Page last updated: 2024-11-07

alpha-aminopimelic acid

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

Description

Alpha-aminopimelic acid (APA) is a non-proteinogenic amino acid that plays a crucial role in the biosynthesis of lysine in bacteria and fungi. It is also a key intermediate in the synthesis of the antibiotic bacitracin. APA is synthesized from diaminopimelic acid (DAP) by a decarboxylase enzyme. Studies have shown that APA can inhibit the growth of certain bacteria, suggesting its potential as an antimicrobial agent. The importance of APA in lysine biosynthesis makes it a target for the development of new herbicides and antimicrobial agents. Research into APA is ongoing to understand its biological roles and its potential applications in agriculture and medicine.'

alpha-aminopimelic acid: antagonizes glutamate-induced inhibitions of Helix neurones [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2-aminopimelic acid : An amino dicarboxylic acid that is heptanedioic acid in which a hydrogen at position 2 is replaced by an amino group. It is a component of the cell wall peptidoglycan of bacteria. [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 CID101122
CHEMBL ID111050
CHEBI ID64305
SCHEMBL ID116556
MeSH IDM0054905

Synonyms (57)

Synonym
bdbm50052549
dl-2-aminopimelic acid(alpha-)
3721-85-5
nsc-402480
nsc402480
2-aminoheptanedioic acid
heptanedioic acid, 2-amino-
2-aminopimelic acid
(+/-)-2-aminopimelic acid, >=99%
SR-01000639310-1
2-aminopimelate
dl-alpha-aminopimelic acid
DB946E0D-C5D0-47E2-A9AA-3E29D190922E
627-76-9
dl-2-aminopimelic acid
A0404
2-amino-heptanedioic acid
chebi:64305 ,
CHEMBL111050 ,
FT-0658289
A833989
(+/-)-2-aminopimelic acid
einecs 211-011-7
heptanedioic acid, 2-amino-, (+-)-
2-aminopimelic acid, dl-
alpha-aminopimelic acid
dl-2-aminopimelate
unii-v76629v970
(+-)-2-aminopimelic acid
v76629v970 ,
nsc 402480
AKOS016003609
CCG-49889
FT-0611264
dl-2-aminoheptanedioic acid
SCHEMBL116556
dl-2-amino pimelic acid
aminopimelic acid
W-204236
(+/-)-2-aminoheptanedioic acid
heptanedioic acid, 2-amino-, (.+/-.)-
dl-.alpha.-aminopimelic acid
2-aminoheptanedioic acid #
.alpha.-aminopimelic acid
mfcd00053314
a-aminopimelic acid
2-amino-(+-)-heptanedioic acid
dl-alpha-aminopimelic acid;h-dl-apm-oh
dl--aminopimelic acid;h-dl-apm-oh
Q27894420
F16285
CS-0201670
AS-47823
DTXSID00978316
d,l- alpha -aminopimelic acid
2-aminoheptanedioicacid
d,l-?-aminopimelic acid
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
bacterial metaboliteAny prokaryotic metabolite produced during a metabolic reaction in bacteria.
[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 (2)

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.
[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]

Protein Targets (3)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Metabotropic glutamate receptor 6Homo sapiens (human)EC50 (µMol)1,000.00000.05502.27864.9000AID107251
Metabotropic glutamate receptor 1Homo sapiens (human)EC50 (µMol)1,000.00000.20004.41009.3000AID108645
Metabotropic glutamate receptor 2Homo sapiens (human)EC50 (µMol)1,000.00000.00061.17848.5000AID109003
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (30)

Processvia Protein(s)Taxonomy
adenylate cyclase-inhibiting G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 6Homo sapiens (human)
G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 6Homo sapiens (human)
chemical synaptic transmissionMetabotropic glutamate receptor 6Homo sapiens (human)
locomotory behaviorMetabotropic glutamate receptor 6Homo sapiens (human)
detection of visible lightMetabotropic glutamate receptor 6Homo sapiens (human)
detection of light stimulus involved in visual perceptionMetabotropic glutamate receptor 6Homo sapiens (human)
retina development in camera-type eyeMetabotropic glutamate receptor 6Homo sapiens (human)
positive regulation of calcium ion import across plasma membraneMetabotropic glutamate receptor 6Homo sapiens (human)
regulation of synaptic transmission, glutamatergicMetabotropic glutamate receptor 6Homo sapiens (human)
G protein-coupled receptor signaling pathwayMetabotropic glutamate receptor 1Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 1Homo sapiens (human)
phospholipase C-activating G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 1Homo sapiens (human)
chemical synaptic transmissionMetabotropic glutamate receptor 1Homo sapiens (human)
locomotory behaviorMetabotropic glutamate receptor 1Homo sapiens (human)
sensory perception of painMetabotropic glutamate receptor 1Homo sapiens (human)
positive regulation of MAPK cascadeMetabotropic glutamate receptor 1Homo sapiens (human)
regulation of sensory perception of painMetabotropic glutamate receptor 1Homo sapiens (human)
regulation of postsynaptic membrane potentialMetabotropic glutamate receptor 1Homo sapiens (human)
cellular response to electrical stimulusMetabotropic glutamate receptor 1Homo sapiens (human)
L-glutamate import across plasma membraneMetabotropic glutamate receptor 1Homo sapiens (human)
regulation of postsynaptic cytosolic calcium ion concentrationMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 1Homo sapiens (human)
regulation of synaptic transmission, glutamatergicMetabotropic glutamate receptor 1Homo sapiens (human)
negative regulation of adenylate cyclase activityMetabotropic glutamate receptor 2Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 2Homo sapiens (human)
chemical synaptic transmissionMetabotropic glutamate receptor 2Homo sapiens (human)
gene expressionMetabotropic glutamate receptor 2Homo sapiens (human)
glutamate secretionMetabotropic glutamate receptor 2Homo sapiens (human)
regulation of glutamate secretionMetabotropic glutamate receptor 2Homo sapiens (human)
regulation of dopamine secretionMetabotropic glutamate receptor 2Homo sapiens (human)
behavioral response to nicotineMetabotropic glutamate receptor 2Homo sapiens (human)
response to cocaineMetabotropic glutamate receptor 2Homo sapiens (human)
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionMetabotropic glutamate receptor 2Homo sapiens (human)
long-term synaptic depressionMetabotropic glutamate receptor 2Homo sapiens (human)
intracellular glutamate homeostasisMetabotropic glutamate receptor 2Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionMetabotropic glutamate receptor 2Homo sapiens (human)
regulation of response to drugMetabotropic glutamate receptor 2Homo sapiens (human)
G protein-coupled glutamate receptor signaling pathwayMetabotropic glutamate receptor 2Homo sapiens (human)
regulation of synaptic transmission, glutamatergicMetabotropic glutamate receptor 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (11)

Processvia Protein(s)Taxonomy
G protein-coupled receptor activityMetabotropic glutamate receptor 6Homo sapiens (human)
protein bindingMetabotropic glutamate receptor 6Homo sapiens (human)
glutamate receptor activityMetabotropic glutamate receptor 6Homo sapiens (human)
protein homodimerization activityMetabotropic glutamate receptor 6Homo sapiens (human)
adenylate cyclase inhibiting G protein-coupled glutamate receptor activityMetabotropic glutamate receptor 6Homo sapiens (human)
G protein-coupled receptor activityMetabotropic glutamate receptor 1Homo sapiens (human)
protein bindingMetabotropic glutamate receptor 1Homo sapiens (human)
glutamate receptor activityMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled neurotransmitter receptor activity involved in regulation of postsynaptic cytosolic calcium ion concentrationMetabotropic glutamate receptor 1Homo sapiens (human)
adenylate cyclase inhibiting G protein-coupled glutamate receptor activityMetabotropic glutamate receptor 1Homo sapiens (human)
neurotransmitter receptor activity involved in regulation of postsynaptic cytosolic calcium ion concentrationMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled receptor activity involved in regulation of postsynaptic membrane potentialMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled receptor activityMetabotropic glutamate receptor 2Homo sapiens (human)
calcium channel regulator activityMetabotropic glutamate receptor 2Homo sapiens (human)
protein bindingMetabotropic glutamate receptor 2Homo sapiens (human)
glutamate receptor activityMetabotropic glutamate receptor 2Homo sapiens (human)
scaffold protein bindingMetabotropic glutamate receptor 2Homo sapiens (human)
group II metabotropic glutamate receptor activityMetabotropic glutamate receptor 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (15)

Processvia Protein(s)Taxonomy
Golgi membraneMetabotropic glutamate receptor 6Homo sapiens (human)
endoplasmic reticulum membraneMetabotropic glutamate receptor 6Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 6Homo sapiens (human)
dendriteMetabotropic glutamate receptor 6Homo sapiens (human)
new growing cell tipMetabotropic glutamate receptor 6Homo sapiens (human)
synapseMetabotropic glutamate receptor 6Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 6Homo sapiens (human)
nucleusMetabotropic glutamate receptor 1Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 1Homo sapiens (human)
dendriteMetabotropic glutamate receptor 1Homo sapiens (human)
Schaffer collateral - CA1 synapseMetabotropic glutamate receptor 1Homo sapiens (human)
glutamatergic synapseMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled receptor dimeric complexMetabotropic glutamate receptor 1Homo sapiens (human)
G protein-coupled receptor homodimeric complexMetabotropic glutamate receptor 1Homo sapiens (human)
postsynaptic density membraneMetabotropic glutamate receptor 1Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 1Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 2Homo sapiens (human)
axonMetabotropic glutamate receptor 2Homo sapiens (human)
dendriteMetabotropic glutamate receptor 2Homo sapiens (human)
presynaptic membraneMetabotropic glutamate receptor 2Homo sapiens (human)
astrocyte projectionMetabotropic glutamate receptor 2Homo sapiens (human)
glutamatergic synapseMetabotropic glutamate receptor 2Homo sapiens (human)
plasma membraneMetabotropic glutamate receptor 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID164718Compound was tested in vitro for antibacterial activity against Pseudomonas aeruginosa 647 strain.1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Peptides of 2-aminopimelic acid: antibacterial agents that inhibit diaminopimelic acid biosynthesis.
AID108645Agonistic activity at mGlu1-alpha receptor expressed in CHO cells1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
A new highly selective metabotropic excitatory amino acid agonist: 2-amino-4-(3-hydroxy-5-methylisoxazol-4-yl)butyric acid.
AID50562Compound was tested in vitro for antibacterial activity against Citrobacter sp 2404 strain.1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Peptides of 2-aminopimelic acid: antibacterial agents that inhibit diaminopimelic acid biosynthesis.
AID70861Compound was tested in vitro for antibacterial activity against Enterobacter cloacae P99 strain1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Peptides of 2-aminopimelic acid: antibacterial agents that inhibit diaminopimelic acid biosynthesis.
AID109003Agonistic activity at mGlu2 receptor expressed in CHO cells1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
A new highly selective metabotropic excitatory amino acid agonist: 2-amino-4-(3-hydroxy-5-methylisoxazol-4-yl)butyric acid.
AID70582Compound was tested in vitro for antibacterial activity against Escherichia coli CB64 strain1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Peptides of 2-aminopimelic acid: antibacterial agents that inhibit diaminopimelic acid biosynthesis.
AID107251Agonistic activity at mGlu6 receptor expressed in CHO cells1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
A new highly selective metabotropic excitatory amino acid agonist: 2-amino-4-(3-hydroxy-5-methylisoxazol-4-yl)butyric acid.
AID200509Compound was tested in vitro for antibacterial activity against Staphylococcus enteritidis E497 strain.1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Peptides of 2-aminopimelic acid: antibacterial agents that inhibit diaminopimelic acid biosynthesis.
AID205391Compound was tested in vitro for antibacterial activity against Serratia marcescens ATCC 13880 strain1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Peptides of 2-aminopimelic acid: antibacterial agents that inhibit diaminopimelic acid biosynthesis.
AID96231Compound was tested in vitro for antibacterial activity against Klebsiella pneumoniae 4200 strain.1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Peptides of 2-aminopimelic acid: antibacterial agents that inhibit diaminopimelic acid biosynthesis.
AID163068Compound was tested in vitro for antibacterial activity against Providencia rettgeri AAB-137 strain; NT is Not Tested1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Peptides of 2-aminopimelic acid: antibacterial agents that inhibit diaminopimelic acid biosynthesis.
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).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (23.08)18.7374
1990's5 (38.46)18.2507
2000's0 (0.00)29.6817
2010's4 (30.77)24.3611
2020's1 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.81

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.81 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.81)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]