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ascaroside C3

PubChem CID
44202063
Structure
ascaroside C3_small.png
ascaroside C3_3D_Structure.png
Molecular Formula
Synonyms
  • ascr#5
  • ascaroside C3
  • 1086696-26-5
  • CHEBI:78829
  • 3-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxypropanoic acid
Molecular Weight
220.22 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2009-09-24
  • Modify:
    2024-12-28
Description
Ascr#5 is 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 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-).
ascaroside C3 has been reported in Caenorhabditis elegans with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
ascaroside C3.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxypropanoic acid
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C9H16O6/c1-5-6(10)4-7(11)9(15-5)14-3-2-8(12)13/h5-7,9-11H,2-4H2,1H3,(H,12,13)/t5-,6+,7+,9+/m0/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

RYYMJVGKZLQYPG-YYWONIAYSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

C[C@H]1[C@@H](C[C@H]([C@@H](O1)OCCC(=O)O)O)O
Computed by OEChem 2.1.5 (PubChem release 2019.06.18)

2.2 Molecular Formula

C9H16O6
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 ChEBI ID

2.3.3 ChEMBL ID

2.3.4 DSSTox Substance ID

2.3.5 Lipid Maps ID (LM_ID)

2.3.6 Metabolomics Workbench ID

2.3.7 Nikkaji Number

2.3.8 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
220.22 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
-1.1
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
220.09468823 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
220.09468823 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
96.2Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
15
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
219
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
4
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2010.01.29)

3.2 Chemical Classes

3.2.1 Lipids

Fatty Acyls [FA] -> Fatty acyl glycosides [FA13] -> Ascarosides [FA1304]

5 Chemical Vendors

6 Literature

6.1 Consolidated References

6.2 Chemical Co-Occurrences in Literature

6.3 Chemical-Gene Co-Occurrences in Literature

7 Patents

7.1 Depositor-Supplied Patent Identifiers

7.2 Chemical Co-Occurrences in Patents

7.3 Chemical-Disease Co-Occurrences in Patents

7.4 Chemical-Gene Co-Occurrences in Patents

8 Biological Test Results

8.1 BioAssay Results

9 Taxonomy

WormJam Metabolites Local CSV for MetFrag | DOI:10.5281/zenodo.3403364
WormJam: A consensus C. elegans Metabolic Reconstruction and Metabolomics Community and Workshop Series, Worm, 6:2, e1373939, DOI:10.1080/21624054.2017.1373939
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

10 Classification

10.1 ChEBI Ontology

10.2 LIPID MAPS Classification

10.3 EPA DSSTox Classification

10.4 LOTUS Tree

10.5 MolGenie Organic Chemistry Ontology

11 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  3. ChEBI
  4. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  5. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  6. ECI Group, LCSB, University of Luxembourg
    LICENSE
    Data: CC-BY 4.0; Code: Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    ascr#5
  7. Natural Product Activity and Species Source (NPASS)
    3-[(2R,3R,5R,6S)-3,5-Dihydroxy-6-Methyloxan-2-Yl]Oxypropanoic Acid
    https://bidd.group/NPASS/compound.php?compoundID=NPC320032
  8. Japan Chemical Substance Dictionary (Nikkaji)
  9. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  10. Metabolomics Workbench
  11. Wikidata
  12. PubChem
  13. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS