ascaroside C9
Basic information
- CAS
946524-26-1- Standard SMILES
C[C@H](CCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O- InChIKey
MWGRRKDIJLJLMO-OSYKULTDSA-N- Molecular formula
- C15H26O6
- Average molar mass
- 302.36 g/mol
- Monoisotopic mass
- 302.17293854
Overview
Ascr#3 is an (1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,8R)-8-hydroxynon-2-enoic acid with ascarylopyranose (the alpha anomer). It is a major component of the dauer pheromone, used by the nematode Caenorhabditis elegans as a population-density signal to promote entry into an alternate larval stage, the nonfeeding and highly persistent dauer diapause, and also synergises with ascr#2, ascr#4, and ascr#8 in male attraction. It has a role as a pheromone and a Caenorhabditis elegans metabolite. It is an alpha,beta-unsaturated monocarboxylic acid and an (omega-1)-hydroxy fatty acid ascaroside. It is functionally related to a (2E,8R)-8-hydroxynon-2-enoic acid. It is a conjugate acid of an ascr#3(1-).
Names & identifiers
- Preferred name
- ascaroside C9
- IUPAC
- (E,8R)-8-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxynon-2-enoic acid
- English name
- 2-Nonenoic acid, 8-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-, (2E,8R)-
- Molecular formula
- C15H26O6
- Molecular weight
- 302.37
Names & synonyms
ascr#3946524-26-1ascaroside C9daumone-3(R,E)-8-(((2R,3R,5R,6S)-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)non-2-enoic acid(E,8R)-8-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxynon-2-enoic acid(2E,8R)-8-[(3,6-dideoxy-alpha-L-arabino-hexopyranosyl)oxy]non-2-enoic acid(-)-8R-(Tetrahydro-3'R,5'R-dihydroxy-6'S-methyl-2H-pyran-2'R-yloxy)-2E-nonenoic acidascaroside C9; ascr#3ASCR NO 3MLS002279963orb1708056
Show more names
2-Nonenoic acid, 8-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-, (2E,8R)-
CHEMBL1221889SCHEMBL13935042CHEBI:78821DTXSID501317699HMS2206B12HY-N6977LMFA13040004AKOS040740707
Database identifiers
- CAS
946524-26-1- PubChem CID
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 96.2 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 8
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 343
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Fatty acyl glycosides [FA13] -> Ascarosides [FA1304]
Physicochemical properties
- Boiling point
- 513 · 513.0±50.0 °C(Predicted)
- Density
- 1.18 · 1.18±0.1 g/cm3(Predicted)
- storage temp.
- 4 °C, · 4°C, protect from light
- solubility
- Soluble in DMSO
- pka
- 4.78 · 4.78±0.10(Predicted)
- form
- Oil
- color
- Colorless to light yellow
Chemistry & industry
Applications
UsesAscr#3 is a type of pheromone found in the beautiful nematode, and when mixed with ascr#2, it can act as a male attractant and also induce the formation of dauer (the dormant larval stage). Ascr#3 can counteract the effects caused by male-enriched Ascr#10[1][2].
Additional notes
DefinitionChEBI: Ascr#3 is an (omega-1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,8R)-8-hydroxynon-2-enoic acid with ascarylopyranose (the alpha anomer). It is a major component of the dauer pheromone, used by the nematode Caenorhabditis elegans as a population-density signal to promote entry into an alternate larval stage, the nonfeeding and highly persistent dauer diapause, and also synergises with ascr#2, ascr#4, and ascr#8 in male attraction. It has a role as a Caenorhabditis elegans metabolite and a pheromone. It is an alpha,beta-unsaturated monocarboxylic acid and an (omega-1)-hydroxy fatty acid ascaroside. It is functionally related to a (2E,8R)-8-hydroxynon-2-enoic acid. It is a conjugate acid of an ascr#3(1-).
Related reactions
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Compound notes
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