P. aeruginosa Metabolome Database: Iminoaspartic acid (PAMDB000267)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000267

Identification

Name:

Iminoaspartic acid

Description:

Iminoaspartic acid (alpha-iminosuccinate) is an intermediate in NAD biosynthesis from aspartate pathwyay. As a general rule, most prokaryotes utilize the aspartate de novo pathway, in which the nicotinate moiety of NAD is synthesized from aspartate, while in eukaryotes, the de novo pathway starts with tryptophan.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

a-Iminosuccinate
a-Iminosuccinic acid
Alpha-Iminosuccinate
Alpha-Iminosuccinic acid
Imino-Butanedioate
Imino-Butanedioic acid
Iminoaspartate
Iminoaspartic acid
Iminosuccinate
Iminosuccinic acid
α-Iminosuccinate
α-Iminosuccinic acid

Chemical Formula:

C₄H₅NO₄

Average Molecular Weight:

131.0868

Monoisotopic Molecular Weight:

131.021857653

InChI Key:

NMUOATVLLQEYHI-UHFFFAOYSA-N

InChI:

InChI=1S/C4H5NO4/c5-2(4(8)9)1-3(6)7/h5H,1H2,(H,6,7)(H,8,9)

CAS number:

79067-61-1

IUPAC Name:

2-iminobutanedioic acid

Traditional IUPAC Name:

iminosuccinic acid

SMILES:

OC(=O)CC(=N)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Fatty acid
Dicarboxylic acid or derivatives
Ketimine
Carboxylic acid
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aspartic acid derivative (CHEBI:50616 )
C4-dicarboxylic acid (CHEBI:50616 )
ketimine (CHEBI:50616 )
Dicarboxylic acids (LMFA01170110 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	4.26 mg/mL	ALOGPS
logP	-0.83	ALOGPS
logP	-0.51	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.28	ChemAxon
pKa (Strongest Basic)	2.48	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	98.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	36.81 m³·mol^-1	ChemAxon
Polarizability	10.55 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:

Dihydroxyacetone phosphate + Iminoaspartic acid <>2 Water + Phosphate + Quinolinic acid
L-Aspartic acid + Fumaric acid > Hydrogen ion + Iminoaspartic acid + Succinic acid
L-Aspartic acid + Oxygen <> Hydrogen ion + Hydrogen peroxide + Iminoaspartic acid
L-Aspartic acid + Ubiquinone-8 > Hydrogen ion + Iminoaspartic acid + Ubiquinol-8
L-Aspartic acid + Menaquinone 8 > Hydrogen ion + Iminoaspartic acid + Menaquinol 8
L-Aspartic acid + Oxygen <> Iminoaspartic acid + Hydrogen peroxide
Dihydroxyacetone phosphate + Iminoaspartic acid > Quinolinic acid +2 Water + Inorganic phosphate
L-Aspartic acid + Oxygen + L-Aspartic acid > Hydrogen peroxide + Hydrogen ion + Iminoaspartic acid

Pathways:

Alanine, aspartate and glutamate metabolism pae00250
Metabolic pathways pae01100
Nicotinate and nicotinamide metabolism pae00760

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03y0-7900000000-1e7dec8cec535849b8dd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00y0-9000000000-ee01d5b059cd84acc52a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-f7639f26eeb1737eca80	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-4900000000-48f2522721d80612277b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q0-9600000000-13c57e1870999d070c90	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066u-9000000000-142f158a200b457f476f	View in MoNA

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
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
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	50616
HMDB ID	HMDB01131
Pubchem Compound ID	796
Kegg ID	C05840
ChemSpider ID	13628208
Wikipedia ID	Not Available
BioCyc ID	IMINOASPARTATE
EcoCyc ID	IMINOASPARTATE

Iminoaspartic acid (PAMDB000267)

Structure for Iminoaspartic acid (PAMDB000267)