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ambruticin

Description

ambruticin: cyclopropyl-polyene-pyran acid from Polyangium cellulosum var. fulvum; RN given refers to parent cpd; structure [MeSH]

Cross-References

ID SourceID
PubMed CID6436037
PubMed CID6918547
CHEMBL ID522783
SCHEMBL ID397001
MeSH IDM0063892

Synonyms (33)

Synonym
ambruticin
ambruticin s
w-7783 ,
w7783 ,
ambruticin (usan/inn)
D02883
smp-78 acid s
w 7783
2h-pyran-2-acetic acid, 6-(2-(2-(5-(6-ethyl-3,6-dihydro-5-methyl-2h-pyran-2-yl)-3-methyl-1,4-hexadienyl)-3-methylcyclopropyl)ethenyl)tetrahydro-4,5-dihydroxy-
antibiotic acid s
ambruticinum [inn-latin]
ambruticine [inn-french]
ambruticin [usan:inn]
ambruticino [inn-spanish]
6-(2-(2-(5-(6-ethyl-3,6-dihydro-5-methyl-2h-pyran-2-yl)-3-methyl-1,4-hexadienyl)-3-methylcyclopropyl)vinyl)tetrahydro-4,5-dihydroxy-2h-pyran-2-acetic acid
nsc-328415
CHEMBL522783
2-[(2s,4s,5r,6s)-6-[(e)-2-[(1s,2s,3r)-2-[(1e,3r,4e)-5-[(2r,6r)-6-ethyl-5-methyl-3,6-dihydro-2h-pyran-2-yl]-3-methylhexa-1,4-dienyl]-3-methylcyclopropyl]ethenyl]-4,5-dihydroxyoxan-2-yl]acetic acid
nsc 328415
x794618736 ,
ambruticine
unii-x794618736
ambruticinum
ambruticino
6-[2-[2-[5-(6-ethyl-3,6-dihydro-5-methyl-2h-pyran-2-yl)-3-methyl-1,4-hexadienyl]-3-methylcyclopropyl]vinyl]tetrahydro-4,5-dihydroxy-2h-pyran-2-acetic acid
ambruticin [usan]
ambruticin [inn]
(+)-ambruticin s
(+)-ambruticin
SCHEMBL397001
Q27293636
DTXSID701024202
AKOS040750394

Bioassays (11)

Assay IDTitleYearJournalArticle
AID1134945Antifungal activity against Microsporum fulvum assessed as growth inhibition by standard broth dilution method1979Journal of medicinal chemistry, Sep, Volume: 22, Issue:9
ISSN: 0022-2623
Antifungal agents. 4. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. Ester and amide analogues of ambruticin.
AID1134946Antifungal activity against Streptococcus pyogenes assessed as growth inhibition by standard broth dilution method1979Journal of medicinal chemistry, Sep, Volume: 22, Issue:9
ISSN: 0022-2623
Antifungal agents. 4. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. Ester and amide analogues of ambruticin.
AID1134944Antifungal activity against Histoplasma capsulatum assessed as growth inhibition by standard broth dilution method1979Journal of medicinal chemistry, Sep, Volume: 22, Issue:9
ISSN: 0022-2623
Antifungal agents. 4. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. Ester and amide analogues of ambruticin.
AID417426Elevation of Hog1 phosphorylation Saccharomyces cerevisiae ATCC 201388 carrying pYES2-HIK1 at 25 ppm after 4 hrs in SD/-Ura medium by Western blot analysis2007Antimicrobial agents and chemotherapy, Oct, Volume: 51, Issue:10
ISSN: 0066-4804
The antifungal polyketide ambruticin targets the HOG pathway.
AID1134909Antifungal activity against Candida albicans by standard broth dilution technique1979Journal of medicinal chemistry, Sep, Volume: 22, Issue:9
ISSN: 0022-2623
Antifungal agents. 5. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. Alcohol, ketone, aldehyde, and oxime analogues of ambruticin.
AID1134910Antifungal activity against Histoplasma capsulatum assessed as growth inhibition after 3 days by standard broth dilution technique1979Journal of medicinal chemistry, Sep, Volume: 22, Issue:9
ISSN: 0022-2623
Antifungal agents. 5. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. Alcohol, ketone, aldehyde, and oxime analogues of ambruticin.
AID1134908Antibacterial activity against Streptococcus pyogenes by standard broth dilution technique1979Journal of medicinal chemistry, Sep, Volume: 22, Issue:9
ISSN: 0022-2623
Antifungal agents. 5. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. Alcohol, ketone, aldehyde, and oxime analogues of ambruticin.
AID1134947Antifungal activity against Candida albicans assessed as growth inhibition by standard broth dilution method1979Journal of medicinal chemistry, Sep, Volume: 22, Issue:9
ISSN: 0022-2623
Antifungal agents. 4. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. Ester and amide analogues of ambruticin.
AID417427Elevation of Hog1 phosphorylation Saccharomyces cerevisiae ATCC 201388 carrying pYES2 at 25 ppm after 4 hrs in SD/-Ura medium by Western blot analysis2007Antimicrobial agents and chemotherapy, Oct, Volume: 51, Issue:10
ISSN: 0066-4804
The antifungal polyketide ambruticin targets the HOG pathway.
AID1134911Antifungal activity against Microsporum fulvum assessed as growth inhibition after 3 days by standard broth dilution technique1979Journal of medicinal chemistry, Sep, Volume: 22, Issue:9
ISSN: 0022-2623
Antifungal agents. 5. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. Alcohol, ketone, aldehyde, and oxime analogues of ambruticin.
AID417300Elevation of Hog1 phosphorylation Saccharomyces cerevisiae ATCC 201388 carrying deltahog1 gene at 25 ppm after 4 hrs in SD/-Ura medium by Western blot analysis2007Antimicrobial agents and chemotherapy, Oct, Volume: 51, Issue:10
ISSN: 0066-4804
The antifungal polyketide ambruticin targets the HOG pathway.

Research

Studies (30)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (16.67)18.7374
1990's3 (10.00)18.2507
2000's14 (46.67)29.6817
2010's5 (16.67)24.3611
2020's3 (10.00)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (8.57%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other32 (91.43%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
vinclozolindicarboximide;
dichlorobenzene;
olefinic compound;
oxazolidinone
2007200717.0low000100
fludioxonilbenzodioxoles;
nitrile;
organofluorine compound;
pyrroles
androgen antagonist;
antifungal agrochemical;
estrogen receptor agonist
2007200717.0low000100
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
glycerolalditol;
triol
algal metabolite;
detergent;
Escherichia coli metabolite;
geroprotector;
human metabolite;
mouse metabolite;
osmolyte;
Saccharomyces cerevisiae metabolite;
solvent
2000200720.5low001100
alaninealanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid
EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite
1990199034.0low001000
aspartic acidaspartate family amino acid;
aspartic acid;
L-alpha-amino acid;
proteinogenic amino acid
Escherichia coli metabolite;
mouse metabolite;
neurotransmitter
1990199034.0low001000
leucineamino acid zwitterion;
L-alpha-amino acid;
leucine;
proteinogenic amino acid;
pyruvate family amino acid
algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
1985198539.0low010000
cyclopropanecycloalkane;
cyclopropanes
inhalation anaesthetic2005201812.5low000110
pyrrolespyrrole;
secondary amine
2009201213.5low000110
oxazoles1,3-oxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
2004200420.0low000100
galactose2004200420.0low000100
alkenes2004201616.2medium000310
glutamic acidglutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid
Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
1990199034.0low001000
fludioxonilbenzodioxoles;
nitrile;
organofluorine compound;
pyrroles
androgen antagonist;
antifungal agrochemical;
estrogen receptor agonist
2009201213.5low000110
alprostadilprostaglandins Eanticoagulant;
human metabolite;
platelet aggregation inhibitor;
vasodilator agent
2004200420.0low000100
amphotericin bantibiotic antifungal drug;
macrolide antibiotic;
polyene antibiotic
antiamoebic agent;
antiprotozoal drug;
bacterial metabolite
1979197945.0low010000
macbecin i1992199232.0medium001000
fr 9014642004200420.0low000100
fostriecin2-pyranones;
olefinic compound;
phosphate monoester;
polyketide;
primary allylic alcohol;
secondary allylic alcohol;
triol
antineoplastic agent;
apoptosis inhibitor;
bacterial metabolite;
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
topoisomerase II inhibitor
2004200420.0low000100
ambruticin201020209.0high000110
ambruticin201020209.0medium000110
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Aspergillosis02006200618.0low000100
Aspergillus Infection02006200618.0low000100
Coccidioides immitis Infection01978200632.0medium010100
Coccidioidomycosis01978200632.0medium010100
Dehydration0202320231.0medium000002
Disease Models, Animal02006200618.0medium000200
Fungal Lung Diseases01978200627.3medium010200
Histoplasma capsulatum Infection01979197945.0low010000
Histoplasmosis01979197945.0low010000

Bioavailability (1)

ArticleYear
Investigating amine derivatives of ambruticin VS-5 and VS-4.
ChemMedChem, , Volume: 3, Issue:6
2008