

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	2	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified						HMDB
Human Urine	Detected and Quantified	0.0591‚Äì0.4024	umol/mmol creatinine	Adult (25-30 years old)	Both		HMDB	23062437
Human Urine	Detected and Quantified	0.0609‚Äì0.6300	umol/mmol creatinine	Adult (25-30 years old)	Both		HMDB	23062437
Human Urine	Detected and Quantified	0.0864‚Äì0.3783	umol/mmol creatinine	Adult (25-30 years old)	Both		HMDB	23062437
Human Urine	Detected and Quantified	0	umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected and Quantified	0	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000783

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022240

KNApSAcK ID

Not Available

Chemspider ID

89122

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5749

PubChem Compound

98681

PDB ID

Not Available

ChEBI ID

89836

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bergstrom T, Greter J, Levin AH, Steen G, Tryding N, Wass U: Propionyl-CoA carboxylase deficiency: case report, effect of low-protein diet and identification of 3-oxo-2-methylvaleric acid 3-hydroxy-2-methylvaleric acid, and maleic acid in urine. Scand J Clin Lab Invest. 1981 Apr;41(2):117-26. doi: 10.3109/00365518109092023. [PubMed:7313494 ]
Prasad C, Nurko S, Borovoy J, Korson MS: The importance of gut motility in the metabolic control of propionic acidemia. J Pediatr. 2004 Apr;144(4):532-5. doi: 10.1016/j.jpeds.2003.12.044. [PubMed:15069406 ]
Wayne A. Fenton; Roy A. Gravel; David S. Rosenblatt (2019). Fenton, W.A., Gravel, R.A., Rosenblatt, D.S. Disorders of propionate and methylmalonate metabolism.. The Online Metabolic and Molecular Bases of Inherited Disease Eds. .
Mayo Medical Laboratories 2005 Test Catalog [Link]

Showing metabocard for Propionylglycine (MMDBc0000545)

MOL for #<Metabolite:0x00007fd102352ca0>

3D MOL for #<Metabolite:0x00007fd102352ca0>

3D SDF for #<Metabolite:0x00007fd102352ca0>

3D-SDF for #<Metabolite:0x00007fd102352ca0>

PDB for #<Metabolite:0x00007fd102352ca0>

3D PDB for #<Metabolite:0x00007fd102352ca0>

SMILES for #<Metabolite:0x00007fd102352ca0>

INCHI for #<Metabolite:0x00007fd102352ca0>

Structure for #<Metabolite:0x00007fd102352ca0>

3D Structure for #<Metabolite:0x00007fd102352ca0>