ECMDB: L-Aspartate-semialdehyde (ECMDB12249) (M2MDB000833)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (6)XML

Proteins (1845)

Record Information

Version

2.0

Creation Date

2012-05-31 14:21:18 -0600

Update Date

2015-06-03 17:19:03 -0600

Secondary Accession Numbers

ECMDB12249

Identification

Name:

L-Aspartate-semialdehyde

Description

L-Aspartate-semialdehyde is involved in both the lysine biosynthesis and homoserine biosynthesis pathways.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

AspSA
L-aspartate β-semialdehyde
L-Aspartate 4-semialdehyde
L-aspartate b-semialdehyde
L-Aspartate beta-semialdehyde
L-Aspartate β-semialdehyde
L-Aspartate-4-semialdehyde
L-Aspartic 4-semialdehyde
L-Aspartic acid β-semialdehyde
L-Aspartic acid 4-semialdehyde
L-Aspartic acid b-semialdehyde
L-Aspartic acid beta-semialdehyde
L-Aspartic acid β-semialdehyde
L-Aspartic acid-4-semialdehyde
L-Aspartic acid-semialdehyde

Chemical Formula:

C₄H₇NO₃

Weight:

Average: 117.1033
Monoisotopic: 117.042593095

InChI Key:

HOSWPDPVFBCLSY-VKHMYHEASA-N

InChI:

InChI=1S/C4H7NO3/c5-3(1-2-6)4(7)8/h2-3H,1,5H2,(H,7,8)/t3-/m0/s1

CAS number:

15106-57-7

IUPAC Name:

(2S)-2-amino-4-oxobutanoic acid

Traditional IUPAC Name:

L-aspartic 4-semialdehyde

SMILES:

N[C@@H](CC=O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Fatty acid
Alpha-hydrogen aldehyde
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Aldehyde
Hydrocarbon derivative
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

amino-acid betaine (CHEBI:537519 )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	225 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-3.6	ChemAxon
logS	0.28	ALOGPS
pKa (Strongest Acidic)	1.95	ChemAxon
pKa (Strongest Basic)	8.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	25.61 m³·mol⁻¹	ChemAxon
Polarizability	10.51 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:

SMPDB Pathways:

Lysine biosynthesis	PW000771
Secondary Metabolites: threonine biosynthesis from aspartate	PW000976
methionine biosynthesis	PW000814
threonine biosynthesis	PW000817

KEGG Pathways:

Arginine and proline metabolism ec00330
Cysteine and methionine metabolism ec00270
Glycine, serine and threonine metabolism ec00260
Lysine biosynthesis ec00300
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
Monobactam biosynthesis eco00261
Phenylalanine, tyrosine and tryptophan biosynthesis ec00400

EcoCyc Pathways:

homoserine biosynthesis HOMOSERSYN-PWY
lysine biosynthesis I DAPLYSINESYN-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9000000000-fc95883465b06fe77fa1	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9600000000-4dda3f4e4df10c3a920a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0v4i-9800000000-aa44dbab9da69646c984	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-58be73453302ce4f7f09	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-e345870892ec8efb1aba	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-6900000000-90fc00407b5ac2f29270	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ba-9200000000-ede87ec86d1914862daf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9000000000-e694b3a8f6038d7455c1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-0b28596cb97f2d4d7a7d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9000000000-7a12e06c4c34bc226441	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-988ff2b32628477425d6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9200000000-c88e1a6c26d62b815d48	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-f667b7d456d3acb3e0f4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-ede149a9baa3d7f48cdb	View in MoNA
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
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	18051
HMDB ID	HMDB12249
Pubchem Compound ID	439235
Kegg ID	C00441
ChemSpider ID	388372
Wikipedia ID	Not Available
BioCyc ID	L-ASPARTATE-SEMIALDEHYDE
EcoCyc ID	L-ASPARTATE-SEMIALDEHYDE

Enzymes

Protein Details

1. Bifunctional aspartokinase/homoserine dehydrogenase 1

General function:: Involved in amino acid binding
Specific function:: L-homoserine + NAD(P)(+) = L-aspartate 4- semialdehyde + NAD(P)H
Gene Name:: thrA
Uniprot ID:: P00561
Molecular weight:: 89119

Reactions

L-homoserine + NAD(P)(+) = L-aspartate 4-semialdehyde + NAD(P)H.
ATP + L-aspartate = ADP + 4-phospho-L-aspartate.

Protein Details

2. Bifunctional aspartokinase/homoserine dehydrogenase 2

General function:: Involved in cellular amino acid biosynthetic process
Specific function:: L-homoserine + NAD(P)(+) = L-aspartate 4- semialdehyde + NAD(P)H
Gene Name:: metL
Uniprot ID:: P00562
Molecular weight:: 88887

Reactions

L-homoserine + NAD(P)(+) = L-aspartate 4-semialdehyde + NAD(P)H.
ATP + L-aspartate = ADP + 4-phospho-L-aspartate.

Protein Details

3. Dihydrodipicolinate synthase

General function:: Involved in catalytic activity
Specific function:: L-aspartate 4-semialdehyde + pyruvate = dihydrodipicolinate + 2 H(2)O
Gene Name:: dapA
Uniprot ID:: P0A6L2
Molecular weight:: 31270

Reactions

L-aspartate 4-semialdehyde + pyruvate = dihydrodipicolinate + 2 H(2)O.

Protein Details

4. Aspartate-semialdehyde dehydrogenase

General function:: Involved in aspartate-semialdehyde dehydrogenase activity
Specific function:: L-aspartate 4-semialdehyde + phosphate + NADP(+) = L-4-aspartyl phosphate + NADPH
Gene Name:: asd
Uniprot ID:: P0A9Q9
Molecular weight:: 40018

Reactions

L-aspartate 4-semialdehyde + phosphate + NADP(+) = L-4-aspartyl phosphate + NADPH.

Protein Details

5. Uncharacterized protein yjhH

General function:: Involved in catalytic activity
Specific function:: Specific function unknown
Gene Name:: yjhH
Uniprot ID:: P39359
Molecular weight:: 32721

Protein Details

6. Uncharacterized protein yagE

General function:: Involved in catalytic activity
Specific function:: Unknown Function
Gene Name:: yagE
Uniprot ID:: P75682
Molecular weight:: 33316

L-Aspartate-semialdehyde (ECMDB12249) (M2MDB000833)

Structure for #<Compound:0xa438ec18>

Enzymes

Reactions

Reactions

Reactions

Reactions