ECMDB: 3-Aminoacrylate (ECMDB21167) (M2MDB001576)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (52)

Record Information

Version

2.0

Creation Date

2012-07-30 14:54:43 -0600

Update Date

2015-06-03 17:20:47 -0600

Secondary Accession Numbers

ECMDB21167

Identification

Name:

3-Aminoacrylate

Description

3-aminoacrylate is a member of the chemical class known as Enones. These are compounds containing the enone functional group, with the structure RC(=O)CR'. Aminoacrylate is involved in amino acid metabolism. A new amino acid is formed when the nucleophiles add to the aminoacrylate. (PMID 8663055)

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms:

(2Z)-3-aminoprop-2-enoate
(2Z)-3-aminoprop-2-enoic acid
(Z)-3-Aminoacrylate
(Z)-3-Aminoacrylic acid
3-Aminoacrylate
3-Aminoacrylic acid
Aminoacrylate
Aminoacrylic acid

Chemical Formula:

C₃H₅NO₂

Weight:

Average: 87.0773
Monoisotopic: 87.032028409

InChI Key:

YTLYLLTVENPWFT-UPHRSURJSA-N

InChI:

InChI=1S/C3H5NO2/c4-2-1-3(5)6/h1-2H,4H2,(H,5,6)/b2-1-

CAS number:

Not Available

IUPAC Name:

(2Z)-3-aminoprop-2-enoic acid

Traditional IUPAC Name:

aminoacrylic acid

SMILES:

N\C=C/C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as acrylic acids and derivatives. These are organic compounds containing acrylic acid CH2=CHCO2H or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Acrylic acids and derivatives

Direct Parent

Acrylic acids and derivatives

Alternative Parents

Substituents

Acrylic acid or derivatives
Vinylogous amide
Amino acid or derivatives
Amino acid
Carboxylic acid
Enamine
Monocarboxylic acid or derivatives
Allylamine
Amine
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha,beta-unsaturated monocarboxylic acid (CHEBI:59893 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	293 g/L	ALOGPS
logP	-0.42	ALOGPS
logP	-2.7	ChemAxon
logS	0.53	ALOGPS
pKa (Strongest Acidic)	2.67	ChemAxon
pKa (Strongest Basic)	6.65	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	20.93 m³·mol⁻¹	ChemAxon
Polarizability	7.62 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

3-Aminoacrylate + Hydrogen ion + Water > Malonic semialdehyde + Ammonium
NADH + Peroxyaminoacrylate > 3-Aminoacrylate + Water + NAD
Ureidoacrylate + Water <> 3-Aminoacrylate + Carbamic acid
Peroxyaminoacrylate <> 3-Aminoacrylate
3-Aminoacrylate + Water <> Malonic semialdehyde + Ammonia
3-ureidoacrylate + Water > Hydrogen ion + Carbamic acid + 3-Aminoacrylate
3-Aminoacrylate + Water > Malonic semialdehyde + Ammonia
Peroxyaminoacrylate + a reduced electron acceptor > 3-Aminoacrylate + Water + Hydrogen ion + an oxidized electron acceptor
(Z)-3-Ureidoacrylate + Water > 3-Aminoacrylate + Carbon dioxide + Ammonia
3-Aminoacrylate + Water > Malonic acid + Ammonia
Ureidoacrylate peracid + Water > Peroxyaminoacrylate + Carbamic acid + Hydrogen ion + 3-Aminoacrylate
Peroxyaminoacrylate + an unknown reduced electron acceptor + 3-Aminoacrylate > 2-Aminoacrylic acid + an unknown oxidized electron acceptor

SMPDB Pathways:

Uracil degradation III

PW002026

KEGG Pathways:

Not Available

EcoCyc Pathways:

uracil degradation III PWY0-1471

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-04ede35a7e8ccb1a1583	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-90549ba6315b89041625	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fu-9000000000-2e75d1ab630a49ed5ffd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-2e5d7401c27942249cdf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ku-9000000000-78d2bc9572a1c23efcd1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-428ecd02d0bf7fc25ac8	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Flint, D. H., Tuminello, J. F., Miller, T. J. (1996). "Studies on the synthesis of the Fe-S cluster of dihydroxy-acid dehydratase in escherichia coli crude extract. Isolation of O-acetylserine sulfhydrylases A and B and beta-cystathionase based on their ability to mobilize sulfur from cysteine and to participate in Fe-S cluster synthesis." J Biol Chem 271:16053-16067. Pubmed: 8663055
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	59894
HMDB ID	Not Available
Pubchem Compound ID	46173135
Kegg ID	C20253
ChemSpider ID	26331746
Wikipedia ID	Not Available
BioCyc ID	CPD0-2339
EcoCyc ID	CPD0-2339

Enzymes

Protein Details

1. UPF0076 protein rutC

General function:: Translation, ribosomal structure and biogenesis
Specific function:: Makes part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
Gene Name:: rutC
Uniprot ID:: P0AFQ5
Molecular weight:: 13763

Protein Details

2. Putative isochorismatase family protein rutB

General function:: Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amides
Specific function:: Makes part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
Gene Name:: rutB
Uniprot ID:: P75897
Molecular weight:: 25209

Reactions

(Z)-3-ureidoacrylate peracid + H(2)O = (Z)-3-peroxyaminoacrylate + NH(3).
(Z)-3-ureidoacrylate + H(2)O = (Z)-3-aminoacrylate + CO(2) + NH(3).
(Z)-2-methyl-ureidoacrylate peracid + H(2)O = (Z)-2-methyl-peroxyaminoacrylate + CO(2) + NH(3).

Protein Details

3. Protein rutD

General function:: Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amides
Specific function:: Makes part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
Gene Name:: rutD
Uniprot ID:: P75895
Molecular weight:: 28898

Reactions

(Z)-3-aminoacrylate + H(2)O = malonate semialdehyde + NH(3).

3-Aminoacrylate (ECMDB21167) (M2MDB001576)

Structure for #<Compound:0xaa409264>

Enzymes

Reactions

Reactions