ECMDB: O-Succinyl-L-homoserine (ECMDB01418) (M2MDB000380)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (400)

Record Information

Version

2.0

Creation Date

2012-05-31 13:52:17 -0600

Update Date

2015-06-03 15:54:06 -0600

Secondary Accession Numbers

ECMDB01418

Identification

Name:

O-Succinyl-L-homoserine

Description

O-succinyl-L-homoserine is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).O-succinyl-L-homoserine is involved in bacterial transfulfuration pathway. Cystathionine gamma-synthase (CGS) is a pyridoxal phosphate-dependent enzyme that catalyzes a gamma-replacement reaction, in which the succinyl group of an O-succinyl-L-homoserine (L-OSHS) is displaced by the thiol of L-cysteine to form L-cystathionine, in the first step of the bacterial transsulfuration pathway. Cystathionine gamma-synthase (CGS) is a pyridoxal phosphate-dependent enzyme that catalyzes a gamma-replacement reaction, in which the succinyl group of an O-succinyl-L-homoserine (L-OSHS) is displaced by the thiol of L-cysteine to form L-cystathionine, in the first step of the bacterial transsulfuration pathway. (PMID 14503880)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(S)-Butanedioate mono(3-amino-3-carboxypropyl) ester
(S)-Butanedioic acid mono(3-amino-3-carboxypropyl) ester
Butanedioate mono(3-amino-3-carboxypropyl) ester
Butanedioate mono[(3S)-3-amino-3-carboxypropyl] ester
Butanedioic acid mono(3-amino-3-carboxypropyl) ester
Butanedioic acid mono[(3S)-3-amino-3-carboxypropyl] ester
L-2-Amino-4-hydroxy-Butyrate hydrogen succinate (ester) (8CI)
L-2-Amino-4-hydroxy-Butyric acid hydrogen succinate (ester) (8CI)
L-2-Amino-4-hydroxy-Butyric acid hydrogen succinic acid (ester) (8CI)
L-Homoserine hydrogen butanedioate (ester)
L-Homoserine hydrogen butanedioate (ester) (9CI)
L-Homoserine hydrogen butanedioic acid (ester)
L-Homoserine hydrogen butanedioic acid (ester) (9CI)
O(4)-succinyl-L-homoserine
O-4-Succinyl-L-homoserine
O-Succinyl-homoserine
O-Succinyl-L-homoserine
O-Succinylhomoserine
Succinate ester with 2-amino-4-hydroxybutyrate
Succinate ester with 2-amino-4-hydroxybutyrate (7ci)
Succinate ester with 2-amino-4-hydroxybutyric acid
Succinate ester with 2-amino-4-hydroxybutyric acid (7CI)
Succinate monoester with 2-amino-4-hydroxybutyrate
Succinate monoester with 2-amino-4-hydroxybutyric acid
Succinate monoester with L-2-amino-4-hydroxybutyrate
Succinate monoester with L-2-amino-4-hydroxybutyrate (8ci)
Succinate monoester with L-2-amino-4-hydroxybutyric acid
Succinate monoester with L-2-amino-4-hydroxybutyric acid (8CI)
Succinic acid ester with 2-amino-4-hydroxybutyric acid
Succinic acid ester with 2-amino-4-hydroxybutyric acid (7CI)
Succinic acid monoester with 2-amino-4-hydroxybutyric acid
Succinic acid monoester with L-2-amino-4-hydroxybutyric acid
Succinic acid monoester with L-2-amino-4-hydroxybutyric acid (8CI)
Succinyl-homoserine
SucHomoSer

Chemical Formula:

C₈H₁₃NO₆

Weight:

Average: 219.1919
Monoisotopic: 219.074287153

InChI Key:

GNISQJGXJIDKDJ-YFKPBYRVSA-N

InChI:

InChI=1S/C8H13NO6/c9-5(8(13)14)3-4-15-7(12)2-1-6(10)11/h5H,1-4,9H2,(H,10,11)(H,13,14)/t5-/m0/s1

CAS number:

1492-23-5

IUPAC Name:

(2S)-2-amino-4-[(3-carboxypropanoyl)oxy]butanoic acid

Traditional IUPAC Name:

O-succinyl-L-homoserine

SMILES:

N[C@@H](CCOC(=O)CCC(O)=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
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Amino acid
Carboxylic acid
Amine
Hydrocarbon derivative
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

o-succinylhomoserine (CHEBI:16160 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
LogP:	-2.96	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	8.69 g/L	ALOGPS
logP	-3.3	ALOGPS
logP	-3.6	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.69	ChemAxon
pKa (Strongest Basic)	9.46	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	126.92 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	46.95 m³·mol⁻¹	ChemAxon
Polarizability	20.51 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:

Sulfur metabolism	PW000922
methionine biosynthesis	PW000814

KEGG Pathways:

Cysteine and methionine metabolism ec00270
Metabolic pathways eco01100
Selenoamino acid metabolism ec00450
Sulfur metabolism ec00920

EcoCyc Pathways:

methionine biosynthesis I HOMOSER-METSYN-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-9600000000-0ee701fa496e19e3d173	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-1950000000-5b18c68cf76a73eb1d8f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pi0-7900000000-3331dd355814be8ede11	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9400000000-146c8b009d4e75570320	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014j-7690000000-0163fcb4afd466414db2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ba-9720000000-dd9470ad7562bdf591b1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05tb-9200000000-ae21c8bfb909ac97af60	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	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:

Aitken, S. M., Kim, D. H., Kirsch, J. F. (2003). "Escherichia coli cystathionine gamma-synthase does not obey ping-pong kinetics. Novel continuous assays for the elimination and substitution reactions." Biochemistry 42:11297-11306. Pubmed: 14503880
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	16160
HMDB ID	Not Available
Pubchem Compound ID	439406
Kegg ID	C01118
ChemSpider ID	388523
Wikipedia ID	Not Available
BioCyc ID	O-SUCCINYL-L-HOMOSERINE
EcoCyc ID	O-SUCCINYL-L-HOMOSERINE

Enzymes

Protein Details

1. Cystathionine gamma-synthase

General function:: Involved in pyridoxal phosphate binding
Specific function:: O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:: metB
Uniprot ID:: P00935
Molecular weight:: 41550

Reactions

O(4)-succinyl-L-homoserine + L-cysteine = L-cystathionine + succinate.

Protein Details

2. Homoserine O-succinyltransferase

General function:: Involved in transferase activity, transferring acyl groups
Specific function:: Succinyl-CoA + L-homoserine = CoA + O- succinyl-L-homoserine
Gene Name:: metA
Uniprot ID:: P07623
Molecular weight:: 35727

Reactions

Succinyl-CoA + L-homoserine = CoA + O-succinyl-L-homoserine.

O-Succinyl-L-homoserine (ECMDB01418) (M2MDB000380)

Structure for #<Compound:0xaff3b290>

Enzymes

Reactions

Reactions