Reaction participants Show >> << Hide
- Name help_outline IC-asc-C7-AMP Identifier CHEBI:166982 Charge -1 Formula C32H40N6O13P InChIKeyhelp_outline FSZCUKZJWUKCBV-MNMXCXDCSA-M SMILEShelp_outline C(CC[C@H](O[C@@H]1O[C@@H](C)[C@@H](C[C@H]1O)OC(C=2C=3C=CC=CC3NC2)=O)C)CC(OP(OC[C@H]4O[C@@H](N5C=6N=CN=C(N)C6N=C5)[C@@H]([C@@H]4O)O)(=O)[O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline CoA Identifier CHEBI:57287 (Beilstein: 11604429) help_outline Charge -4 Formula C21H32N7O16P3S InChIKeyhelp_outline RGJOEKWQDUBAIZ-IBOSZNHHSA-J SMILEShelp_outline CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCS 2D coordinates Mol file for the small molecule Search links Involved in 1,567 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline IC-asc-C7-CoA Identifier CHEBI:166976 Charge -4 Formula C43H59N8O22P3S InChIKeyhelp_outline JCDSEEFGQRURNN-LRZHQNEJSA-J SMILEShelp_outline C(CC(SCCNC(CCNC(=O)[C@@H](C(COP(OP(OC[C@H]1O[C@@H](N2C3=C(C(=NC=N3)N)N=C2)[C@@H]([C@@H]1OP([O-])([O-])=O)O)(=O)[O-])(=O)[O-])(C)C)O)=O)=O)CC[C@H](O[C@@H]4O[C@@H](C)[C@@H](C[C@H]4O)OC(C=5C=6C=CC=CC6NC5)=O)C 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline AMP Identifier CHEBI:456215 Charge -2 Formula C10H12N5O7P InChIKeyhelp_outline UDMBCSSLTHHNCD-KQYNXXCUSA-L SMILEShelp_outline Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 529 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,932 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:66260 | RHEA:66261 | RHEA:66262 | RHEA:66263 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Related reactions help_outline
More general form(s) of this reaction
Publications
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Biosynthetic tailoring of existing ascaroside pheromones alters their biological function in C. elegans.
Zhou Y., Wang Y., Zhang X., Bhar S., Jones Lipinski R.A., Han J., Feng L., Butcher R.A.
<i>Caenorhabditis elegans</i> produces ascaroside pheromones to control its development and behavior. Even minor structural differences in the ascarosides have dramatic consequences for their biological activities. Here, we identify a mechanism that enables <i>C. elegans</i> to dynamically tailor ... >> More
<i>Caenorhabditis elegans</i> produces ascaroside pheromones to control its development and behavior. Even minor structural differences in the ascarosides have dramatic consequences for their biological activities. Here, we identify a mechanism that enables <i>C. elegans</i> to dynamically tailor the fatty-acid side chains of the indole-3-carbonyl (IC)-modified ascarosides it has produced. In response to starvation, <i>C. elegans</i> uses the peroxisomal acyl-CoA synthetase ACS-7 to activate the side chains of medium-chain IC-ascarosides for β-oxidation involving the acyl-CoA oxidases ACOX-1.1 and ACOX-3. This pathway rapidly converts a favorable ascaroside pheromone that induces aggregation to an unfavorable one that induces the stress-resistant dauer larval stage. Thus, the pathway allows the worm to respond to changing environmental conditions and alter its chemical message without having to synthesize new ascarosides de novo. We establish a new model for biosynthesis of the IC-ascarosides in which side-chain β-oxidation is critical for controlling the type of IC-ascarosides produced. << Less
Elife 7:0-0(2018) [PubMed] [EuropePMC]
This publication is cited by 14 other entries.
Comments
RHEA:66260 part of RHEA:66252