Page last updated: 2024-11-04

2,2',3,3',4,4'-hexahydroxy-1,1'-biphenyl-6,6'-dimethanol dimethyl ether

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Description

2,2',3,3',4,4'-hexahydroxy-1,1'-biphenyl-6,6'-dimethanol dimethyl ether: potent inhibitor of protein kinase C; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3568
CHEMBL ID437222
CHEMBL ID59451
CHEMBL ID537897
CHEBI ID94660
SCHEMBL ID1272421
MeSH IDM0226681

Synonyms (48)

Synonym
bdbm50043774
6,6''-bis-methoxymethyl-biphenyl-2,3,4,2'',3'',4''-hexaol
BRD-K56064827-001-03-9
BRD-K56064827-001-04-7
BIO2_000388
BIO2_000868
BIOMOLKI2_000071
BIOMOLKI_000067
hbdde
NCGC00163390-01
NCGC00163390-02
KBIOGR_000455
KBIO3_000849
KBIO2_003023
KBIO3_000850
KBIOSS_000455
KBIO2_005591
KBIO2_000455
IDI1_002143
BSPBIO_001115
NCGC00163390-03
HMS1990G17
CHEMBL437222 ,
CHEMBL59451 ,
CHEMBL537897 ,
BMK1-G7
2,2',3,3',4,4'-hexahydroxy-1,1'-biphenyl-6,6'-dimethanol dimethyl ether
HMS1362G17
HMS1792G17
154675-18-0
5-(methoxymethyl)-4-[2,3,4-trihydroxy-6-(methoxymethyl)phenyl]benzene-1,2,3-triol
NCGC00163390-04
hhbpdde
[1,1'-biphenyl]-2,2',3,3',4,4'-hexol,6,6'-bis(methoxymethyl)-
CCG-100671
bdbm50375658
bdbm50375660
SCHEMBL1272421
HMS3403G17
AKOS030533055
CHEBI:94660
J-009130
Q27166474
hbdde - cas 154675-18-0
DTXSID20935042
6,6'-bis(methoxymethyl)[1,1'-biphenyl]-2,2',3,3',4,4'-hexol
HY-131305
CS-0132740
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
tanninAny of a group of astringent polyphenolic vegetable principles or compounds, chiefly complex glucosides of catechol and pyrogallol.
[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 (34)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency0.27010.003245.467312,589.2998AID2517; AID2572
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency0.10740.004023.8416100.0000AID485290
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency3.97160.140911.194039.8107AID2451
Chain A, ATP-DEPENDENT DNA HELICASE Q1Homo sapiens (human)Potency1.00000.125919.1169125.8920AID2549
endonuclease IVEscherichia coliPotency4.46680.707912.432431.6228AID2565
thioredoxin reductaseRattus norvegicus (Norway rat)Potency14.12540.100020.879379.4328AID588453
phosphopantetheinyl transferaseBacillus subtilisPotency10.26630.141337.9142100.0000AID1490
TDP1 proteinHomo sapiens (human)Potency4.73940.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency4.73590.180013.557439.8107AID1460; AID1468
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency25.11890.011212.4002100.0000AID1030
regulator of G-protein signaling 4Homo sapiens (human)Potency0.03360.531815.435837.6858AID504845
67.9K proteinVaccinia virusPotency11.22020.00018.4406100.0000AID720579
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency1.00000.035520.977089.1251AID504332
runt-related transcription factor 1 isoform AML1bHomo sapiens (human)Potency1.43480.02007.985839.8107AID504374; AID504375
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency17.90080.354828.065989.1251AID504847
core-binding factor subunit beta isoform 2Homo sapiens (human)Potency1.43480.02007.985839.8107AID504374; AID504375
flap endonuclease 1Homo sapiens (human)Potency1.58490.133725.412989.1251AID588795
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency2.81840.050127.073689.1251AID588590
DNA polymerase kappa isoform 1Homo sapiens (human)Potency0.44080.031622.3146100.0000AID588579
Glutamate receptor 1Rattus norvegicus (Norway rat)Potency0.31620.01418.602439.8107AID2572
Glutamate receptor 2Rattus norvegicus (Norway rat)Potency0.31620.001551.739315,848.9004AID2572
Glutamate receptor 3Rattus norvegicus (Norway rat)Potency0.31620.01418.602439.8107AID2572
Glutamate receptor 4Rattus norvegicus (Norway rat)Potency0.31620.01418.602439.8107AID2572
C-terminal-binding protein 1Homo sapiens (human)Potency6.74670.30149.321019.0148AID720541
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Protein kinase C gamma typeHomo sapiens (human)IC50 (µMol)50.00000.00011.035410.0000AID163878
Protein kinase C alpha typeRattus norvegicus (Norway rat)IC50 (µMol)98.00000.00000.21931.0000AID165112
Protein kinase C delta typeRattus norvegicus (Norway rat)IC50 (µMol)98.00000.00000.25851.0000AID165112
Protein kinase C epsilon typeRattus norvegicus (Norway rat)IC50 (µMol)98.00000.00000.25851.0000AID165112
Protein kinase C zeta typeRattus norvegicus (Norway rat)IC50 (µMol)98.00000.00000.25851.0000AID165112
Protein kinase C alpha typeHomo sapiens (human)IC50 (µMol)43.00000.00010.972010.0000AID163163
Protein kinase C gamma typeRattus norvegicus (Norway rat)IC50 (µMol)98.00000.00000.26401.1000AID165112
Protein kinase C beta typeRattus norvegicus (Norway rat)IC50 (µMol)98.00000.00000.21641.1000AID165112
Protein kinase C eta typeRattus norvegicus (Norway rat)IC50 (µMol)98.00000.00000.25851.0000AID165112
Protein kinase C theta typeRattus norvegicus (Norway rat)IC50 (µMol)98.00000.00000.25851.0000AID165112
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (62)

Processvia Protein(s)Taxonomy
protein phosphorylationProtein kinase C gamma typeHomo sapiens (human)
chemical synaptic transmissionProtein kinase C gamma typeHomo sapiens (human)
learning or memoryProtein kinase C gamma typeHomo sapiens (human)
chemosensory behaviorProtein kinase C gamma typeHomo sapiens (human)
response to toxic substanceProtein kinase C gamma typeHomo sapiens (human)
phosphorylationProtein kinase C gamma typeHomo sapiens (human)
negative regulation of protein ubiquitinationProtein kinase C gamma typeHomo sapiens (human)
regulation of response to foodProtein kinase C gamma typeHomo sapiens (human)
positive regulation of mismatch repairProtein kinase C gamma typeHomo sapiens (human)
negative regulation of protein catabolic processProtein kinase C gamma typeHomo sapiens (human)
regulation of circadian rhythmProtein kinase C gamma typeHomo sapiens (human)
response to morphineProtein kinase C gamma typeHomo sapiens (human)
negative regulation of neuron apoptotic processProtein kinase C gamma typeHomo sapiens (human)
response to painProtein kinase C gamma typeHomo sapiens (human)
rhythmic processProtein kinase C gamma typeHomo sapiens (human)
regulation of phagocytosisProtein kinase C gamma typeHomo sapiens (human)
long-term synaptic potentiationProtein kinase C gamma typeHomo sapiens (human)
innervationProtein kinase C gamma typeHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionProtein kinase C gamma typeHomo sapiens (human)
negative regulation of proteasomal protein catabolic processProtein kinase C gamma typeHomo sapiens (human)
response to psychosocial stressProtein kinase C gamma typeHomo sapiens (human)
regulation of synaptic vesicle exocytosisProtein kinase C gamma typeHomo sapiens (human)
intracellular signal transductionProtein kinase C gamma typeHomo sapiens (human)
peptidyl-serine phosphorylationProtein kinase C gamma typeHomo sapiens (human)
angiogenesisProtein kinase C alpha typeHomo sapiens (human)
positive regulation of endothelial cell proliferationProtein kinase C alpha typeHomo sapiens (human)
desmosome assemblyProtein kinase C alpha typeHomo sapiens (human)
chromatin remodelingProtein kinase C alpha typeHomo sapiens (human)
protein phosphorylationProtein kinase C alpha typeHomo sapiens (human)
mitotic nuclear membrane disassemblyProtein kinase C alpha typeHomo sapiens (human)
cell adhesionProtein kinase C alpha typeHomo sapiens (human)
positive regulation of endothelial cell migrationProtein kinase C alpha typeHomo sapiens (human)
positive regulation of cardiac muscle hypertrophyProtein kinase C alpha typeHomo sapiens (human)
peptidyl-serine phosphorylationProtein kinase C alpha typeHomo sapiens (human)
peptidyl-threonine phosphorylationProtein kinase C alpha typeHomo sapiens (human)
positive regulation of cell migrationProtein kinase C alpha typeHomo sapiens (human)
positive regulation of lipopolysaccharide-mediated signaling pathwayProtein kinase C alpha typeHomo sapiens (human)
negative regulation of glial cell apoptotic processProtein kinase C alpha typeHomo sapiens (human)
regulation of mRNA stabilityProtein kinase C alpha typeHomo sapiens (human)
positive regulation of blood vessel endothelial cell migrationProtein kinase C alpha typeHomo sapiens (human)
post-translational protein modificationProtein kinase C alpha typeHomo sapiens (human)
positive regulation of macrophage differentiationProtein kinase C alpha typeHomo sapiens (human)
positive regulation of angiogenesisProtein kinase C alpha typeHomo sapiens (human)
positive regulation of bone resorptionProtein kinase C alpha typeHomo sapiens (human)
positive regulation of cell adhesionProtein kinase C alpha typeHomo sapiens (human)
positive regulation of mitotic cell cycleProtein kinase C alpha typeHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeProtein kinase C alpha typeHomo sapiens (human)
response to interleukin-1Protein kinase C alpha typeHomo sapiens (human)
regulation of platelet aggregationProtein kinase C alpha typeHomo sapiens (human)
apoptotic signaling pathwayProtein kinase C alpha typeHomo sapiens (human)
positive regulation of adenylate cyclase-activating G protein-coupled receptor signaling pathwayProtein kinase C alpha typeHomo sapiens (human)
positive regulation of angiotensin-activated signaling pathwayProtein kinase C alpha typeHomo sapiens (human)
positive regulation of dense core granule biogenesisProtein kinase C alpha typeHomo sapiens (human)
intracellular signal transductionProtein kinase C alpha typeHomo sapiens (human)
positive regulation of insulin secretionProtein kinase C alpha typeHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIC-terminal-binding protein 1Homo sapiens (human)
protein phosphorylationC-terminal-binding protein 1Homo sapiens (human)
negative regulation of cell population proliferationC-terminal-binding protein 1Homo sapiens (human)
viral genome replicationC-terminal-binding protein 1Homo sapiens (human)
negative regulation of DNA-templated transcriptionC-terminal-binding protein 1Homo sapiens (human)
positive regulation of DNA-templated transcriptionC-terminal-binding protein 1Homo sapiens (human)
synaptic vesicle endocytosisC-terminal-binding protein 1Homo sapiens (human)
white fat cell differentiationC-terminal-binding protein 1Homo sapiens (human)
regulation of cell cycleC-terminal-binding protein 1Homo sapiens (human)
synaptic vesicle clusteringC-terminal-binding protein 1Homo sapiens (human)
regulation of transcription by RNA polymerase IIC-terminal-binding protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (24)

Processvia Protein(s)Taxonomy
protein kinase activityProtein kinase C gamma typeHomo sapiens (human)
diacylglycerol-dependent serine/threonine kinase activityProtein kinase C gamma typeHomo sapiens (human)
calcium,diacylglycerol-dependent serine/threonine kinase activityProtein kinase C gamma typeHomo sapiens (human)
protein serine/threonine/tyrosine kinase activityProtein kinase C gamma typeHomo sapiens (human)
protein bindingProtein kinase C gamma typeHomo sapiens (human)
ATP bindingProtein kinase C gamma typeHomo sapiens (human)
zinc ion bindingProtein kinase C gamma typeHomo sapiens (human)
protein serine kinase activityProtein kinase C gamma typeHomo sapiens (human)
protein serine/threonine kinase activityProtein kinase C gamma typeHomo sapiens (human)
diacylglycerol-dependent serine/threonine kinase activityProtein kinase C delta typeRattus norvegicus (Norway rat)
protein kinase activityProtein kinase C alpha typeHomo sapiens (human)
diacylglycerol-dependent serine/threonine kinase activityProtein kinase C alpha typeHomo sapiens (human)
calcium,diacylglycerol-dependent serine/threonine kinase activityProtein kinase C alpha typeHomo sapiens (human)
integrin bindingProtein kinase C alpha typeHomo sapiens (human)
protein bindingProtein kinase C alpha typeHomo sapiens (human)
ATP bindingProtein kinase C alpha typeHomo sapiens (human)
zinc ion bindingProtein kinase C alpha typeHomo sapiens (human)
enzyme bindingProtein kinase C alpha typeHomo sapiens (human)
histone H3T6 kinase activityProtein kinase C alpha typeHomo sapiens (human)
protein serine kinase activityProtein kinase C alpha typeHomo sapiens (human)
protein serine/threonine kinase activityProtein kinase C alpha typeHomo sapiens (human)
diacylglycerol bindingProtein kinase C alpha typeHomo sapiens (human)
transcription corepressor bindingC-terminal-binding protein 1Homo sapiens (human)
chromatin bindingC-terminal-binding protein 1Homo sapiens (human)
transcription corepressor activityC-terminal-binding protein 1Homo sapiens (human)
protein bindingC-terminal-binding protein 1Homo sapiens (human)
oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptorC-terminal-binding protein 1Homo sapiens (human)
protein domain specific bindingC-terminal-binding protein 1Homo sapiens (human)
identical protein bindingC-terminal-binding protein 1Homo sapiens (human)
NAD bindingC-terminal-binding protein 1Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingC-terminal-binding protein 1Homo sapiens (human)
DNA-binding transcription factor bindingC-terminal-binding protein 1Homo sapiens (human)
transcription coactivator activityC-terminal-binding protein 1Homo sapiens (human)
transcription coregulator bindingC-terminal-binding protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (23)

Processvia Protein(s)Taxonomy
nucleusProtein kinase C gamma typeHomo sapiens (human)
cytosolProtein kinase C gamma typeHomo sapiens (human)
plasma membraneProtein kinase C gamma typeHomo sapiens (human)
cell-cell junctionProtein kinase C gamma typeHomo sapiens (human)
postsynaptic densityProtein kinase C gamma typeHomo sapiens (human)
dendriteProtein kinase C gamma typeHomo sapiens (human)
calyx of HeldProtein kinase C gamma typeHomo sapiens (human)
perinuclear region of cytoplasmProtein kinase C gamma typeHomo sapiens (human)
synaptic membraneProtein kinase C gamma typeHomo sapiens (human)
presynaptic cytosolProtein kinase C gamma typeHomo sapiens (human)
postsynaptic cytosolProtein kinase C gamma typeHomo sapiens (human)
cytosolProtein kinase C delta typeRattus norvegicus (Norway rat)
cytosolProtein kinase C zeta typeRattus norvegicus (Norway rat)
ciliary basal bodyProtein kinase C alpha typeHomo sapiens (human)
nucleoplasmProtein kinase C alpha typeHomo sapiens (human)
cytoplasmProtein kinase C alpha typeHomo sapiens (human)
mitochondrionProtein kinase C alpha typeHomo sapiens (human)
endoplasmic reticulumProtein kinase C alpha typeHomo sapiens (human)
cytosolProtein kinase C alpha typeHomo sapiens (human)
plasma membraneProtein kinase C alpha typeHomo sapiens (human)
mitochondrial membraneProtein kinase C alpha typeHomo sapiens (human)
perinuclear region of cytoplasmProtein kinase C alpha typeHomo sapiens (human)
extracellular exosomeProtein kinase C alpha typeHomo sapiens (human)
alphav-beta3 integrin-PKCalpha complexProtein kinase C alpha typeHomo sapiens (human)
plasma membraneGlutamate receptor 1Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
nucleusC-terminal-binding protein 1Homo sapiens (human)
nucleoplasmC-terminal-binding protein 1Homo sapiens (human)
presynaptic active zone cytoplasmic componentC-terminal-binding protein 1Homo sapiens (human)
glutamatergic synapseC-terminal-binding protein 1Homo sapiens (human)
GABA-ergic synapseC-terminal-binding protein 1Homo sapiens (human)
transcription repressor complexC-terminal-binding protein 1Homo sapiens (human)
nucleusC-terminal-binding protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID165112Inhibitory activity against protein kinase C of rat brain1994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
New hexahydroxybiphenyl derivatives as inhibitors of protein kinase C.
AID163163Inhibition of protein kinase C alpha1994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
New hexahydroxybiphenyl derivatives as inhibitors of protein kinase C.
AID163878Inhibition of protein kinase C gamma1994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
New hexahydroxybiphenyl derivatives as inhibitors of protein kinase C.
AID219159Inhibition of c-AMP dependent kinase (PKA) catalytic subunit1994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
New hexahydroxybiphenyl derivatives as inhibitors of protein kinase C.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (20.00)18.2507
2000's2 (40.00)29.6817
2010's2 (40.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.58

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 Index12.58 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.58)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]