Nomega-hydroxy-nor-l-arginine

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

Cross-References

ID Source	ID
PubMed CID	446124
CHEMBL ID	1234777
CHEBI ID	191070
SCHEMBL ID	4097591
SCHEMBL ID	17905716

Synonyms (43)

Synonym
nnh ,
nor-n-omega-hydroxy-l-arginine
n-hydroxy-nor-arginine
DB02381
(2s)-2-amino-4-(((hydroxyamino)iminomethyl)amino)butanoic acid
n-hydroxy-nor-l-arginine
nomega-hydroxy-nor-l-arginine
nor-noha
HSCI1_000281
chembl1234777 ,
bdbm50008099
CHEBI:191070
(2s)-2-amino-4-[[amino-(hydroxyamino)methylidene]amino]butanoic acid
189302-40-7
AKOS006279536
nomega-hydroxy-nor-l-arginine dihydrochloride
291758-32-2
n\|o-hydroxy-nor-l-arginine dihydrochloride
(2s)-2-amino-4-[(e)-2-hydroxycarbamimidamido]butanoic acid
gtpl5091
SCHEMBL4097591
n?-hydroxy-nor-l-arginine dihydrochloride
J842.499C ,
U0F1149OFR ,
n.omega.-hydroxy-nor-l-arginine
butanoic acid, 2-amino-4-(((hydroxyamino)iminomethyl)amino)-, (s)-
HMS3650A03
butanoic acid,2-amino-4-[[(hydroxyamino)iminomethyl]amino]-,(2s)-
DTXSID40332211
unii-u0f1149ofr
SCHEMBL17905716
J-012212
n-omega'-hydroxy-l-norarginine
n--hydroxy-l-norarginine acetate salt
(2s)-2-amino-4-(n'-hydroxycarbamimidamido)butanoic acid
n-omega-hydroxy-nor-l-arginine dihydrochloride
n-omega-hydroxy-l-norarginine
Q27088086
SR-01000946755-1
sr-01000946755
(2s)-4-[[amino-(hydroxyamino)methylidene]amino]-2-azaniumylbutanoate
(s)-2-amino-4-(3-hydroxyguanidino)butanoic acid
(2s)-2-amino-4-{[amino(hydroxyamino)methylidene]amino}butanoic acid

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

Class	Description
L-alpha-amino acid	Any alpha-amino acid having L-configuration at the alpha-carbon.
[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 (4)

Inhibition Measurements

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Arginase-1	Homo sapiens (human)	IC50 (µMol)	3.6800	0.3110	1.6054	6.0000	AID1540248; AID1695181
Arginase-1	Rattus norvegicus (Norway rat)	IC50 (µMol)	1.4000	0.8000	1.2000	2.0000	AID1128922; AID1724055
Arginase-2, mitochondrial	Homo sapiens (human)	Ki	0.0510	0.0085	0.3438	1.6000	AID1370773; AID1724057
Arginase-1	Bos taurus (cattle)	IC50 (µMol)	2.7000	2.7000	2.7000	2.7000	AID1695179
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Arginase-1	Homo sapiens (human)	Kd	0.2820	0.0050	0.6987	3.6000	AID1370772; AID1724056
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (27)

Process	via Protein(s)	Taxonomy
urea cycle	Arginase-1	Homo sapiens (human)
adaptive immune response	Arginase-1	Homo sapiens (human)
arginine catabolic process	Arginase-1	Homo sapiens (human)
negative regulation of T cell proliferation	Arginase-1	Homo sapiens (human)
defense response to protozoan	Arginase-1	Homo sapiens (human)
innate immune response	Arginase-1	Homo sapiens (human)
negative regulation of activated T cell proliferation	Arginase-1	Homo sapiens (human)
negative regulation of type II interferon-mediated signaling pathway	Arginase-1	Homo sapiens (human)
positive regulation of neutrophil mediated killing of fungus	Arginase-1	Homo sapiens (human)
negative regulation of T-helper 2 cell cytokine production	Arginase-1	Homo sapiens (human)
arginine catabolic process to ornithine	Arginase-1	Homo sapiens (human)
urea cycle	Arginase-2, mitochondrial	Homo sapiens (human)
ureteric bud development	Arginase-2, mitochondrial	Homo sapiens (human)
adaptive immune response	Arginase-2, mitochondrial	Homo sapiens (human)
negative regulation of type 2 immune response	Arginase-2, mitochondrial	Homo sapiens (human)
nitric oxide biosynthetic process	Arginase-2, mitochondrial	Homo sapiens (human)
striated muscle contraction	Arginase-2, mitochondrial	Homo sapiens (human)
regulation of interleukin-1 beta production	Arginase-2, mitochondrial	Homo sapiens (human)
negative regulation of interleukin-13 production	Arginase-2, mitochondrial	Homo sapiens (human)
negative regulation of interleukin-17 production	Arginase-2, mitochondrial	Homo sapiens (human)
negative regulation of tumor necrosis factor production	Arginase-2, mitochondrial	Homo sapiens (human)
innate immune response	Arginase-2, mitochondrial	Homo sapiens (human)
negative regulation of macrophage inflammatory protein 1 alpha production	Arginase-2, mitochondrial	Homo sapiens (human)
negative regulation of chemokine (C-C motif) ligand 4 production	Arginase-2, mitochondrial	Homo sapiens (human)
negative regulation of chemokine (C-C motif) ligand 5 production	Arginase-2, mitochondrial	Homo sapiens (human)
negative regulation of defense response to bacterium	Arginase-2, mitochondrial	Homo sapiens (human)
regulation of reactive oxygen species biosynthetic process	Arginase-2, mitochondrial	Homo sapiens (human)
negative regulation of activated CD8-positive, alpha-beta T cell apoptotic process	Arginase-2, mitochondrial	Homo sapiens (human)
negative regulation of CD4-positive, alpha-beta T cell proliferation	Arginase-2, mitochondrial	Homo sapiens (human)
positive regulation of cellular senescence	Arginase-2, mitochondrial	Homo sapiens (human)
arginine catabolic process to ornithine	Arginase-2, mitochondrial	Homo sapiens (human)
urea cycle	Arginase-1	Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Process	via Protein(s)	Taxonomy
protein binding	Arginase-1	Homo sapiens (human)
arginase activity	Arginase-1	Homo sapiens (human)
manganese ion binding	Arginase-1	Homo sapiens (human)
arginase activity	Arginase-2, mitochondrial	Homo sapiens (human)
protein binding	Arginase-2, mitochondrial	Homo sapiens (human)
manganese ion binding	Arginase-2, mitochondrial	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Process	via Protein(s)	Taxonomy
extracellular region	Arginase-1	Homo sapiens (human)
extracellular space	Arginase-1	Homo sapiens (human)
nucleus	Arginase-1	Homo sapiens (human)
cytosol	Arginase-1	Homo sapiens (human)
azurophil granule lumen	Arginase-1	Homo sapiens (human)
specific granule lumen	Arginase-1	Homo sapiens (human)
cytosol	Arginase-1	Homo sapiens (human)
cytoplasm	Arginase-1	Homo sapiens (human)
mitochondrial matrix	Arginase-2, mitochondrial	Homo sapiens (human)
cytoplasm	Arginase-2, mitochondrial	Homo sapiens (human)
