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CHEBI:141361 - aigialone
| ChEBI ID | CHEBI:141361 |
| ChEBI Name | aigialone |
| Stars | |
| Definition | A furopyran that is 5,6-dihydro-4H-furo[2,3-b]pyran-3(2H)-one which is substituted by hydroxy groups at positions 4 and 5, methyl groups at positions 2 and 5, and a heptyl group at position 6 (the 2R,4R,5S,6R stereoisomer). Isolated from the mangrove fungus Aigialus parvus BCC 5311 and from Phaeoacremonium sp., an endophytic fungus from Senna spectabilis. |
| Last Modified | 8 November 2024 |
| Submitter | R. Stephan |
| Downloads |
| Formula | C16H26O5 |
| Net Charge | 0 |
| Average Mass | 298.379 |
| Monoisotopic Mass | 298.17802 |
| SMILES | CCCCCCC[C@H]1OC2=C(C(=O)[C@@H](C)O2)[C@@H](O)[C@]1(C)O |
| InChI | InChI=1S/C16H26O5/c1-4-5-6-7-8-9-11-16(3,19)14(18)12-13(17)10(2)20-15(12)21-11/h10-11,14,18-19H,4-9H2,1-3H3/t10-,11-,14-,16-/m1/s1 |
| InChIKey | YVCGKKHYXVEPMA-MMYVAXCBSA-N |
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Phaeoacremonium sp. (ncbitaxon:1769363) | - | PubMed (28425292 ) |
| Roles Classification |
|---|
| Biological Roles: | antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. fungal metabolite Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| aigialone (CHEBI:141361) has role antifungal agent (CHEBI:35718) |
| aigialone (CHEBI:141361) has role fungal metabolite (CHEBI:76946) |
| aigialone (CHEBI:141361) is a cyclic ketone (CHEBI:3992) |
| aigialone (CHEBI:141361) is a furopyran (CHEBI:74927) |
| aigialone (CHEBI:141361) is a ketene acetal (CHEBI:145408) |
| aigialone (CHEBI:141361) is a secondary alcohol (CHEBI:35681) |
| aigialone (CHEBI:141361) is a tertiary alcohol (CHEBI:26878) |
| IUPAC Name |
|---|
| (2R,4R,5S,6R)-6-heptyl-4,5-dihydroxy-2,5-dimethyl-5,6-dihydro-4H-furo[2,3-b]pyran-3(2H)-one |
| Synonym | Source |
|---|---|
| (−)-aigialone | KNApSAcK |
| Manual Xrefs | Databases |
|---|---|
| C00043254 | KNApSAcK |
| Registry Numbers | Sources |
|---|---|
| CAS:666735-72-4 | KNApSAcK |
| Citations |
|---|