Page last updated: 2024-12-11

ambruticin

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

Description

ambruticin: cyclopropyl-polyene-pyran acid from Polyangium cellulosum var. fulvum; RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ambruticin S: antifungal from myxobacterium Polyangium cellulosum; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	6436037
MeSH ID	M0063892
PubMed CID	6918547
CHEMBL ID	522783
SCHEMBL ID	397001
MeSH ID	M0063892

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

Research Excerpts

Overview

Ambruticins are a family of polyketides.

Excerpt	Reference	Relevance
"Ambruticins are a family of polyketides. "	( Efficacy of ambruticin analogs in a murine model of invasive pulmonary aspergillosis. Chiang, LY; Ejzykowicz, DE; Filler, SG; Katz, L; Tian, ZQ, 2006)	2.16

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (11)

Assay ID	Title	Year	Journal	Article
AID1134945	Antifungal activity against Microsporum fulvum assessed as growth inhibition by standard broth dilution method	1979	Journal of medicinal chemistry, Sep, Volume: 22, Issue:9	Antifungal agents. 4. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. Ester and amide analogues of ambruticin.
AID1134946	Antifungal activity against Streptococcus pyogenes assessed as growth inhibition by standard broth dilution method	1979	Journal of medicinal chemistry, Sep, Volume: 22, Issue:9	Antifungal agents. 4. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. Ester and amide analogues of ambruticin.
AID1134944	Antifungal activity against Histoplasma capsulatum assessed as growth inhibition by standard broth dilution method	1979	Journal of medicinal chemistry, Sep, Volume: 22, Issue:9	Antifungal agents. 4. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. Ester and amide analogues of ambruticin.
AID417426	Elevation of Hog1 phosphorylation Saccharomyces cerevisiae ATCC 201388 carrying pYES2-HIK1 at 25 ppm after 4 hrs in SD/-Ura medium by Western blot analysis	2007	Antimicrobial agents and chemotherapy, Oct, Volume: 51, Issue:10	The antifungal polyketide ambruticin targets the HOG pathway.
AID1134909	Antifungal activity against Candida albicans by standard broth dilution technique	1979	Journal of medicinal chemistry, Sep, Volume: 22, Issue:9	Antifungal agents. 5. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. Alcohol, ketone, aldehyde, and oxime analogues of ambruticin.
AID1134910	Antifungal activity against Histoplasma capsulatum assessed as growth inhibition after 3 days by standard broth dilution technique	1979	Journal of medicinal chemistry, Sep, Volume: 22, Issue:9	Antifungal agents. 5. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. Alcohol, ketone, aldehyde, and oxime analogues of ambruticin.
AID1134908	Antibacterial activity against Streptococcus pyogenes by standard broth dilution technique	1979	Journal of medicinal chemistry, Sep, Volume: 22, Issue:9	Antifungal agents. 5. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. Alcohol, ketone, aldehyde, and oxime analogues of ambruticin.
AID1134947	Antifungal activity against Candida albicans assessed as growth inhibition by standard broth dilution method	1979	Journal of medicinal chemistry, Sep, Volume: 22, Issue:9	Antifungal agents. 4. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. Ester and amide analogues of ambruticin.
AID417427	Elevation of Hog1 phosphorylation Saccharomyces cerevisiae ATCC 201388 carrying pYES2 at 25 ppm after 4 hrs in SD/-Ura medium by Western blot analysis	2007	Antimicrobial agents and chemotherapy, Oct, Volume: 51, Issue:10	The antifungal polyketide ambruticin targets the HOG pathway.
AID1134911	Antifungal activity against Microsporum fulvum assessed as growth inhibition after 3 days by standard broth dilution technique	1979	Journal of medicinal chemistry, Sep, Volume: 22, Issue:9	Antifungal agents. 5. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. Alcohol, ketone, aldehyde, and oxime analogues of ambruticin.
AID417300	Elevation of Hog1 phosphorylation Saccharomyces cerevisiae ATCC 201388 carrying deltahog1 gene at 25 ppm after 4 hrs in SD/-Ura medium by Western blot analysis	2007	Antimicrobial agents and chemotherapy, Oct, Volume: 51, Issue:10	The antifungal polyketide ambruticin targets the HOG pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (30)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	5 (16.67)	18.7374
1990's	3 (10.00)	18.2507
2000's	14 (46.67)	29.6817
2010's	5 (16.67)	24.3611
2020's	3 (10.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.97

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.

Metric	This Compound (vs All)
Research Demand Index	21.97 (24.57)
Research Supply Index	3.43 (2.92)
Research Growth Index	4.82 (4.65)
Search Engine Demand Index	21.17 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (21.97)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Trials	0 (0.00%)	5.53%
Reviews	2 (6.67%)	6.00%
Reviews	1 (20.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Observational	0 (0.00%)	0.25%
Other	28 (93.33%)	84.16%
Other	4 (80.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	2.42	2	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	1.97	1	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	1.97	1	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	1.96	1	amino 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
cyclopropane cyclopropane : A cycloalkane composed of three carbon atoms to form a ring.	7.47	2	cycloalkane; cyclopropanes	inhalation anaesthetic
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	2.46	2	pyrrole; secondary amine
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	3.12	1	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	3.12	1
alkenes [no description available]	4.05	4
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	1.97	1	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
fludioxonil fludioxonil: structure in first source. fludioxonil : A member of the class of benzodioxoles that is 2,2-difluoro-1,3-benzodioxole substituted at position 4 by a 3-cyanopyrrol-4-yl group. A fungicide seed treatment for control of a range of diseases including Fusarium, Rhizoctonia and Alternaria.	2.46	2	benzodioxoles; nitrile; organofluorine compound; pyrroles	androgen antagonist; antifungal agrochemical; estrogen receptor agonist
alprostadil [no description available]	3.12	1	prostaglandins E	anticoagulant; human metabolite; platelet aggregation inhibitor; vasodilator agent
amphotericin b Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.	1.95	1	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
macbecin i macbecin I: from Norcardia sp. No. C-14919; belongs to ansamycin group of antibiotics; RN given refers to (6S,15R)-isomer; structure in second source	1.98	1
fr 901464 FR 901464: isolated from Pseudomonas; structure in first source	3.12	1
fostriecin fostriecin: compound contains a conjugated triene and an unsaturated lactone; from Streptomyces pulveraceus; structure given in second source. fostriecin : A structurally unique, naturally-occurring phosphate monoester isolated from the soil bacterium Streptomyces pulveraceus. It inhibits DNA topoisomerase II as well as several protein phosphatase including PP2A and PPA4, and exhibits potent antitumor activity against several cancer cell lines.	3.12	1	2-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
vinclozolin vinclozolin : A racemate comprising equimolar amounts of (R)- and (S)-vinclozolin. A fungicide used mainly on oilseed rape, vines, fruit and vegetables to control Botrytis, Sclerotinia and Monilia spp.. 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione : A member of the class of oxazolidinones that is 5-ethenyl-5-methyl-2,4-oxazolidinedione in which the imide hydrogen is replaced by a 3,5-dichlorophenyl group.	2.03	1	dicarboximide; dichlorobenzene; olefinic compound; oxazolidinone
fludioxonil fludioxonil: structure in first source. fludioxonil : A member of the class of benzodioxoles that is 2,2-difluoro-1,3-benzodioxole substituted at position 4 by a 3-cyanopyrrol-4-yl group. A fungicide seed treatment for control of a range of diseases including Fusarium, Rhizoctonia and Alternaria.	2.03	1	benzodioxoles; nitrile; organofluorine compound; pyrroles	androgen antagonist; antifungal agrochemical; estrogen receptor agonist

Condition	Relationship Strength	Studies
Dehydration The condition that results from excessive loss of water from a living organism.	3.52	4
Aspergillus Infection [description not available]	2.03	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.43	2
Fungal Lung Diseases [description not available]	2.68	3
Aspergillosis Infections with fungi of the genus ASPERGILLUS.	7.03	1
Coccidioides immitis Infection [description not available]	2.38	2
Coccidioidomycosis Infection with a fungus of the genus COCCIDIOIDES, endemic to the SOUTHWESTERN UNITED STATES. It is sometimes called valley fever but should not be confused with RIFT VALLEY FEVER. Infection is caused by inhalation of airborne, fungal particles known as arthroconidia, a form of FUNGAL SPORES. A primary form is an acute, benign, self-limited respiratory infection. A secondary form is a virulent, severe, chronic, progressive granulomatous disease with systemic involvement. It can be detected by use of COCCIDIOIDIN.	2.38	2
Histoplasma capsulatum Infection [description not available]	1.95	1
Histoplasmosis Infection resulting from exposure to the fungus HISTOPLASMA. It is worldwide in distribution and particularly common in the central and eastern states, especially areas around the Ohio and Mississippi River valleys.	1.95	1

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