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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

2006-01-27 11:06:50 UTC

Update Date

2023-02-21 17:15:49 UTC

HMDB ID

HMDB0001843

Secondary Accession Numbers

HMDB01843

Metabolite Identification

Common Name

N-Acryloylglycine

Description

N-Acryloylglycine 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. N-Acryloylglycine is an acylglycines found in normal human biofluids (PMID 7364920 ; 912020; 7438429).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Aminopropenal acetic acid	HMDB
N-(1-oxo-2-Propenyl)-glycine	HMDB
N-Acryloyl-glycine	HMDB
APAA	HMDB
2-[(1-Hydroxyprop-2-en-1-ylidene)amino]acetate	HMDB

Chemical Formula

C₅H₇NO₃

Average Molecular Weight

129.114

Monoisotopic Molecular Weight

129.042593095

IUPAC Name

2-(prop-2-enamido)acetic acid

Traditional Name

N-acryloylglycine

CAS Registry Number

24599-25-5

SMILES

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

InChI Identifier

InChI=1S/C5H7NO3/c1-2-4(7)6-3-5(8)9/h2H,1,3H2,(H,6,7)(H,8,9)

InChI Key

LZCXCXDOGAEFQX-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
Acrylic acid or derivatives
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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0001843)

Source

Endogenous

Endogenous (HMDB: HMDB0001843)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

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	63.6 g/L	ALOGPS
logP	-0.28	ALOGPS
logP	-0.57	ChemAxon
logS	-0.31	ALOGPS
pKa (Strongest Acidic)	3.84	ChemAxon
pKa (Strongest Basic)	-0.63	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	30.09 m³·mol⁻¹	ChemAxon
Polarizability	11.92 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]+	126.598	31661259
DarkChem	[M-H]-	122.021	31661259
AllCCS	[M+H]+	130.4	32859911
AllCCS	[M-H]-	125.552	32859911
DeepCCS	[M+H]+	124.039	30932474
DeepCCS	[M-H]-	120.65	30932474
DeepCCS	[M-2H]-	157.792	30932474
DeepCCS	[M+Na]+	132.911	30932474
AllCCS	[M+H]+	130.4	32859911
AllCCS	[M+H-H2O]+	126.3	32859911
AllCCS	[M+NH4]+	134.3	32859911
AllCCS	[M+Na]+	135.4	32859911
AllCCS	[M-H]-	125.6	32859911
AllCCS	[M+Na-2H]-	128.3	32859911
AllCCS	[M+HCOO]-	131.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acryloylglycine	OC(=O)CNC(=O)C=C	2071.0	Standard polar	33892256
N-Acryloylglycine	OC(=O)CNC(=O)C=C	1106.5	Standard non polar	33892256
N-Acryloylglycine	OC(=O)CNC(=O)C=C	1388.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acryloylglycine,1TMS,isomer #1	C=CC(=O)NCC(=O)O[Si](C)(C)C	1371.3	Semi standard non polar	33892256
N-Acryloylglycine,1TMS,isomer #2	C=CC(=O)N(CC(=O)O)[Si](C)(C)C	1404.6	Semi standard non polar	33892256
N-Acryloylglycine,2TMS,isomer #1	C=CC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1418.8	Semi standard non polar	33892256
N-Acryloylglycine,2TMS,isomer #1	C=CC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1386.7	Standard non polar	33892256
N-Acryloylglycine,2TMS,isomer #1	C=CC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C	1571.5	Standard polar	33892256
N-Acryloylglycine,1TBDMS,isomer #1	C=CC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C	1631.2	Semi standard non polar	33892256
N-Acryloylglycine,1TBDMS,isomer #2	C=CC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	1627.1	Semi standard non polar	33892256
N-Acryloylglycine,2TBDMS,isomer #1	C=CC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1878.2	Semi standard non polar	33892256
N-Acryloylglycine,2TBDMS,isomer #1	C=CC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1801.9	Standard non polar	33892256
N-Acryloylglycine,2TBDMS,isomer #1	C=CC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1854.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acryloylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-5696c0e42a06c47cf8b7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acryloylglycine GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-9100000000-24a928243f8f9100db11	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acryloylglycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acryloylglycine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-053r-9300000000-2802258cfc542054fcb4	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acryloylglycine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4i-9000000000-7e7bd17503bfa7395d45	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acryloylglycine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0a4i-9000000000-285bc2264e30ec8661e6	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acryloylglycine 10V, Positive-QTOF	splash10-053r-9800000000-8a9d3ec8bd310d5e1054	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acryloylglycine 20V, Positive-QTOF	splash10-0a6r-9000000000-2e90beda6bee67bb9493	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acryloylglycine 40V, Positive-QTOF	splash10-0a6r-9000000000-4d8ae6a5538548b2ff80	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acryloylglycine 10V, Negative-QTOF	splash10-004i-2900000000-180967d33262d5a62115	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acryloylglycine 20V, Negative-QTOF	splash10-00b9-9700000000-826ef5ca3fe09b06deb8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acryloylglycine 40V, Negative-QTOF	splash10-0ab9-9000000000-88dc019451d6fff02eec	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acryloylglycine 10V, Positive-QTOF	splash10-053r-9000000000-6ade5e377c74732a4673	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acryloylglycine 20V, Positive-QTOF	splash10-053r-9000000000-567c6ce87890d5f22146	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acryloylglycine 40V, Positive-QTOF	splash10-0a4i-9000000000-8a5d1614f47f2b0cf6a4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acryloylglycine 10V, Negative-QTOF	splash10-001i-9100000000-248ae8281c13b7a1405c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acryloylglycine 20V, Negative-QTOF	splash10-053r-9000000000-8e94320e0e497fc726e7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acryloylglycine 40V, Negative-QTOF	splash10-05fu-9000000000-2f13c8b54478f07e39ba	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	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	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

Cytoplasm (predicted from logP)

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

FDB022703

KNApSAcK ID

Not Available

Chemspider ID

90657

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6343

PubChem Compound

100321

PDB ID

Not Available

ChEBI ID

Not Available

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, Tanak K: Gas chromatographic retention indices of twenty metabolically important acylglycines as trimethylsilyl derivatives. J Chromatogr. 1980 Jan 11;181(1):90-4. [PubMed:7364920 ]

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 N-Acryloylglycine (HMDB0001843)

MOL for HMDB0001843 (N-Acryloylglycine)

3D MOL for HMDB0001843 (N-Acryloylglycine)

3D SDF for HMDB0001843 (N-Acryloylglycine)

3D-SDF for HMDB0001843 (N-Acryloylglycine)

PDB for HMDB0001843 (N-Acryloylglycine)

3D PDB for HMDB0001843 (N-Acryloylglycine)

SMILES for HMDB0001843 (N-Acryloylglycine)

INCHI for HMDB0001843 (N-Acryloylglycine)

Structure for HMDB0001843 (N-Acryloylglycine)

3D Structure for HMDB0001843 (N-Acryloylglycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes