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Record Information
Version	2.0
Creation Date	2012-05-31 10:27:06 -0600
Update Date	2015-09-13 12:56:08 -0600
Secondary Accession Numbers	ECMDB00510
Identification
Name:	Aminoadipic acid
Description	Aminoadipic acid is metabolite in the principal biochemical pathway of lysine. The major outer membrane proteins from Escherichia coli K-12 are often modified to contain alpha-aminoadipic acid delta-semialdehyde (allysine). [PMID:358196]. Amiinoadipic acid can be decarboxylated by glutmate decarboxylase [PMID:379598]
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xb0157308> Close
Synonyms:	(+/-)-2-Aminoadipate (+/-)-2-Aminoadipic acid 2-Aminoadipate 2-Aminoadipic acid a-amino-Adipate a-amino-Adipic acid A-Aminoadipate A-Aminoadipic acid alpha-amino-Adipate Alpha-Amino-adipic acid Alpha-Aminoadipate Alpha-Aminoadipic acid Aminoadipate DL-2-Aminoadipate DL-2-Aminoadipic acid DL-2-Aminohexanedioate DL-2-Aminohexanedioic acid DL-a-Aminoadipate DL-a-Aminoadipic acid DL-alpha-Aminoadipate DL-alpha-Aminoadipic acid DL-α-Aminoadipate DL-α-Aminoadipic acid L-2-aminoadipate L-2-Aminoadipic acid L-2-Aminohexanedioate L-2-Aminohexanedioic acid L-a-Aminoadipate L-a-Aminoadipic acid L-alpha-Aminoadipate L-alpha-Aminoadipic acid L-α-Aminoadipate L-α-Aminoadipic acid α-amino-Adipate α-amino-Adipic acid α-Aminoadipate α-Aminoadipic acid
Chemical Formula:	C6H11NO4
Weight:	Average: 161.1558 Monoisotopic: 161.068807845
InChI Key:	OYIFNHCXNCRBQI-BYPYZUCNSA-N
InChI:	InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)/t4-/m0/s1
CAS number:	542-32-5
IUPAC Name:	(2S)-2-aminohexanedioic acid
Traditional IUPAC Name:	aminoadipate
SMILES:	N[C@@H](CCCC(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	Medium-chain fatty acids Amino fatty acids Dicarboxylic acids and derivatives Amino acids Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
Substituents	L-alpha-amino acid Medium-chain fatty acid Amino fatty acid Dicarboxylic acid or derivatives Fatty acid Fatty acyl Amino acid Carboxylic acid Organopnictogen compound Organic nitrogen compound Amine Organic oxygen compound Primary amine Organooxygen compound Organonitrogen compound Primary aliphatic amine Carbonyl group Hydrocarbon derivative Organic oxide Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	2-aminoadipic acid (CHEBI:37023 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	196-198 °C
Experimental Properties:	Property Value Source Water Solubility: 2.2 mg/ml [YALKOWSKY,SH & DANNENFELSER,RM (1992)] PhysProp LogP: -2.936 PhysProp
Predicted Properties	Property Value Source Water Solubility 32.7 g/L ALOGPS logP -3.4 ALOGPS logP -2.8 ChemAxon logS -0.69 ALOGPS pKa (Strongest Acidic) 2.01 ChemAxon pKa (Strongest Basic) 9.53 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 100.62 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 35.89 m³·mol⁻¹ ChemAxon Polarizability 15.53 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:
SMPDB Pathways:	Lysine biosynthesis PW000771
KEGG Pathways:	Lysine biosynthesis ec00300 Lysine degradation ec00310
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-MS (3 TMS) splash10-02vi-1890000000-cb81ff688a4a1d2ee926 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-00xu-9200000000-2a666aa0f9c15fd2295b View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-0002-9600000000-77ab58046847c3ea82f0 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Positive splash10-0a4j-9000000000-fced5385ac147b0fd6a0 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-9000000000-3f7c5858ac3e97d89e6e View in MoNA LC-MS/MS LC-MS/MS Spectrum - 30V, Positive splash10-0a4i-9000000000-af6e2d829df2d68bd262 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-9000000000-3664a98748e89e99cd2d View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-0002-9700000000-e1040cea3fd3c274b468 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Positive splash10-052b-9000000000-c9da617e7f36084d0276 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-00kb-9800000000-2738b9d8b78b33fed9f7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 35V, Positive splash10-00ke-7900000000-461c76f7d777bbdee97e View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-9000000000-b096dea8b50a6e2c75c4 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-00ke-7900000000-cfb9ae7bd0906a939368 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Positive splash10-0a4j-9000000000-7c27445e72a5da0c3bb6 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-014j-6900000000-f349746a9f0635231c65 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 0V, Positive splash10-03di-0900000000-1bc82027155d45c9a43d View in MoNA LC-MS/MS LC-MS/MS Spectrum - 30V, Positive splash10-0a4i-9000000000-2749c34e547a235a0f78 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 0V, Positive splash10-03di-0900000000-97545962897518937c04 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 30V, Positive splash10-0a4i-9000000000-0e2bf30c88b4dafc0c5f View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-0002-9500000000-83d347e56da993118fba View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Negative splash10-03xu-1900000000-db1ee9542c240bfe00b7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00kg-2900000000-3e45ac769d3b229221a3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-01ba-9600000000-c51318834cc371625d46 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-05fu-9000000000-edbc970f12ea186bcf06 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-1900000000-0f7002659f604cc69395 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-01ox-4900000000-bf42ddc971a2a05516a2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0abc-9100000000-1979c27463bab7d33d58 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 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
References
References:	Diedrich, D. L., Schnaitman, C. A. (1978). "Lysyl-derived aldehydes in outer membrane proteins of Escherichia coli." Proc Natl Acad Sci U S A 75:3708-3712. Pubmed: 358196 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 Sukhareva, B. S., Malikova, D. G. (1977). "[Substrate specificity of E. coli glutamate decarboxylase]." Mol Biol (Mosk) 11:394-402. Pubmed: 379598 Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
Synthesis Reference:	Waalkes, T.P. etal., J.A.C.S., 1950, 72, 5760; Trown, P.W. etal., Biochem. J., 1963, 86, 280-284; Lerch, E. etal., Helv. Chim. Acta, 1974, 57, 1584-1597; Kondo, M. etal., Bull. Chem. Soc. Jpn., 1985, 58, 1171-1173
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 17082 HMDB ID HMDB00510 Pubchem Compound ID 92136 Kegg ID C00956 ChemSpider ID 83182 Wikipedia alpha-Aminoadipate BioCyc ID Not Available Ligand Expo UN1

Enzymes