Compounds > 1-nitrosocyclohexyl acetate
Page last updated: 2024-11-12

1-nitrosocyclohexyl acetate

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

Description

1-nitrosocyclohexyl acetate: a nitric oxide donor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11843278
CHEMBL ID1681831
SCHEMBL ID2269851
MeSH IDM0552892

Synonyms (7)

Synonym
(1-nitrosocyclohexyl) acetate
CHEMBL1681831
1-nitrosocyclohexyl acetate
bdbm50439263
SCHEMBL2269851
10259-08-2
PD156468

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" The slow HNO-donor 1 demonstrates weak thiol-insensitive vasorelaxation, indicating HNO release kinetics determine HNO bioavailability and activity."( Acyloxy nitroso compounds as nitroxyl (HNO) donors: kinetics, reactions with thiols, and vasodilation properties.
Brandon, A; Crawford, JH; DuMond, JF; Honovar, J; Isbell, TS; King, SB; Patel, RP; Shoman, ME; Vitturi, DA; White, CR, 2011)		0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glyceraldehyde-3-phosphate dehydrogenaseOryctolagus cuniculus (rabbit)IC50 (µMol)0.20000.20000.20000.2000AID766218
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID577799Vasodilatory activity in Sprague-Dawley rat thoracic aorta assessed as relaxation of phenylephrine-induced vasoconstriction at 0.01 nM to 1 uM in presence 100 U/ml SOD at 21% oxygen2011Journal of medicinal chemistry, Feb-24, Volume: 54, Issue:4
Acyloxy nitroso compounds as nitroxyl (HNO) donors: kinetics, reactions with thiols, and vasodilation properties.
AID766216Binding affinity to alkyl hydroperoxide reductase subunit C C165S mutant (unknown origin) assessed as structural modifications by SDS-PAGE2013Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17
Direct and nitroxyl (HNO)-mediated reactions of acyloxy nitroso compounds with the thiol-containing proteins glyceraldehyde 3-phosphate dehydrogenase and alkyl hydroperoxide reductase subunit C.
AID766218Inhibition of rabbit muscle GAPDH assessed as residual enzyme activity after 60 mins by spectrophotometry2013Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17
Direct and nitroxyl (HNO)-mediated reactions of acyloxy nitroso compounds with the thiol-containing proteins glyceraldehyde 3-phosphate dehydrogenase and alkyl hydroperoxide reductase subunit C.
AID577796Vasodilatory activity in Sprague-Dawley rat thoracic aorta assessed as relaxation of phenylephrine-induced vasoconstriction compound treated 5 mins after 200 uM NO-scavenger C-PTIO treatment2011Journal of medicinal chemistry, Feb-24, Volume: 54, Issue:4
Acyloxy nitroso compounds as nitroxyl (HNO) donors: kinetics, reactions with thiols, and vasodilation properties.
AID577807Vasodilatory activity in rabbit thoracic aorta assessed as relaxation of phenylephrine-induced vasoconstriction2011Journal of medicinal chemistry, Feb-24, Volume: 54, Issue:4
Acyloxy nitroso compounds as nitroxyl (HNO) donors: kinetics, reactions with thiols, and vasodilation properties.
AID766215Binding affinity to rabbit muscle GAPDH assessed as structural modifications at 5 mM after 60 mins by SDS-PAGE2013Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17
Direct and nitroxyl (HNO)-mediated reactions of acyloxy nitroso compounds with the thiol-containing proteins glyceraldehyde 3-phosphate dehydrogenase and alkyl hydroperoxide reductase subunit C.
AID577808Vasodilatory activity in bovine intrapulmonary artery assessed as relaxation of phenylephrine-induced vasoconstriction2011Journal of medicinal chemistry, Feb-24, Volume: 54, Issue:4
Acyloxy nitroso compounds as nitroxyl (HNO) donors: kinetics, reactions with thiols, and vasodilation properties.
AID766206Binding affinity to alkyl hydroperoxide reductase subunit C C165S mutant (unknown origin) assessed as formation of sulfinic acid of Cys46 of peptide D41 to G51 by LC-MS analysis2013Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17
Direct and nitroxyl (HNO)-mediated reactions of acyloxy nitroso compounds with the thiol-containing proteins glyceraldehyde 3-phosphate dehydrogenase and alkyl hydroperoxide reductase subunit C.
AID766213Binding affinity to rabbit muscle GAPDH tryptic peptide I143 to K159 assessed as formation of disulfide bond by LC-MS analysis2013Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17
Direct and nitroxyl (HNO)-mediated reactions of acyloxy nitroso compounds with the thiol-containing proteins glyceraldehyde 3-phosphate dehydrogenase and alkyl hydroperoxide reductase subunit C.
AID766212Binding affinity to rabbit muscle GAPDH peptide V232 to R245 assessed as formation of sulfinic acid of Cys244 by LC-MS analysis2013Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17
Direct and nitroxyl (HNO)-mediated reactions of acyloxy nitroso compounds with the thiol-containing proteins glyceraldehyde 3-phosphate dehydrogenase and alkyl hydroperoxide reductase subunit C.
AID766217Reversible inhibition of rabbit muscle GAPDH assessed as residual enzyme activity at 1 uM after 60 mins followed by incubation with DTT by spectrophotometry relative to control2013Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17
Direct and nitroxyl (HNO)-mediated reactions of acyloxy nitroso compounds with the thiol-containing proteins glyceraldehyde 3-phosphate dehydrogenase and alkyl hydroperoxide reductase subunit C.
AID577803Potentiation of MahmaNonoate induced- vasodilatory activity in Sprague-Dawley rat thoracic aorta at 1 mM2011Journal of medicinal chemistry, Feb-24, Volume: 54, Issue:4
Acyloxy nitroso compounds as nitroxyl (HNO) donors: kinetics, reactions with thiols, and vasodilation properties.
AID577798Vasodilatory activity in Sprague-Dawley rat thoracic aorta assessed as relaxation of phenylephrine-induced vasoconstriction at 0.01 nM to 1 uM in presence of 1% oxygen2011Journal of medicinal chemistry, Feb-24, Volume: 54, Issue:4
Acyloxy nitroso compounds as nitroxyl (HNO) donors: kinetics, reactions with thiols, and vasodilation properties.
AID577794Vasodilatory activity in Sprague-Dawley rat thoracic aorta assessed as relaxation of phenylephrine-induced vasoconstriction at 0.01 nM to 100 uM2011Journal of medicinal chemistry, Feb-24, Volume: 54, Issue:4
Acyloxy nitroso compounds as nitroxyl (HNO) donors: kinetics, reactions with thiols, and vasodilation properties.
AID766208Binding affinity to alkyl hydroperoxide reductase subunit C C165S mutant (unknown origin) assessed as unreacted thiol in peptide D41 to G51 by LC-MS analysis2013Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17
Direct and nitroxyl (HNO)-mediated reactions of acyloxy nitroso compounds with the thiol-containing proteins glyceraldehyde 3-phosphate dehydrogenase and alkyl hydroperoxide reductase subunit C.
AID766200Inhibition of rabbit muscle GAPDH at 1 uM after 60 mins by spectrophotometry2013Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17
Direct and nitroxyl (HNO)-mediated reactions of acyloxy nitroso compounds with the thiol-containing proteins glyceraldehyde 3-phosphate dehydrogenase and alkyl hydroperoxide reductase subunit C.
AID577797Vasodilatory activity in Sprague-Dawley rat thoracic aorta assessed as relaxation of phenylephrine-induced vasoconstriction at 0.01 nM to 1 uM in presence of 21% oxygen2011Journal of medicinal chemistry, Feb-24, Volume: 54, Issue:4
Acyloxy nitroso compounds as nitroxyl (HNO) donors: kinetics, reactions with thiols, and vasodilation properties.
AID577806Inhibition of 1-Nitrosocyclohexyl acetate induced- vasodilatory activity in Sprague-Dawley rat thoracic aorta at 0.1 to 1 mM2011Journal of medicinal chemistry, Feb-24, Volume: 54, Issue:4
Acyloxy nitroso compounds as nitroxyl (HNO) donors: kinetics, reactions with thiols, and vasodilation properties.
AID766219Binding affinity to rabbit muscle GAPDH assessed as structural modifications of Cys149, Cys153 and Cys244 at 5 mM after 60 mins by MALDI-TOF MS2013Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17
Direct and nitroxyl (HNO)-mediated reactions of acyloxy nitroso compounds with the thiol-containing proteins glyceraldehyde 3-phosphate dehydrogenase and alkyl hydroperoxide reductase subunit C.
AID766209Binding affinity to alkyl hydroperoxide reductase subunit C C165S mutant peptide D41 to G51 (unknown origin) assessed as sulfinic acid or sulfinamide modification by MALDI-TOF MS2013Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17
Direct and nitroxyl (HNO)-mediated reactions of acyloxy nitroso compounds with the thiol-containing proteins glyceraldehyde 3-phosphate dehydrogenase and alkyl hydroperoxide reductase subunit C.
AID577795Vasodilatory activity in Sprague-Dawley rat thoracic aorta assessed as relaxation of phenylephrine-induced vasoconstriction compound treated 5 mins after 1 uM soluble guanylate cyclase inhibitor ODQ treatment2011Journal of medicinal chemistry, Feb-24, Volume: 54, Issue:4
Acyloxy nitroso compounds as nitroxyl (HNO) donors: kinetics, reactions with thiols, and vasodilation properties.
AID577802Potentiation of 1-Nitrosocyclohexyl acetate induced- vasodilatory activity in Sprague-Dawley rat thoracic aorta at 1 mM2011Journal of medicinal chemistry, Feb-24, Volume: 54, Issue:4
Acyloxy nitroso compounds as nitroxyl (HNO) donors: kinetics, reactions with thiols, and vasodilation properties.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's7 (87.50)24.3611
2020's1 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.24

