Compounds > n(alpha)-acetylfusarinines
Page last updated: 2024-11-13

n(alpha)-acetylfusarinines

Description

N(alpha)-acetylfusarinines: group of naturally occurring hydroxamic acids produced by unidentified species of Penicillium when grown on iron deficient media; monohydroxamate more active than trimer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

desferricoprogen : A member of the class of 2,5-diketopiperazines that is 2,5-diketopiperazine which is substituted at positions 3 and 6 by 3-(hydroxyamino)propyl groups in which the nitrogens have been acylated by (2E)-5-hydroxy-3-methylpent-2-enoyl groups. The substituent at position 3 has been further modified by having its terminal hydroxy group esterified by condensation with the carboxy group of N(2)-acetyl-N(5)-hydroxy-L-ornithine in which the N(5) nitrogen has been acylated by a (2E)-5-hydroxy-3-methylpent-2-enoyl group. [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 CID23636677
CHEMBL ID4074181
CHEBI ID83125
MeSH IDM0059934

Synonyms (16)

Synonym
n-alpha-acetylfusarinines
l-ornithine, n2-acetyl-n5-hydroxy-n5-(5-hydroxy-3-methyl-1-oxo-2-pentenyl)-, 5-(hydroxy(3-(5-(3-(hydroxy(5-hydroxy-3-methyl-1-oxo-2-pentenyl)amino)propyl)-3,6-dioxo-2-piperazinyl)propyl)amino)-3-methyl-5-oxo-3-pentenyl ester, (n5(e),1(2s-(2alpha(e),5alpha
kj1hg53l71 ,
nalpha-acetylfusarinines
30315-65-2
unii-kj1hg53l71
n(alpha)-acetylfusarinines
desferricoprogen
desferricoprogen [mi]
deferricoprogen
(3e)-5-(hydroxy{3-[(2s,5s)-5-(3-{hydroxy[(2e)-5-hydroxy-3-methylpent-2-enoyl]amino}propyl)-3,6-dioxopiperazin-2-yl]propyl}amino)-3-methyl-5-oxopent-3-en-1-yl n(2)-acetyl-n(5)-hydroxy-n(5)-[(2e)-5-hydroxy-3-methylpent-2-enoyl]-l-ornithinate
CHEBI:83125
Q27156652
(e)-5-((3-((2s,5s)-5-(3-((e)-n,5-dihydroxy-3-methylpent-2-enamido)propyl)-3,6-dioxopiperazin-2-yl)propyl)(hydroxy)amino)-3-methyl-5-oxopent-3-en-1-yl (s)-2-acetamido-5-((e)-n,5-dihydroxy-3-methylpent-2-enamido)pentanoate
[(e)-5-[hydroxy-[3-[(2s,5s)-5-[3-[hydroxy-[(e)-5-hydroxy-3-methylpent-2-enoyl]amino]propyl]-3,6-dioxopiperazin-2-yl]propyl]amino]-3-methyl-5-oxopent-3-enyl] (2s)-2-acetamido-5-[hydroxy-[(e)-5-hydroxy-3-methylpent-2-enoyl]amino]pentanoate
CHEMBL4074181

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" In similar dose-response fashion, these siderophores also inhibited the generation of LDL products cytotoxic to human vascular endothelium."( Fungal siderophores function as protective agents of LDL oxidation and are promising anti-atherosclerotic metabolites in functional food.
Balla, G; Balla, J; Emri, T; Fésüs, L; Gyémánt, G; Jeney, V; Kertai, P; Pócsi, I, 2008)		0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
siderophoreAny of low-molecular-mass iron(III)-chelating compounds produced by microorganisms for the purpose of the transport and sequestration of iron.
[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 (6)

ClassDescription
hydroxamic acidA compound, RkE(=O)lNHOH, derived from an oxoacid RkE(=O)l(OH) (l =/= 0) by replacing -OH with -NHOH, and derivatives thereof. Specific examples of hydroxamic acids are preferably named as N-hydroxy amides.
carboxylic esterAn ester of a carboxylic acid, R(1)C(=O)OR(2), where R(1) = H or organyl and R(2) = organyl.
primary alcoholA primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.
acetamidesCompounds with the general formula RNHC(=O)CH3.
2,5-diketopiperazinesAny piperazinone that has a piperazine-2,5-dione skeleton.
homoallylic alcoholAn aliphatic alcohol where the hydroxy carbon is beta to a double bond.
[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]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID1483624Cytotoxicity against human SW620 cells assessed as reduction in cell viability up to 30 uM after 68 hrs by MTT assay2017Journal of natural products, 03-24, Volume: 80, Issue:3
Talarazines A-E: Noncytotoxic Iron(III) Chelators from an Australian Mud Dauber Wasp-Associated Fungus, Talaromyces sp. (CMB-W045).
AID1483619Growth inhibition of Pseudomonas aeruginosa ATCC 27853 after 24 by broth micro-dilution method2017Journal of natural products, 03-24, Volume: 80, Issue:3
Talarazines A-E: Noncytotoxic Iron(III) Chelators from an Australian Mud Dauber Wasp-Associated Fungus, Talaromyces sp. (CMB-W045).
AID1483625Cytotoxicity against human NCI-H460 cells assessed as reduction in cell viability up to 30 uM after 68 hrs by MTT assay2017Journal of natural products, 03-24, Volume: 80, Issue:3
Talarazines A-E: Noncytotoxic Iron(III) Chelators from an Australian Mud Dauber Wasp-Associated Fungus, Talaromyces sp. (CMB-W045).
AID1483622Metal chelating activity of the compound assessed as fluorescence recovery of calcein-Fe3 complex formation up to 40 uM measured after overnight incubation by CAFe based fluorescence spectrophotometry2017Journal of natural products, 03-24, Volume: 80, Issue:3
Talarazines A-E: Noncytotoxic Iron(III) Chelators from an Australian Mud Dauber Wasp-Associated Fungus, Talaromyces sp. (CMB-W045).
AID1483620Growth inhibition of Candida albicans ATCC 90028 after 48 by broth micro-dilution method2017Journal of natural products, 03-24, Volume: 80, Issue:3
Talarazines A-E: Noncytotoxic Iron(III) Chelators from an Australian Mud Dauber Wasp-Associated Fungus, Talaromyces sp. (CMB-W045).
AID1483617Growth inhibition of Staphylococcus aureus ATCC 25923 after 24 by broth micro-dilution method2017Journal of natural products, 03-24, Volume: 80, Issue:3
Talarazines A-E: Noncytotoxic Iron(III) Chelators from an Australian Mud Dauber Wasp-Associated Fungus, Talaromyces sp. (CMB-W045).
AID1483621Metal chelating activity of the compound assessed as fluorescence recovery of calcein-Fe3 complex formation up to 10 uM measured after overnight incubation by CAFe based fluorescence spectrophotometry2017Journal of natural products, 03-24, Volume: 80, Issue:3
Talarazines A-E: Noncytotoxic Iron(III) Chelators from an Australian Mud Dauber Wasp-Associated Fungus, Talaromyces sp. (CMB-W045).
AID1483623Cytotoxicity against human KB-3-1 cells assessed as reduction in cell viability up to 30 uM after 68 hrs by MTT assay2017Journal of natural products, 03-24, Volume: 80, Issue:3
Talarazines A-E: Noncytotoxic Iron(III) Chelators from an Australian Mud Dauber Wasp-Associated Fungus, Talaromyces sp. (CMB-W045).
AID1483618Growth inhibition of Escherichia coli ATCC 25922 after 24 by broth micro-dilution method2017Journal of natural products, 03-24, Volume: 80, Issue:3
Talarazines A-E: Noncytotoxic Iron(III) Chelators from an Australian Mud Dauber Wasp-Associated Fungus, Talaromyces sp. (CMB-W045).
[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-19901 (9.09)18.7374
1990's0 (0.00)18.2507
2000's2 (18.18)29.6817
2010's8 (72.73)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.49

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 Index12.49 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.97 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.49)

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
deferoxamine
Deferoxamine: Natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form.. desferrioxamine B : An acyclic desferrioxamine that is butanedioic acid in which one of the carboxy groups undergoes formal condensation with the primary amino group of N-(5-aminopentyl)-N-hydroxyacetamide and the second carboxy group undergoes formal condensation with the hydroxyamino group of N(1)-(5-aminopentyl)-N(1)-hydroxy-N(4)-[5-(hydroxyamino)pentyl]butanediamide. It is a siderophore native to Streptomyces pilosus biosynthesised by the DesABCD enzyme cluster as a high affinity Fe(III) chelator.		2.7630acyclic desferrioxaminebacterial metabolite;
ferroptosis inhibitor;
iron chelator;
siderophore
oxidopamine
Oxidopamine: A neurotransmitter analogue that depletes noradrenergic stores in nerve endings and induces a reduction of dopamine levels in the brain. Its mechanism of action is related to the production of cytolytic free-radicals.. oxidopamine : A benzenetriol that is phenethylamine in which the hydrogens at positions 2, 4, and 5 on the phenyl ring are replaced by hydroxy groups. It occurs naturally in human urine, but is also produced as a metabolite of the drug DOPA (used for the treatment of Parkinson's disease).		2.5320benzenetriol;
catecholamine;
primary amino compound		drug metabolite;
human metabolite;
neurotoxin
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.		2.07101,3-oxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
chromium
Chromium: A trace element that plays a role in glucose metabolism. It has the atomic symbol Cr, atomic number 24, and atomic weight 52. According to the Fourth Annual Report on Carcinogens (NTP85-002,1985), chromium and some of its compounds have been listed as known carcinogens.. chromium ion : An chromium atom having a net electric charge.. chromium atom : A chromium group element atom that has atomic number 24.		2.420chromium group element atom;
metal allergen		micronutrient
ferrioxamine e
ferrioxamine E: structure. ferrioxamine E : An Fe(III)-complexed hydroxamate siderophore consisting of norcardamine (desferrioxamine E) complexed to iron(III).		2.0710
rhodotorulic acid
rhodotorulic acid: RN given refers to (1S-cis)-isomer; structure. rhodotorulic acid : A member of the class of 2,5-diketopiperazines obtained by cyclodimerisation of N(5)-acetyl-N(5)-hydroxy-L-ornithine.		2.07102,5-diketopiperazines;
hydroxamic acid;
L-ornithine derivative		fungal metabolite;
siderophore
lead
Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.		2.0410carbon group element atom;
elemental lead;
metal atom		neurotoxin
dimerum acid
dimerum acid: structure		2.1310
acinetobactin
acinetobactin: structurally related to anguibactin; isolated from Acinetobacter baumannii; structure given in first source		2.0710
citrinin
Citrinin: Antibiotic and mycotoxin from Aspergillus niveus and Penicillium citrinum.		2.0710
ferricrocin
ferricrocin: close structural analog of ferrichrome, mediating iron uptake with same rate. ferricrocin : A member of the class of ferrichromes that is an iron(III) chelate of the homodetic cyclic hexapeptide cyclo(glycyl-L-serylglycyl-N(5)-acetyl-N(5)-hydroxy-L-ornithyl-N(5)-acetyl-N(5)-hydroxy-L-ornithyl-N(5)-acetyl-N(5)-hydroxy-L-ornithyl).		1.9610
coprogen
coprogen: siderochrome found in Penicillium & Neurospora; structure. coprogen : An iron(III) hydroxamate isolated from fungi and bacteria including Penicillium species and Neurospora crassa. It is a growth factor for coprophilous fungi.		2.7130Fe(III)-complexed hydroxamate siderophore;
homoallylic alcohol		Penicillium metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Aspergilloses, Bronchopulmonary
[description not available]		02.0710
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.0710
Pulmonary Aspergillosis
Infections of the respiratory tract with fungi of the genus ASPERGILLUS.		02.0710
Iron Overload
An excessive accumulation of iron in the body due to a greater than normal absorption of iron from the gastrointestinal tract or from parenteral injection. This may arise from idiopathic hemochromatosis, excessive iron intake, chronic alcoholism, certain types of refractory anemia, or transfusional hemosiderosis. (From Churchill's Illustrated Medical Dictionary, 1989)		02.2110
Atherogenesis
[description not available]		02.0410
Atherosclerosis
A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.		02.0410
Idiopathic Parkinson Disease
[description not available]		02.1310
Parkinson Disease
A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)		02.1310
Kidney Diseases
Pathological processes of the KIDNEY or its component tissues.		02.0710
chemdatabank.com