Compounds > sargahydroquinoic acid
Page last updated: 2024-11-12

sargahydroquinoic acid

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

Description

sargahydroquinoic acid: vasodilatator from the brown alga Sargassum macrocarpum; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10202734
CHEMBL ID261063
SCHEMBL ID14212076
MeSH IDM0521391

Synonyms (5)

Synonym
CHEMBL261063
sargahydroquinoic acid
SCHEMBL14212076
(2z,6e,10e)-12-(2,5-dihydroxy-3-methylphenyl)-6,10-dimethyl-2-(4-methylpent-3-enyl)dodeca-2,6,10-trienoic acid
bdbm50267969

Research Excerpts

Overview

Sargahydroquinoic acid (SHQA) is a major component of MES.

ExcerptReferenceRelevance
"Sargahydroquinoic acid (SHQA) is a major component of MES."( Hypothalamic administration of sargahydroquinoic acid elevates peripheral thermogenic signaling and ameliorates high fat diet-induced obesity through the sympathetic nervous system.
Choi, CW; Hwang, H; Kang, T; Kim, D; Kim, HR; Kim, MS; Lee, B; Lee, Y; Park, YJ; Rhim, H, 2021)		1.63
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AcetylcholinesteraseElectrophorus electricus (electric eel)IC50 (µMol)124.30000.00000.94539.9400AID1486115
Beta-secretase 1Homo sapiens (human)IC50 (µMol)4.40000.00061.619410.0000AID1486117
Beta-secretase 1Homo sapiens (human)Ki1.60000.00031.35248.0000AID1486118
CholinesteraseEquus caballus (horse)IC50 (µMol)15.20000.00002.22149.4000AID1486116
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
proteolysisBeta-secretase 1Homo sapiens (human)
membrane protein ectodomain proteolysisBeta-secretase 1Homo sapiens (human)
response to lead ionBeta-secretase 1Homo sapiens (human)
protein processingBeta-secretase 1Homo sapiens (human)
amyloid-beta formationBeta-secretase 1Homo sapiens (human)
amyloid precursor protein catabolic processBeta-secretase 1Homo sapiens (human)
positive regulation of neuron apoptotic processBeta-secretase 1Homo sapiens (human)
amyloid-beta metabolic processBeta-secretase 1Homo sapiens (human)
detection of mechanical stimulus involved in sensory perception of painBeta-secretase 1Homo sapiens (human)
prepulse inhibitionBeta-secretase 1Homo sapiens (human)
cellular response to copper ionBeta-secretase 1Homo sapiens (human)
cellular response to manganese ionBeta-secretase 1Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionBeta-secretase 1Homo sapiens (human)
signaling receptor ligand precursor processingBeta-secretase 1Homo sapiens (human)
cellular response to amyloid-betaBeta-secretase 1Homo sapiens (human)
amyloid fibril formationBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
amyloid-beta bindingBeta-secretase 1Homo sapiens (human)
endopeptidase activityBeta-secretase 1Homo sapiens (human)
aspartic-type endopeptidase activityBeta-secretase 1Homo sapiens (human)
protein bindingBeta-secretase 1Homo sapiens (human)
peptidase activityBeta-secretase 1Homo sapiens (human)
beta-aspartyl-peptidase activityBeta-secretase 1Homo sapiens (human)
enzyme bindingBeta-secretase 1Homo sapiens (human)
protein serine/threonine kinase bindingBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (20)

Processvia Protein(s)Taxonomy
lysosomeBeta-secretase 1Homo sapiens (human)
endosomeBeta-secretase 1Homo sapiens (human)
early endosomeBeta-secretase 1Homo sapiens (human)
late endosomeBeta-secretase 1Homo sapiens (human)
multivesicular bodyBeta-secretase 1Homo sapiens (human)
endoplasmic reticulum lumenBeta-secretase 1Homo sapiens (human)
Golgi apparatusBeta-secretase 1Homo sapiens (human)
trans-Golgi networkBeta-secretase 1Homo sapiens (human)
plasma membraneBeta-secretase 1Homo sapiens (human)
synaptic vesicleBeta-secretase 1Homo sapiens (human)
cell surfaceBeta-secretase 1Homo sapiens (human)
endosome membraneBeta-secretase 1Homo sapiens (human)
membraneBeta-secretase 1Homo sapiens (human)
axonBeta-secretase 1Homo sapiens (human)
dendriteBeta-secretase 1Homo sapiens (human)
neuronal cell bodyBeta-secretase 1Homo sapiens (human)
membrane raftBeta-secretase 1Homo sapiens (human)
recycling endosomeBeta-secretase 1Homo sapiens (human)
Golgi-associated vesicle lumenBeta-secretase 1Homo sapiens (human)
hippocampal mossy fiber to CA3 synapseBeta-secretase 1Homo sapiens (human)
endosomeBeta-secretase 1Homo sapiens (human)
plasma membraneBeta-secretase 1Homo sapiens (human)
trans-Golgi networkBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID1486116Inhibition of equine serum BChE using butyrylthiocholine chloride as substrate incubated for 15 mins by spectrophotometric analysis2017Bioorganic & medicinal chemistry, 08-01, Volume: 25, Issue:15
BACE1 inhibitory activity and molecular docking analysis of meroterpenoids from Sargassum serratifolium.
AID1486117Inhibition of recombinant human BACE1 using Rh-EVNLDAEFK-Quencher as substrate after 60 mins by FRET assay2017Bioorganic & medicinal chemistry, 08-01, Volume: 25, Issue:15
BACE1 inhibitory activity and molecular docking analysis of meroterpenoids from Sargassum serratifolium.
AID329646Vasodialative effect on high K+-induced vasoconstriction in rabbit carotid artery2008Bioorganic & medicinal chemistry letters, Apr-15, Volume: 18, Issue:8
Selective vasodilatation effect of sargahydroquinoic acid, an active constituent of Sargassum micracanthum, on the basilar arteries of rabbits.
AID329645Vasodialative effect on high K+-induced vasoconstriction in rabbit basilar artery2008Bioorganic & medicinal chemistry letters, Apr-15, Volume: 18, Issue:8
Selective vasodilatation effect of sargahydroquinoic acid, an active constituent of Sargassum micracanthum, on the basilar arteries of rabbits.
AID1486115Inhibition of electric eel AChE using acetylthiocholine iodide as substrate incubated for 15 mins by spectrophotometric analysis2017Bioorganic & medicinal chemistry, 08-01, Volume: 25, Issue:15
BACE1 inhibitory activity and molecular docking analysis of meroterpenoids from Sargassum serratifolium.
AID390886Inhibition of Candida albicans isocitrate lyase2008Journal of natural products, Oct, Volume: 71, Issue:10
Meroditerpenoids from the brown alga Sargassum siliquastrum.
AID329647Selectivity index, ratio of EC50 for vasodialative effect on high K+-induced vasoconstriction in rabbit carotid artery to basilar artery2008Bioorganic & medicinal chemistry letters, Apr-15, Volume: 18, Issue:8
Selective vasodilatation effect of sargahydroquinoic acid, an active constituent of Sargassum micracanthum, on the basilar arteries of rabbits.
AID390885Inhibition of Staphylococcus aureus sortase A2008Journal of natural products, Oct, Volume: 71, Issue:10
Meroditerpenoids from the brown alga Sargassum siliquastrum.
AID1486118Mixed type inhibition of recombinant human BACE1 using Rh-EVNLDAEFK-Quencher as substrate after 60 mins by Dixon plot analysis2017Bioorganic & medicinal chemistry, 08-01, Volume: 25, Issue:15
BACE1 inhibitory activity and molecular docking analysis of meroterpenoids from Sargassum serratifolium.
AID390884Antioxidant activity assessed as DPPH radical scavenging activity2008Journal of natural products, Oct, Volume: 71, Issue:10
Meroditerpenoids from the brown alga Sargassum siliquastrum.
AID1486120Mixed type inhibition of recombinant human BACE1 using Rh-EVNLDAEFK-Quencher as substrate after 60 mins by Lineweaver-Burk plot analysis2017Bioorganic & medicinal chemistry, 08-01, Volume: 25, Issue:15
BACE1 inhibitory activity and molecular docking analysis of meroterpenoids from Sargassum serratifolium.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (20.00)29.6817
2010's6 (40.00)24.3611
2020's6 (40.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.19

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 Index12.19 (24.57)
Research Supply Index2.77 (2.92)
Research Growth Index4.97 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.19)

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%
Other15 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
methanol
Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.		2.2110alkyl alcohol;
one-carbon compound;
primary alcohol;
volatile organic compound		amphiprotic solvent;
Escherichia coli metabolite;
fuel;
human metabolite;
mouse metabolite;
Mycoplasma genitalium metabolite
berberine
[no description available]		2.1510alkaloid antibiotic;
berberine alkaloid;
botanical anti-fungal agent;
organic heteropentacyclic compound		antilipemic drug;
antineoplastic agent;
antioxidant;
EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor;
EC 1.21.3.3 (reticuline oxidase) inhibitor;
EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor;
EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor;
EC 2.7.11.10 (IkappaB kinase) inhibitor;
EC 3.1.1.4 (phospholipase A2) inhibitor;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor;
EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
geroprotector;
hypoglycemic agent;
metabolite;
potassium channel blocker
2-methylpentane
Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.		2.2110alkane
n-hexane
hexane : An unbranched alkane containing six carbon atoms.		2.2110alkane;
volatile organic compound		neurotoxin;
non-polar solvent
ethyl acetate
ethyl acetate : The acetate ester formed between acetic acid and ethanol.		2.2110acetate ester;
ethyl ester;
volatile organic compound		EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor;
metabolite;
polar aprotic solvent;
Saccharomyces cerevisiae metabolite
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.		2.2110benzenes;
phenyl acetates
alkenes
[no description available]		4.09130
quercetin
[no description available]		2.15107-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
sargachromenol
sargachromenol: nerve growth factor-potentiating substance from Sargassum macrocarpum; structure in first source		2.8630
ConditionIndicatedRelationship StrengthStudiesTrials
Acute Confusional Senile Dementia
[description not available]		02.3110
Alzheimer Disease
A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)		02.3110
Cardiometabolic Syndrome
A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.		02.3110
Obesity
A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).		07.3110
Metabolic Syndrome
A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.		02.3110
Anaphylactic Reaction
[description not available]		02.4110
Anaphylaxis
An acute hypersensitivity reaction due to exposure to a previously encountered ANTIGEN. The reaction may include rapidly progressing URTICARIA, respiratory distress, vascular collapse, systemic SHOCK, and death.		07.4110
Adjuvant Arthritis
[description not available]		02.2510
Rheumatoid Arthritis
[description not available]		02.2510
Arthritis, Rheumatoid
A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.		02.2510
Innate Inflammatory Response
[description not available]		02.1310
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.1310
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.0710
Diabetes Mellitus, Adult-Onset
[description not available]		02.0710
Enlarged Liver
[description not available]		02.0710
Diabetes Mellitus, Type 2
A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.		02.0710