Livestock Metabolome Database: Showing metabocard for Aminoadipic acid (LMDB00168)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:43:51 UTC

Update Date

2021-04-30 20:57:41 UTC

Lmdb

LMDB00168

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Aminoadipic acid

Description

Aminoadipic acid (2-aminoadipate) is a metabolite in the principal biochemical pathway of lysine. It is an intermediate in the metabolism (i.e. breakdown or degradation) of lysine and saccharopine.(Wikipedia). It antagonizes neuroexcitatory activity modulated by the glutamate receptor, N-methyl-D-aspartate; (NMDA). Aminoadipic has also been shown to inhibit the production of kynurenic acid in brain tissue slices (PMID: 8566117 ). Kynurenic acid is a broad spectrum excitatory amino acid receptor antagonist. Recent studies have shown that aminoadipic acid is elevated in prostate biopsy tissues from prostate cancer patients (PMID: 23737455 ). Mutations in DHTKD1 (dehydrogenase E1 and transketolase domain-containing protein 1) have been shown to cause animal 2-aminoadipic and 2-oxoadipic aciduria via impaired turnover of decarboxylation 2-oxoadipate to glutaryl-CoA, which is the last step in the lysine degradation pathway (PMID: 23141293 ). Aging, diabetes, sepsis and renal failure are known to catalyze the oxidation of lysyl residues to 2-aminoadipic acid in animal skin collagen and potentially other tissues (PMID: 18448817 ). Proteolytic breakdown of these tissues can lead to the release of free 2-aminoadipic acid. Studies in rats indicate that aminoadipic acid (along with the 3 branched chain amino acid ñ Leu, Val and Ile) levels are elevated in the pre-diabetic phase and so aminoadipic acid may serve as a predictive biomarker for the development of diabetes. (PMID: 15389298 ). Long-term hyperglycemia of endothelial cells leads to elevated levels of aminoadipate which is though to be a sign of lysine breakdown through oxidative stress and reactive oxygen species (ROS) (PMID: 21961526 ). 2-aminoadipate is a potential small-molecule marker of oxidative stress (PMID: 21647514 )

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(+/-)-2-aminoadipic acid	ChEBI
Aad	ChEBI
alpha-Aminoadipic acid	ChEBI
DL-2-Aminoadipic acid	ChEBI
DL-2-Aminohexanedioic acid	ChEBI
DL-alpha-Aminoadipic acid	ChEBI
(+/-)-2-aminoadipate	Generator
a-Aminoadipate	Generator
a-Aminoadipic acid	Generator
alpha-Aminoadipate	Generator
Α-aminoadipate	Generator
Α-aminoadipic acid	Generator
DL-2-Aminoadipate	Generator
DL-2-Aminohexanedioate	Generator
DL-a-Aminoadipate	Generator
DL-a-Aminoadipic acid	Generator
DL-alpha-Aminoadipate	Generator
DL-Α-aminoadipate	Generator
DL-Α-aminoadipic acid	Generator
Aminoadipate	Generator
2 Aminoadipic acid	MeSH
2 Aminohexanedioic acid	MeSH
2-Aminoadipic acid	MeSH
Acid, 2 aminoadipic	MeSH
Acid, 2-aminoadipic	MeSH
Acid, 2-aminohexanedioic	MeSH
Acid, alpha-aminoadipic	MeSH
Aminoadipic acid, 2	MeSH
alpha Aminoadipic acid	MeSH
2-Aminoadipate	HMDB
alpha-amino-Adipic acid	HMDB
L-2-Aminoadipate	HMDB
L-2-Aminoadipic acid	HMDB
L-2-Aminohexanedioate	HMDB
L-2-Aminohexanedioic acid	HMDB
L-alpha-Aminoadipate	HMDB
L-alpha-Aminoadipic acid	HMDB
2-Aminohexanedioic acid	MeSH, HMDB

Chemical Formula

C₆H₁₁NO₄

Average Molecular Weight

161.1558

Monoisotopic Molecular Weight

161.068807845

IUPAC Name

2-aminohexanedioic acid

Traditional Name

aminoadipic acid

CAS Registry Number

542-32-5

SMILES

NC(CCCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)

InChI Key

OYIFNHCXNCRBQI-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Dicarboxylic acid or derivatives
Fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

amino dicarboxylic acid (CHEBI:37024 )
non-proteinogenic alpha-amino acid (CHEBI:37024 )
Dicarboxylic acids (LMFA01170098 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	35.89 m³·mol⁻¹	ChemAxon
Polarizability	15.53 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-02di-0950000000-ec4fd991a53a8b6bc6ae	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-02di-0950000000-ec4fd991a53a8b6bc6ae	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00r6-9300000000-9ef33042820e032c1af3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00ri-9620000000-052fe671da5a64787657	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03xv-2900000000-58b4f0b3e06cbb7abb90	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4j-9000000000-cc9c0c03f7c3890b531c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9000000000-7b74167f01c922da9ef7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-9400000000-71832a0d1e49341749a7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 20V, negative	splash10-014l-2900000000-08df6df87d0bea6dce31	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, negative	splash10-0006-0900000000-99e7d8729f7099c6e9ea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-03di-0900000000-f542aa2756da9aa3ecb6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-03di-0900000000-3133117467ce925161cb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-03di-0900000000-9e5f27d91fd799c059d6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-03xu-0900000000-b801b3a34049e54a2915	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-014i-1900000000-2ef33d8640c4e5788618	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-014i-1900000000-281e4277990becc84832	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-014i-2900000000-a56c711aeb57c767fed8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, negative	splash10-0006-0900000000-862ae5fa10820c14bdf1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, negative	splash10-006t-9400000000-e007d0e2c3cec7f1a02c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, negative	splash10-0002-9000000000-4755db14192225e1eebf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kg-2900000000-3e45ac769d3b229221a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ba-9600000000-c51318834cc371625d46	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fu-9000000000-edbc970f12ea186bcf06	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-0f7002659f604cc69395	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-4900000000-bf42ddc971a2a05516a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abc-9100000000-1979c27463bab7d33d58	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-4900000000-7913a597d0c94eebe02d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dj-9100000000-523aa25ee55f888299e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-0dcf3a7ca5d4e20885ee	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Feces
Follicular Fluid
Milk
Plasma
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Feces	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Follicular Fluid	Detected and Quantified	27 +/- 4-37+/-4 uM	Not Available	Porcine	183842	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details
Milk	Detected and Quantified	195-427 uM	Not Available	Bovine	20338431	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Plasma	Detected and Quantified	44 +/- 2-37+/-4 uM	Not Available	Porcine	22513987	details
Plasma	Detected and Quantified	54 +/- 8-83+/-13 uM	Not Available	Porcine	22513987	details
Plasma	Detected and Quantified	55 +/- 7-75+/-15 uM	Not Available	Porcine	22513987	details
Serum	Detected and Quantified	1.4316 +/- 0.4262 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.4892 +/- 0.5005 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.1757 +/- 0.7708 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.5796 +/- 0.4215 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.6284 +/- 0.4872 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.89 +/- 3.95 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	1.6636 +/- 0.6341 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.9958 +/- 0.7143 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3 +/- 9 uM	Not Available	Porcine	183842	details
Serum	Detected and Quantified	1.6302 +/- 0.798 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.9 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	3.6 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	4.2 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	4.3 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	1.8689 +/- 0.6061 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.3136 +/- 0.5757 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.4315 +/- 0.4727 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.1748 +/- 0.6959 uM	Normal	Ovine	Goldansaz et al.,...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0302754

FooDB ID

FDB007648

Phenol Explorer ID

Not Available

KNApSAcK ID

C00007393

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Alpha-Aminoadipic_acid

Chemspider ID

456

ChEBI ID

37024

PubChem Compound ID

469

Kegg Compound ID

Not Available

YMDB ID

YMDB00305

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Wu HQ, Ungerstedt U, Schwarcz R: L-alpha-aminoadipic acid as a regulator of kynurenic acid production in the hippocampus: a microdialysis study in freely moving rats. Eur J Pharmacol. 1995 Jul 25;281(1):55-61. [8566117 ]
Jung K, Reszka R, Kamlage B, Bethan B, Stephan C, Lein M, Kristiansen G: Tissue metabolite profiling identifies differentiating and prognostic biomarkers for prostate carcinoma. Int J Cancer. 2013 Dec 15;133(12):2914-24. doi: 10.1002/ijc.28303. Epub 2013 Jun 29. [23737455 ]
Danhauser K, Sauer SW, Haack TB, Wieland T, Staufner C, Graf E, Zschocke J, Strom TM, Traub T, Okun JG, Meitinger T, Hoffmann GF, Prokisch H, Kolker S: DHTKD1 mutations cause 2-aminoadipic and 2-oxoadipic aciduria. Am J Hum Genet. 2012 Dec 7;91(6):1082-7. doi: 10.1016/j.ajhg.2012.10.006. Epub 2012 Nov 8. [23141293 ]
Sell DR, Strauch CM, Shen W, Monnier VM: Aging, diabetes, and renal failure catalyze the oxidation of lysyl residues to 2-aminoadipic acid in human skin collagen: evidence for metal-catalyzed oxidation mediated by alpha-dicarbonyls. Ann N Y Acad Sci. 2008 Apr;1126:205-9. doi: 10.1196/annals.1433.065. [18448817 ]
Wijekoon EP, Skinner C, Brosnan ME, Brosnan JT: Amino acid metabolism in the Zucker diabetic fatty rat: effects of insulin resistance and of type 2 diabetes. Can J Physiol Pharmacol. 2004 Jul;82(7):506-14. [15389298 ]
Yuan W, Zhang J, Li S, Edwards JL: Amine metabolomics of hyperglycemic endothelial cells using capillary LC-MS with isobaric tagging. J Proteome Res. 2011 Nov 4;10(11):5242-50. doi: 10.1021/pr200815c. Epub 2011 Oct 17. [21961526 ]
Zeitoun-Ghandour S, Leszczyszyn OI, Blindauer CA, Geier FM, Bundy JG, Sturzenbaum SR: C. elegans metallothioneins: response to and defence against ROS toxicity. Mol Biosyst. 2011 Aug;7(8):2397-406. doi: 10.1039/c1mb05114h. Epub 2011 Jun 7. [21647514 ]

Showing metabocard for Aminoadipic acid (LMDB00168)

Structure for LMDB00168 (Aminoadipic acid)