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Record Information
Version	2.0
Creation Date	2012-05-31 14:21:24 -0600
Update Date	2015-06-03 17:19:04 -0600
Secondary Accession Numbers	ECMDB12266
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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa7e80c7c> Close
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
Weight:	Average: 289.2387 Monoisotopic: 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
Description	belongs to the class of organic compounds 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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	N-acyl-L-alpha-amino acids
Alternative Parents	Tricarboxylic acids and derivatives N-acyl amines Alpha-keto acids and derivatives Alpha-hydroxy ketones Secondary carboxylic acid amides Carboxylic acids Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
Substituents	N-acyl-l-alpha-amino acid Tricarboxylic acid or derivatives Alpha-keto acid Fatty amide Keto acid Fatty acyl N-acyl-amine Alpha-hydroxy ketone Carboxamide group Secondary carboxylic acid amide Ketone Carboxylic acid Organooxygen compound Hydrocarbon derivative Organic oxide Organopnictogen compound Carbonyl group Organic oxygen compound Organic nitrogen compound Organonitrogen compound Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	tricarboxylic acid (CHEBI:35266 )
Physical Properties
State:	Solid
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 1.41 g/L ALOGPS logP -0.78 ALOGPS logP -0.55 ChemAxon logS -2.3 ALOGPS pKa (Strongest Acidic) 2.78 ChemAxon pKa (Strongest Basic) -1.5 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 158.07 Ų ChemAxon Rotatable Bond Count 10 ChemAxon Refractivity 61.57 m³·mol⁻¹ ChemAxon Polarizability 25.89 ų 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:	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 N-succinyl-L-2,6-diaminoheptanedioate + Oxoglutaric acid > N-Succinyl-2-amino-6-ketopimelate + L-Glutamate Succinyl-CoA + (S)-2,3,4,5-tetrahydropyridine-2,6-dicarboxylate + Water > CoA + 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 alpha-Ketoglutarate + N-Succinyl-L,L-2,6-diaminopimelate <> L-Glutamate + N-Succinyl-2-amino-6-ketopimelate Water + Succinyl-CoA + Tetrahydrodipicolinate <> Coenzyme A + N-Succinyl-2-amino-6-ketopimelate
SMPDB Pathways:	Lysine biosynthesis PW000771
KEGG Pathways:	Lysine biosynthesis ec00300 Metabolic pathways eco01100 Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:	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 splash10-0006-9880000000-0f0ff4f7e373c0b3162c View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive splash10-00du-9408600000-fd466a0230c24aa5db92 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 splash10-0fkc-0290000000-2cf1a6c8c873c44c176a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0fdo-1970000000-e6da5433a70177935ddd View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-05i3-7900000000-a6e1749a519577b39b0b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-007c-0190000000-cfcf85c3db41c68abca2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-009g-1590000000-73abaab210b9727b9f16 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-5910000000-b01ea1042bed0446bc1c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0006-0790000000-d2b9c6f92d7b00453793 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0abc-4930000000-f2f2e3269f8edd762cf8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0pb9-9700000000-787d11c10df4c3cb6d65 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000l-0590000000-2961efd3a4f8e021c893 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-002g-0960000000-6adfe9927596ba357d75 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9500000000-70678263ddcfe89f4fb6 View in MoNA 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:	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 35266 HMDB ID HMDB12266 Pubchem Compound ID 440349 Kegg ID C04462 ChemSpider ID 389314 Wikipedia ID Not Available BioCyc ID N-SUCCINYL-2-AMINO-6-KETOPIMELATE EcoCyc ID N-SUCCINYL-2-AMINO-6-KETOPIMELATE

Enzymes