mitochondrion	Arginase-2, mitochondrial	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay ID	Title	Year	Journal	Article
AID1370772	Binding affinity to arginase 1 (unknown origin)	2018	Bioorganic & medicinal chemistry letters, 02-01, Volume: 28, Issue:3	Small molecule immuno-oncology therapeutic agents.
AID1724057	Inhibition of human Arg2 at pH 7.5	2020	Bioorganic & medicinal chemistry, 09-15, Volume: 28, Issue:18	Boronic acid-based arginase inhibitors in cancer immunotherapy.
AID1695179	Inhibition of recombinant bovine liver ARGI using L-arginine as substrate incubated for 60 mins by spectroscopic analysis	2020	RSC medicinal chemistry, May-01, Volume: 11, Issue:5	Synthesis, evaluation and molecular modelling of piceatannol analogues as arginase inhibitors.
AID1128922	Inhibition of rat liver arginase	2014	European journal of medicinal chemistry, Apr-09, Volume: 76	The applications of binuclear metallohydrolases in medicine: recent advances in the design and development of novel drug leads for purple acid phosphatases, metallo-β-lactamases and arginases.
AID1501188	Inhibition of bovine liver arginase assessed as reduction in urea production using L-arginine as substrate after 60 mins in presence of MnCl2 by alpha-isonitrosopropiophenone reagent based spectrophotometric analysis	2017	Journal of natural products, 09-22, Volume: 80, Issue:9	Cyperaceae Species Are Potential Sources of Natural Mammalian Arginase Inhibitors with Positive Effects on Vascular Function.
AID1724056	Binding affinity to human Arg1 at pH 8.5	2020	Bioorganic & medicinal chemistry, 09-15, Volume: 28, Issue:18	Boronic acid-based arginase inhibitors in cancer immunotherapy.
AID1695181	Inhibition of recombinant human liver ARGI using L-arginine as substrate incubated for 60 mins by spectroscopic analysis	2020	RSC medicinal chemistry, May-01, Volume: 11, Issue:5	Synthesis, evaluation and molecular modelling of piceatannol analogues as arginase inhibitors.
AID1370774	Oral bioavailability in rat	2018	Bioorganic & medicinal chemistry letters, 02-01, Volume: 28, Issue:3	Small molecule immuno-oncology therapeutic agents.
AID1370775	Half life in rat	2018	Bioorganic & medicinal chemistry letters, 02-01, Volume: 28, Issue:3	Small molecule immuno-oncology therapeutic agents.
AID1540248	Inhibition of human recombinant arginase 1 expressed in Escherichia coli BL21 (DE3) assessed as reduction in urea production using L-arginine as substrate in presence of MnSO4 incubated for 60 mins by o-phthaldialdehyde/N-(1-naphthyl)ethylene-diamine dihy	2019	Journal of medicinal chemistry, 09-12, Volume: 62, Issue:17	Discovery of
AID1724055	Inhibition of rat Arg1 at pH 7.4	2020	Bioorganic & medicinal chemistry, 09-15, Volume: 28, Issue:18	Boronic acid-based arginase inhibitors in cancer immunotherapy.
AID1540249	Inhibition of human recombinant arginase 2 H331 to I354 deletion mutant expressed in Escherichia coli BL21 (DE3) assessed as reduction in urea production using L-arginine as substrate in presence of MnSO4 incubated for 60 mins by colorimetric assay	2019	Journal of medicinal chemistry, 09-12, Volume: 62, Issue:17	Discovery of
AID1370773	Inhibition of arginase 2 (unknown origin)	2018	Bioorganic & medicinal chemistry letters, 02-01, Volume: 28, Issue:3	Small molecule immuno-oncology therapeutic agents.
AID1128921	Inhibition of mouse macrophage arginase	2014	European journal of medicinal chemistry, Apr-09, Volume: 76	The applications of binuclear metallohydrolases in medicine: recent advances in the design and development of novel drug leads for purple acid phosphatases, metallo-β-lactamases and arginases.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	0 (0.00)	29.6817
2010's	4 (66.67)	24.3611
2020's	2 (33.33)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.56

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.

Metric	This Compound (vs All)
Research Demand Index	12.56 (24.57)
Research Supply Index	1.95 (2.92)
Research Growth Index	4.51 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (12.56)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	3 (50.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	3 (50.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
catechol [no description available]	2.25	1	catechols	allelochemical; genotoxin; plant metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	2.25	1	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
phosphonoacetic acid Phosphonoacetic Acid: A simple organophosphorus compound that inhibits DNA polymerase, especially in viruses and is used as an antiviral agent.. phosphonoacetic acid : A member of the class of phosphonic acids that is phosphonic acid in which the hydrogen attached to the phosphorous is replaced by a carboxymethyl group.	3.19	1	monocarboxylic acid; phosphonic acids	antiviral agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor
2-mercaptoacetate [no description available]	3.19	1	sulfur-containing carboxylic acid
mercaptoethanol Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.	3.19	1	alkanethiol; primary alcohol	geroprotector
beta-phosphonopropionic acid beta-phosphonopropionic acid: structure	3.19	1
resorcinol resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951. resorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.	2.25	1	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser
salicyl alcohol salicyl alcohol: RN given refers to parent cpd; saligenin is the aglycone of salicin; structure; it is oxidatively metabolized to gentisic acid. salicyl alcohol : A hydroxybenzyl alcohol that is phenol substituted by a hydroxymethyl group at C-2.	2.25	1	aromatic primary alcohol; hydroxybenzyl alcohol	human urinary metabolite
salicylamide salamide: a major impurity of hydrochlorothiazide; structure in first source	2.25	1	phenols; salicylamides	antirheumatic drug; non-narcotic analgesic
2-thiosalicylic acid 2-thiosalicylic acid: a degradation product of thimerosal; RN given refers to parent cpd. thiosalicylic acid : A sulfanylbenzoic acid that is the 2-sulfanyl derivative of benzoic acid.	3.19	1	sulfanylbenzoic acid	antipyretic; non-narcotic analgesic
2-aminophenol [no description available]	2.25	1	aminophenol	bacterial metabolite
3-mercaptopropionic acid 3-Mercaptopropionic Acid: An inhibitor of glutamate decarboxylase. It decreases the GAMMA-AMINOBUTYRIC ACID concentration in the brain, thereby causing convulsions.. 3-mercaptopropanoic acid : A mercaptopropanoic acid that is propanoic acid carrying a sulfanyl group at position 3.	3.19	1	mercaptopropanoic acid	algal metabolite
salicylaldehyde o-hydroxybenzaldehyde: structure in first source	2.25	1	hydroxybenzaldehyde	nematicide; plant metabolite
1,2-diaminobenzene 1,2-diaminobenzene: RN given refers to parent cpd. 1,2-phenylenediamine : A phenylenediamine in which the two amino groups are ortho to each other.	2.25	1	phenylenediamine	hydrogen donor
ethyl salicylate ethyl salicylate: causes erythema after topical application as an aerosol; found in blood	2.25	1	hydroxybenzoic acid
1,3-benzodioxole 1,3-benzodioxole : A benzodioxole consisting of a benzene ring substituted by a the methylenedioxy group.	2.25	1	benzodioxole
dipicolinic acid dipicolinic acid : A pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6.	3.19	1	pyridinedicarboxylic acid	bacterial metabolite
hydroxyhydroquinone benzene-1,2,4-triol : A benzenetriol carrying hydroxy groups at positions 1, 2 and 4.	2.25	1	benzenetriol	mouse metabolite
methylene diphosphonate medronic acid : A 1,1-bis(phosphonic acid) consisting of methane substituted by two phosphonic acid groups.	3.19	1	1,1-bis(phosphonic acid)	bone density conservation agent; chelator
thiolactic acid thiolactic acid: RN given refers to parent cpd	3.19	1	mercaptopropanoic acid
1,8-dihydroxynaphthalene 1,8-dihydroxynaphthalene: isolated from mutant of Wangiella dermatitidis; structure given in first source. naphthalene-1,8-diol : A member of the class of naphthalenediols that is naphthalene in which the hydrogens at positions 1 and 8 are replaced by hydroxy groups.	2.25	1	naphthalenediol	fungal metabolite
1,2-benzenedithiol 1,2-benzenedithiol: structure in first source	2.25	1
3-mercaptopropanol 3-mercaptopropanol: structure in first source	3.19	1
3,4-dihydroxybenzylamine 3,4-dihydroxybenzylamine: RN given refers to parent cpd; structure	2.25	1	catechols
3,4-dihydroxybenzyl alcohol 3,4-dihydroxybenzyl alcohol: structure given in first source	2.25	1
n(omega)-hydroxyarginine N(omega)-hydroxyarginine: can cause vasorelaxation of bovine intrapulmonary artery; structure given in first source. N(5)-[(Z)-amino(hydroxyimino)methyl]-L-ornithine : An N(5)-[amino(hydroxyimino)methyl]-L-ornithine in which the double bond has Z-configuration.	3.35	1	amino acid zwitterion; N(5)-[(E)-amino(hydroxyimino)methyl]ornithine; N(5)-[(hydroxyamino)(imino)methyl]ornithine; N(5)-[(Z)-amino(hydroxyimino)methyl]ornithine; N(5)-[amino(hydroxyimino)methyl]-L-ornithine; N(5)-[amino(hydroxyimino)methyl]ornithine; N(omega)-hydroxy-L-arginine
a 3253 4-aminocatechol: RN given refers to parent cpd	2.25	1	catechols
methyl 3,4-dihydroxybenzoate [no description available]	2.25	1	catechols; methyl ester	antioxidant; neuroprotective agent; plant metabolite
dithioerythritol [no description available]	3.19	1	1,4-dimercaptobutane-2,3-diol	reducing agent
bulgecin a bulgecin A: structure in first source; do not confuse with bulgecin	3.19	1
kobophenol a kobophenol A: structure in first source	2.15	1
3,3',4,5'-tetrahydroxystilbene 3,3',4,5'-tetrahydroxystilbene: demethyl derivative of isorhapontigenin; structure in first source; a Syk kinase inhibitor; found in heartwood of FABACEAE; inhibitor of photosynthesis in spinach chloroplasts; may be inhibitor of plant growth; RN given refers to (E)-isomer. piceatannol : A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5.	2.59	2	catechols; polyphenol; resorcinols; stilbenol	antineoplastic agent; apoptosis inducer; geroprotector; hypoglycemic agent; plant metabolite; protein kinase inhibitor; tyrosine kinase inhibitor
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	2.25	1	caffeic acid	geroprotector; mouse metabolite
thiosemicarbazide thiosemicarbazide: glutamate decarboxylase antagonist; structure given in first source. hydrazinecarbothioamide : A member of the class of thioureas that is thiourea in which a hydrogen of one of the amino groups is replaced by an amino group.	3.19	1	hydrazines; thiocarboxamide; thioureas
(+)-trans-epsilon-viniferin (+)-trans-epsilon-viniferin : A stilbenoid that is the (+)-trans-stereoisomer of epsilon-viniferin, obtained by cyclodimerisation of trans-resveratrol.	2.15	1	1-benzofurans; polyphenol; stilbenoid
(S)-2-amino-6-boronohexanoic acid (S)-2-amino-6-boronohexanoic acid : L-Norleucine substituted at C-6 with a borono group.	4.03	3	non-proteinogenic L-alpha-amino acid; organoboron compound
thiomandelic acid thiomandelic acid: structure in first source	3.19	1
3-mercaptopropylphosphonic acid [no description available]	3.19	1

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