Compounds > mucronulatol
Page last updated: 2024-11-08

mucronulatol

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

Description

mucronulatol: compound from Caribbean propolis that exerts cytotoxic effects on human tumor cell lines [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

mucronulatol : A methoxyisoflavan that is (S)-isoflavan substituted by methoxy groups at positions 2' and 4' and hydroxy groups at positions 7 and 3' respectively. [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]

Cross-References

ID SourceID
PubMed CID442811
CHEMBL ID253474
CHEBI ID7014
MeSH IDM0523891
PubMed CID4484949
CHEMBL ID478971
CHEBI ID174890
SCHEMBL ID4290208
MeSH IDM0523891

Synonyms (35)

Synonym
20878-97-1
mucronulatol
(3s)-mucronulatol
CHEMBL253474
chebi:7014 ,
(3s)-3-(3-hydroxy-2,4-dimethoxyphenyl)-3,4-dihydro-2h-chromen-7-ol
LMPK12080024
(-)-mucronulatol
(3s)-3-(3-hydroxy-2,4-dimethoxyphenyl)-3,4-dihydro-2h-1-benzopyran-7-ol
DTXSID70331959
Q27107401
CHEBI:174890
3-(3-hydroxy-2,4-dimethoxyphenyl)-3,4-dihydro-2h-chromen-7-ol
(r)-3',7-dihydroxy-2',4'-dimethoxyisoflavan
DIVK1C_006795
smr000470933
MLS000697594
KBIO1_001739
SPECPLUS_000699
SPECTRUM2_001834
SPBIO_001907
CHEMBL478971
(+/-)-mucronulatol
HMS2270J22
CCG-38462
SCHEMBL4290208
27213-18-9
20878-98-2
mucronulatol(+/-)
3,4-dihydro-3-(3-hydroxy-2,4-dimethoxyphenyl)-2h-1-benzopyran-7-ol
(+)-mucronulatol
(r)-mucronulatol
FS-8458
3',7-dihydroxy-2',4'-dimethoxyisoflavan
AKOS040735371
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role 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]

Drug Classes (3)

ClassDescription
methoxyisoflavanAny member of the class of isoflavans in which one or more ring hydrogens are replaced by methoxy groups.
hydroxyisoflavansA member of the class of isoflavans in which one or more ring hydrogens are replaced by hydroxy groups.
isoflavonoidAny 1-benzopyran with an aryl substituent at position 3. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.
[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 (10)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
glp-1 receptor, partialHomo sapiens (human)Potency10.00000.01846.806014.1254AID624417
TDP1 proteinHomo sapiens (human)Potency17.35820.000811.382244.6684AID686978; AID686979
apical membrane antigen 1, AMA1Plasmodium falciparum 3D7Potency39.81070.707912.194339.8107AID720542
IDH1Homo sapiens (human)Potency29.09290.005210.865235.4813AID686970
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency79.43280.050127.073689.1251AID588590
urokinase-type plasminogen activator precursorMus musculus (house mouse)Potency28.18380.15855.287912.5893AID540303
plasminogen precursorMus musculus (house mouse)Potency28.18380.15855.287912.5893AID540303
urokinase plasminogen activator surface receptor precursorMus musculus (house mouse)Potency28.18380.15855.287912.5893AID540303
gemininHomo sapiens (human)Potency24.84460.004611.374133.4983AID624296; AID624297
DNA dC->dU-editing enzyme APOBEC-3G isoform 1Homo sapiens (human)Potency15.84890.058010.694926.6086AID602310
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (39)

