Record Information
Version2.0
Creation Date2012-05-31 13:47:03 -0600
Update Date2015-06-03 15:53:49 -0600
Secondary Accession Numbers
  • ECMDB01180
Identification
Name:N2-Succinyl-L-glutamic acid 5-semialdehyde
Description:N2-Succinyl-L-glutamic acid 5-semialdehyde is a substrate for Succinate semialdehyde dehydrogenase (mitochondrial) and Ornithine aminotransferase (mitochondrial).
Structure
Thumb
Synonyms:
  • N2-Succinyl-L-glutamate 5-semialdehyde
  • N2-succinylglutamate semialdehyde
  • N2-succinylglutamic acid semialdehyde
  • N2-succinylglutamic semialdehyde
  • N2-succinylglutamic-semialdehyde
  • N2SucGluSA
  • N2-succinylglutamate semialdehyde
  • N2-succinylglutamic semialdehyde
  • N2-succinylglutamic-semialdehyde
Chemical Formula:C9H13NO6
Weight:Average: 231.2026
Monoisotopic: 231.074287153
InChI Key:XTOKIEIBKARFSZ-LURJTMIESA-N
InChI:InChI=1S/C9H13NO6/c11-5-1-2-6(9(15)16)10-7(12)3-4-8(13)14/h5-6H,1-4H2,(H,10,12)(H,13,14)(H,15,16)/t6-/m0/s1
CAS number:Not Available
IUPAC Name:(2S)-2-(3-carboxypropanamido)-5-oxopentanoic acid
Traditional IUPAC Name:(2S)-2-(3-carboxypropanamido)-5-oxopentanoic acid
SMILES:OC(=O)CCC(=O)N[C@@H](CCC=O)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentN-acyl-L-alpha-amino acids
Alternative Parents
Substituents
  • N-acyl-l-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • Fatty acyl
  • Fatty acid
  • N-acyl-amine
  • Alpha-hydrogen aldehyde
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Aldehyde
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.57 mg/mLALOGPS
logP-0.81ALOGPS
logP-1.4ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.38ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area120.77 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity50.7 m3·mol-1ChemAxon
Polarizability21.38 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
arginine metabolismPW000790 Pw000790Pw000790 greyscalePw000790 simple
KEGG Pathways:
  • Arginine and proline metabolism ec00330
EcoCyc Pathways:
  • arginine degradation II (AST pathway) AST-PWY
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-06rf-8920000000-de0373c383031c38b98dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0fk9-9616000000-e905acfb4421fd9a292dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1980000000-74015f7ab3858792898cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q0-5910000000-c37e86034167b574deb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6u-9300000000-4a69a3cdc96a6c8c5c40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1590000000-5a28fbbff5308518ce1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02ai-3930000000-12821be6f464ccdfdba0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-2070a656d13619fb7663View 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
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID27657
HMDB IDHMDB01180
Pubchem Compound ID556
Kegg IDC05932
ChemSpider ID389690
Wikipedia IDNot Available
BioCyc IDCPD-822
EcoCyc IDCPD-822

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NAD-dependent reduction of succinylglutamate semialdehyde into succinylglutamate. Also shows activity with decanal or succinic semialdehyde as the electron donor and NAD as the electron acceptor. No activity is detected with NADP as the electron acceptor. Therefore, is an aldehyde dehydrogenase with broad substrate specificity
Gene Name:
astD
Uniprot ID:
P76217
Molecular weight:
53026
Reactions
N-succinyl-L-glutamate 5-semialdehyde + NAD(+) + H(2)O = N-succinyl-L-glutamate + NADH.
General function:
Involved in transaminase activity
Specific function:
Catalyzes the transamination of N(2)-succinylornithine and alpha-ketoglutarate into N(2)-succinylglutamate semialdehyde and glutamate. Can also act as an acetylornithine aminotransferase
Gene Name:
astC
Uniprot ID:
P77581
Molecular weight:
43665
Reactions
N(2)-succinyl-L-ornithine + 2-oxoglutarate = N-succinyl-L-glutamate 5-semialdehyde + L-glutamate.