Page last updated: 2024-12-04

pipecolic acid

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

Description

pipecolic acid: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

pipecolic acid : A piperidinemonocarboxylic acid in which the carboxy group is located at position C-2. [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]

pipecolate : A piperidinecarboxylate that is the conjugate base of pipecolic acid. [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 CID849
CHEMBL ID308408
CHEBI ID17964
SCHEMBL ID22016
MeSH IDM0098557

Synonyms (120)

Synonym
AC-691
CHEMBL308408
acide pipecolique
h254gw7pvv ,
acide piperidine-carboxylique-2
unii-h254gw7pvv
EN300-20680
CHEBI:17964 ,
2-piperidinecarboxylic acid, (.+/-.)-
NCIOPEN2_001582
dl-pipecolinic acid
nsc17125
pipecolate
nsc-17125
dihydrobaikiane
homoproline
hexahydropicolinic acid
535-75-1
.alpha.-pipecolinic acid
piperidine-2-carboxylic acid
pipecolic acid, l-
pipecolic acid, (s)-(-)-
nsc93089
2-piperidinecarboxylic acid, (s)-
einecs 208-616-3
piperolinic acid
einecs 223-737-1
acide pipecolique [french]
nsc 17125
acide piperidine-carboxylique-2 [french]
2-piperidinecarboxylic acid
pipecolinic acid
pipecolic acid
pipecolinic acid, 98%
inchi=1/c6h11no2/c8-6(9)5-3-1-2-4-7-5/h5,7h,1-4h2,(h,8,9)
hxeaclliillprg-uhfffaoysa-
2-piperidinic acid
dl-pipecolic acid
83680-83-5
FT-0650084
dl-homoproline
P0442
(+/-)-2-piperidinecarboxylic acid
AKOS000120345
A23910
A7793
(d)-(+)-pipercolicacid
l-pipecolicacid
dl-pipecolicacid
4043-87-2
(+/-)-pipecolic acid
FT-0673913
FT-0625508
FT-0613361
FT-0601108
FT-0601107
PS-5851
AB00554
AM90343
S6322
hexahydro-2-picolinic acid
2-carboxypiperidine
2-piperidine carboxylic acid
(+/-) pipecolic acid
2-piperidine-carboxylic acid
AKOS016050399
SCHEMBL22016
SY003076
SY002975
SY003075
mfcd00064347
W-106353
2-pipecolinic acid
pipecolic acid dl-form [mi]
(+/-)-pipecolinic acid
pipecolic acid [mi]
piperidine-6-carboxylic acid
2-piperidinecarboxylic acid #
W-111701
F2191-0193
AC-2835
dl-piperidine-2-carboxylic acid
CS-B1313
dl-2-piperidinecarboxylate
pipecolinate
(.+/-.)-2-piperidinecarboxylic acid
piperolinate
a-pipecolinate
(+/-)-pipecolate
2-piperidinylcarboxylic acid
dl-pipecolate
a-pipecolinic acid
hexahydro-2-picolinate
(rs)-2-piperidinecarboxylate
hexahydropicolinate
pipecolic acid free base
alpha-pipecolinate
dl-pipecolinate
()-piperidine-2-carboxylic acid
alpha-pipecolinic acid
(+/-)-pipecolinate
dl-2-piperidinecarboxylic acid
(+/-)-2-piperidinecarboxylate
(rs)-2-piperidinecarboxylic acid
HY-Y0669
DTXSID40862144
2-pyridine(carboxylic acid-13c1)
rac piperidine-2-carboxylic acid
Q7197255
h-dl-hopro-oh
STL183326
( inverted exclamation marka)-piperidine-2-carboxylic acid
dl-pipecolic acid;h-dl-pip-oh
h-dl-homopro-oh
dl-2-piperidine-d9-carboxylic acid
pipecolinicacid
2-piperidinecarboxylic acid, (a+/-)-
(+/-)-piperidine-2-carboxylic acid
2-piperidinecarboxylic acidd
Z104479780

Research Excerpts

Overview

Pipecolic acid (PA) is an alicyclic amino acid and putative neurotransmitter. It may modulate GABAergic transmission in the central nervous system. Pipecolic Acid is an important biochemical marker for the diagnosis of peroxisomal disorders.

ExcerptReferenceRelevance
"Pipecolic acid (PA) is an alicyclic amino acid and putative neurotransmitter which may modulate GABAergic transmission in the central nervous system. "( Inhibition of intrathecally administered picrotoxin- and bicuculline-induced convulsions in mice by pipecolic acid or GABA.
Beitz, AJ; Larson, AA, 1985
)
1.93
"Pipecolic acid (Pip) is an ALD1-dependent bioactive product induced by P."( ALD1 Regulates Basal Immune Components and Early Inducible Defense Responses in Arabidopsis.
Cecchini, NM; Engle, NL; Greenberg, JT; Jung, HW; Tschaplinski, TJ, 2015
)
1.14
"Pipecolic acid (PA) is an important biochemical marker for the diagnosis of peroxisomal disorders. "( Determination of plasma pipecolic acid by an easy and rapid liquid chromatography-tandem mass spectrometry method.
Barraco, GM; Boenzi, S; Catesini, G; Dionisi-Vici, C; Iacovone, F; Inglese, R; Manco, M; Muraca, M; Rizzo, C; Semeraro, M, 2015
)
2.17
"L-Pipecolic acid is a key component of biologically active molecules and a pharmaceutically important chiral building block. "( Functional expression of L-lysine α-oxidase from Scomber japonicus in Escherichia coli for one-pot synthesis of L-pipecolic acid from DL-lysine.
China, H; Dekishima, Y; Kawabata, H; Mihara, H; Miyake, R; Saito, S; Tani, Y; Yukami, R, 2015
)
1.35
"Pipecolic acid is an important precursor of many useful microbial secondary metabolites. "( Pipecolic acid in microbes: biosynthetic routes and enzymes.
He, M, 2006
)
3.22
"L-Pipecolic acid is a chiral pharmaceutical intermediate. "( Enzymatic synthesis of L-pipecolic acid by Delta1-piperideine-2-carboxylate reductase from Pseudomonas putida.
Esaki, N; Kurihara, T; Mihara, H; Muramatsu, H; Ueda, M; Yasuda, M, 2006
)
1.36
"Pipecolic acid is a biochemical marker frequently detected in group 1 peroxisomal disorders (peroxisomal biogenesis disorders). "( Hyperpipecolic acidemia: clinical, biochemical, and radiologic observations.
Al-Essa, MA; Chaves-Carballo, E; Ozand, PT, 1999
)
2.26
"Pipecolic acid is a component of several secondary metabolites in plants and fungi. "( Conversion of pipecolic acid into lysine in Penicillium chrysogenum requires pipecolate oxidase and saccharopine reductase: characterization of the lys7 gene encoding saccharopine reductase.
Bañuelos, O; Casqueiro, J; Lopez, P; Martin de Valmaseda, E; Martin, JF; Naranjo, L; Riaño, J, 2001
)
2.11

Actions

ExcerptReferenceRelevance
"DL-Pipecolic acid (DL-PIP) promotes growth restoration of Sinorhizobium meliloti cells facing inhibitory hyperosmolarity. "( Osmoprotection by pipecolic acid in Sinorhizobium meliloti: specific effects of D and L isomers.
Bernard, T; Blanco, C; Gouffi, K, 2000
)
1.26

Toxicity

ExcerptReferenceRelevance
" In conclusion, the present study demonstrated that PPX is more toxic than expected since we found that its induced mortality was approximately three times that found for bupivacaine and its CNS toxicity was about two times that of bupivacaine."( Acute toxicity of bupivacaine metabolites in mice.
Attolini, L; Bruguerolle, B; Gantenbein, M, 1994
)
0.29

Dosage Studied

ExcerptRelevanceReference
" The dose-response relationship followed simple Michaelis-Menten kinetics, with a half-maximal response elicited at approximately 110 microM."( Effects of gamma-aminobutyric acid on skate retinal horizontal cells: evidence for an electrogenic uptake mechanism.
Malchow, RP; Ripps, H, 1990
)
0.28
"5 mM shifted the dose-response curve for GABA to the left."( The effect of GABA on neurotransmission in frog tectal slices.
Arakawa, T; Okada, Y, 1989
)
0.28
" Bicuculline 1 microM shifted the dose-response curve of GABA to the right and the excitatory effect was also enhanced."( Excitatory and inhibitory action of GABA on synaptic transmission in slices of guinea pig superior colliculus.
Arakawa, T; Okada, Y, 1988
)
0.27
" Dopa accumulation was significantly inhibited at a high dosage by nipecotic acid alone and by low dosages of nipecotic acid in rats pretreated with either aminooxyacetic acid or gabaculine."( Use of gamma-aminobutyric acid (GABA)-transaminase inhibitors and a GABA uptake inhibitor to investigate the influence of GABA neurons on dopamine-containing amacrine cells of the rat retina.
Morgan, WW; Proll, MA, 1983
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
piperidinemonocarboxylic acidAny member of the class of piperidines in which one of the carbons of the piperidine ring is substituted by a carboxy group.
[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 (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (2)

