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salicyluric beta-D-glucuronide

PubChem CID
121596205
Structure
salicyluric beta-D-glucuronide_small.png
salicyluric beta-D-glucuronide_3D_Structure.png
Molecular Formula
Synonyms
  • salicyluric beta-D-glucuronide
  • salicyluric glucuronide
  • Salicyluric-glucuronide
  • CHEBI:133026
  • 1-O-salicyluroyl-beta-D-glucuronic acid
Molecular Weight
371.30 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2016-09-14
  • Modify:
    2025-01-18
Description
Salicyluric beta-D-glucuronide is a carboxylic ester resulting from the formal condensation of the carboxy group of salicyluric acid with the anomeric hydroxy group of beta-D-glucuronic acid. It is a beta-D-glucosiduronic acid and an O-acyl carbohydrate. It is functionally related to a salicyluric acid. It is a conjugate acid of a salicyluric beta-D-glucuronide(1-).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
salicyluric beta-D-glucuronide.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-[(2-hydroxybenzoyl)amino]acetyl]oxyoxane-2-carboxylic acid
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C15H17NO10/c17-7-4-2-1-3-6(7)13(22)16-5-8(18)25-15-11(21)9(19)10(20)12(26-15)14(23)24/h1-4,9-12,15,17,19-21H,5H2,(H,16,22)(H,23,24)/t9-,10-,11+,12-,15+/m0/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

OEPADIDIUZTYOX-QKZHPOIUSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

C1=CC=C(C(=C1)C(=O)NCC(=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C(=O)O)O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H17NO10
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 ChEBI ID

2.3.2 HMDB ID

2.3.3 Metabolomics Workbench ID

2.3.4 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
371.30 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
-0.6
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
6
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
10
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
371.08524574 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
371.08524574 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
183 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
26
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
541
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
5
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 2019.01.04)

3.2 Chemical Classes

3.2.1 Drugs

Pharmaceuticals -> Metabolite of Carbasalate calcium
S113 | SWISSPHARMA24 | 2024 Swiss Pharmaceutical List with Metabolites | DOI:10.5281/zenodo.10501043

5 Associated Disorders and Diseases

Disease
Colorectal cancer
References

PubMed: 7482520, 22148915, 19006102, 23940645, 24424155, 20156336, 19678709, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

6 Literature

6.1 Consolidated References

7 Classification

7.1 ChEBI Ontology

7.2 NORMAN Suspect List Exchange Classification

7.3 MolGenie Organic Chemistry Ontology

8 Information Sources

  1. ChEBI
  2. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
    Salicyluric beta-D-glucuronide
    http://www.hmdb.ca/metabolites/HMDB0240252
  3. Metabolomics Workbench
  4. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Salicyluric-glucuronide
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  5. Wikidata
    (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-[(2-hydroxybenzoyl)amino]acetyl]oxyoxane-2-carboxylic acid
    https://www.wikidata.org/wiki/Q76854664
  6. PubChem
  7. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS