Bovine Metabolome Database: Showing metabocard for Aminoadipic acid (BMDB0000510)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:31:53 UTC

Update Date

2020-06-04 20:23:43 UTC

BMDB ID

BMDB0000510

Secondary Accession Numbers

BMDB00510

Metabolite Identification

Common Name

Aminoadipic acid

Description

Aminoadipic acid, also known as aminoadipic acid or Aminoadipic acid, 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). Aminoadipic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Aminoadipic acid exists in all eukaryotes, ranging from yeast to humans. Aminoadipic acid participates in a number of enzymatic reactions, within cattle. In particular, Aminoadipic acid can be biosynthesized from allysine through the action of the enzyme Alpha-aminoadipic semialdehyde dehydrogenase. In addition, Aminoadipic acid and oxoglutaric acid can be converted into oxoadipic acid and L-glutamic acid through its interaction with the enzyme kynurenine/alphaminoadipic acid aminotransferase, mitochondrial. In cattle, aminoadipic acid is involved in the metabolic pathway called the lysine degradation pathway. Aminoadipic acid is a potentially toxic compound.

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

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	196 - 198 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.2 mg/mL	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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-02di-0950000000-ec4fd991a53a8b6bc6ae	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-02di-0950000000-ec4fd991a53a8b6bc6ae	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00r6-9300000000-9ef33042820e032c1af3	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00ri-9620000000-052fe671da5a64787657	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03xv-2900000000-58b4f0b3e06cbb7abb90	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4j-9000000000-cc9c0c03f7c3890b531c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9000000000-7b74167f01c922da9ef7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-9400000000-71832a0d1e49341749a7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 20V, negative	splash10-014l-2900000000-08df6df87d0bea6dce31	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, negative	splash10-0006-0900000000-99e7d8729f7099c6e9ea	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-03di-0900000000-f542aa2756da9aa3ecb6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-03di-0900000000-3133117467ce925161cb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-03di-0900000000-9e5f27d91fd799c059d6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-03xu-0900000000-b801b3a34049e54a2915	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-014i-1900000000-2ef33d8640c4e5788618	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-014i-1900000000-281e4277990becc84832	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-014i-2900000000-a56c711aeb57c767fed8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, negative	splash10-0006-0900000000-862ae5fa10820c14bdf1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, negative	splash10-006t-9400000000-e007d0e2c3cec7f1a02c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 11V, negative	splash10-0002-9000000000-4755db14192225e1eebf	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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-4900000000-7913a597d0c94eebe02d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dj-9100000000-523aa25ee55f888299e1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-0dcf3a7ca5d4e20885ee	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Blood
Liver
Longissimus Thoracis Muscle
Mammary Gland
Milk
Placenta
Prostate Tissue
Ruminal Fluid
Semimembranosus Muscle
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Lysine Degradation		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.28 +/- 0.52 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Blood	Detected and Quantified	7.3-8.1 uM	Not Specified	Not Specified	Normal	PMID: 28036059	details
Liver	Detected and Quantified	68 +/- 27 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Longissimus Thoracis Muscle	Detected and Quantified	7 +/- 2 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Milk	Detected and Quantified	4.3 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	6.1 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	5.4 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	5.0 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	195 - 427 uM	Not Specified	Not Specified	Normal	PMID: 20338431	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23438684	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	1 +/- 1 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Semimembranosus Muscle	Detected and Quantified	10 +/- 4 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	98 +/- 39 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0302754

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007648

KNApSAcK ID

C00007393

Chemspider ID

456

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alpha-Aminoadipic_acid

METLIN ID

Not Available

PubChem Compound

469

PDB ID

Not Available

ChEBI ID

37024

References

Synthesis Reference

Khan, Naseem H.; Ali, Mohd.; Panda, H.; Rakhshinda. Synthesis of a-aminoadipic acid. Journal of the Indian Chemical Society (1982), 59(9), 1077-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

Enzyme Details

1. Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial

General function:: Transcription
Specific function:: Transaminase with broad substrate specificity. Has transaminase activity towards aminoadipate, kynurenine, methionine and glutamate. Shows activity also towards tryptophan, aspartate and hydroxykynurenine. Accepts a variety of oxo-acids as amino-group acceptors, with a preference for 2-oxoglutarate, 2-oxocaproic acid, phenylpyruvate and alpha-oxo-gamma-methiol butyric acid. Can also use glyoxylate as amino-group acceptor (in vitro) (By similarity).
Gene Name:: AADAT
Uniprot ID:: Q5E9N4
Molecular weight:: 47901.0

Reactions

Aminoadipic acid + Oxoglutaric acid → Oxoadipic acid + L-Glutamic acid	details

Enzyme Details

2. Alpha-aminoadipic semialdehyde dehydrogenase

General function:: Energy production and conversion
Specific function:: Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism (By similarity).
Gene Name:: ALDH7A1
Uniprot ID:: Q2KJC9
Molecular weight:: 58582.0

Reactions

Allysine + NAD + Water → Aminoadipic acid + NADH	details

Showing metabocard for Aminoadipic acid (BMDB0000510)

Structure for BMDB0000510 (Aminoadipic acid)

Enzymes

Reactions

Reactions