Page last updated: 2024-12-11

helicide

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

Description

helicide: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID12896796
CHEMBL ID201358
CHEBI ID189486
SCHEMBL ID17822698
MeSH IDM0156615
PubMed CID7573800
CHEMBL ID461515
SCHEMBL ID987981
MeSH IDM0156615

Synonyms (57)

Synonym
helicide
F0542
4-(beta-d-allopyranosyloxy)benzaldehyde
4-formylphenyl beta-d-allopyranoside
CHEMBL201358 ,
4-((2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2h-pyran-2-yloxy)benzaldehyde
4-((2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)benzaldehyde
bdbm50177404
4-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzaldehyde
CHEBI:189486
A839856
4-(((2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)benzaldehyde
S3797
AKOS025310966
4-(beta-d-allopyranosyloxy)-benzaldehyde
mfcd00210992
benzaldehyde, 4-(b-d-allopyranosyloxy)-
SCHEMBL17822698
4-formylphenyl b-d-allopyranoside
hilicidum
helicid,(s)
4-formylphenyl-o-b-d-allopyranoside
AS-30535
HMS3885A06
CS-0008901
CCG-267289
HY-N0343
helicide; helicidum;4-formylphenyl--d-allopyranoside
80154-34-3
4-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2h-pyran-2-yloxy)benzaldehyde
bdbm50245886
4-formylphenyl-o-beta-d-glucopyranoside
4-formylphenyl-o-beta-dglucopyranoside
4-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)benzaldehyde
CHEMBL461515 ,
4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzaldehyde
helicin hydrate
4'-formylphenyl-beta-d-glucopyranoside
4-formylphenyl b-d-glucopyranoside
4-(beta-d-glucopyranosyloxy)benzaldehyde
26993-16-8
AKOS015960450
N88424
SCHEMBL987981
Q-201187
W-202142
4-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)benzaldehyde
mfcd08704111
AC-7974
gastrodin impurity 1
AS-49890
A925039
4-formylphenyl-beta-d-glucopyranoside
4-formylphenyl |a-d-glucopyranoside
CS-0139019
PD182179
(2s,3r,4s,5s,6r)-4-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzaldehyde

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" The method was successfully applied to a pharmacokinetic study in rats after intragastric administration of helicid with a dose of 50mg/kg."( Quantitative determination of helicid in rat plasma by liquid chromatography-electrospray ionization mass spectrometry and its application to preliminary pharmacokinetic studies.
Dai, X; Jia, Y; Wang, G; Wang, R; Wang, W; Wang, Y; Xie, H; Xu, M; Yao, C, 2007
)
0.34
"To report the pharmacokinetic parameters of helicid HD in rats after intravenous administration at different doses."( [Investigation on pharmacokinetics of helicid in rats].
Chen, Z; Jiang, XH; Liu, TM; Ma, G; Ren, J; Wang, L, 2008
)
0.35
" To facilitate pharmacokinetic studies of helicid in man, a sensitive and specific LC-MS/MS method for the quantitative detection of helicid in human plasma was developed and validated."( LC-MS/MS determination of helicid in human plasma and its application in pharmacokinetic studies.
Chen, R; Jia, Y; Shen, J; Sun, H; Tan, Z; Xie, H; Zhang, W; Zhou, H, 2011
)
0.37
" Bioavailability and pharmacokinetic parameters of helicid in beagle dogs were researched from a two period crossover design study."( Bioavailability and pharmacokinetics profile of helicid in beagle dogs using gradient elution high performance liquid chromatography electrospray ionization mass spectrometry.
Jia, Y; Shen, J; Sun, J; Wang, W; Xie, H, 2015
)
0.42

Bioavailability

ExcerptReferenceRelevance
" Bioavailability and pharmacokinetic parameters of helicid in beagle dogs were researched from a two period crossover design study."( Bioavailability and pharmacokinetics profile of helicid in beagle dogs using gradient elution high performance liquid chromatography electrospray ionization mass spectrometry.
Jia, Y; Shen, J; Sun, J; Wang, W; Xie, H, 2015
)
0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
glycosideA glycosyl compound resulting from the attachment of a glycosyl group to a non-acyl group RO-, RS-, RSe-, etc. The bond between the glycosyl group and the non-acyl group is called a glycosidic bond. By extension, the terms N-glycosides and C-glycosides are used as class names for glycosylamines and for compounds having a glycosyl group attached to a hydrocarbyl group respectively. These terms are misnomers and should not be used. The preferred terms are glycosylamines and C-glycosyl compounds, respectively.
[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 (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Polyphenol oxidase 2Agaricus bisporusIC50 (µMol)2,540.00000.03403.987110.0000AID411681
AcetylcholinesteraseElectrophorus electricus (electric eel)IC50 (µMol)0.45000.00000.94539.9400AID383238
AcetylcholinesteraseElectrophorus electricus (electric eel)Ki0.73000.00121.25638.9000AID383238
Polyphenol oxidase 2Agaricus bisporusIC50 (µMol)940.00000.03403.987110.0000AID411681; AID430880
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (28)

Processvia Protein(s)Taxonomy
succinate metabolic processSuccinate-semialdehyde dehydrogenase, mitochondrialHomo sapiens (human)
glutamate metabolic processSuccinate-semialdehyde dehydrogenase, mitochondrialHomo sapiens (human)
central nervous system developmentSuccinate-semialdehyde dehydrogenase, mitochondrialHomo sapiens (human)
gamma-aminobutyric acid catabolic processSuccinate-semialdehyde dehydrogenase, mitochondrialHomo sapiens (human)
post-embryonic developmentSuccinate-semialdehyde dehydrogenase, mitochondrialHomo sapiens (human)
synaptic transmission, GABAergicSuccinate-semialdehyde dehydrogenase, mitochondrialHomo sapiens (human)
response to hypoxia4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
copulation4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
locomotory behavior4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
response to xenobiotic stimulus4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
gamma-aminobutyric acid metabolic process4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
gamma-aminobutyric acid biosynthetic process4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
response to iron ion4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
negative regulation of gamma-aminobutyric acid secretion4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
cerebellum development4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
positive regulation of heat generation4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
positive regulation of insulin secretion4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
negative regulation of dopamine secretion4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
response to nicotine4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
exploration behavior4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
response to ethanol4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
negative regulation of blood pressure4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
positive regulation of dopamine metabolic process4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
behavioral response to cocaine4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
positive regulation of uterine smooth muscle contraction4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
positive regulation of inhibitory postsynaptic potential4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
positive regulation of prolactin secretion4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
positive regulation of aspartate secretion4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
gamma-aminobutyric acid catabolic process4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
succinate-semialdehyde dehydrogenase (NAD+) activitySuccinate-semialdehyde dehydrogenase, mitochondrialHomo sapiens (human)
identical protein bindingSuccinate-semialdehyde dehydrogenase, mitochondrialHomo sapiens (human)
4-aminobutyrate transaminase activity4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
pyridoxal phosphate binding4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
succinate-semialdehyde dehydrogenase binding4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
4-aminobutyrate:2-oxoglutarate transaminase activity4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
identical protein binding4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
metal ion binding4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
(S)-3-amino-2-methylpropionate transaminase activity4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
iron-sulfur cluster binding4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
mitochondrionSuccinate-semialdehyde dehydrogenase, mitochondrialHomo sapiens (human)
mitochondrial matrixSuccinate-semialdehyde dehydrogenase, mitochondrialHomo sapiens (human)
synapseSuccinate-semialdehyde dehydrogenase, mitochondrialHomo sapiens (human)
mitochondrionSuccinate-semialdehyde dehydrogenase, mitochondrialHomo sapiens (human)
mitochondrion4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
mitochondrial matrix4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
4-aminobutyrate transaminase complex4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
mitochondrion4-aminobutyrate aminotransferase, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID260087Inhibitory activity against SSADH2006Bioorganic & medicinal chemistry letters, Feb, Volume: 16, Issue:3
Inhibition of GABA shunt enzymes' activity by 4-hydroxybenzaldehyde derivatives.
AID444074Inhibition of mushroom tyrosinase at 200 uM2009Bioorganic & medicinal chemistry letters, Nov-01, Volume: 19, Issue:21
Discovery of 4-functionalized phenyl-O-beta-D-glycosides as a new class of mushroom tyrosinase inhibitors.
AID383242Inhibition of horse serum BuChE upto 500 uM by Ellman's method2008European journal of medicinal chemistry, Jan, Volume: 43, Issue:1
Synthesis and biological evaluation of helicid analogues as novel acetylcholinesterase inhibitors.
AID1442887Antiproliferative activity against human MCF7 cells by SRB assay2017Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8
Bioactive drimane sesquiterpenoids and aromatic glycosides from Cinnamosma fragrans.
AID455418Inhibition of Torpedo california AChE at 1 mM by Ellman's method2009Bioorganic & medicinal chemistry, Oct-01, Volume: 17, Issue:19
Rational design and synthesis of highly potent anti-acetylcholinesterase activity huperzine A derivatives.
AID411681Inhibition of mushroom tyrosinase assessed as 3,4-dihydroxy-L-phenylalanine oxidation2008Bioorganic & medicinal chemistry letters, Dec-15, Volume: 18, Issue:24
Synthesis and biological evaluation of helicid analogues as mushroom tyrosinase inhibitors.
AID411682Inhibition of mushroom tyrosinase assessed as 3,4-dihydroxy-L-phenylalanine oxidation at 0.1 mM2008Bioorganic & medicinal chemistry letters, Dec-15, Volume: 18, Issue:24
Synthesis and biological evaluation of helicid analogues as mushroom tyrosinase inhibitors.
AID383241Inhibition of Electrophorus electricus AChE upto 500 uM by Ellman's method2008European journal of medicinal chemistry, Jan, Volume: 43, Issue:1
Synthesis and biological evaluation of helicid analogues as novel acetylcholinesterase inhibitors.
AID260086Inhibitory activity against GABAT2006Bioorganic & medicinal chemistry letters, Feb, Volume: 16, Issue:3
Inhibition of GABA shunt enzymes' activity by 4-hydroxybenzaldehyde derivatives.
AID383242Inhibition of horse serum BuChE upto 500 uM by Ellman's method2008European journal of medicinal chemistry, Jan, Volume: 43, Issue:1
Synthesis and biological evaluation of helicid analogues as novel acetylcholinesterase inhibitors.
AID411681Inhibition of mushroom tyrosinase assessed as 3,4-dihydroxy-L-phenylalanine oxidation2008Bioorganic & medicinal chemistry letters, Dec-15, Volume: 18, Issue:24
Synthesis and biological evaluation of helicid analogues as mushroom tyrosinase inhibitors.
AID411684Toxicity in mouse assessed by autopsy at 1200 mg/kg, po administered as single gavage dose after 20 days2008Bioorganic & medicinal chemistry letters, Dec-15, Volume: 18, Issue:24
Synthesis and biological evaluation of helicid analogues as mushroom tyrosinase inhibitors.
AID1717384Binding affinity to rat FPPS expressed in Escherichia coli BL21 (DE3) by isothermal titration calorimetry2020European journal of medicinal chemistry, Jan-15, Volume: 186Structure-based virtual screening and biological evaluation of novel non-bisphosphonate farnesyl pyrophosphate synthase inhibitors.
AID411682Inhibition of mushroom tyrosinase assessed as 3,4-dihydroxy-L-phenylalanine oxidation at 0.1 mM2008Bioorganic & medicinal chemistry letters, Dec-15, Volume: 18, Issue:24
Synthesis and biological evaluation of helicid analogues as mushroom tyrosinase inhibitors.
AID1717383Inhibition of rat FPPS expressed in Escherichia coli BL21 (DE3) using GPP and IPP as substrate at 10 uM incubated for 10 mins by microplate reader2020European journal of medicinal chemistry, Jan-15, Volume: 186Structure-based virtual screening and biological evaluation of novel non-bisphosphonate farnesyl pyrophosphate synthase inhibitors.
AID444074Inhibition of mushroom tyrosinase at 200 uM2009Bioorganic & medicinal chemistry letters, Nov-01, Volume: 19, Issue:21
Discovery of 4-functionalized phenyl-O-beta-D-glycosides as a new class of mushroom tyrosinase inhibitors.
AID383238Inhibition of Electrophorus electricus AChE by Ellman's method2008European journal of medicinal chemistry, Jan, Volume: 43, Issue:1
Synthesis and biological evaluation of helicid analogues as novel acetylcholinesterase inhibitors.
AID430880Inhibition of diphenolase activity of mushroom tyrosinase2009Bioorganic & medicinal chemistry letters, Aug-01, Volume: 19, Issue:15
Synthesis and evaluation of 5-benzylidene(thio)barbiturate-beta-D-glycosides as mushroom tyrosinase inhibitors.
AID411683Toxicity in mouse assessed as mortality at 1200 mg/kg, po administered as single gavage dose after 20 days2008Bioorganic & medicinal chemistry letters, Dec-15, Volume: 18, Issue:24
Synthesis and biological evaluation of helicid analogues as mushroom tyrosinase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (27)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (7.41)18.7374
1990's0 (0.00)18.2507
2000's10 (37.04)29.6817
2010's10 (37.04)24.3611
2020's5 (18.52)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.93

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 Index34.93 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.30 (4.65)
Search Engine Demand Index44.85 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (34.93)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other25 (100.00%)84.16%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]