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5-Hydroxy-2-(4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one

PubChem CID
12304405
Structure
5-Hydroxy-2-(4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one_small.png
Molecular Formula
Synonyms
  • 5-hydroxy-2-(4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
  • Poncirenin
  • (2S)-Poncirenin
Molecular Weight
448.4 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2007-02-07
  • Modify:
    2025-01-11
Description
Isosakuranin has been reported in Prunus cerasoides with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
5-Hydroxy-2-(4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one.png

1.2 3D Status

Conformer generation is disallowed since too many undefined stereo centers

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-hydroxy-2-(4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C22H24O10/c1-29-11-4-2-10(3-5-11)15-8-14(25)18-13(24)6-12(7-16(18)31-15)30-22-21(28)20(27)19(26)17(9-23)32-22/h2-7,15,17,19-24,26-28H,8-9H2,1H3
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

KEEWIHDTSNESJZ-UHFFFAOYSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

COC1=CC=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C22H24O10
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 CAS

491-69-0

2.3.2 HMDB ID

2.3.3 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
448.4 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
0.9
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
10
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
448.13694696 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
448.13694696 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
155 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
32
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
638
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
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
6
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 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Melting Point

214 °C

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 MS-MS

1 of 6
View All
Spectra ID
Instrument Type
LC-ESI-TOF
Ionization Mode
negative
Top 5 Peaks

285.0771 100

286.0798 15.62

287.0815 1.40

270.0541 0.50

243.0645 0.40

Thumbnail
Thumbnail
Notes
instrument=impact HD
2 of 6
View All
Spectra ID
Instrument Type
LC-ESI-TOF
Ionization Mode
negative
Top 5 Peaks

285.0638 100

286.0673 7.31

243.0501 0.70

270.0429 0.60

285.1056 0.50

Thumbnail
Thumbnail
Notes
instrument=impact HD

4.1.2 LC-MS

1 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
447.1
Instrument
impact HD
Instrument Type
LC-ESI-TOF
Ionization
ESI
Ionization Mode
negative
Collision Energy
40
Retention Time
603
Top 5 Peaks

285.0795 100

286.0823 15.92

270.0551 12.81

241.0883 9.41

243.0678 9.41

Thumbnail
Thumbnail
License
License CC-BY-NC-SA 4.0 International
2 of 3
View All
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
447.1
Instrument
impact HD
Instrument Type
LC-ESI-TOF
Ionization
ESI
Ionization Mode
negative
Collision Energy
50
Retention Time
603
Top 5 Peaks

285.0789 100

164.0125 56.86

151.0047 45.55

243.0679 36.74

270.0555 30.43

Thumbnail
Thumbnail
License
License CC-BY-NC-SA 4.0 International

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Human Metabolite Information

7.1.1 Cellular Locations

  • Cytoplasm
  • Extracellular

8 Literature

8.1 Consolidated References

8.2 Chemical Co-Occurrences in Literature

8.3 Chemical-Gene Co-Occurrences in Literature

8.4 Chemical-Disease Co-Occurrences in Literature

9 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

10 Classification

10.1 LOTUS Tree

10.2 MolGenie Organic Chemistry Ontology

11 Information Sources

  1. 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
  2. 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/
  3. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  4. Wikidata
  5. PubChem
  6. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS