Compounds > 7-hydroxytropolone
Page last updated: 2024-12-06

7-hydroxytropolone

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

Description

7-Hydroxytropolone, a natural product isolated from various plant sources, exhibits diverse biological activities, including antibacterial, antifungal, and anticancer properties. Its unique structure, featuring a seven-membered tropolone ring with a hydroxyl group at the 7-position, contributes to its biological potency. The compound has been investigated for its potential as a drug candidate due to its ability to inhibit the growth of various cancer cell lines. Synthetic routes for 7-hydroxytropolone involve multistep reactions starting from readily available starting materials. Notably, its metal-binding properties have been explored for applications in coordination chemistry and catalysis.'

7-hydroxytropolone: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID36917
CHEMBL ID3357560
SCHEMBL ID122963
MeSH IDM0109920

Synonyms (24)

Synonym
2,3-dihydroxy-2,4,6-cycloheptatrien-1-one
2,4,6-cycloheptatrien-1-one, 2,3-dihydroxy-
3-hydroxytropolone
brn 3236699
abnpyudygcgotk-uhfffaoysa-
inchi=1/c7h6o3/c8-5-3-1-2-4-6(9)7(5)10/h1-4h,(h2,8,9,10)
2,3-dihydroxycyclohepta-2,4,6-trien-1-one
nsc742578
nsc-742578
AKOS004902643
2,7-DIHYDROXY-2,4,6-CYCLOHEPTATRIEN-1-ONE ,
2,7-dihydroxy-cyclohepta-2,4,6-trien-1-one
33739-50-3
2,4,6-cycloheptatrien-1-one, 2,7-dihydroxy-
7-hydroxytropolone
4-08-00-01740 (beilstein handbook reference)
34777-04-3
2,7-dihydroxycyclohepta-2,4,6-trien-1-one
SCHEMBL122963
ABNPYUDYGCGOTK-UHFFFAOYSA-N
CHEMBL3357560 ,
bdbm50498342
DTXSID80955342
2,3-dihydroxycyclohepta-2,4,6-trienone
[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)
Dopamine beta-hydroxylaseHomo sapiens (human)IC50 (µMol)2.00001.20232.07793.0000AID1232066
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (23)

Processvia Protein(s)Taxonomy
blood vessel remodelingDopamine beta-hydroxylaseHomo sapiens (human)
response to amphetamineDopamine beta-hydroxylaseHomo sapiens (human)
leukocyte mediated immunityDopamine beta-hydroxylaseHomo sapiens (human)
chemical synaptic transmissionDopamine beta-hydroxylaseHomo sapiens (human)
memoryDopamine beta-hydroxylaseHomo sapiens (human)
locomotory behaviorDopamine beta-hydroxylaseHomo sapiens (human)
visual learningDopamine beta-hydroxylaseHomo sapiens (human)
homoiothermyDopamine beta-hydroxylaseHomo sapiens (human)
vasoconstrictionDopamine beta-hydroxylaseHomo sapiens (human)
dopamine catabolic processDopamine beta-hydroxylaseHomo sapiens (human)
norepinephrine biosynthetic processDopamine beta-hydroxylaseHomo sapiens (human)
glucose homeostasisDopamine beta-hydroxylaseHomo sapiens (human)
fear responseDopamine beta-hydroxylaseHomo sapiens (human)
maternal behaviorDopamine beta-hydroxylaseHomo sapiens (human)
positive regulation of vasoconstrictionDopamine beta-hydroxylaseHomo sapiens (human)
behavioral response to ethanolDopamine beta-hydroxylaseHomo sapiens (human)
response to painDopamine beta-hydroxylaseHomo sapiens (human)
leukocyte migrationDopamine beta-hydroxylaseHomo sapiens (human)
positive regulation of cold-induced thermogenesisDopamine beta-hydroxylaseHomo sapiens (human)
regulation of vascular associated smooth muscle cell proliferationDopamine beta-hydroxylaseHomo sapiens (human)
regulation of vascular endothelial cell proliferationDopamine beta-hydroxylaseHomo sapiens (human)
regulation of extrinsic apoptotic signaling pathwayDopamine beta-hydroxylaseHomo sapiens (human)
octopamine biosynthetic processDopamine beta-hydroxylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
catalytic activityDopamine beta-hydroxylaseHomo sapiens (human)
dopamine beta-monooxygenase activityDopamine beta-hydroxylaseHomo sapiens (human)
copper ion bindingDopamine beta-hydroxylaseHomo sapiens (human)
protein bindingDopamine beta-hydroxylaseHomo sapiens (human)
L-ascorbic acid bindingDopamine beta-hydroxylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
extracellular regionDopamine beta-hydroxylaseHomo sapiens (human)
extracellular spaceDopamine beta-hydroxylaseHomo sapiens (human)
cytoplasmDopamine beta-hydroxylaseHomo sapiens (human)
endoplasmic reticulumDopamine beta-hydroxylaseHomo sapiens (human)
membraneDopamine beta-hydroxylaseHomo sapiens (human)
transport vesicle membraneDopamine beta-hydroxylaseHomo sapiens (human)
secretory granule membraneDopamine beta-hydroxylaseHomo sapiens (human)
centriolar satelliteDopamine beta-hydroxylaseHomo sapiens (human)
chromaffin granule lumenDopamine beta-hydroxylaseHomo sapiens (human)
secretory granule lumenDopamine beta-hydroxylaseHomo sapiens (human)
chromaffin granule membraneDopamine beta-hydroxylaseHomo sapiens (human)
intracellular membrane-bounded organelleDopamine beta-hydroxylaseHomo sapiens (human)
synapseDopamine beta-hydroxylaseHomo sapiens (human)
extracellular spaceDopamine beta-hydroxylaseHomo sapiens (human)
secretory granule membraneDopamine beta-hydroxylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID1363742Inhibition of bacterial NDM1 at 200 uM using chromacef as substrate preincubated for 10 mins followed by substrate addition2018Journal of medicinal chemistry, 11-21, Volume: 61, Issue:22
Structure-Activity Relationships in Metal-Binding Pharmacophores for Influenza Endonuclease.
AID1363741Inhibition of full length human arginase 1 expressed in Escherichia coli BL21(DE3) at 200 uM using unlabeled L-arginine/L-[guanidino-14C]arginine as substrate after 5 mins by liquid scintillation counting method relative to control2018Journal of medicinal chemistry, 11-21, Volume: 61, Issue:22
Structure-Activity Relationships in Metal-Binding Pharmacophores for Influenza Endonuclease.
AID1167669Inhibition of Escherichia coli W677/JR76.2 2''-O-adenylyltransferase 1a using [14C]ATP at 55 uM by liquid scintillation counting analysis2014Bioorganic & medicinal chemistry letters, Nov-01, Volume: 24, Issue:21
Inhibition of the ANT(2")-Ia resistance enzyme and rescue of aminoglycoside antibiotic activity by synthetic α-hydroxytropolones.
AID1232045Antibacterial activity against Staphylococcus aureus2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1232082Inhibition of phosphotidylcholine-preferring phospholipase C (unknown origin) at pH 9.52014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1232047Antibacterial activity against Micrococcus luteus2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1363739Inhibition of Influenza A (A/California/04/2009) (H1N1) clinical isolate N-terminal truncated PA endonuclease using 5'-FAM/3-TAMRA quencer labeled 17-mer ssDNA-oligo as substrate measured over 45 mins by FRET assay2018Journal of medicinal chemistry, 11-21, Volume: 61, Issue:22
Structure-Activity Relationships in Metal-Binding Pharmacophores for Influenza Endonuclease.
AID1232049Antibacterial activity against Klebsiella pneumoniae2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1232050Antibacterial activity against Escherichia coli NIHJ2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1232058Antimalarial activity against chloroquine-resistant Plasmodium falciparum K12014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1232085Inhibition of Escherichia coli W677/JR76.2 2'-O-adenylyltransferase at 5.5 uM using aminoglycoside and [14C]ATP incubated for 15 mins by liquid scintillation counting based radiochemical assay2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1232059Antimalarial activity against Plasmodium falciparum FCR-3/Gambia2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1232065Inhibition of alkaline phosphatase (unknown origin)2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1232051Cytotoxicity against mouse B16 cells2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1232084Inhibition of Escherichia coli W677/JR76.2 2'-O-adenylyltransferase at 55 uM using aminoglycoside and [14C]ATP incubated for 15 mins by liquid scintillation counting based radiochemical assay2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1232083Inhibition of Escherichia coli W677/JR76.2 2'-O-adenylyltransferase at 550 uM using aminoglycoside and [14C]ATP incubated for 15 mins by liquid scintillation counting based radiochemical assay2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1167670Inhibition of Escherichia coli W677/JR76.2 2''-O-adenylyltransferase 1a using [14C]ATP at 5.5 uM by liquid scintillation counting analysis2014Bioorganic & medicinal chemistry letters, Nov-01, Volume: 24, Issue:21
Inhibition of the ANT(2")-Ia resistance enzyme and rescue of aminoglycoside antibiotic activity by synthetic α-hydroxytropolones.
AID1232046Antifungal activity against Aspergillus fumigatus IAM23502014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1232081Inhibition of phosphotidylcholine-preferring phospholipase C (unknown origin) at pH 7.32014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1232064Inhibition of inositol monophosphatase (unknown origin)2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1232048Antibacterial activity against Pseudomonas aeruginosa2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1232060Cytotoxicity against human MRC5 cells2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
AID1363750Inhibition of human MetAP2 Mn2+ isoform at 200 uM using Met-AMC as substrate by fluorescence assay relative to control2018Journal of medicinal chemistry, 11-21, Volume: 61, Issue:22
Structure-Activity Relationships in Metal-Binding Pharmacophores for Influenza Endonuclease.
AID1167668Inhibition of Escherichia coli W677/JR76.2 2''-O-adenylyltransferase 1a using [14C]ATP at 550 uM by liquid scintillation counting analysis2014Bioorganic & medicinal chemistry letters, Nov-01, Volume: 24, Issue:21
Inhibition of the ANT(2")-Ia resistance enzyme and rescue of aminoglycoside antibiotic activity by synthetic α-hydroxytropolones.
AID1363740Inhibition of Influenza A (A/California/04/2009) (H1N1) clinical isolate N-terminal truncated PA endonuclease at 500 nM using 5'-FAM/3-TAMRA quencer labeled 17-mer ssDNA-oligo as substrate measured over 45 mins by FRET assay relative to control2018Journal of medicinal chemistry, 11-21, Volume: 61, Issue:22
Structure-Activity Relationships in Metal-Binding Pharmacophores for Influenza Endonuclease.
AID1232066Inhibition of dopamine beta-oxygenase (unknown origin)2014MedChemComm, Jul-01, Volume: 5, Issue:7
The biology and synthesis of α-hydroxytropolones.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (18.18)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's5 (45.45)24.3611
2020's4 (36.36)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.82

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 Index12.82 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index5.30 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.82)

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%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
2,3-dihydroxybenzoic acid
2,3-dihydroxybenzoic acid: RN given refers to parent cpd. dihydroxybenzoic acid : Any member of the class of hydroxybenzoic acids carrying two phenolic hydroxy groups on the benzene ring and its derivatives.. 2,3-dihydroxybenzoic acid : A dihydroxybenzoic acid that is benzoic acid substituted by hydroxy groups at positions 2 and 3. It occurs naturally in Phyllanthus acidus and in the aquatic fern Salvinia molesta.		2.1710dihydroxybenzoic acidhuman xenobiotic metabolite;
plant metabolite
gallic acid
gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.		2.1710trihydroxybenzoic acidantineoplastic agent;
antioxidant;
apoptosis inducer;
astringent;
cyclooxygenase 2 inhibitor;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
geroprotector;
human xenobiotic metabolite;
plant metabolite
phenylacetic acid
phenylacetic acid : A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.		2.610benzenes;
monocarboxylic acid;
phenylacetic acids		allergen;
Aspergillus metabolite;
auxin;
EC 6.4.1.1 (pyruvate carboxylase) inhibitor;
Escherichia coli metabolite;
human metabolite;
plant growth retardant;
plant metabolite;
Saccharomyces cerevisiae metabolite;
toxin
pyrogallol
benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.		2.1710benzenetriol;
phenolic donor		plant metabolite
anthralin
Anthralin: An anthracene derivative that disrupts MITOCHONDRIA function and structure and is used for the treatment of DERMATOSES, especially PSORIASIS. It may cause FOLLICULITIS.. anthralin : An anthracene compound derived by the substitution of -OH groups for hydrogen at C-1 and C-8, and with an oxo group at C-9.		2.1710anthracenesantipsoriatic
mitomycin
Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.		2.110mitomycinalkylating agent;
antineoplastic agent
pantothenic acid
Pantothenic Acid: A butyryl-beta-alanine that can also be viewed as pantoic acid complexed with BETA ALANINE. It is incorporated into COENZYME A and protects cells against peroxidative damage by increasing the level of GLUTATHIONE.. pantothenic acid : A member of the class of pantothenic acids that is an amide formed from pantoic acid and beta-alanine.. vitamin B5 : Any member of a group of vitamers that belong to the chemical structural class called pantothenic acids that exhibit biological activity against vitamin B5 deficiency. Deficiency of vitamin B5 is rare due to its widespread distribution in whole grain cereals, legumes and meat. Symptoms associated with vitamin B5 deficiency are difficult to asses since they are subtle and resemble those of other B vitamin deficiencies. The vitamers include (R)-pantothenic acid and its ionized and salt forms.. (R)-pantothenate : A pantothenate that is the conjugate base of (R)-pantothenic acid, obtained by deprotonation of the carboxy group.. (R)-pantothenic acid : A pantothenic acid having R-configuration.		7.2510pantothenic acid;
vitamin B5		antidote to curare poisoning;
geroprotector;
human blood serum metabolite
dipicolinic acid
dipicolinic acid : A pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6.		2.1710pyridinedicarboxylic acidbacterial metabolite
n-hydroxyphthalimide
N-hydroxyphthalimide: causes contact dermititis		2.1710
tropolone
Tropolone: A seven-membered aromatic ring compound. It is structurally related to a number of naturally occurring antifungal compounds (ANTIFUNGAL AGENTS).. tropolone : A cyclic ketone that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2. It is a toxin produced by the agricultural pathogen Burkholderia plantarii.		3.5480alpha-hydroxy ketone;
cyclic ketone;
enol		bacterial metabolite;
fungicide;
toxin
2,3,4-Trihydroxybenzoic acid
[no description available]		2.1710hydroxybenzoic acid
gamma-thujaplicin
2-hydroxy-5-isopropyl- 2,4,6-cycloheptatrienone: a metal chelating agent		2.110cyclic ketone
dihydrostreptomycin sulfate
Dihydrostreptomycin Sulfate: A semi-synthetic aminoglycoside antibiotic that is used in the treatment of TUBERCULOSIS.		1.9610
pyromeconic acid
pyromeconic acid: from herb Dengzhanhua; structure		2.1710
allomaltol
allomaltol: structure in first source		2.1710
beta-thujaplicinol
beta-thujaplicinol: inhibits ribonuclease H activity of HIV-1 reverse transcriptase; structure in first source		2.520
alpha-thujaplicin
alpha-thujaplicin: structure in first source		2.110
3,7-dihydroxytropolone
3,7-dihydroxytropolone: from Streptomyces tropolofaciens; active against B16 melanoma; structure given in first source. 3,7-dihydroxytropolone : A cyclic ketone that is tropolone in which the hydrogens at positions 3 and 7 are substituted by hydroxy groups. It is isolated from the soil bacterium Streptomyces tropolofaciens strain K611-97.		2.110alpha-hydroxy ketone;
cyclic ketone;
enol;
triol		antineoplastic agent;
bacterial metabolite
artesunate
artesunic acid: RN given for (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,(2aR*))-isomer; succinic ester of artemether		2.110artemisinin derivative;
cyclic acetal;
dicarboxylic acid monoester;
hemisuccinate;
semisynthetic derivative;
sesquiterpenoid		antimalarial;
antineoplastic agent;
ferroptosis inducer
gentamicin sulfate
[no description available]		2.110
ConditionIndicatedRelationship StrengthStudiesTrials
Infections, Pseudomonas
[description not available]		02.2510
Pseudomonas Infections
Infections with bacteria of the genus PSEUDOMONAS.		02.2510