Record Information
Version2.0
Creation Date2012-05-31 13:52:17 -0600
Update Date2015-06-03 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
Thumb
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
DescriptionThis compound belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentD-alpha-amino acids
Alternative Parents
Substituents
  • D-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • Amino fatty acid
  • Fatty acyl
  • Carboxylic acid ester
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-2.96PhysProp
Predicted Properties
PropertyValueSource
Water Solubility8.69 g/LALOGPS
logP-3.3ALOGPS
logP-3.6ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.69ChemAxon
pKa (Strongest Basic)9.46ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area126.92 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity46.95 m³·mol⁻¹ChemAxon
Polarizability20.51 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Sulfur metabolismPW000922 ThumbThumb?image type=greyscaleThumb?image type=simple
methionine biosynthesisPW000814 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uk9-9600000000-0ee701fa496e19e3d173View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-1950000000-5b18c68cf76a73eb1d8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pi0-7900000000-3331dd355814be8ede11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9400000000-146c8b009d4e75570320View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-7690000000-0163fcb4afd466414db2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-9720000000-dd9470ad7562bdf591b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05tb-9200000000-ae21c8bfb909ac97af60View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView 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
External Links:
ResourceLink
CHEBI ID16160
HMDB IDNot Available
Pubchem Compound ID439406
Kegg IDC01118
ChemSpider ID388523
Wikipedia IDNot Available
BioCyc IDO-SUCCINYL-L-HOMOSERINE
EcoCyc IDO-SUCCINYL-L-HOMOSERINE

Enzymes

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.
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.