Compounds > nectandrin-b
Page last updated: 2024-12-08

nectandrin-b

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Description

nectandrin-B: antifungal lignan from the seeds of Myristica fragrans; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID156517
CHEMBL ID228326
SCHEMBL ID893437
MeSH IDM0516130

Synonyms (10)

Synonym
nectandrin b
CHEMBL228326 ,
bdbm50216278
nectandrin-b
phenol, 4,4'-((2r,3r,4s,5s)-tetrahydro-3,4-dimethyl-2,5-furandiyl)bis(2-methoxy-, rel-
74683-16-2
phenol, 4,4'-(tetrahydro-3,4-dimethyl-2,5-furandiyl)bis(2-methoxy-, (2alpha,3beta,4beta,5alpha)-
SCHEMBL893437
DTXSID50225660
nectandrinb
[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)
Glucocorticoid receptorHomo sapiens (human)IC50 (µMol)27.00000.00000.495310.0000AID291923
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (31)

Processvia Protein(s)Taxonomy
negative regulation of transcription by RNA polymerase IIGlucocorticoid receptorHomo sapiens (human)
regulation of gluconeogenesisGlucocorticoid receptorHomo sapiens (human)
chromatin organizationGlucocorticoid receptorHomo sapiens (human)
regulation of DNA-templated transcriptionGlucocorticoid receptorHomo sapiens (human)
apoptotic processGlucocorticoid receptorHomo sapiens (human)
chromosome segregationGlucocorticoid receptorHomo sapiens (human)
signal transductionGlucocorticoid receptorHomo sapiens (human)
glucocorticoid metabolic processGlucocorticoid receptorHomo sapiens (human)
gene expressionGlucocorticoid receptorHomo sapiens (human)
microglia differentiationGlucocorticoid receptorHomo sapiens (human)
adrenal gland developmentGlucocorticoid receptorHomo sapiens (human)
regulation of glucocorticoid biosynthetic processGlucocorticoid receptorHomo sapiens (human)
synaptic transmission, glutamatergicGlucocorticoid receptorHomo sapiens (human)
maternal behaviorGlucocorticoid receptorHomo sapiens (human)
intracellular glucocorticoid receptor signaling pathwayGlucocorticoid receptorHomo sapiens (human)
glucocorticoid mediated signaling pathwayGlucocorticoid receptorHomo sapiens (human)
positive regulation of neuron apoptotic processGlucocorticoid receptorHomo sapiens (human)
negative regulation of DNA-templated transcriptionGlucocorticoid receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIGlucocorticoid receptorHomo sapiens (human)
astrocyte differentiationGlucocorticoid receptorHomo sapiens (human)
cell divisionGlucocorticoid receptorHomo sapiens (human)
mammary gland duct morphogenesisGlucocorticoid receptorHomo sapiens (human)
motor behaviorGlucocorticoid receptorHomo sapiens (human)
cellular response to steroid hormone stimulusGlucocorticoid receptorHomo sapiens (human)
cellular response to glucocorticoid stimulusGlucocorticoid receptorHomo sapiens (human)
cellular response to dexamethasone stimulusGlucocorticoid receptorHomo sapiens (human)
cellular response to transforming growth factor beta stimulusGlucocorticoid receptorHomo sapiens (human)
neuroinflammatory responseGlucocorticoid receptorHomo sapiens (human)
positive regulation of miRNA transcriptionGlucocorticoid receptorHomo sapiens (human)
intracellular steroid hormone receptor signaling pathwayGlucocorticoid receptorHomo sapiens (human)
regulation of transcription by RNA polymerase IIGlucocorticoid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (20)

Processvia Protein(s)Taxonomy
RNA polymerase II transcription regulatory region sequence-specific DNA bindingGlucocorticoid receptorHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingGlucocorticoid receptorHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificGlucocorticoid receptorHomo sapiens (human)
core promoter sequence-specific DNA bindingGlucocorticoid receptorHomo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specificGlucocorticoid receptorHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificGlucocorticoid receptorHomo sapiens (human)
DNA-binding transcription factor activityGlucocorticoid receptorHomo sapiens (human)
RNA bindingGlucocorticoid receptorHomo sapiens (human)
nuclear receptor activityGlucocorticoid receptorHomo sapiens (human)
nuclear glucocorticoid receptor activityGlucocorticoid receptorHomo sapiens (human)
steroid bindingGlucocorticoid receptorHomo sapiens (human)
protein bindingGlucocorticoid receptorHomo sapiens (human)
zinc ion bindingGlucocorticoid receptorHomo sapiens (human)
TBP-class protein bindingGlucocorticoid receptorHomo sapiens (human)
protein kinase bindingGlucocorticoid receptorHomo sapiens (human)
identical protein bindingGlucocorticoid receptorHomo sapiens (human)
Hsp90 protein bindingGlucocorticoid receptorHomo sapiens (human)
steroid hormone bindingGlucocorticoid receptorHomo sapiens (human)
sequence-specific double-stranded DNA bindingGlucocorticoid receptorHomo sapiens (human)
estrogen response element bindingGlucocorticoid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
nucleusGlucocorticoid receptorHomo sapiens (human)
nucleusGlucocorticoid receptorHomo sapiens (human)
nucleoplasmGlucocorticoid receptorHomo sapiens (human)
cytoplasmGlucocorticoid receptorHomo sapiens (human)
mitochondrial matrixGlucocorticoid receptorHomo sapiens (human)
centrosomeGlucocorticoid receptorHomo sapiens (human)
spindleGlucocorticoid receptorHomo sapiens (human)
cytosolGlucocorticoid receptorHomo sapiens (human)
membraneGlucocorticoid receptorHomo sapiens (human)
nuclear speckGlucocorticoid receptorHomo sapiens (human)
synapseGlucocorticoid receptorHomo sapiens (human)
chromatinGlucocorticoid receptorHomo sapiens (human)
protein-containing complexGlucocorticoid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID1239176Cytotoxicity against mouse HT22 cells assessed as induction of cell proliferation at 30 uM after 24 hrs by MTT assay2015Journal of natural products, Aug-28, Volume: 78, Issue:8
Neolignans from Aristolochia fordiana Prevent Oxidative Stress-Induced Neuronal Death through Maintaining the Nrf2/HO-1 Pathway in HT22 Cells.
AID399193Antitrypanosomal activity against Trypanosoma cruzi Y trypomastigotes infected in mouse macrophage2004Journal of natural products, Jan, Volume: 67, Issue:1
Tetrahydrofuran lignans from Nectandra megapotamica with trypanocidal activity.
AID1239178Neuroprotective activity in mouse HT22 cells assessed as decrease of glutamate-induced decrease in Nrf2/HO-1 protein expression at 30 uM pretreated 30 mins before glutamate challenge measured after 12 hrs by Western blotting assay2015Journal of natural products, Aug-28, Volume: 78, Issue:8
Neolignans from Aristolochia fordiana Prevent Oxidative Stress-Induced Neuronal Death through Maintaining the Nrf2/HO-1 Pathway in HT22 Cells.
AID399190Trypanocidal activity against Trypanosoma cruzi Y trypomastigotes infected in mouse macrophage at 32 uM2004Journal of natural products, Jan, Volume: 67, Issue:1
Tetrahydrofuran lignans from Nectandra megapotamica with trypanocidal activity.
AID1239171Cytotoxicity against mouse HT22 cells assessed as cell viability at 30 uM after 24 hrs by MTT assay2015Journal of natural products, Aug-28, Volume: 78, Issue:8
Neolignans from Aristolochia fordiana Prevent Oxidative Stress-Induced Neuronal Death through Maintaining the Nrf2/HO-1 Pathway in HT22 Cells.
AID489316Activation of AMPK in mouse CDC12 cells at 5 uM by Western blotting2010Bioorganic & medicinal chemistry letters, Jul-15, Volume: 20, Issue:14
AMP-activated protein kinase (AMPK) activators from Myristica fragrans (nutmeg) and their anti-obesity effect.
AID1239175Neuroprotective activity in mouse HT22 cells assessed as protection against glutamate-induced change in cell morphology at 1 to 30 uM pretreated 30 mins before glutamate challenge measured after 24 hrs by MTT assay2015Journal of natural products, Aug-28, Volume: 78, Issue:8
Neolignans from Aristolochia fordiana Prevent Oxidative Stress-Induced Neuronal Death through Maintaining the Nrf2/HO-1 Pathway in HT22 Cells.
AID1239174Neuroprotective activity in mouse HT22 cells assessed as protection against glutamate-induced cell death pretreated 30 mins before glutamate challenge measured after 24 hrs by MTT assay2015Journal of natural products, Aug-28, Volume: 78, Issue:8
Neolignans from Aristolochia fordiana Prevent Oxidative Stress-Induced Neuronal Death through Maintaining the Nrf2/HO-1 Pathway in HT22 Cells.
AID1239180Neuroprotective activity in mouse HT22 cells assessed as decrease of glutamate-induced decrease in Bcl-2 protein expression at 30 uM pretreated 30 mins before glutamate challenge measured after 12 hrs by Western blotting assay2015Journal of natural products, Aug-28, Volume: 78, Issue:8
Neolignans from Aristolochia fordiana Prevent Oxidative Stress-Induced Neuronal Death through Maintaining the Nrf2/HO-1 Pathway in HT22 Cells.
AID1239172Neuroprotective activity in mouse HT22 cells assessed as protection against glutamate-induced cell death at 1 to 30 uM pretreated 30 mins before glutamate challenge measured after 24 hrs by MTT assay2015Journal of natural products, Aug-28, Volume: 78, Issue:8
Neolignans from Aristolochia fordiana Prevent Oxidative Stress-Induced Neuronal Death through Maintaining the Nrf2/HO-1 Pathway in HT22 Cells.
AID1327072Antagonist activity at human EGFP-fused CCR3 expressed in mouse L1.2 cells assessed as inhibition of CCL11-induced chemotaxis at 1 uM measured after 1.5 hrs by PicoGreen dsDNA reagent-based assay2016Journal of natural products, 08-26, Volume: 79, Issue:8
Neolignans from the Arils of Myristica fragrans as Potent Antagonists of CC Chemokine Receptor 3.
AID291923Binding affinity to glucocorticoid receptor by GR binding assay2007Journal of natural products, Jul, Volume: 70, Issue:7
Endiandrin A, a potent glucocorticoid receptor binder isolated from the Australian plant Endiandra anthropophagorum.
AID1239173Neuroprotective activity in mouse HT22 cells assessed as decrease of glutamate-induced increase in LDH level at 10 to 30 uM pretreated 30 mins before glutamate challenge measured after 24 hrs2015Journal of natural products, Aug-28, Volume: 78, Issue:8
Neolignans from Aristolochia fordiana Prevent Oxidative Stress-Induced Neuronal Death through Maintaining the Nrf2/HO-1 Pathway in HT22 Cells.
AID1239177Neuroprotective activity in mouse HT22 cells assessed as decrease of glutamate-induced ROS production at 30 uM pretreated 30 mins before glutamate challenge measured after 12 hrs using H2DCF-DA staining by fluorescence assay2015Journal of natural products, Aug-28, Volume: 78, Issue:8
Neolignans from Aristolochia fordiana Prevent Oxidative Stress-Induced Neuronal Death through Maintaining the Nrf2/HO-1 Pathway in HT22 Cells.
AID399192Trypanocidal activity against Trypanosoma cruzi Y trypomastigotes infected in mouse macrophage at 8 uM2004Journal of natural products, Jan, Volume: 67, Issue:1
Tetrahydrofuran lignans from Nectandra megapotamica with trypanocidal activity.
AID1239179Effect on Nrf2/HO-1 protein expression in mouse HT22 cells at 30 uM after 24 hrs by Western blotting assay2015Journal of natural products, Aug-28, Volume: 78, Issue:8
Neolignans from Aristolochia fordiana Prevent Oxidative Stress-Induced Neuronal Death through Maintaining the Nrf2/HO-1 Pathway in HT22 Cells.
AID399191Trypanocidal activity against Trypanosoma cruzi Y trypomastigotes infected in mouse macrophage at 2 uM2004Journal of natural products, Jan, Volume: 67, Issue:1
Tetrahydrofuran lignans from Nectandra megapotamica with trypanocidal activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (23.08)29.6817
2010's9 (69.23)24.3611
2020's1 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.32

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 Index29.32 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.77 (4.65)
Search Engine Demand Index34.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.32)

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%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
guaiacol
Guaiacol: An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747). methylcatechol : Any member of the class of catechols carrying one or more methyl substituents.. guaiacol : A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.		2.0310guaiacolsdisinfectant;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
expectorant;
plant metabolite
myristicin
myristicin: asaricin is an isomer; structure; a methylene dioxy version of elemicin;		2.1310organic molecular entitymetabolite
tert-butylhydroperoxide
tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.		2.1310alkyl hydroperoxideantibacterial agent;
oxidising agent
2-naphthol
2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.		2.0710naphtholantinematodal drug;
genotoxin;
human urinary metabolite;
human xenobiotic metabolite;
mouse metabolite;
radical scavenger
catechin
Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.		2.0710catechinantioxidant;
plant metabolite
gentian violet
Gentian Violet: A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.. crystal violet : An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.		2.0210organic chloride saltanthelminthic drug;
antibacterial agent;
antifungal agent;
antiseptic drug;
histological dye
secoisolariciresinol
secoisolariciresinol: RN given refers to ((R-(R*,R*))-isomer); RN for cpd without isomeric designation not available 8/89; precursor of lignans found in human urine; structure given in first source. secoisolariciresinol : A lignan that is butane-1,4-diol in which the 2 and 3 positions are substituted by 4-hydroxy-3-methoxybenzyl groups. (-)-secoisolariciresinol : An enantiomer of secoisolariciresinol having (-)-(2R,3R)-configuration.		2.0710secoisolariciresinolantidepressant;
phytoestrogen;
plant metabolite
galgravin
galgravin: an anti-PAF constituent from the stems of Piper futokadsura, the Chinese drug haifengteng; structures of the isomers galgravin, galbelgin (10569-12-7) and veraguensin (19950-55-1) given in first source; RN given refers to galgravin, the (2alpha,3beta,4beta,5alpha)-isomer. galgravin : A member of the class of aryltetrahydrofurans carrying two 3,4-dimethoxyphenyl substituents at positions 2 and 5 as well as two methyl groups at positions 3 and 4.		2.0210aryltetrahydrofuran;
dimethoxybenzene;
lignan;
ring assembly		bone density conservation agent;
neuroprotective agent;
plant metabolite;
platelet aggregation inhibitor
isolariciresinol
isolariciresinol: RN given refers to ((1-S-(1alpha,2beta,3alpha))-isomer); structure given in first source. (+)-isolariciresinol : A lignan that is 5,6,7,8-tetrahydronaphthalen-2-ol substituted by hydroxymethyl groups at positions 6 and 7, a methoxy group at position 3 and a 4-hydroxy-3-methoxyphenyl group at position 8. It has been isolated from the roots of Rubia yunnanensis.		2.0710guaiacols;
lignan;
polyphenol;
primary alcohol		plant metabolite
dihydroguaiaretic acid
dihydroguaiaretic acid: lignan extracted form Larrea divaricata; inhibitory to beef heart mitochondrial succinoxidase & NADH-oxidase; RN given refers to cpd without isomeric designation		2.0310
lignin
Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.		2.0710
lignans
Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)		3.7190
eupomatenoid 6
eupomatenoid 6: RN given for (E)-isomer; structure in first source. rataniaphenol II : A member of the class of benzofurans that is 1-benzofuran substituted by a 4-hydroxyphenyl group at position 2, a methyl group at position 3 and a prop-1-en-1-yl group at position 5. It is a lignan derivative isolated from the roots of Krameria lappacea.		2.1110benzofurans;
phenols		anti-inflammatory agent;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
NF-kappaB inhibitor;
plant metabolite
sb 328437
SB 328437: a CC chemokine receptor-3 antagonist that inhibits binding of eotaxin and monocyte chemotactic protein-4 to eosinophils; structure in first source		2.1310
verrucosin
verrucosin: disrupts ion homeostasis in the presence of acridine orange; isolated from Virola oleifera; structure in first source; do not confuse with either verrucosin A or verrucosin B		2.5220
endiandrin a
endiandrin A: a potent glucocorticoid receptor binder isolated from the Australian plant Endiandra anthropophagorum; structure in first source		2.0310
ConditionIndicatedRelationship StrengthStudiesTrials
Liver Steatosis
[description not available]		02.1110
Fatty Liver
Lipid infiltration of the hepatic parenchymal cells resulting in a yellow-colored liver. The abnormal lipid accumulation is usually in the form of TRIGLYCERIDES, either as a single large droplet or multiple small droplets. Fatty liver is caused by an imbalance in the metabolism of FATTY ACIDS.		02.1110
Vascular Injuries
[description not available]		02.0810
Neointima
The new and thickened layer of scar tissue that forms on a PROSTHESIS, or as a result of vessel injury especially following ANGIOPLASTY or stent placement.		02.0810