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Diuvaretin

PubChem CID
3085222
Structure
Diuvaretin_small.png
Diuvaretin_3D_Structure.png
Molecular Formula
Synonyms
  • diuvaretin
  • 61463-04-5
  • 1-[2,4-dihydroxy-3,5-bis[(2-hydroxyphenyl)methyl]-6-methoxyphenyl]-3-phenylpropan-1-one
  • CHEBI:65802
  • 1-Propanone, 1-(2,4-dihydroxy-3,5-bis((2-hydroxyphenyl)methyl)-6-metoxyphenyl)-3-phenyl-
Molecular Weight
484.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-09
  • Modify:
    2025-01-18
Description
Diuvaretin is a member of the class of dihydrochalcones that is dihydrochalcone substituted by 2-hydroxybenzyl groups at positions 3 and 5, hydroxy groups at positions 2 and 4 and a methoxy group at position 6. Isolated from the roots of Uvaria acuminata and Uvaria chamae, it exhibits cytotoxicity towards human promyelocytic leukemia HL-60 cells. It has a role as a metabolite, an antineoplastic agent and an antimalarial. It is a member of dihydrochalcones, a member of resorcinols and a monomethoxybenzene.
Diuvaretin has been reported in Uvaria angolensis, Uvaria acuminata, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Diuvaretin.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[2,4-dihydroxy-3,5-bis[(2-hydroxyphenyl)methyl]-6-methoxyphenyl]-3-phenylpropan-1-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C30H28O6/c1-36-30-23(18-21-12-6-8-14-25(21)32)28(34)22(17-20-11-5-7-13-24(20)31)29(35)27(30)26(33)16-15-19-9-3-2-4-10-19/h2-14,31-32,34-35H,15-18H2,1H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

KDEMELRYKGOXDL-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

COC1=C(C(=C(C(=C1C(=O)CCC2=CC=CC=C2)O)CC3=CC=CC=C3O)O)CC4=CC=CC=C4O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C30H28O6
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

61463-04-5

2.3.2 ChEBI ID

2.3.3 ChEMBL ID

2.3.4 DSSTox Substance ID

2.3.5 Lipid Maps ID (LM_ID)

2.3.6 Metabolomics Workbench ID

2.3.7 Nikkaji Number

2.3.8 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
484.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
6.4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
484.18858861 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
484.18858861 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
107 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
36
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
678
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
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
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 2021.10.14)

3.2 Chemical Classes

3.2.1 Lipids

Polyketides [PK] -> Flavonoids [PK12] -> Chalcones and dihydrochalcones [PK1212]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

1 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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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

1 of 2
Source of Spectrum
X2-48-579-2
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
Y1-32-1051-2
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Literature

7.1 Consolidated References

7.2 Chemical Co-Occurrences in Literature

7.3 Chemical-Gene Co-Occurrences in Literature

7.4 Chemical-Disease Co-Occurrences in Literature

8 Patents

8.1 Depositor-Supplied Patent Identifiers

9 Biological Test Results

9.1 BioAssay Results

10 Taxonomy

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

11 Classification

11.1 ChEBI Ontology

11.2 LIPID MAPS Classification

11.3 ChemIDplus

11.4 EPA DSSTox Classification

11.5 LOTUS Tree

11.6 MolGenie Organic Chemistry Ontology

12 Information Sources

  1. ChEBI
  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. 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
  4. ChemIDplus
    1-Propanone, 1-(2,4-dihydroxy-3,5-bis((2-hydroxyphenyl)methyl)-6-metoxyphenyl)-3-phenyl-
    https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0061463045
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  5. EPA DSSTox
    1-Propanone, 1-(2,4-dihydroxy-3,5-bis((2-hydroxyphenyl)methyl)-6-metoxyphenyl)-3-phenyl-
    https://comptox.epa.gov/dashboard/DTXSID20210407
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. Japan Chemical Substance Dictionary (Nikkaji)
  7. KNApSAcK Species-Metabolite Database
  8. Natural Product Activity and Species Source (NPASS)
  9. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  10. Metabolomics Workbench
  11. SpectraBase
  12. Wikidata
  13. PubChem
  14. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS