Basic information
- CAS
1086696-26-5- Standard SMILES
C[C@@H]1O[C@@H](OCCC(=O)O)[C@H](O)C[C@H]1O- InChIKey
RYYMJVGKZLQYPG-YYWONIAYSA-N- Molecular formula
- C9H16O6
- Average molar mass
- 220.22 g/mol
- Monoisotopic mass
- 220.09468823
Overview
Ascr#5 is an -hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of 3-hydroxypropanoic acid with ascarylopyranose (the alpha anomer). A major component of the dauer pheromone of the nematode Caenorhabditis elegans, it synergises with ascr#2 and ascr#3 as a population-density signal to promote entry into an alternate larval stage, the nonfeeding and highly persistent dauer diapause. It has a role as a pheromone and a Caenorhabditis elegans metabolite. It is a monocarboxylic acid and an omega-hydroxy fatty acid ascaroside. It is functionally related to a 3-hydroxypropionic acid. It is a conjugate acid of an ascr#5(1-).
Names & identifiers
- Preferred name
- ascaroside C3
- IUPAC
- 3-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxypropanoic acid
- English name
- 3-(((2R,3R,5R,6S)-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)propanoic acid
- Molecular formula
- C9H16O6
- Molecular weight
- 220.22
Names & synonyms
ascr#51086696-26-5ascaroside C33-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxypropanoic acid3-(((2R,3R,5R,6S)-3,5-Dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)propanoic acid3-[(3,6-dideoxy-alpha-L-arabino-hexopyranosyl)oxy]propanoic acidMLS002460583orb1708055CHEMBL1714874SCHEMBL30163822CHEBI:78829DTXSID001317806
Show more names
Reaxys ID: 22233379Propanoic acid, 3-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-
HMS2200P19HY-N6978LMFA13040005AKOS040740708DA-60179MS-23222SMR001382724CS-0101359
Database identifiers
- CAS
1086696-26-5- PubChem CID
- 44202063
- DTXSID
DTXSID001317806- ChEMBL
CHEMBL1714874- ChEBI
CHEBI:78829- Nikkaji
- J3.560.909A
Properties
Computed structural properties
- XLogP
- -1.1
- Topological polar surface area
- 96.2 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 4
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 219
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Fatty acyl glycosides [FA13] -> Ascarosides [FA1304]
Physicochemical properties
- storage temp.
- 4 °C, · 4°C, protect from light
- solubility
- Soluble in DMSO
- form
- Solid
- color
- White to light yellow
Chemistry & industry
Applications
UsesAscr#5 is a highly conserved ascaroside isolated from Caenorhabditis elegans.
Suppliers11 total
常州市华阳科技有限公司+8615250961469 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
北京秦岭医药科技有限公司010-61241352 18901327973 · [email protected]
career henan chemical co+86-0371-86658258 · [email protected]
海蔚化学86-21-51086038 · [email protected]
爆牛贸易重庆有限公司+86-023-6139-8061 +86-86-13650506873 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
TargetMol中国（陶术生物）15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]
上海阿摩尔生物科技有限公司13370042665 18916960931 · [email protected]
Additional notes
DefinitionChEBI: An omega-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of 3-hydroxypropanoic acid with ascarylopyranose (the alpha anomer). A major component of the dauer pheromone of the nem tode Caenorhabditis elegans, it synergises with ascr#2 and ascr#3 as a population-density signal to promote entry into an alternate larval stage, the nonfeeding and highly persistent dauer diapause.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…