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 Index13.24 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index5.43 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.24)

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
nitroxyl
nitroxyl: hydroxamic acid oxidized to nitroxyl free radical. nitroxyl : A nitrogen oxoacid consisting of an oxygen atom double-bonded to an NH group.		7.9840nitrogen oxoacid
isoflurane
Isoflurane: A stable, non-explosive inhalation anesthetic, relatively free from significant side effects.		2.0610organofluorine compoundinhalation anaesthetic
tromethamine
Tromethamine: An organic amine proton acceptor. It is used in the synthesis of surface-active agents and pharmaceuticals; as an emulsifying agent for cosmetic creams and lotions, mineral oil and paraffin wax emulsions, as a biological buffer, and used as an alkalizer. (From Merck, 11th ed; Martindale, The Extra Pharmacopoeia, 30th ed, p1424)		2.0610primary amino compound;
triol		buffer
nitrosobenzene
[no description available]		2.0810benzenes;
nitroso compound		xenobiotic metabolite
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		2.0610acetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid		antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
phenyl acetate
phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.		3.3460benzenes;
phenyl acetates
s-nitrosoglutathione
[no description available]		2.0810glutathione derivative;
nitrosothio compound		bronchodilator agent;
nitric oxide donor;
platelet aggregation inhibitor;
signalling molecule
ryanodine
Ryanodine: A methylpyrrole-carboxylate from RYANIA that disrupts the RYANODINE RECEPTOR CALCIUM RELEASE CHANNEL to modify CALCIUM release from SARCOPLASMIC RETICULUM resulting in alteration of MUSCLE CONTRACTION. It was previously used in INSECTICIDES. It is used experimentally in conjunction with THAPSIGARGIN and other inhibitors of CALCIUM ATPASE uptake of calcium into SARCOPLASMIC RETICULUM.. ryanodine : An insecticide alkaloid isolated from South American plant Ryania speciosa.		2.0610
diamide
Diamide: A sulfhydryl reagent which oxidizes sulfhydryl groups to the disulfide form. It is a radiation-sensitizing agent of anoxic bacterial and mammalian cells.		2.25101,1'-azobis(N,N-dimethylformamide)
cysteine
Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.		2.0710cysteiniumfundamental metabolite
noc 9
NOC 9: nitrogen oxide releaser		2.0610
ConditionIndicatedRelationship StrengthStudiesTrials
Left Ventricular Hypertrophy
[description not available]		02.1110
Left Ventricular Dysfunction
[description not available]		02.1110
Cardiac Remodeling, Ventricular
[description not available]		02.1110
Alloxan Diabetes
[description not available]		02.1110
Hypertrophy, Left Ventricular
Enlargement of the LEFT VENTRICLE of the heart. This increase in ventricular mass is attributed to sustained abnormal pressure or volume loads and is a contributor to cardiovascular morbidity and mortality.		02.1110
Ventricular Dysfunction, Left
A condition in which the LEFT VENTRICLE of the heart was functionally impaired. This condition usually leads to HEART FAILURE; MYOCARDIAL INFARCTION; and other cardiovascular complications. Diagnosis is made by measuring the diminished ejection fraction and a depressed level of motility of the left ventricular wall.		02.1110
Diabetic Cardiomyopathies
Diabetes complications in which VENTRICULAR REMODELING in the absence of CORONARY ATHEROSCLEROSIS and hypertension results in cardiac dysfunctions, typically LEFT VENTRICULAR DYSFUNCTION. The changes also result in myocardial hypertrophy, myocardial necrosis and fibrosis, and collagen deposition due to impaired glucose tolerance.		02.1110
Muscle Contraction
A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.		02.0510
Cardiac Failure
[description not available]		02.0710
Heart Failure
A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.		02.0710
Atherogenesis
[description not available]		02.0810
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.0810
Atherosclerosis
A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.		02.0810