Page last updated: 2024-12-10
australifungin
Description
australifungin: contains a combination of alpha-diketone and beta-ketoaldehyde groups; from Sporormiella australis; inhibits sphinganine N-acyltransferase (ceramide synthetase); structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
australifungin : A carbobicyclic compound that is 4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one substituted by hydroxy groups at positions 2, 5 and 8, a (2Z)-3-hydroxyprop-2-enoyl group at position 4, methyl groups at positions 4 and 7 and a 2R-octan-2-yl group at position 3 (the 4S,4aR,5S,7R,8R,8aS stereoisomer). It is isolated from the fermentation extracts of Sporormiella australis and exhibits antifungal activity by interfering with the fungal lipid metabolism. [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 Source | ID |
|---|
| PubMed CID | 5276375 |
| CHEMBL ID | 512638 |
| CHEBI ID | 65459 |
| SCHEMBL ID | 1229477 |
| MeSH ID | M0248583 |
Synonyms (10)
| Synonym |
|---|
| (4s,4ar,5s,7r,8r,8as)-2,5,8-trihydroxy-4-[(z)-3-hydroxyprop-2-enoyl]-4,7-dimethyl-3-[(2r)-octan-2-yl]-4a,5,6,7,8,8a-hexahydronaphthalen-1-one |
| (4s,4ar,5s,7r,8r,8as)-2,5,8-trihydroxy-4-[(z)-3-hydroxyprop-2-enoyl]-4,7-dimethyl-3-[(1r)-1-methylheptyl]-4a,5,6,7,8,8a-hexahydronaphthalen-1-one |
| australifungin |
| 1(4h)-naphthalenone, 4a,5,6,7,8,8a-hexahydro-2,5,8-trihydroxy-4-[(2z)-3-hydroxy-1-oxo-2-propenyl]-4,7-dimethyl-3-[(1r)-1-methylheptyl]-, (4s,4ar,5s,7r,8r,8as)- |
| chebi:65459 , |
| CHEMBL512638 |
| (4s,4ar,5s,7r,8r,8as)-2,5,8-trihydroxy-4-[(2z)-3-hydroxyprop-2-enoyl]-4,7-dimethyl-3-[(2r)-octan-2-yl]-4a,5,6,7,8,8a-hexahydronaphthalen-1(4h)-one |
| SCHEMBL1229477 |
| bdbm50478534 |
| Q27133902 |
Roles (4)
| Role | Description |
|---|
| metabolite | Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. |
| EC 2.3.1.24 (sphingosine N-acyltransferase) inhibitor | An EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the action of sphingosine N-acyltransferase (EC 2.3.1.24). |
| HIV-1 integrase inhibitor | An inhibitor of HIV-1 integrase, an enzyme required for the integration of the genetic material of the retrovirus into the DNA of the infected cells. |
| antifungal agent | An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. |
| [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 (4)
| Class | Description |
|---|
| enol | Alkenols; the term refers specifically to vinylic alcohols, which have the structure HOCR'=CR2. Enols are tautomeric with aldehydes (R' = H) or ketones (R' =/= H). |
| enone | An alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position. |
| secondary alcohol | A secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it. |
| carbobicyclic compound | A bicyclic compound in which all the ring atoms are carbon. |
| [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 (1)
Inhibition Measurements
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|
| Integrase | Human immunodeficiency virus 1 | IC50 (µMol) | 20.0000 | 0.0005 | 1.5443 | 10.0000 | AID355749 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Research
Studies (8)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 3 (37.50) | 18.2507 |
| 2000's | 3 (37.50) | 29.6817 |
| 2010's | 2 (25.00) | 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] |
Market Indicators
Research Demand Index: 12.12
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.
| Metric | This Compound (vs All) |
|---|
| Research Demand Index | 12.12 (24.57) | | Research Supply Index | 2.30 (2.92) | | Research Growth Index | 4.42 (4.65) | | Search Engine Demand Index | 0.00 (26.88) | | Search Engine Supply Index | 0.00 (0.95) |
| |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (11.11%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 8 (88.89%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |