Page last updated: 2024-12-05

norleucine

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

Description

Norleucine: An unnatural amino acid that is used experimentally to study protein structure and function. It is structurally similar to METHIONINE, however it does not contain SULFUR. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

L-norleucine : A non-proteinogenic L-alpha-amino acid comprising hexanoic acid carrying an amino group at C-2. It does not occur naturally. [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 CID21236
CHEMBL ID292439
CHEBI ID18347
SCHEMBL ID8393
MeSH IDM0014987

Synonyms (72)

Synonym
CHEBI:18347 ,
(2s)-2-aminohexanoic acid
l(+)-norleucine
einecs 206-321-4
alpha-aminocaproic acid
nsc 10378
norleucine (van)
hexanoic acid, 2-amino-, (s)-
brn 1721750
norleucine
.alpha.-aminocaproic acid
2-aminocaproic acid
caprine
nsc-10378
norleucine, l-
glycoleucine
l-(+)-norleucine
2s-amino-hexanoic acid
LMFA01100042
NLE ,
(s)-2-aminohexanoic acid
327-57-1
l-norleucine
l-2-aminohexanoic acid
l-2-aminohexanoate ,
C01933
l-aminohexanoic acid
l-norleucine, >=98% (tlc)
l-norleucine, suitable for amino acid analysis, bioreagent
N6877_SIGMA ,
N-8800
B9CD20C9-2708-47D2-BEF1-0BA8BB0628AC
CHEMBL292439
2-amino-hexanoic acid
BMSE000411
(s)-2-aminocaproic acid
(s)-()-2-aminohexanoic acid
N0303
4-04-00-02686 (beilstein handbook reference)
unii-832c8ov84s
832c8ov84s ,
496-90-2
A827805
AKOS006240047
h-nle-oh
norleucine [mi]
FD3031
AM82584
SCHEMBL8393
J-300345
CS-W020710
n-c4h9ch(nh2)cooh
(s)-norleucine
(s)-(+)-2-aminohexanoic acid
AC-22372
mfcd00064423
h-nle-oh l-norleucine
M03242
2-aminocaproate
(s)-2-amino-hexanoate
(s)-2-amino-hexanoic acid
(s)-aminohexanoate
(s)-aminohexanoic acid
2-aminohexanoate
HY-Y0017
Q415428
DB15458
AS-13136
DTXSID70883362
EN300-134822
(s)-2-aminohexanoicacid
Z1203162297

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Indospicine, a toxic amino acid found in the genus Indigofera, was detected in samples of suspect horsemeat."( Hepatotoxicity to dogs of horse meat contaminated with indospicine.
Cameron, R; Hegarty, MP; Kelly, WR; McEwan, D; Williams, OJ, 1988
)
0.27
" Taken together, our findings suggest that at the studied conditions NAC protects against 2,5-HD neurotoxicity and DMPN may be proposed as a new sensitive and specific biomarker of 2,5-HD neurotoxicity in animals treated with a toxic amount of 2,5-hexanedione."( Role of N-acetylcysteine in protecting against 2,5-hexanedione neurotoxicity in a rat model: changes in urinary pyrroles levels and motor activity performance.
Andrade, V; Batoréu, MC; dos Santos, AP; Gonçalves, LL; Mateus, ML; Torres, ME, 2014
)
0.4

Pharmacokinetics

ExcerptReferenceRelevance
"The study provides pharmacokinetic data for exogenous synthetic and endogenous natural motilin in man."( Pharmacokinetics of motilin in man.
Bloom, SR; Demling, L; Domschke, S; Domschke, W; Mitznegg, P; Wuensch, E, 1977
)
0.26
" The native hGLP-2, a 33 amino acid gastrointestinal peptide, is not a suitable clinical candidate, due to its very short half-life in humans."( Synthesis and Pharmacological Characterization of Novel Glucagon-like Peptide-2 (GLP-2) Analogues with Low Systemic Clearance.
Alagarsamy, S; Croston, G; Dwyer, JJ; Ferdyan, N; Galyean, R; Hargrove, DM; Hartwig, J; Jiang, G; Kraus, J; Laporte, R; Lu, M; Mares, M; Posch, A; Qi, S; Rivière, PJ; Schteingart, CD; Srinivasan, K; Sueiras-Diaz, J; Thompson, D; Wang, YC; Wiśniewska, H; Wiśniewski, K, 2016
)
0.43

Bioavailability

ExcerptReferenceRelevance
" Thus, lipophilic peptide fragments offer bioavailability and stability, providing lead compounds for drug design against neurodegenerative diseases."( Mapping the active site in vasoactive intestinal peptide to a core of four amino acids: neuroprotective drug design.
Ashur-Fabian, O; Davidson, A; Fridkin, M; Giladi, E; Gozes, I; Perl, O; Rubinraut, S, 1999
)
0.3
" The results suggest that the oral bioavailability of maltosine can be increased significantly by applying this drug candidate in peptide-bound form."( Synthesis and intestinal transport of the iron chelator maltosine in free and dipeptide form.
Brandsch, M; Geissler, S; Hellwig, M; Henle, T; Markwardt, F, 2011
)
0.37
" Peptide-enriched drinks (PEDs) are broadly consumed worldwide due to rapid rate of absorption and perceived health effects."( Determination of Free-Form and Peptide Bound Pyrraline in the Commercial Drinks Enriched with Different Protein Hydrolysates.
Li, B; Li, L; Liang, Z; Qi, H; Xu, Z; Zhang, X, 2016
)
0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
L-alpha-amino acid zwitterionZwitterionic form of an L-alpha-amino acid having an anionic carboxy group and a protonated amino group.
2-aminohexanoic acidAn alpha-amino acid that is caproic acid substituted by an amino group at position 2.
non-proteinogenic L-alpha-amino acidAny L-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]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID26797Partition coefficient (logP)1987Journal of medicinal chemistry, Oct, Volume: 30, Issue:10
Quantitative structure-activity relationships of the bitter thresholds of amino acids, peptides, and their derivatives.
AID233318Bitter threshold value1987Journal of medicinal chemistry, Oct, Volume: 30, Issue:10
Quantitative structure-activity relationships of the bitter thresholds of amino acids, peptides, and their derivatives.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (480)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990206 (42.92)18.7374
1990's75 (15.63)18.2507
2000's93 (19.38)29.6817
2010's90 (18.75)24.3611
2020's16 (3.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (0.40%)5.53%
Reviews17 (3.42%)6.00%
Case Studies1 (0.20%)4.05%
Observational0 (0.00%)0.25%
Other477 (95.98%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]