N-Succinyl-2-amino-6-ketopimelate (PAMDB000835)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000835
Identification
Name: N-Succinyl-2-amino-6-ketopimelate
Description:N-Succinyl-2-amino-6-ketopimelate is an intermediate in lysine biosynthesis. It is the fourth to last step in n the synthesis of lysine and is converted from tetrahydrodipicolinate via the enzyme tetrahydrodipicolinate N-succinyltransferase (EC 2.3.1.117). It is then converted to N-succinyl-L,L-2,6-diaminopimelate via the enzyme Succinyldiaminopimelate transferase (EC 2.6.1.17).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2S)-2-(3-carboxypropanamido)-6-oxoheptanedioate
  • (2S)-2-(3-carboxypropanamido)-6-oxoheptanedioic acid
  • (S)-2-(Succinylamino)-6-oxoheptanedioate
  • (S)-2-(Succinylamino)-6-oxoheptanedioic acid
  • N-succinyl-L-2-amino-6-oxoheptanedioate
  • L-2-Succinylamino-6-oxoheptanedioate
  • L-2-Succinylamino-6-oxoheptanedioic acid
  • N-Succinyl-2-amino-6-ketopimelic acid
  • N-Succinyl-2-amino-6-oxo-L-pimelate
  • N-Succinyl-2-amino-6-oxo-L-pimelic acid
  • N-Succinyl-2-L-amino-6-oxoheptanedioate
  • N-Succinyl-2-L-amino-6-oxoheptanedioic acid
  • N-Succinyl-epsilon-keto-L-aminopimelate
  • N-Succinyl-epsilon-keto-L-aminopimelic acid
  • N-Succinyl-L-2-amino-6-oxoheptanedioate
  • N-Succinyl-L-2-amino-6-oxoheptanedioic acid
  • N-Succinyl-L-2-amino-6-oxopimelate
  • N-Succinyl-L-2-amino-6-oxopimelic acid
  • SAKPA
  • Succinyl-ε-keto-α-aminopimelate
  • Succinyl-ε-keto-α-aminopimelic acid
  • Succinyl-epsilon-keto-a-aminopimelate
  • Succinyl-epsilon-keto-a-aminopimelic acid
  • Succinyl-epsilon-keto-alpha-aminopimelate
  • Succinyl-epsilon-keto-alpha-aminopimelic acid
  • Succinyl-epsilon-keto-α-aminopimelate
  • Succinyl-epsilon-keto-α-aminopimelic acid
Chemical Formula: C11H15NO8
Average Molecular Weight: 289.2387
Monoisotopic Molecular Weight: 289.079766461
InChI Key: SDVXSCSNVVZWDD-LURJTMIESA-N
InChI:InChI=1S/C11H15NO8/c13-7(11(19)20)3-1-2-6(10(17)18)12-8(14)4-5-9(15)16/h6H,1-5H2,(H,12,14)(H,15,16)(H,17,18)(H,19,20)/t6-/m0/s1
CAS number: Not Available
IUPAC Name:(2S)-2-(3-carboxypropanamido)-6-oxoheptanedioic acid
Traditional IUPAC Name: (2S)-2-(3-carboxypropanamido)-6-oxoheptanedioic acid
SMILES:OC(=O)CCC(=O)N[C@@H](CCCC(=O)C(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as n-acyl-aliphatic-alpha amino acids. These are alpha amino acids carrying a N-acylated aliphatic chain.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent N-acyl-aliphatic-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-l-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Amino fatty acid
  • Fatty acyl
  • N-acyl-amine
  • Keto acid
  • Fatty amide
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Secondary carboxylic acid amide
  • Ketone
  • Carboxamide group
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.41 mg/mLALOGPS
logP-0.78ALOGPS
logP-0.55ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)2.78ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area158.07 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity61.57 m3·mol-1ChemAxon
Polarizability25.89 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Water + Succinyl-CoA + Tetrahydrodipicolinate <> Coenzyme A + N-Succinyl-2-amino-6-ketopimelate
alpha-Ketoglutarate + N-Succinyl-L,L-2,6-diaminopimelate <> L-Glutamate + N-Succinyl-2-amino-6-ketopimelate
Oxoglutaric acid + N-Succinyl-L,L-2,6-diaminopimelate <> L-Glutamate + N-Succinyl-2-amino-6-ketopimelate
(S)-2,3,4,5-tetrahydrodipicolinate + Succinyl-CoA + Water + Succinyl-CoA > Coenzyme A + N-Succinyl-2-amino-6-ketopimelate
N-Succinyl-2-amino-6-ketopimelate + L-Glutamic acid + L-Glutamate > N-Succinyl-L,L-2,6-diaminopimelate + Oxoglutaric acid
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fkc-0290000000-2cf1a6c8c873c44c176aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fdo-1970000000-e6da5433a70177935dddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i3-7900000000-a6e1749a519577b39b0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-007c-0190000000-cfcf85c3db41c68abca2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-009g-1590000000-73abaab210b9727b9f16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-5910000000-b01ea1042bed0446bc1cView 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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID35266
HMDB IDHMDB12266
Pubchem Compound ID440349
Kegg IDC04462
ChemSpider ID389314
Wikipedia IDNot Available
BioCyc IDN-SUCCINYL-2-AMINO-6-KETOPIMELATE
EcoCyc IDN-SUCCINYL-2-AMINO-6-KETOPIMELATE