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(2S,3R,4S,5S,6R)-2-(4-Aminophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

PubChem CID
88702
Structure
(2S,3R,4S,5S,6R)-2-(4-Aminophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol_small.png
(2S,3R,4S,5S,6R)-2-(4-Aminophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol_3D_Structure.png
Molecular Formula
Synonyms
  • 20818-25-1
  • 4-Aminophenyl beta-D-glucopyranoside
  • 4-Aminophenyl |A-D-glucopyranoside
  • (2S,3R,4S,5S,6R)-2-(4-Aminophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
  • 4-Aminophenyl-beta-D-glucopyranoside
Molecular Weight
271.27 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2005-08-01
  • Modify:
    2025-01-25

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(2S,3R,4S,5S,6R)-2-(4-Aminophenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
Glc(b)-O-Ph(4-NH2)
IUPAC
(4-aminophenyl) beta-D-gluco-hexopyranoside

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(2S,3R,4S,5S,6R)-2-(4-aminophenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

3.1.2 InChI

InChI=1S/C12H17NO6/c13-6-1-3-7(4-2-6)18-12-11(17)10(16)9(15)8(5-14)19-12/h1-4,8-12,14-17H,5,13H2/t8-,9-,10+,11-,12-/m1/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.3 InChIKey

MIAKOEWBCMPCQR-RMPHRYRLSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.4 SMILES

C1=CC(=CC=C1N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C12H17NO6
Computed by PubChem 2.1 (PubChem release 2019.06.18)

3.3 Other Identifiers

3.3.1 CAS

20818-25-1

3.3.2 European Community (EC) Number

3.3.3 UNII

3.3.4 DSSTox Substance ID

3.3.5 Nikkaji Number

3.3.6 Wikidata

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • 4-aminophenyl glucoside
  • 4-aminophenyl glucoside, (alpha-D)-isomer
  • 4-aminophenyl-beta-D-glucopyranoside
  • p-aminophenyl-beta-D-glucoside
  • PAPB-DG

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
271.27 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3
Property Value
-1
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
7
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
271.10558726 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
271.10558726 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
125 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
19
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
283
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)

6 Chemical Vendors

7 Safety and Hazards

7.1 Hazards Identification

7.1.1 GHS Classification

GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 1 of 1 companies. For more detailed information, please visit ECHA C&L website.

7.1.2 Hazard Classes and Categories

Not Classified

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Springer Nature References

8.4 Nature Journal References

8.5 Chemical Co-Occurrences in Literature

8.6 Chemical-Gene Co-Occurrences in Literature

8.7 Chemical-Disease Co-Occurrences in Literature

9 Patents

9.1 Depositor-Supplied Patent Identifiers

9.2 WIPO PATENTSCOPE

9.3 Chemical Co-Occurrences in Patents

9.4 Chemical-Disease Co-Occurrences in Patents

9.5 Chemical-Gene Co-Occurrences in Patents

10 Classification

10.1 MeSH Tree

10.2 ChemIDplus

10.3 UN GHS Classification

10.4 EPA DSSTox Classification

10.5 MolGenie Organic Chemistry Ontology

11 Information Sources

  1. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  2. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  3. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  4. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  5. Japan Chemical Substance Dictionary (Nikkaji)
  6. Nature Chemistry
  7. Springer Nature
  8. Wikidata
  9. PubChem
  10. 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
  11. GHS Classification (UNECE)
  12. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  13. PATENTSCOPE (WIPO)
CONTENTS