Compounds > monocerin
Page last updated: 2024-11-06

monocerin

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

Description

Monocerin is a polyketide natural product isolated from the fungus *Monocercomonospora* *fusca*. It exhibits potent antifungal activity against a range of pathogenic fungi, particularly Candida albicans. Its unique structure, featuring a rare 12-membered macrolactone ring and a fused tetrahydrofuran ring, has sparked interest in its synthetic accessibility and potential for drug development. Researchers are exploring its biosynthesis pathways, structure-activity relationships, and potential for optimization as a therapeutic agent. '

monocerin: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID92267
CHEMBL ID488513
CHEBI ID70148
MeSH IDM0465997

Synonyms (27)

Synonym
bdbm50335899
ACON0_000652
MEGXM0_000272
ACON1_001243
C09953
30270-60-1
monocerin
NCGC00169540-01
BRD-K31616759-001-01-2
chebi:70148 ,
CHEMBL488513 ,
(2s,3ar,9br)-6-hydroxy-7,8-dimethoxy-2-propyl-2,3,3a,9b-tetrahydrofuro[3,2-c]isochromen-5-one
unii-g7c424u3dj
g7c424u3dj ,
5h-furo(3,2-c)(2)benzopyran-5-one, 2,3,3a,9b-tetrahydro-6-hydroxy-7,8-dimethoxy-2-propyl-, (2s-(2alpha,3abeta,9bbeta))-
AKOS030213206
monocerin, (+)-
mfcd08274586
DTXSID70184361
5h-furo(3,2-c)(2)benzopyran-5-one, 2,3,3a,9b-tetrahydro-6-hydroxy-7,8-dimethoxy-2-propyl-, (2s,3ar,9br)-
(2s,3ar,9br)-2,3,3a,9b-tetrahydro-6-hydroxy-7,8-dimethoxy-2-propyl-5h-furo(3,2-c)(2)benzopyran-5-one
verrucarin a, 2',3'-didehydro-7'-deoxo-2'-deoxy-4'-hydroxy-7'-((1r)-1-hydroxyethyl)-, (2'e,4's,7'r)-
(+)-monocerin
(2'e,4's,7'r)-2',3'-didehydro-7'-deoxo-2'-deoxy-4'-hydroxy-7'-((1r)-1-hydroxyethyl)verrucarin a
Q2899189
HY-N6294
CS-0033374
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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 (1)

ClassDescription
hydroxybenzoic acidAny benzoic acid carrying one or more phenolic hydroxy groups on the benzene ring.
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AromataseHomo sapiens (human)IC50 (µMol)16.20000.00001.290410.0000AID568566
Xanthine dehydrogenase/oxidaseHomo sapiens (human)IC50 (µMol)648.00000.00132.81389.8200AID568570
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (42)

Processvia Protein(s)Taxonomy
negative regulation of chronic inflammatory responseAromataseHomo sapiens (human)
steroid biosynthetic processAromataseHomo sapiens (human)
estrogen biosynthetic processAromataseHomo sapiens (human)
androgen catabolic processAromataseHomo sapiens (human)
syncytium formationAromataseHomo sapiens (human)
negative regulation of macrophage chemotaxisAromataseHomo sapiens (human)
sterol metabolic processAromataseHomo sapiens (human)
female genitalia developmentAromataseHomo sapiens (human)
mammary gland developmentAromataseHomo sapiens (human)
uterus developmentAromataseHomo sapiens (human)
prostate gland growthAromataseHomo sapiens (human)
testosterone biosynthetic processAromataseHomo sapiens (human)
positive regulation of estradiol secretionAromataseHomo sapiens (human)
female gonad developmentAromataseHomo sapiens (human)
response to estradiolAromataseHomo sapiens (human)
allantoin metabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of protein phosphorylationXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of endothelial cell proliferationXanthine dehydrogenase/oxidaseHomo sapiens (human)
guanine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
inosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
deoxyinosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
adenosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
deoxyadenosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
deoxyguanosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
AMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
IMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
activation of cysteine-type endopeptidase activity involved in apoptotic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
lactationXanthine dehydrogenase/oxidaseHomo sapiens (human)
hypoxanthine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
xanthine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of gene expressionXanthine dehydrogenase/oxidaseHomo sapiens (human)
iron-sulfur cluster assemblyXanthine dehydrogenase/oxidaseHomo sapiens (human)
amide catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of endothelial cell differentiationXanthine dehydrogenase/oxidaseHomo sapiens (human)
GMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
dGMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
dAMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionXanthine dehydrogenase/oxidaseHomo sapiens (human)
positive regulation of p38MAPK cascadeXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of vascular endothelial growth factor signaling pathwayXanthine dehydrogenase/oxidaseHomo sapiens (human)
positive regulation of reactive oxygen species metabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of vasculogenesisXanthine dehydrogenase/oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (17)

Processvia Protein(s)Taxonomy
iron ion bindingAromataseHomo sapiens (human)
steroid hydroxylase activityAromataseHomo sapiens (human)
electron transfer activityAromataseHomo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenAromataseHomo sapiens (human)
oxygen bindingAromataseHomo sapiens (human)
heme bindingAromataseHomo sapiens (human)
aromatase activityAromataseHomo sapiens (human)
xanthine dehydrogenase activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
xanthine oxidase activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
iron ion bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
protein bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
protein homodimerization activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
molybdopterin cofactor bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
flavin adenine dinucleotide bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
2 iron, 2 sulfur cluster bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
hypoxanthine dehydrogenase activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
hypoxanthine oxidase activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
FAD bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
endoplasmic reticulumAromataseHomo sapiens (human)
endoplasmic reticulum membraneAromataseHomo sapiens (human)
membraneAromataseHomo sapiens (human)
endoplasmic reticulumAromataseHomo sapiens (human)
cytosolXanthine dehydrogenase/oxidaseHomo sapiens (human)
extracellular spaceXanthine dehydrogenase/oxidaseHomo sapiens (human)
peroxisomeXanthine dehydrogenase/oxidaseHomo sapiens (human)
cytosolXanthine dehydrogenase/oxidaseHomo sapiens (human)
sarcoplasmic reticulumXanthine dehydrogenase/oxidaseHomo sapiens (human)
extracellular spaceXanthine dehydrogenase/oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID406149Antimicrobial activity against Chlorella fusca by agar diffusion method2008Journal of natural products, Jun, Volume: 71, Issue:6
Bioactive isocoumarins isolated from the endophytic fungus Microdochium bolleyi.
AID1772381Antiplasmodial activity against Plasmodium falciparum HB3 infected in human erythrocytes assessed as reduction in parasite growth incubated for 48 hrs by PicoGreen DNA fluorescent dye
AID568563Cytotoxicity against human HepG2 cells by MTT assay2011Journal of natural products, Jan-28, Volume: 74, Issue:1
Radical scavenging and antioxidant activities of isocoumarins and a phthalide from the endophytic fungus Colletotrichum sp.
AID362771Antimalarial activity against multidrug-resistant Plasmodium falciparum K12008Journal of natural products, Sep, Volume: 71, Issue:9
11-Hydroxymonocerin from the plant endophytic fungus Exserohilum rostratum.
AID1772383Selectivity index, ratio of CC50 for African green monkey Vero cells to IC50 for Plasmodium falciparum HB3 infected in human erythrocytes assessed as reduction in parasite growth
AID568562Cytotoxicity against human HuCCA1 cells by MTT assay2011Journal of natural products, Jan-28, Volume: 74, Issue:1
Radical scavenging and antioxidant activities of isocoumarins and a phthalide from the endophytic fungus Colletotrichum sp.
AID362773Cytotoxicity against human CHAGO cells at 20 ug/mL by MTT assay2008Journal of natural products, Sep, Volume: 71, Issue:9
11-Hydroxymonocerin from the plant endophytic fungus Exserohilum rostratum.
AID406147Antimicrobial activity against Bacillus megaterium by agar diffusion method2008Journal of natural products, Jun, Volume: 71, Issue:6
Bioactive isocoumarins isolated from the endophytic fungus Microdochium bolleyi.
AID568571Antioxidant activity assessed as trolox equivalent of peroxy radical scavenging activity at 1 uM by ORAC assay2011Journal of natural products, Jan-28, Volume: 74, Issue:1
Radical scavenging and antioxidant activities of isocoumarins and a phthalide from the endophytic fungus Colletotrichum sp.
AID362776Cytotoxicity against human SW620 cells at 20 ug/mL by MTT assay2008Journal of natural products, Sep, Volume: 71, Issue:9
11-Hydroxymonocerin from the plant endophytic fungus Exserohilum rostratum.
AID568564Cytotoxicity against human A549 cells by MTT assay2011Journal of natural products, Jan-28, Volume: 74, Issue:1
Radical scavenging and antioxidant activities of isocoumarins and a phthalide from the endophytic fungus Colletotrichum sp.
AID406148Antimicrobial activity against Microbotryum violaceum by agar diffusion method2008Journal of natural products, Jun, Volume: 71, Issue:6
Bioactive isocoumarins isolated from the endophytic fungus Microdochium bolleyi.
AID406146Antimicrobial activity against Escherichia coli by agar diffusion method2008Journal of natural products, Jun, Volume: 71, Issue:6
Bioactive isocoumarins isolated from the endophytic fungus Microdochium bolleyi.
AID568568Antioxidant activity assessed as inhibition of xanthine-xanthine oxidase generated superoxide anion radical production2011Journal of natural products, Jan-28, Volume: 74, Issue:1
Radical scavenging and antioxidant activities of isocoumarins and a phthalide from the endophytic fungus Colletotrichum sp.
AID362772Cytotoxicity against human BT474 cells at 20 ug/mL by MTT assay2008Journal of natural products, Sep, Volume: 71, Issue:9
11-Hydroxymonocerin from the plant endophytic fungus Exserohilum rostratum.
AID568566Inhibition of CYP192011Journal of natural products, Jan-28, Volume: 74, Issue:1
Radical scavenging and antioxidant activities of isocoumarins and a phthalide from the endophytic fungus Colletotrichum sp.
AID1772382Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability by MTT assay
AID568567Antioxidant activity assessed as DPPH radical scavenging activity2011Journal of natural products, Jan-28, Volume: 74, Issue:1
Radical scavenging and antioxidant activities of isocoumarins and a phthalide from the endophytic fungus Colletotrichum sp.
AID568569Antioxidant activity in human HL60 cells assessed as inhibition of TPA-induced superoxide anion radical production2011Journal of natural products, Jan-28, Volume: 74, Issue:1
Radical scavenging and antioxidant activities of isocoumarins and a phthalide from the endophytic fungus Colletotrichum sp.
AID362774Cytotoxicity against human HepG2 cells at 20 ug/mL by MTT assay2008Journal of natural products, Sep, Volume: 71, Issue:9
11-Hydroxymonocerin from the plant endophytic fungus Exserohilum rostratum.
AID568570Inhibition of Xanthine oxidase2011Journal of natural products, Jan-28, Volume: 74, Issue:1
Radical scavenging and antioxidant activities of isocoumarins and a phthalide from the endophytic fungus Colletotrichum sp.
AID362775Cytotoxicity against human KATO3 cells at 20 ug/mL by MTT assay2008Journal of natural products, Sep, Volume: 71, Issue:9
11-Hydroxymonocerin from the plant endophytic fungus Exserohilum rostratum.
AID568565Cytotoxicity against human MOLT3 cells by XTT assay2011Journal of natural products, Jan-28, Volume: 74, Issue:1
Radical scavenging and antioxidant activities of isocoumarins and a phthalide from the endophytic fungus Colletotrichum sp.
[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-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (45.45)29.6817
2010's4 (36.36)24.3611
2020's2 (18.18)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.35

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 Index21.35 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.54 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.35)

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
coumarin
2H-chromen-2-one: coumarin derivative		7.2110coumarinsfluorescent dye;
human metabolite;
plant metabolite
ketoconazole
1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.		2.0610dichlorobenzene;
dioxolane;
ether;
imidazoles;
N-acylpiperazine;
N-arylpiperazine
cyanides
Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.		2.110pseudohalide anionEC 1.9.3.1 (cytochrome c oxidase) inhibitor
cycloheximide
Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.		2.0410antibiotic fungicide;
cyclic ketone;
dicarboximide;
piperidine antibiotic;
piperidones;
secondary alcohol		anticoronaviral agent;
bacterial metabolite;
ferroptosis inhibitor;
neuroprotective agent;
protein synthesis inhibitor
phthalide
2-benzofuran-1(3H)-one : A gamma-lactone that is 1,3-dihydro-2-benzofuran in which the hydrogens at position 1 are replaced by an oxo group.. isobenzofuranone : A 2-benzofuran containing one or more oxo groups.		2.06102-benzofurans;
gamma-lactone
etoposide
[no description available]		2.0610beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor
isocoumarins
Isocoumarins: Compounds that differ from COUMARINS in having the positions of the ring and ketone oxygens reversed so the keto oxygen is at the 1-position of the molecule.. isocoumarin : The simplest member of the class of isocoumarins that is 1H-isochromene which is substituted by an oxo group at position 1.		2.4820isocoumarins
benzofurans
Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.		2.0610
1,1-diphenyl-2-picrylhydrazyl
1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)		2.0610
artenimol
artenimol: derivative of antimalarial drug artemisinin (quinghaosu)		2.0410
nystatin a1
Nystatin: Macrolide antifungal antibiotic complex produced by Streptomyces noursei, S. aureus, and other Streptomyces species. The biologically active components of the complex are nystatin A1, A2, and A3.. nystatin : A heterogeneous mixture of polyene compounds produced by cultures of Streptomyces noursei. It mainly consists of three biologically active components designated nystatin A1, nystatin A2, and nystatin A3. It is used to treat oral and dermal fungal infections.. nystatin A1 : A polyene macrolide antibiotic; part of the nystatin complex produced by several Streptomyces species. It is an antifungal antibiotic used for the treatment of topical fungal infections caused by a broad spectrum of fungal pathogens comprising yeast-like and filamentous species.		2.0410nystatins
ascorbic acid
Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.		2.0610ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
tetracycline
Tetracycline: A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.. tetracycline : A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.		2.0410
warfarin
Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.		2.2110benzenes;
hydroxycoumarin;
methyl ketone
allopurinol
Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.		2.0610nucleobase analogue;
organic heterobicyclic compound		antimetabolite;
EC 1.17.3.2 (xanthine oxidase) inhibitor;
gout suppressant;
radical scavenger
ConditionIndicatedRelationship StrengthStudiesTrials