Processvia Protein(s)Taxonomy
lysine catabolic processPeroxisomal sarcosine oxidaseHomo sapiens (human)
L-lysine catabolic process to acetyl-CoA via L-pipecolatePeroxisomal sarcosine oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
protein bindingPeroxisomal sarcosine oxidaseHomo sapiens (human)
sarcosine oxidase activityPeroxisomal sarcosine oxidaseHomo sapiens (human)
L-pipecolate oxidase activityPeroxisomal sarcosine oxidaseHomo sapiens (human)
flavin adenine dinucleotide bindingPeroxisomal sarcosine oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
peroxisomePeroxisomal sarcosine oxidaseHomo sapiens (human)
peroxisomal matrixPeroxisomal sarcosine oxidaseHomo sapiens (human)
cytosolPeroxisomal sarcosine oxidaseHomo sapiens (human)
peroxisomePeroxisomal sarcosine oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID49192Affinity of compound towards the carnitine/acylcarnitine translocase was determined by monitoring the efflux of [14C]L-carnitine from isolated rat heart mitochondria1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Synthesis and biological evaluation of cyclic analogues of 1-carnitine as potential agents in the treatment of myocardial ischemia.
AID336478Inhibition of COX2 at 100 uM by scintillation proximity assay2002Journal of natural products, Nov, Volume: 65, Issue:11
Screening of ubiquitous plant constituents for COX-2 inhibition with a scintillation proximity based assay.
AID500816Inhibition of nitrogen-starved wild type sigma1278b yeast Gap1-mediated amino acid uptake at 5 mM after 60 secs relative to L-citrulline2009Nature chemical biology, Jan, Volume: 5, Issue:1
Transport and signaling via the amino acid binding site of the yeast Gap1 amino acid transceptor.
AID227699Virtual screen for compounds with anticonvulsant activity2003Bioorganic & medicinal chemistry letters, Aug-18, Volume: 13, Issue:16
Topological virtual screening: a way to find new anticonvulsant drugs from chemical diversity.
AID95422determined in L-pipecolate oxidase from Rehsus monkey1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
Mechanism-based inhibition of L-pipecolate oxidase by 4,5-dehydro-L-pipecolic acid.
AID95423Kinetic parameter Vmax (maximum velocity) was determined on L-pipecolate oxidase from Rhesus monkey1996Journal of medicinal chemistry, Aug-02, Volume: 39, Issue:16
Mechanism-based inhibition of L-pipecolate oxidase by 4,5-dehydro-L-pipecolic acid.
AID1632443Inhibition of Shh-N-induced Gli1 (unknown origin) expressed in mouse Shh Light2 cells assessed as Gli1-mediated mediated transcription up to 50 uM incubated for 30 hrs by firefly luciferase assay2016Bioorganic & medicinal chemistry letters, 09-15, Volume: 26, Issue:18
Piperazic acid derivatives inhibit Gli1 in Hedgehog signaling pathway.
AID1632444Inhibition of Gli1 (unknown origin) expression in mouse Shh Light2 cells at 1 to 100 uM by Western blot analysis2016Bioorganic & medicinal chemistry letters, 09-15, Volume: 26, Issue:18
Piperazic acid derivatives inhibit Gli1 in Hedgehog signaling pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (483)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990146 (30.23)18.7374
1990's141 (29.19)18.2507
2000's66 (13.66)29.6817
2010's96 (19.88)24.3611
2020's34 (7.04)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 51.37

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index51.37 (24.57)
Research Supply Index6.21 (2.92)
Research Growth Index4.62 (4.65)
Search Engine Demand Index83.22 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (51.37)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (0.81%)5.53%
Reviews18 (3.66%)6.00%
Case Studies32 (6.50%)4.05%
Observational0 (0.00%)0.25%
Other438 (89.02%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]