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(1R,2S)-3-oxo-2-(5'-O-beta-D-glucopyranosyloxy-2'Z-pentenyl)-cyclopentaneacetic acid

PubChem CID
52922085
Structure
(1R,2S)-3-oxo-2-(5'-O-beta-D-glucopyranosyloxy-2'Z-pentenyl)-cyclopentaneacetic acid_small.png
(1R,2S)-3-oxo-2-(5'-O-beta-D-glucopyranosyloxy-2'Z-pentenyl)-cyclopentaneacetic acid_3D_Structure.png
Molecular Formula
Synonyms
  • Tuberonic acid glucoside
  • (1R,2S)-3-oxo-2-(5'-O-beta-D-glucopyranosyloxy-2'Z-pentenyl)-cyclopentaneacetic acid
  • SCHEMBL5438842
  • LMFA13010032
Molecular Weight
388.4 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2011-06-09
  • Modify:
    2025-01-25

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(1R,2S)-3-oxo-2-(5'-O-beta-D-glucopyranosyloxy-2'Z-pentenyl)-cyclopentaneacetic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[(1R,2S)-3-oxo-2-[(Z)-5-[(2R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypent-2-enyl]cyclopentyl]acetic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

2.1.2 InChI

InChI=1S/C18H28O9/c19-9-13-15(23)16(24)17(25)18(27-13)26-7-3-1-2-4-11-10(8-14(21)22)5-6-12(11)20/h1-2,10-11,13,15-19,23-25H,3-9H2,(H,21,22)/b2-1-/t10-,11+,13-,15?,16?,17?,18-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.3 InChIKey

JFDNMLUPLXZXGV-YXDAKWILSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.4 SMILES

C1CC(=O)[C@H]([C@H]1CC(=O)O)C/C=C\CCO[C@H]2C(C(C([C@H](O2)CO)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C18H28O9
Computed by PubChem 2.1 (PubChem release 2021.05.07)

2.3 Other Identifiers

2.3.1 KEGG ID

2.3.2 Metabolomics Workbench ID

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • tuberonic acid beta-D-glucoside
  • tuberonic acid glucoside

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
388.4 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
-1.2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
388.17333247 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
388.17333247 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
154 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
27
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
535
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
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
3
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
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 2019.01.04)

5 Literature

5.1 Consolidated References

5.2 NLM Curated PubMed Citations

5.3 Chemical Co-Occurrences in Literature

5.4 Chemical-Gene Co-Occurrences in Literature

5.5 Chemical-Disease Co-Occurrences in Literature

6 Patents

6.1 Depositor-Supplied Patent Identifiers

7 Classification

7.1 MeSH Tree

8 Information Sources

  1. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  2. Metabolomics Workbench
  3. PubChem
  4. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
CONTENTS