ChemFOnt: Showing chemical card for Aminoadipic acid (CFc000000390)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:46 UTC

Chemfont ID

CFc000000390

Molecule Identification

Common Name

Aminoadipic acid

Definition

Aminoadipic acid (CAS: 542-32-5), also known as 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. It antagonizes neuroexcitatory activity modulated by the glutamate receptor N-methyl-D-aspartate (NMDA). Aminoadipic acid has also been shown to inhibit the production of kynurenic acid, a broad spectrum excitatory amino acid receptor antagonist, in brain tissue slices (PMID: 8566117 ). 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 human 2-aminoadipic aciduria and 2-oxoadipic aciduria via impaired decarboxylation of 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 form 2-aminoadipic acid in human 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 three branched-chain amino acids: leucine, valine, and isoleucine) 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 can also lead to elevated levels of aminoadipate which is thought 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 ). Therefore, depending on the circumstances aminoadipic acid can act as an acidogen, a diabetogen, an atherogen, and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A diabetogen is a compound that can lead to type 2 diabetes. An atherogen is a compound that leads to atherosclerosis and cardiovascular disease. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of aminoadipic acid are associated with at least two inborn errors of metabolism including 2-aminoadipic aciduria and 2-oxoadipic aciduria. Aminoadipic acid is an organic acid and abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, kidney abnormalities, liver damage, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. As a diabetogen, serum aminoadipic levels appear to regulate glucose homeostasis and have been highly predictive of individuals who later develop diabetes (PMID: 24091325 ). In particular, aminoadipic acid lowers fasting plasma glucose levels and enhances insulin secretion from human islets. As an atherogen, aminoadipic acid has been found to be produced at high levels via protein lysine oxidation in atherosclerotic plaques (PMID: 28069522 ).

Structure

MOL SDF PDB SMILES InChI

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

1118-90-7

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 )

Functional Ontology

Physiological effect

Health effect

Genetic disorder

Nontypified gene mutation

Organic acidemia

2-Aminoadipic acidemia (HMDB: HMDB0000510)
2-ketoadipic acidemia (HMDB: HMDB0000510)

2-aminoadipic aciduria (HMDB: HMDB0000510)

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0000510)

Observation

Aciduria (HMDB: HMDB0000510)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8764822)
Saliva (HMDB: HMDB0000510)

Organ

Prostate (HMDB: HMDB0000510)
Placenta (HMDB: HMDB0000510)

Excreta

Biofluid or Excreta

Urine (PMID: 19309105)
Feces (PMID: 27609529)

Cellular substructure

Cytoplasm (HMDB: HMDB0000510)
Membrane (HMDB: HMDB0000510)

Organelle

Mitochondrion (HMDB: HMDB0000510)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000510)

Source

Endogenous

Endogenous (HMDB: HMDB0000510)

Plant

Animal

Animal (HMDB: HMDB0000510)

Exogenous

Food

Food (HMDB: HMDB0000510)

Broccoli (FooDB: FOOD00034)
White cabbage (FooDB: FOOD00887)

Leaf vegetable

Tuber

Potato (FooDB: FOOD00175)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)
Rye (FooDB: FOOD00169)
Wheat (FooDB: FOOD00561)

Gourd

Cucumber (FooDB: FOOD00065)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)

Herb and spice

Herb

Dill (FooDB: FOOD00013)
Turnip (FooDB: FOOD00036)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)
Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Pulse

Bean

Yellow wax bean (FooDB: FOOD00882)
Green bean (FooDB: FOOD00883)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Lysine Degradation (HMDB: HMDB0000510)
Lysine Degradation (HMDB: HMDB0000510)
Lysine Metabolism (PathBank: SMP0002434)

Disease pathway

2-Aminoadipic 2-Oxoadipic Aciduria (HMDB: HMDB0000510)
Pyridoxine Dependency with Seizures (PathBank: SMP0120635)
Glutaric Aciduria Type I (PathBank: SMP0120704)
Hyperlysinemia I, Familial (PathBank: SMP0120811)
Hyperlysinemia II or Saccharopinuria (PathBank: SMP0120812)
Pyridoxine Dependency with Seizures (HMDB: HMDB0000510)
Saccharopinuria/Hyperlysinemia II (PathBank: SMP0120746)

Role

Industrial application

Food and nutrition

Food and nutrition (HMDB: HMDB0000510)

Pharmaceutical industry

Biomarker

Alpha Aminoadipic Aciduria (MarkerDB: MDB00000178)

Indirect biological role

Metabotoxin

Metabotoxin (HMDB: HMDB0000510)

Biological role

Human metabolite (HMDB: HMDB0000510)
Metabolite (HMDB: HMDB0000510)
Escherichia coli metabolite (HMDB: HMDB0000510)
Metabolite (HMDB: HMDB0000510)

Physical Properties

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 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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon