Page last updated: 2024-12-06

homocitrulline

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

Description

Homocitrulline is an amino acid that is a structural isomer of citrulline. It is formed through the enzymatic conversion of arginine by the enzyme peptidylarginine deiminase (PAD). PAD enzymes are involved in a variety of biological processes, including immune responses and inflammation. Homocitrulline has been linked to autoimmune diseases, particularly rheumatoid arthritis (RA), where it is a target of autoantibodies. The presence of anti-homocitrulline antibodies (ACPA) in the blood is a highly specific marker for RA. While the precise role of homocitrulline in RA pathogenesis is not fully understood, research suggests that PAD enzymes may play a role in the generation of citrullinated proteins, which are then recognized by the immune system as foreign, leading to autoimmune responses. The study of homocitrulline and ACPA is crucial for understanding the pathogenesis of RA and for developing diagnostic and therapeutic approaches for this debilitating disease.'

L-homocitrulline : A L-lysine derivative that is L-lysine having a carbamoyl group at the N(6)-position. It is found in individuals with urea cycle disorders. [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 CID65072
CHEBI ID17443
SCHEMBL ID56915
MeSH IDM0041495

Synonyms (42)

Synonym
l-lysine, n6-(aminocarbonyl)-
n(6)-carbamoyl-l-lysine
(2s)-2-amino-6-(carbamoylamino)hexanoic acid
n(6)-(aminocarbonyl)-l-lysine
CHEBI:17443
1190-49-4
C02427
l-homocitrulline
homocitrulline
2-amino-6-carbamoylamino-hexanoic acid
inchi=1/c7h15n3o3/c8-5(6(11)12)3-1-2-4-10-7(9)13/h5h,1-4,8h2,(h,11,12)(h3,9,10,13)/t5-/m0/s1
xigsagmebxlvjj-yfkpbyrvsa-
l-lysine, n(6)-(aminocarbonyl)-
BMSE000442
n6-carbamoyl-lysine
AKOS006272047
einecs 214-722-0
unii-133t7a0y5k
133t7a0y5k ,
nsc 27428
n-.epsilon.-carbamyl-l-lysine
lysine, n6-carbamoyl-
homo-l-citrulline
homocitrulline, l-
lysine, n6-carbamoyl-, l-
S6128
SCHEMBL56915
(s)-2-amino-6-ureidohexanoic acid
CS-W018790
(s)-2-amino-6-ureidocaproic acid
J-004062
h-homocit-oh
n-e-carbamyl-l-lysine
n-epsilon-carbamyl-l-lysine
n6-carbamoyl-l-lysine
HY-W018004
DS-15012
Q18207833
AMY22717
A892674
DTXSID301317386
n~6~-carbamoyl-l-lysine

Research Excerpts

Overview

Homocitrulline (HCit) is a carbamylation-derived product (CDP) that has been identified as a valuable biomarker of morbidity and mortality in patients with chronic kidney disease.

ExcerptReferenceRelevance
"Homocitrulline (HCit) is a carbamylation-derived product (CDP) that has been identified as a valuable biomarker of morbidity and mortality in patients with chronic kidney disease (CKD). "( Homocitrulline as marker of protein carbamylation in hemodialyzed patients.
Desmons, A; Fadel, F; Gillery, P; Jaisson, S; Kazes, I; Millart, H; Oudart, JB; Rieu, P; Santos-Weiss, IC; Touré, F, 2016
)
3.32

Actions

ExcerptReferenceRelevance
"Homocitrulline excretion was lower with all additions compared to the control period."( Hyperornithinemia-hyperammonemia-homocitrullinuria syndrome: low creatine excretion and effect of citrulline, arginine, or ornithine supplement.
Bachmann, C; Colombo, JP; Dionisi Vici, C; Gambarara, M; Sabetta, G, 1987
)
0.99

Dosage Studied

ExcerptRelevanceReference
" We could not demonstrate a gene dosage effect in oxidation values."( Comparison of ornithine metabolism in hyperornithinaemia-hyperammonaemia-homocitrullinuria syndrome, lysinuric protein intolerance and gyrate atrophy fibroblasts.
Botschner, J; Scriver, CR; Simell, O; Smith, DW, 1989
)
0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[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 (4)

ClassDescription
ureas
L-lysine derivativeA proteinogenic amino acid derivative resulting from reaction of L-lysine at the amino group or the carboxy group, or from the replacement of any hydrogen of L-lysine by a heteroatom.
non-proteinogenic L-alpha-amino acidAny L-alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids.
amino acid zwitterionThe zwitterionic form of an amino acid having a negatively charged carboxyl group and a positively charged amino 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]

Research

Studies (135)

TimeframeStudies, This Drug (%)All Drugs %
pre-199036 (26.67)18.7374
1990's21 (15.56)18.2507
2000's23 (17.04)29.6817
2010's50 (37.04)24.3611
2020's5 (3.70)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.81

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

MetricThis Compound (vs All)
Research Demand Index30.81 (24.57)
Research Supply Index4.93 (2.92)
Research Growth Index4.70 (4.65)
Search Engine Demand Index42.09 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (30.81)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews9 (6.52%)6.00%
Case Studies27 (19.57%)4.05%
Observational0 (0.00%)0.25%
Other102 (73.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]