ECMDB: Peroxyaminoacrylate (ECMDB21275) (M2MDB001682)

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

Proteins (36)

Record Information

Version

2.0

Creation Date

2012-07-30 14:55:10 -0600

Update Date

2015-06-03 17:21:04 -0600

Secondary Accession Numbers

ECMDB21275

Identification

Name:

Peroxyaminoacrylate

Description

Peroxyaminoacrylate is a member of the chemical class known as Enones. These are compounds containing the enone functional group, with the structure RC(=O)CR'.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(2Z)-3-aminoprop-2-eneperoxoate
(2Z)-3-aminoprop-2-eneperoxoic acid
(Z)-3-Peroxyaminoacrylate
(Z)-3-Peroxyaminoacrylic acid
Aminoacrylate peracid
Aminoacrylic acid peracid
Peroxy aminoacrylate
Peroxy aminoacrylic acid
Peroxyaminoacrylate
Peroxyaminoacrylic acid

Chemical Formula:

C₃H₅NO₃

Weight:

Average: 103.0767
Monoisotopic: 103.026943031

InChI Key:

WQKGFGLGYOHJOG-UPHRSURJSA-N

InChI:

InChI=1S/C3H5NO3/c4-2-1-3(5)7-6/h1-2,6H,4H2/b2-1-

CAS number:

Not Available

IUPAC Name:

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

Traditional IUPAC Name:

peroxyaminoacrylate

SMILES:

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as peroxycarboxylic acids. These are organic acids with the general formula [H]OOC(R)=O (R = H, organyl group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Peroxycarboxylic acids and derivatives

Direct Parent

Peroxycarboxylic acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

peroxy acid (CHEBI:59892 )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	159 g/L	ALOGPS
logP	-0.64	ALOGPS
logP	-0.54	ChemAxon
logS	0.19	ALOGPS
pKa (Strongest Acidic)	7.39	ChemAxon
pKa (Strongest Basic)	3.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	72.55 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	22.56 m³·mol⁻¹	ChemAxon
Polarizability	8.39 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:

NADH + Peroxyaminoacrylate > 3-Aminoacrylate + Water + NAD
Water + Ureidoacrylate peracid > Carbamic acid + Hydrogen ion + Peroxyaminoacrylate
Ureidoacrylate peracid + Water <> Peroxyaminoacrylate + Carbamic acid
Peroxyaminoacrylate <> 3-Aminoacrylate
Peroxyaminoacrylate + a reduced electron acceptor > 3-Aminoacrylate + Water + Hydrogen ion + an oxidized electron acceptor
Ureidoacrylate peracid + Water > Peroxyaminoacrylate + Ammonia
Ureidoacrylate peracid + Water + Carbamic acid + (Z)-2-Methyl-ureidoacrylate peracid <> Peroxyaminoacrylate + Carbon dioxide + Ammonia + (Z)-2-Methyl-peroxyaminoacrylate
Uracil + FMNH2 + Oxygen > Ureidoacrylate peracid + Flavin Mononucleotide + Hydrogen ion + Peroxyaminoacrylate
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:

Pyrimidine metabolism	PW000942
Uracil degradation III	PW002026

KEGG Pathways:

Metabolic pathways eco01100
Pyrimidine metabolism ec00240

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_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fki-9100000000-db715a15c2c4b6f132a6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-9000000000-37efe41c00992a9fdb1a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-710b7105b933dbcc1dcb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-7900000000-97e05fdfcf0d580a19c9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gb9-9200000000-0ad740a68dd63cb5df10	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uyl-9000000000-83e544387003edc8c285	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:

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	59892
HMDB ID	Not Available
Pubchem Compound ID	46173085
Kegg ID	C20249
ChemSpider ID	26331745
Wikipedia ID	Not Available
BioCyc ID	CPD0-2340
EcoCyc ID	CPD0-2340

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 monooxygenase rutA

General function:: Involved in oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen
Specific function:: Part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
Gene Name:: rutA
Uniprot ID:: P75898
Molecular weight:: 42219

Reactions

Uracil + FMNH(2) + O(2) = (Z)-3-ureidoacrylate peracid + FMN + H(2)O.
Thymine + FMNH(2) + O(2) = (Z)-2-methylureidoacrylate peracid + FMN + H(2)O.

Protein Details

3. 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).

Peroxyaminoacrylate (ECMDB21275) (M2MDB001682)

Structure for #<Compound:0xaee5f28c>

Enzymes

Reactions

Reactions