Assay IDTitleYearJournalArticle
AID345142Cytotoxicity against human HCT8 cells after 24 hrs2008Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22
The contribution of plukenetione A to the anti-tumoral activity of Cuban propolis.
AID404184Cytotoxicity against human HT1080 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID313354Cytotoxicity against human PANC1 cells in nutrient deprived medium after 24 hrs2008Bioorganic & medicinal chemistry, Jan-01, Volume: 16, Issue:1
Constituents of Brazilian red propolis and their preferential cytotoxic activity against human pancreatic PANC-1 cancer cell line in nutrient-deprived condition.
AID345153Cytotoxicity against human LAN1 cells after 24 hrs2008Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22
The contribution of plukenetione A to the anti-tumoral activity of Cuban propolis.
AID345155Cytotoxicity against cisplatin-resistant human LAN1 cells after 24 hrs2008Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22
The contribution of plukenetione A to the anti-tumoral activity of Cuban propolis.
AID404181Cytotoxicity against mouse LLC cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID404182Cytotoxicity against human A549 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID345163Cytotoxicity against HEK293 cells after 24 hrs2008Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22
The contribution of plukenetione A to the anti-tumoral activity of Cuban propolis.
AID345145Cytotoxicity against human MCF7 cells after 24 hrs2008Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22
The contribution of plukenetione A to the anti-tumoral activity of Cuban propolis.
AID404180Cytotoxicity against mouse B16-BL6 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID345146Cytotoxicity against doxorubicin-resistant human MCF7 cells after 24 hrs2008Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22
The contribution of plukenetione A to the anti-tumoral activity of Cuban propolis.
AID404179Cytotoxicity against mouse colon 26-L5 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID404183Cytotoxicity against human HeLa cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID345154Cytotoxicity against etoposide-resistant human LAN1 cells after 24 hrs2008Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22
The contribution of plukenetione A to the anti-tumoral activity of Cuban propolis.
AID345156Cytotoxicity against 5-FU-resistant human LAN1 cells after 24 hrs2008Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22
The contribution of plukenetione A to the anti-tumoral activity of Cuban propolis.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID338054Antibacterial activity against Escherichia coli ATCC 25922 after 16 hrs by microdilution assay
AID338056Antifungal activity against Penicillium expansum ATCC 7861 after 3 days by microdilution assay
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID338052Antibacterial activity against Staphylococcus aureus ATCC 25923 after 16 hrs by microdilution assay
AID338053Antibacterial activity against Bacillus subtilis ATCC 6633 after 16 hrs by microdilution assay
AID338055Antifungal activity against Candida albicans ATCC 10259 after 3 days by microdilution assay
AID338057Antifungal activity against Aspergillus niger ATCC 6275 after 3 days by microdilution assay
AID338058Antifungal activity against Trichophyton mentagrophytes ATCC 9533 after 3 days by microdilution assay
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (41.67)29.6817
2010's5 (41.67)24.3611
2020's2 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews1 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
Other7 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
fluorouracil
Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.		2.7330nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		2.0410taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
arctigenin
arctigenin: precursor to catechols; in many plants		2.0410lignan
pinocembrin
pinocembrin : A dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea.		2.0510(2S)-flavan-4-one;
dihydroxyflavanone		antineoplastic agent;
antioxidant;
metabolite;
neuroprotective agent;
vasodilator agent
medicarpin, (6as-cis)-isomer
(+)-medicarpin : The (+)-enantiomer of medicarpin.		2.4420medicarpin
(+)-Eudesmin
[no description available]		2.4420lignan
liquiritigenin
liquiritigenin: structure given in first source; isolated from Pterocarpus marsupium. 4',7-dihydroxyflavanone : A dihydroxyflavanone in which the two hydroxy substituents are located at positions 4' and 7.. liquiritigenin : A dihydroxyflavanone compound having the two hydroxy substituents at the 4'- and 7-positions. Isolated from the root of Glycyrrhizae uralensis, it is a selective agonist for oestrogen receptor beta.		2.44204',7-dihydroxyflavanonehormone agonist;
plant metabolite
naringenin
(S)-naringenin : The (S)-enantiomer of naringenin.		2.4420(2S)-flavan-4-one;
naringenin		expectorant;
plant metabolite
syringaresinol
(+)-syringaresinol : The (7alpha,7'alpha,8alpha,8'alpha)-stereoisomer of syringaresinol.		2.4420syringaresinolantineoplastic agent
nemorosone
[no description available]		2.0410
isoliquiritigenin
[no description available]		2.4420chalconesantineoplastic agent;
biological pigment;
EC 1.14.18.1 (tyrosinase) inhibitor;
GABA modulator;
geroprotector;
metabolite;
NMDA receptor antagonist
(2S)-7-hydroxyflavanone
[no description available]		2.44207-hydroxyflavanone
biochanin a
[no description available]		2.44204'-methoxyisoflavones;
7-hydroxyisoflavones		antineoplastic agent;
EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor;
phytoestrogen;
plant metabolite;
tyrosine kinase inhibitor
formononetin
[no description available]		2.44204'-methoxyisoflavones;
7-hydroxyisoflavones		phytoestrogen;
plant metabolite
7,3'-dihydroxy-4'-methoxyisoflavone
7,3'-dihydroxy-4'-methoxyisoflavone: isolated from Astragali radix; structure in first source. calycosin : A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at the 3' position and a methoxy group at the 4' position.		2.44204'-methoxyisoflavones;
7-hydroxyisoflavones		antioxidant;
metabolite
2'-hydroxyformononetin
2'-hydroxyformononetin : A member of the class of 4'-methoxyisoflavones that is formononetin with a hydroxy group at the 2'position.		2.44204'-methoxyisoflavones;
7-hydroxyisoflavones		anti-inflammatory agent
daidzein
[no description available]		2.44207-hydroxyisoflavonesantineoplastic agent;
EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
phytoestrogen;
plant metabolite
4'-methoxy-3',5,7-trihydroxyisoflavone
4'-methoxy-3',5,7-trihydroxyisoflavone: structure in first source. pratensein : A member of the class of 7-hydroxyisoflavones in which isoflavone is substituted by hydroxy groups at the 5, 7, and 3' positions, and by a methoxy group at the 4' position.		2.44204'-methoxyisoflavones;
7-hydroxyisoflavones
3-deoxysappanchalcone
3-deoxysappanchalcone: Anti-allergic from the roots and heartwood of Caesalpinia sappan; structure in first source. 2'-O-methylisoliquiritigenin : A member of the class of chalcones that is isoliquiritigenin in which one of the hydroxy groups at position 2' is replaced by a methoxy group.		2.4420chalcones;
monomethoxybenzene;
phenols		metabolite
2',4'-dihydroxychalcone
2',4'-dihydroxychalcone: RN given refers to (E)-isomer; RN for cpd without isomeric designation not available 6/89; structure given in first source		2.4420
(-)-pinoresinol
(-)-pinoresinol : An enantiomer of pinoresinol having (-)-1R,3aS,4R,6aS-configuration.		2.4420pinoresinolplant metabolite
plukenetione a
plukenetione A: produced by honey bees from various plant sources; structure in first source		2.0410
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Pancreas
[description not available]		02.0410
Necrosis
The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.		02.0410
Pancreatic Neoplasms
Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).		02.0410
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.0410
Benign Neoplasms
[description not available]		03.3920
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		03.3920
Innate Inflammatory Response
[description not available]		02.0510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.0510