Page last updated: 2024-12-04

2-aminoadipic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

2-Aminoadipic Acid: A metabolite in the principal biochemical pathway of lysine. It antagonizes neuroexcitatory activity modulated by the glutamate receptor, N-METHYL-D-ASPARTATE; (NMDA). [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2-aminoadipic acid : An alpha-amino acid that is adipic acid bearing a single amino substituent at position 2. An intermediate in the formation of lysine. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID469
CHEMBL ID433238
CHEBI ID37024
SCHEMBL ID41328
MeSH IDM0023188

Synonyms (79)

Synonym
alpha-aminoadipic acid
NSC46994 ,
2-aminoadipate
nsc-46994
hexanedioic acid, 2-amino-
aminoadipic acid, alpha
2-aminoadipic acid
.alpha.-aminoadipate
.alpha.-aminoadipic acid
CHEBI:37024 ,
dl-2-aminohexanedioic acid
2-aminohexanedioic acid
(+/-)-2-aminoadipic acid
dl-alpha-aminoadipic acid
dl-2-aminoadipic acid ,
aminoadipic acid
nsc 46994
cb 1710
brn 1773077
einecs 208-809-2
542-32-5
dl-2-aminoadipic acid, >=99%
A-4920
D3202D09-2C52-46F4-B662-00E096B3EC6D
adipic acid, 2-amino-
CHEMBL433238
AKOS000487360
BMSE000429
2-amino-hexanedioic acid
LMFA01170098
STK099993
l-2-aminoadipicacid
2-amino adipic acid
alpha-aminoadipic acid, dl-
2-04-00-00913 (beilstein handbook reference)
unii-1k7b1oed4n
1k7b1oed4n ,
einecs 210-960-4
dl-alpha-aminoadipate
FT-0625426
FT-0627628
FT-0636535
aminoadipate
F3146-3326
l-.alpha.-aminoadipic acid
S5442
AKOS016352194
l-|a-aminoadipic acid
AM82414
SCHEMBL41328
2-aminoadipic acid, dl-
.alpha.-aminoadipic acid [mi]
2-aminoadipic acid, (+-)-
(+/-)-.alpha.-aminoadipic acid
dl-.alpha.-aminoadipic acid
mfcd00063119
VU0510757-1
J-521626
d-|a inverted exclamation mark-aminoadipic acid
l-alpha-aminoadipic acid;(s)-2-aminohexanedioic acid;h-homoglu-oh
h-dl-aad-oh
h-d-aad-oh
dl-alpha-aminoadipic acid;(rs)-2-aminohexanedioic acid;h-dl-homoglu-oh
d-alpha-aminoadipic acid;(r)-2-aminohexanedioic acid;h-d-homoglu-oh
CS-0059618
HY-113328
SY034135
SY034127
racemic alpha-aminoadipic acid
racemic 2-aminoadipic acid
DTXSID90862154
Q2823204
DS-13288
rac ?-aminoadipic acid
PB47596
2-amino-adipic acid
2-aminohexanedioicacid
EN300-86284
SY062169

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"The toxic effects of DL-alpha-aminoadipic acid on retinal glial cells were examined histologically following intravitreal injection to rats or rabbits."( Aminoadipic acid toxic effects on retinal glial cells.
Ishikawa, Y; Mine, S, 1983
)
0.27
" Among related amino acids, DL-alpha-aminoadipic acid (DL-alpha-AAA), which is well known as a selective gliotoxin in the retina, is also toxic to these cells."( Cystine/glutamate antiporter expression in retinal Müller glial cells: implications for DL-alpha-aminoadipate toxicity.
Ishita, S; Kato, S; Mawatari, K; Sugawara, K, 1993
)
0.29
" The enhancement was highly synergistic because MeHg and L-Glu alone had little toxic effect in the conditions used."( L-glutamate enhances methylmercury toxicity by synergistically increasing oxidative stress.
Amonpatumrat, S; Kanai, Y; Khunweeraphong, N; Nagamori, S; Piyachaturawat, P; Sakurai, H; Tanaka, H; Wiriyasermkul, P, 2008
)
0.35

Compound-Compound Interactions

ExcerptReferenceRelevance
" Lysine combined with cadaverine influenced production positively, but only at low lysine concentrations."( Enhancing effect of lysine combined with other compounds on cephamycin C production in Streptomyces clavuligerus.
Araujo, ML; Cavallieri, AP; Leite, CA, 2013
)
0.39
"This study demonstrated that different combinations of lysine with diamines or lysine with alpha-aminoadipic acid engender significant differences with respect to antibiotic volumetric production, with emphasis on the benefits observed for lysine combined with alpha-aminoadipic acid or 1,3-diaminopropane."( Enhancing effect of lysine combined with other compounds on cephamycin C production in Streptomyces clavuligerus.
Araujo, ML; Cavallieri, AP; Leite, CA, 2013
)
0.39

Bioavailability

ExcerptReferenceRelevance
" P6C forms a complex with pyridoxal phosphate (PLP), a key vitamer of pyridoxine, thereby reducing PLP bioavailability and subsequently causing epilepsy."( Inherited Disorders of Lysine Metabolism: A Review.
Bouchereau, J; Schiff, M, 2020
)
0.56

Dosage Studied

ExcerptRelevanceReference
" The animals were randomized into groups and were administered one of the following treatments: saline, PILO, saline+L-α-aminoadipic acid (L-AAA; one dosage tested), PILO+L-AAA, or PILO+L-methionine sulfoximine (three dosages tested)."( A sub-threshold dose of pilocarpine increases glutamine synthetase in reactive astrocytes and enhances the progression of amygdaloid-kindling epilepsy in rats.
Bai, XY; Chen, XM; Deng, DP; Li, SC; Liu, YX; Pan, XH; Sun, HL; Wang, CH; Wang, CY; Zhang, XL; Zhu, W, 2016
)
0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
mammalian metaboliteAny animal metabolite produced during a metabolic reaction in mammals.
Caenorhabditis elegans metaboliteA nematode metabolite produced by Caenorhabditis elegans.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
amino dicarboxylic acid
non-proteinogenic alpha-amino acidAny alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids.
dicarboxylic fatty acid
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (10)

PathwayProteinsCompounds
Lysine Degradation1324
Saccharopinuria/Hyperlysinemia II1324
Hyperlysinemia I, Familial1324
Hyperlysinemia II or Saccharopinuria1324
Pyridoxine Dependency with Seizures1324
2-Aminoadipic 2-Oxoadipic Aciduria1324
Lysine Metabolism722
Vitamin B6-dependent and responsive disorders219
Cerebral organic acidurias, including diseases527
Lysine degradation II318

Bioassays (3)

Assay IDTitleYearJournalArticle
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
AID144457Ability to displace [3H]CPP from NMDA receptor in rat brain membrane1992Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8
Generation of N-methyl-D-aspartate agonist and competitive antagonist pharmacophore models. Design and synthesis of phosphonoalkyl-substituted tetrahydroisoquinolines as novel antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (541)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990213 (39.37)18.7374
1990's99 (18.30)18.2507
2000's97 (17.93)29.6817
2010's111 (20.52)24.3611
2020's21 (3.88)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.26

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index30.26 (24.57)
Research Supply Index6.31 (2.92)
Research Growth Index4.48 (4.65)
Search Engine Demand Index39.96 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (30.26)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (0.73%)5.53%
Reviews20 (3.66%)6.00%
Case Studies21 (3.85%)4.05%
Observational0 (0.00%)0.25%
Other501 (91.76%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]