nectandrin-b

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

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 Source	ID
PubMed CID	156517
CHEMBL ID	228326
SCHEMBL ID	893437
MeSH ID	M0516130

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

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Glucocorticoid receptor	Homo sapiens (human)	IC50 (µMol)	27.0000	0.0000	0.4953	10.0000	AID291923
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (31)

Process	via Protein(s)	Taxonomy
negative regulation of transcription by RNA polymerase II	Glucocorticoid receptor	Homo sapiens (human)
regulation of gluconeogenesis	Glucocorticoid receptor	Homo sapiens (human)
chromatin organization	Glucocorticoid receptor	Homo sapiens (human)
regulation of DNA-templated transcription	Glucocorticoid receptor	Homo sapiens (human)
apoptotic process	Glucocorticoid receptor	Homo sapiens (human)
chromosome segregation	Glucocorticoid receptor	Homo sapiens (human)
signal transduction	Glucocorticoid receptor	Homo sapiens (human)
glucocorticoid metabolic process	Glucocorticoid receptor	Homo sapiens (human)
gene expression	Glucocorticoid receptor	Homo sapiens (human)
microglia differentiation	Glucocorticoid receptor	Homo sapiens (human)
adrenal gland development	Glucocorticoid receptor	Homo sapiens (human)
regulation of glucocorticoid biosynthetic process	Glucocorticoid receptor	Homo sapiens (human)
synaptic transmission, glutamatergic	Glucocorticoid receptor	Homo sapiens (human)
maternal behavior	Glucocorticoid receptor	Homo sapiens (human)
intracellular glucocorticoid receptor signaling pathway	Glucocorticoid receptor	Homo sapiens (human)
glucocorticoid mediated signaling pathway	Glucocorticoid receptor	Homo sapiens (human)
positive regulation of neuron apoptotic process	Glucocorticoid receptor	Homo sapiens (human)
negative regulation of DNA-templated transcription	Glucocorticoid receptor	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Glucocorticoid receptor	Homo sapiens (human)
astrocyte differentiation	Glucocorticoid receptor	Homo sapiens (human)
cell division	Glucocorticoid receptor	Homo sapiens (human)
mammary gland duct morphogenesis	Glucocorticoid receptor	Homo sapiens (human)
motor behavior	Glucocorticoid receptor	Homo sapiens (human)
cellular response to steroid hormone stimulus	Glucocorticoid receptor	Homo sapiens (human)
cellular response to glucocorticoid stimulus	Glucocorticoid receptor	Homo sapiens (human)
cellular response to dexamethasone stimulus	Glucocorticoid receptor	Homo sapiens (human)
cellular response to transforming growth factor beta stimulus	Glucocorticoid receptor	Homo sapiens (human)
neuroinflammatory response	Glucocorticoid receptor	Homo sapiens (human)
positive regulation of miRNA transcription	Glucocorticoid receptor	Homo sapiens (human)
intracellular steroid hormone receptor signaling pathway	Glucocorticoid receptor	Homo sapiens (human)
regulation of transcription by RNA polymerase II	Glucocorticoid receptor	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (20)

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

Ceullar Components (12)

Process	via Protein(s)	Taxonomy
nucleus	Glucocorticoid receptor	Homo sapiens (human)
nucleus	Glucocorticoid receptor	Homo sapiens (human)
nucleoplasm	Glucocorticoid receptor	Homo sapiens (human)
cytoplasm	Glucocorticoid receptor	Homo sapiens (human)
mitochondrial matrix	Glucocorticoid receptor	Homo sapiens (human)
centrosome	Glucocorticoid receptor	Homo sapiens (human)
spindle	Glucocorticoid receptor	Homo sapiens (human)
cytosol	Glucocorticoid receptor	Homo sapiens (human)
membrane	Glucocorticoid receptor	Homo sapiens (human)
nuclear speck	Glucocorticoid receptor	Homo sapiens (human)
synapse	Glucocorticoid receptor	Homo sapiens (human)
chromatin	Glucocorticoid receptor	Homo sapiens (human)
protein-containing complex	Glucocorticoid receptor	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay ID	Title	Year	Journal	Article
AID1239176	Cytotoxicity against mouse HT22 cells assessed as induction of cell proliferation at 30 uM after 24 hrs by MTT assay	2015	Journal 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.
AID399193	Antitrypanosomal activity against Trypanosoma cruzi Y trypomastigotes infected in mouse macrophage	2004	Journal of natural products, Jan, Volume: 67, Issue:1	Tetrahydrofuran lignans from Nectandra megapotamica with trypanocidal activity.
AID1239178	Neuroprotective 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 assay	2015	Journal 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.
AID399190	Trypanocidal activity against Trypanosoma cruzi Y trypomastigotes infected in mouse macrophage at 32 uM	2004	Journal of natural products, Jan, Volume: 67, Issue:1	Tetrahydrofuran lignans from Nectandra megapotamica with trypanocidal activity.
AID1239171	Cytotoxicity against mouse HT22 cells assessed as cell viability at 30 uM after 24 hrs by MTT assay	2015	Journal 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.
AID489316	Activation of AMPK in mouse CDC12 cells at 5 uM by Western blotting	2010	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 20, Issue:14	AMP-activated protein kinase (AMPK) activators from Myristica fragrans (nutmeg) and their anti-obesity effect.
AID1239175	Neuroprotective 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 assay	2015	Journal 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.
AID1239174	Neuroprotective 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 assay	2015	Journal 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.
AID1239180	Neuroprotective 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 assay	2015	Journal 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.
AID1239172	Neuroprotective 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 assay	2015	Journal 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.
AID1327072	Antagonist 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 assay	2016	Journal of natural products, 08-26, Volume: 79, Issue:8	Neolignans from the Arils of Myristica fragrans as Potent Antagonists of CC Chemokine Receptor 3.
AID291923	Binding affinity to glucocorticoid receptor by GR binding assay	2007	Journal of natural products, Jul, Volume: 70, Issue:7	Endiandrin A, a potent glucocorticoid receptor binder isolated from the Australian plant Endiandra anthropophagorum.
AID1239173	Neuroprotective 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 hrs	2015	Journal 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.
AID1239177	Neuroprotective 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 assay	2015	Journal 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.
AID399192	Trypanocidal activity against Trypanosoma cruzi Y trypomastigotes infected in mouse macrophage at 8 uM	2004	Journal of natural products, Jan, Volume: 67, Issue:1	Tetrahydrofuran lignans from Nectandra megapotamica with trypanocidal activity.
AID1239179	Effect on Nrf2/HO-1 protein expression in mouse HT22 cells at 30 uM after 24 hrs by Western blotting assay	2015	Journal 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.
AID399191	Trypanocidal activity against Trypanosoma cruzi Y trypomastigotes infected in mouse macrophage at 2 uM	2004	Journal 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)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	3 (23.08)	29.6817
2010's	9 (69.23)	24.3611
2020's	1 (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.

Metric	This Compound (vs All)
Research Demand Index	29.32 (24.57)
Research Supply Index	2.64 (2.92)
Research Growth Index	4.77 (4.65)
Search Engine Demand Index	34.37 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (29.32)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	13 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
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.	2.03	1	guaiacols	disinfectant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; expectorant; plant metabolite
myristicin myristicin: asaricin is an isomer; structure; a methylene dioxy version of elemicin;	2.13	1	organic molecular entity	metabolite
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.	2.13	1	alkyl hydroperoxide	antibacterial 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.	2.07	1	naphthol	antinematodal 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.	2.07	1	catechin	antioxidant; 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.	2.02	1	organic chloride salt	anthelminthic 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.	2.07	1	secoisolariciresinol	antidepressant; 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.	2.02	1	aryltetrahydrofuran; 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.	2.07	1	guaiacols; 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	2.03	1
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.	2.07	1
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)	3.71	9
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.	2.11	1	benzofurans; 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	2.13	1
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	2.52	2
endiandrin a endiandrin A: a potent glucocorticoid receptor binder isolated from the Australian plant Endiandra anthropophagorum; structure in first source	2.03	1

Condition	Relationship Strength	Studies
Liver Steatosis [description not available]	2.11	1
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.	2.11	1
Vascular Injuries [description not available]	2.08	1
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.	2.08	1

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