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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 01:22:37 UTC

Update Date

2023-02-21 17:16:45 UTC

HMDB ID

HMDB0003609

Secondary Accession Numbers

HMDB0006356
HMDB03609
HMDB06356

Metabolite Identification

Common Name

2-Aminoacrylic acid

Description

2-Aminoacrylic acid, also known as 2,3-didehydroalanine or 2-aminoacrylate, 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). 2-Aminoacrylic acid is a very strong basic compound (based on its pKa). 2-Aminoacrylic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, 2-Aminoacrylic acid has been detected, but not quantified in, several different foods, such as wax gourds, soursops, durians, green beans, and grapes. This could make 2-aminoacrylic acid a potential biomarker for the consumption of these foods. A 2,3-dehydroamino acid that is alanine which has been dehydrogenated to introduce a double bond between positions 2 and 3.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,3-Didehydroalanine	ChEBI
2-Aminoacrylate	ChEBI
alpha,beta-Dehydroalanine	ChEBI
Anhydroserine2-aminopropenoic acid	ChEBI
Dehydroalanine	ChEBI
2-Aminoprop-2-enoate	Kegg
a,b-Dehydroalanine	Generator
Α,β-dehydroalanine	Generator
Anhydroserine2-aminopropenoate	Generator
2-Aminoprop-2-enoic acid	Generator
(alpha)-(beta)-Di-dehydroalanine	HMDB
a-b-Di-dehydroalanine	HMDB
alpha-beta-Di-dehydroalanine	HMDB
alpha-Aminoacrylate	HMDB
2-Amino-2-propenoic acid	HMDB
Aminoacrylic acid	HMDB
Dehydro-L-alanine	HMDB
alpha,beta-Didehydroalanine	HMDB
alpha-Aminoacrylic acid	HMDB
α,β-Didehydroalanine	HMDB
α-Aminoacrylic acid	HMDB

Chemical Formula

C₃H₅NO₂

Average Molecular Weight

87.0773

Monoisotopic Molecular Weight

87.032028409

IUPAC Name

2-aminoprop-2-enoic acid

Traditional Name

dehydroalanine

CAS Registry Number

28453-71-6

SMILES

NC(=C)C(O)=O

InChI Identifier

InChI=1S/C3H5NO2/c1-2(4)3(5)6/h1,4H2,(H,5,6)

InChI Key

UQBOJOOOTLPNST-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
Enamine
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Organopnictogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:17123 )
enamine (CHEBI:17123 )
alpha,beta-unsaturated monocarboxylic acid (CHEBI:17123 )
dehydroamino acid (CHEBI:17123 )

Ontology

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	-2.651	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	233 g/L	ALOGPS
logP	-0.13	ALOGPS
logP	-2.9	ChemAxon
logS	0.43	ALOGPS
pKa (Strongest Acidic)	2.58	ChemAxon
pKa (Strongest Basic)	8.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	20.92 m³·mol⁻¹	ChemAxon
Polarizability	7.72 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]+	115.674	31661259
DarkChem	[M-H]-	109.74	31661259
DeepCCS	[M+H]+	122.8	30932474
DeepCCS	[M-H]-	120.002	30932474
DeepCCS	[M-2H]-	156.38	30932474
DeepCCS	[M+Na]+	130.951	30932474
AllCCS	[M+H]+	124.9	32859911
AllCCS	[M+H-H2O]+	120.5	32859911
AllCCS	[M+NH4]+	129.0	32859911
AllCCS	[M+Na]+	130.2	32859911
AllCCS	[M-H]-	121.7	32859911
AllCCS	[M+Na-2H]-	126.4	32859911
AllCCS	[M+HCOO]-	131.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Aminoacrylic acid	NC(=C)C(O)=O	2001.7	Standard polar	33892256
2-Aminoacrylic acid	NC(=C)C(O)=O	1005.6	Standard non polar	33892256
2-Aminoacrylic acid	NC(=C)C(O)=O	1058.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Aminoacrylic acid,1TMS,isomer #1	C=C(N)C(=O)O[Si](C)(C)C	1027.4	Semi standard non polar	33892256
2-Aminoacrylic acid,1TMS,isomer #2	C=C(N[Si](C)(C)C)C(=O)O	1123.8	Semi standard non polar	33892256
2-Aminoacrylic acid,2TMS,isomer #1	C=C(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1215.4	Semi standard non polar	33892256
2-Aminoacrylic acid,2TMS,isomer #1	C=C(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1260.8	Standard non polar	33892256
2-Aminoacrylic acid,2TMS,isomer #1	C=C(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1388.4	Standard polar	33892256
2-Aminoacrylic acid,2TMS,isomer #2	C=C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1326.1	Semi standard non polar	33892256
2-Aminoacrylic acid,2TMS,isomer #2	C=C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1237.1	Standard non polar	33892256
2-Aminoacrylic acid,2TMS,isomer #2	C=C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1493.0	Standard polar	33892256
2-Aminoacrylic acid,3TMS,isomer #1	C=C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1353.6	Semi standard non polar	33892256
2-Aminoacrylic acid,3TMS,isomer #1	C=C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1315.2	Standard non polar	33892256
2-Aminoacrylic acid,3TMS,isomer #1	C=C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1338.2	Standard polar	33892256
2-Aminoacrylic acid,1TBDMS,isomer #1	C=C(N)C(=O)O[Si](C)(C)C(C)(C)C	1257.8	Semi standard non polar	33892256
2-Aminoacrylic acid,1TBDMS,isomer #2	C=C(N[Si](C)(C)C(C)(C)C)C(=O)O	1369.7	Semi standard non polar	33892256
2-Aminoacrylic acid,2TBDMS,isomer #1	C=C(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1634.0	Semi standard non polar	33892256
2-Aminoacrylic acid,2TBDMS,isomer #1	C=C(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1620.2	Standard non polar	33892256
2-Aminoacrylic acid,2TBDMS,isomer #1	C=C(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1641.0	Standard polar	33892256
2-Aminoacrylic acid,2TBDMS,isomer #2	C=C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1760.8	Semi standard non polar	33892256
2-Aminoacrylic acid,2TBDMS,isomer #2	C=C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1634.4	Standard non polar	33892256
2-Aminoacrylic acid,2TBDMS,isomer #2	C=C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1680.3	Standard polar	33892256
2-Aminoacrylic acid,3TBDMS,isomer #1	C=C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1961.5	Semi standard non polar	33892256
2-Aminoacrylic acid,3TBDMS,isomer #1	C=C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1929.2	Standard non polar	33892256
2-Aminoacrylic acid,3TBDMS,isomer #1	C=C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1735.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Aminoacrylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-91e0ae8251c533ccb7ad	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Aminoacrylic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9500000000-d9a0c6188aef6b8aec5a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Aminoacrylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Aminoacrylic acid 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminoacrylic acid 10V, Positive-QTOF	splash10-000f-9000000000-15dc8dc52e98be913462	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminoacrylic acid 20V, Positive-QTOF	splash10-0006-9000000000-dc312ec6c67a0557dea5	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminoacrylic acid 40V, Positive-QTOF	splash10-0006-9000000000-6abf262be2b6f2447777	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminoacrylic acid 10V, Negative-QTOF	splash10-000i-9000000000-8d7c53619f483f86f61a	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminoacrylic acid 20V, Negative-QTOF	splash10-000i-9000000000-e78e6283f6f0fd640c07	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminoacrylic acid 40V, Negative-QTOF	splash10-014u-9000000000-f45341969a54a57e8b77	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminoacrylic acid 10V, Positive-QTOF	splash10-0006-9000000000-ff7f2c935a022bb6caf6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminoacrylic acid 20V, Positive-QTOF	splash10-0006-9000000000-ff7f2c935a022bb6caf6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminoacrylic acid 40V, Positive-QTOF	splash10-0006-9000000000-ff7f2c935a022bb6caf6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminoacrylic acid 10V, Negative-QTOF	splash10-000i-9000000000-cb7bf9d7a9fec42be16c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminoacrylic acid 20V, Negative-QTOF	splash10-000i-9000000000-56882758237b475e8194	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminoacrylic acid 40V, Negative-QTOF	splash10-0006-9000000000-f6f1fa2beae1e80da0d0	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

Name	SMPDB/PathBank	KEGG
Thyroid hormone synthesis		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02688

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023206

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

123991

PDB ID

Not Available

ChEBI ID

17123

Food Biomarker Ontology

Not Available

VMH ID

2AMAC

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Thyroid peroxidase

General function:: Involved in calcium ion binding
Specific function:: Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
Gene Name:: TPO
Uniprot ID:: P07202
Molecular weight:: 102961.63

Reactions

3,5-Diiodo-L-tyrosine + Hydrogen peroxide → Thyroxine + 2-Aminoacrylic acid + Water	details
Iodotyrosine + 3,5-Diiodo-L-tyrosine + Hydrogen peroxide → Liothyronine + 2-Aminoacrylic acid + Water	details

Enzyme Details

2. L-serine dehydratase/L-threonine deaminase

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: SDS
Uniprot ID:: P20132
Molecular weight:: 34625.105

Reactions

Serine → 2-Aminoacrylic acid + Water	details

Showing metabocard for 2-Aminoacrylic acid (HMDB0003609)

MOL for HMDB0003609 (2-Aminoacrylic acid)

3D MOL for HMDB0003609 (2-Aminoacrylic acid)

3D SDF for HMDB0003609 (2-Aminoacrylic acid)

3D-SDF for HMDB0003609 (2-Aminoacrylic acid)

PDB for HMDB0003609 (2-Aminoacrylic acid)

3D PDB for HMDB0003609 (2-Aminoacrylic acid)

SMILES for HMDB0003609 (2-Aminoacrylic acid)

INCHI for HMDB0003609 (2-Aminoacrylic acid)

Structure for HMDB0003609 (2-Aminoacrylic acid)

3D Structure for HMDB0003609 (2-Aminoacrylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions