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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:17 UTC

HMDB ID

HMDB0000894

Secondary Accession Numbers

HMDB0006723
HMDB0006724
HMDB00894
HMDB06723
HMDB06724

Metabolite Identification

Common Name

Vinylacetylglycine

Description

Vinylacetylglycine 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-acylglycine. Vinylacetylglycine is a human metabolite that had been identified in a GC/MS urine screen. Increased amounts of this metabolite in the urine has been linked to a metabolomic disorder termed Isovaleric acidemia. (Gas-Chromatographic Method of Analysis for Urinary Organic Acids. I. Retention indices of 155 metaboically Important Compounds; Kay Tanaka, David G. Hine, Agnes West-Dull, and Theodore B. Lynn.).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(But-3-enamido)acetic acid	ChEBI
2-(But-3-enamido)acetate	Generator

Chemical Formula

C₆H₉NO₃

Average Molecular Weight

143.1406

Monoisotopic Molecular Weight

143.058243159

IUPAC Name

2-(but-3-enamido)acetic acid

Traditional Name

but-3-enamidoacetic acid

CAS Registry Number

73122-61-9

SMILES

OC(=O)CNC(=O)CC=C

InChI Identifier

InChI=1S/C6H9NO3/c1-2-3-5(8)7-4-6(9)10/h2H,1,3-4H2,(H,7,8)(H,9,10)

InChI Key

UKISAGFGRDHYFO-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
N-acyl-amine
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acylglycine (CHEBI:74435 )

Ontology

Not Available

Endogenous (HMDB: HMDB0000894)

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)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	55.3 g/L	ALOGPS
logP	-0.48	ALOGPS
logP	-0.49	ChemAxon
logS	-0.41	ALOGPS
pKa (Strongest Acidic)	3.98	ChemAxon
pKa (Strongest Basic)	-2.4	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	4	ChemAxon
Refractivity	34.72 m³·mol⁻¹	ChemAxon
Polarizability	13.8 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	131.887	31661259
DarkChem	[M-H]-	128.699	31661259
AllCCS	[M+H]+	133.35	32859911
AllCCS	[M-H]-	129.729	32859911
DeepCCS	[M+H]+	132.601	30932474
DeepCCS	[M-H]-	130.289	30932474
DeepCCS	[M-2H]-	166.188	30932474
DeepCCS	[M+Na]+	141.101	30932474
AllCCS	[M+H]+	133.3	32859911
AllCCS	[M+H-H2O]+	129.3	32859911
AllCCS	[M+NH4]+	137.1	32859911
AllCCS	[M+Na]+	138.2	32859911
AllCCS	[M-H]-	129.7	32859911
AllCCS	[M+Na-2H]-	132.0	32859911
AllCCS	[M+HCOO]-	134.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vinylacetylglycine	OC(=O)CNC(=O)CC=C	2334.0	Standard polar	33892256
Vinylacetylglycine	OC(=O)CNC(=O)CC=C	1223.9	Standard non polar	33892256
Vinylacetylglycine	OC(=O)CNC(=O)CC=C	1417.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vinylacetylglycine,1TMS,isomer #1	C=CCC(=O)NCC(=O)O[Si](C)(C)C	1420.6	Semi standard non polar	33892256
Vinylacetylglycine,1TMS,isomer #2	C=CCC(=O)N(CC(=O)O)[Si](C)(C)C	1423.9	Semi standard non polar	33892256
Vinylacetylglycine,2TMS,isomer #1	C=CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1462.2	Semi standard non polar	33892256
Vinylacetylglycine,2TMS,isomer #1	C=CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1477.8	Standard non polar	33892256
Vinylacetylglycine,2TMS,isomer #1	C=CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1645.5	Standard polar	33892256
Vinylacetylglycine,1TBDMS,isomer #1	C=CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C	1652.1	Semi standard non polar	33892256
Vinylacetylglycine,1TBDMS,isomer #2	C=CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	1660.5	Semi standard non polar	33892256
Vinylacetylglycine,2TBDMS,isomer #1	C=CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1918.9	Semi standard non polar	33892256
Vinylacetylglycine,2TBDMS,isomer #1	C=CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1890.2	Standard non polar	33892256
Vinylacetylglycine,2TBDMS,isomer #1	C=CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1924.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vinylacetylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-9000000000-ee4dafe242d7b3a25b37	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vinylacetylglycine GC-MS (1 TMS) - 70eV, Positive	splash10-01bd-9200000000-d5452b4615c0101900f1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vinylacetylglycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vinylacetylglycine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vinylacetylglycine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vinylacetylglycine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vinylacetylglycine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-9000000000-a3036bdbe74f1665bb9b	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vinylacetylglycine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-014r-9000000000-d09a783c09e0f2b1061b	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vinylacetylglycine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-014r-9000000000-6c0914193049d59e4305	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinylacetylglycine 10V, Positive-QTOF	splash10-002f-9800000000-5aefea4a1f5958127955	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinylacetylglycine 20V, Positive-QTOF	splash10-056u-9000000000-7282b4d50a81e85e26fd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinylacetylglycine 40V, Positive-QTOF	splash10-054o-9000000000-e011facd59167c71ef22	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinylacetylglycine 10V, Negative-QTOF	splash10-0006-2900000000-62444f45e0908221bc67	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinylacetylglycine 20V, Negative-QTOF	splash10-006x-9700000000-8371d2bb5ea318537d21	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinylacetylglycine 40V, Negative-QTOF	splash10-05fu-9000000000-69be79618946966c31c7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinylacetylglycine 10V, Positive-QTOF	splash10-0006-9000000000-279914ea2f886d4d7d28	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinylacetylglycine 20V, Positive-QTOF	splash10-00kf-9000000000-bfb50c5c1402d0b8ef30	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinylacetylglycine 40V, Positive-QTOF	splash10-052f-9000000000-8a0e8da17968af912e48	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinylacetylglycine 10V, Negative-QTOF	splash10-0002-9200000000-793087dba3b379b67ea7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinylacetylglycine 20V, Negative-QTOF	splash10-006t-9000000000-0f9e57db8b82bb8feae4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vinylacetylglycine 40V, Negative-QTOF	splash10-00dl-9000000000-0860c46254feca10147d	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022303

KNApSAcK ID

Not Available

Chemspider ID

27976741

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5851

PubChem Compound

53477718

PDB ID

Not Available

ChEBI ID

74435

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Ramsdell HS, Baretz BH, Tanaka K: Mass spectrometric studies of twenty-one metabolically important acylglycines. Biomed Mass Spectrom. 1977 Aug;4(4):220-5. [PubMed:912020 ]

Enzymes

Enzyme Details

1. Glycine N-acyltransferase

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:: GLYAT
Uniprot ID:: Q6IB77
Molecular weight:: 18506.33

Enzyme Details

2. Glycine N-acyltransferase-like protein 1

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:: GLYATL1
Uniprot ID:: Q969I3
Molecular weight:: 35100.895

Enzyme Details

3. Glycine N-acyltransferase-like protein 2

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:: GLYATL2
Uniprot ID:: Q8WU03
Molecular weight:: 34277.055

Enzyme Details

4. Glycine N-acyltransferase-like protein 3

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers the acyl group to the N- terminus of glycine
Gene Name:: GLYATL3
Uniprot ID:: Q5SZD4
Molecular weight:: 32703.3

Showing metabocard for Vinylacetylglycine (HMDB0000894)

MOL for HMDB0000894 (Vinylacetylglycine)

3D MOL for HMDB0000894 (Vinylacetylglycine)

3D SDF for HMDB0000894 (Vinylacetylglycine)

3D-SDF for HMDB0000894 (Vinylacetylglycine)

PDB for HMDB0000894 (Vinylacetylglycine)

3D PDB for HMDB0000894 (Vinylacetylglycine)

SMILES for HMDB0000894 (Vinylacetylglycine)

INCHI for HMDB0000894 (Vinylacetylglycine)

Structure for HMDB0000894 (Vinylacetylglycine)

3D Structure for HMDB0000894 (Vinylacetylglycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes