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]
ID Source | ID |
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PubMed CID | 23636677 |
CHEMBL ID | 4074181 |
CHEBI ID | 83125 |
MeSH ID | M0059934 |
Synonym |
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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 |
Excerpt | Relevance | Reference |
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" 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 |
Role | Description |
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siderophore | Any 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] |
Class | Description |
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hydroxamic acid | A 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 ester | An ester of a carboxylic acid, R(1)C(=O)OR(2), where R(1) = H or organyl and R(2) = organyl. |
primary alcohol | A 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. |
acetamides | Compounds with the general formula RNHC(=O)CH3. |
2,5-diketopiperazines | Any piperazinone that has a piperazine-2,5-dione skeleton. |
homoallylic alcohol | An 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] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1483624 | Cytotoxicity against human SW620 cells assessed as reduction in cell viability up to 30 uM after 68 hrs by MTT assay | 2017 | Journal 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). |
AID1483619 | Growth inhibition of Pseudomonas aeruginosa ATCC 27853 after 24 by broth micro-dilution method | 2017 | Journal 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). |
AID1483625 | Cytotoxicity against human NCI-H460 cells assessed as reduction in cell viability up to 30 uM after 68 hrs by MTT assay | 2017 | Journal 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). |
AID1483622 | Metal 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 spectrophotometry | 2017 | Journal 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). |
AID1483620 | Growth inhibition of Candida albicans ATCC 90028 after 48 by broth micro-dilution method | 2017 | Journal 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). |
AID1483617 | Growth inhibition of Staphylococcus aureus ATCC 25923 after 24 by broth micro-dilution method | 2017 | Journal 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). |
AID1483621 | Metal 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 spectrophotometry | 2017 | Journal 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). |
AID1483623 | Cytotoxicity against human KB-3-1 cells assessed as reduction in cell viability up to 30 uM after 68 hrs by MTT assay | 2017 | Journal 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). |
AID1483618 | Growth inhibition of Escherichia coli ATCC 25922 after 24 by broth micro-dilution method | 2017 | Journal 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] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 1 (9.09) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 2 (18.18) | 29.6817 |
2010's | 8 (72.73) | 24.3611 |
2020's | 0 (0.00) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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.
| This Compound (12.49) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 11 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |