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Myricetin 3-rhamnoside

PubChem CID
5352000
Structure
Myricetin 3-rhamnoside_small.png
Myricetin 3-rhamnoside_3D_Structure.png
Molecular Formula
Synonyms
  • Myricetin 3-rhamnoside
  • MLS000737865
  • Rhamnoside,myricetin-3
  • Myricetin 3-O-L-rhamnoside
  • SMR000528196
Molecular Weight
464.4 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-10
Description
Myricetin 3-rhamnoside has been reported in Mycoacia fuscoatra, Glochidion sphaerogynum, and other organisms with data available.
See also: Myricitrin (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Myricetin 3-rhamnoside.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

5,7-dihydroxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C21H20O12/c1-6-14(26)17(29)18(30)21(31-6)33-20-16(28)13-9(23)4-8(22)5-12(13)32-19(20)7-2-10(24)15(27)11(25)3-7/h2-6,14,17-18,21-27,29-30H,1H3
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

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

2.1.4 SMILES

CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C(=C4)O)O)O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C21H20O12
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 CAS

17912-87-7

2.3.2 ChEMBL ID

2.3.3 DSSTox Substance ID

2.3.4 HMDB ID

2.3.5 Metabolomics Workbench ID

2.3.6 NSC Number

2.3.7 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
464.4 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
0.5
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
8
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
12
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
464.09547607 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
464.09547607 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
207 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
33
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
760
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
5
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

194 - 197 °C

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

Instrument Name
Varian CFT-20
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

Source of Spectrum
O1-60-2561-2
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2.2 LC-MS

1 of 25
View All
Authors
Sawada Y, Matsuda F, and Hirai MY. Plant Science Center, RIKEN
Instrument
TQD, Waters
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10
Precursor m/z
465.41
Top 5 Peaks

319 999

465 634

318 297

464 165

466 111

Thumbnail
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License
CC BY-NC
Reference
Sawada, Y.; Akiyama, K.; Sakata, A.; Kuwahara, A.; Otsuki, H.; Sakurai, T.; Saito, K.; Hirai, M. Y. Widely Targeted Metabolomics Based on Large-Scale MS/MS Data for Elucidating Metabolite Accumulation Patterns in Plants. Plant and Cell Physiology 2008, 50 (1), 37-47. DOI:10.1093/pcp/pcn183
2 of 25
View All
Authors
Sawada Y, Matsuda F, and Hirai MY. Plant Science Center, RIKEN
Instrument
TQD, Waters
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20
Precursor m/z
465.41
Top 5 Peaks

319 999

318 268

147 251

129 179

85 157

Thumbnail
Thumbnail
License
CC BY-NC
Reference
Sawada, Y.; Akiyama, K.; Sakata, A.; Kuwahara, A.; Otsuki, H.; Sakurai, T.; Saito, K.; Hirai, M. Y. Widely Targeted Metabolomics Based on Large-Scale MS/MS Data for Elucidating Metabolite Accumulation Patterns in Plants. Plant and Cell Physiology 2008, 50 (1), 37-47. DOI:10.1093/pcp/pcn183

6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Cellular Locations

  • Cytoplasm
  • Extracellular

9 Literature

9.1 Consolidated References

9.2 Chemical Co-Occurrences in Literature

9.3 Chemical-Gene Co-Occurrences in Literature

9.4 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 WIPO PATENTSCOPE

11 Biological Test Results

11.1 BioAssay Results

12 Taxonomy

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

13 Classification

13.1 NORMAN Suspect List Exchange Classification

13.2 EPA DSSTox Classification

13.3 LOTUS Tree

13.4 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. 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
  2. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  3. 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
  4. EPA DSSTox
    5,7-Dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-3-yl 6-deoxyhexopyranoside
    https://comptox.epa.gov/dashboard/DTXSID60864807
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. FooDB
    LICENSE
    FooDB 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 (FooDB) and the original publication.
    https://foodb.ca/about
  6. 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/
  7. Natural Product Activity and Species Source (NPASS)
    5,7-Dihydroxy-3-(3,4,5-Trihydroxy-6-Methyloxan-2-Yl)Oxy-2-(3,4,5-Trihydroxyphenyl)Chromen-4-One
    https://bidd.group/NPASS/compound.php?compoundID=NPC277174
  8. MassBank Europe
  9. Metabolomics Workbench
    5,7-Dihydroxy-3-(3,4,5-Trihydroxy-6-Methyloxan-2-Yl)Oxy-2-(3,4,5-Trihydroxyphenyl)Chromen-4-One
    https://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=123692
  10. SpectraBase
  11. Wikidata
  12. PubChem
  13. 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/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  14. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  15. PATENTSCOPE (WIPO)
CONTENTS