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Bisdemethoxycurcumin

PubChem CID
5315472
Structure
Bisdemethoxycurcumin_small.png
Bisdemethoxycurcumin_3D_Structure.png
Molecular Formula
Synonyms
  • Bisdemethoxycurcumin
  • 33171-05-0
  • 24939-16-0
  • Curcumin III
  • Didemethoxycurcumin
Molecular Weight
308.3 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-18
Description
Bisdemethoxycurcumin is a beta-diketone that is methane in which two of the hydrogens are substituted by 4-hydroxycinnamoyl groups. It has a role as a metabolite and an EC 3.2.1.1 (alpha-amylase) inhibitor. It is a beta-diketone, a polyphenol, an enone and a diarylheptanoid. It is functionally related to a 4-coumaric acid.
Bisdemethoxycurcumin has been reported in Curcuma xanthorrhiza, Curcuma kwangsiensis, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Bisdemethoxycurcumin.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

PREBVFJICNPEKM-YDWXAUTNSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1=CC(=CC=C1/C=C/C(=O)CC(=O)/C=C/C2=CC=C(C=C2)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C19H16O4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

24939-16-0

2.3.2 Deprecated CAS

104024-29-5, 22608-12-4, 85801-92-9, 91884-88-7
104024-29-5, 85801-92-9, 91884-88-7

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 Metabolomics Workbench ID

2.3.10 Nikkaji Number

2.3.11 NSC Number

2.3.12 Pharos Ligand ID

2.3.13 Wikidata

2.3.14 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 1,6-heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-
  • bis(4-hydroxycinnamoyl)methane
  • bisdemethoxy-curcumin
  • bisdemethoxycurcumin

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
308.3 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
3.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
308.10485899 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
308.10485899 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
74.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
23
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
408
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
2
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 Experimental Properties

3.2.1 Physical Description

Solid

3.3 Chemical Classes

3.3.1 Endocrine Disruptors

Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 2
Source of Spectrum
CD-590-0-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
EMC-32-325-VUF9014
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 MS-MS

1 of 2
Spectra ID
Instrument Type
LC-ESI-ITTOF
Ionization Mode
negative
Top 5 Peaks

143.0506 100

187.0366 69.45

119.0507 18.47

145.0343 16.10

144.0523 15.28

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Notes
instrument=LCMS-IT-TOF
2 of 2
NIST Number
1185290
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
309.1121
Total Peaks
27
m/z Top Peak
225
m/z 2nd Highest
147
m/z 3rd Highest
189
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4.1.3 LC-MS

1 of 6
View All
Authors
Ken TANAKA
Instrument
Shimadzu LC20A-IT-TOFMS
Instrument Type
LC-ESI-ITTOF
MS Level
MS
Ionization Mode
POSITIVE
Column Name
Waters Atlantis T3 (2.1 x 150 mm, 5 um)
Retention Time
1278.200 sec
Top 5 Peaks

309.1127 999

310.1166 232

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License
CC BY-SA
2 of 6
View All
Authors
Ken TANAKA
Instrument
Shimadzu LC20A-IT-TOFMS
Instrument Type
LC-ESI-ITTOF
MS Level
MS
Ionization Mode
NEGATIVE
Column Name
Waters Atlantis T3 (2.1 x 150 mm, 5 um)
Retention Time
1261.200 sec
Top 5 Peaks

307.0971 999

308.0987 250

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License
CC BY-SA

4.1.4 Other MS

MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
307.09771609564166
Ionization Mode
negative
Retention Time
4.238934058901076
Top 5 Peaks

119.04914855957031 100

143.04922485351562 31.96

187.03936767578125 9.18

115.05412292480469 2.70

93.0334701538086 2.17

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6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Metabolism / Metabolites

Bisdemethoxycurcumin has known human metabolites that include Bisdemethoxycurcumin, 4-O-glucuronide.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

7.2 Human Metabolite Information

7.2.1 Cellular Locations

Membrane

7.3 Biochemical Reactions

7.4 Transformations

8 Use and Manufacturing

8.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

1 of 2
View All
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Precautionary Statement Codes

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

9.1.2 Hazard Classes and Categories

Skin Irrit. 2 (100%)

Eye Irrit. 2 (100%)

Not Classified

10 Associated Disorders and Diseases

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Chemical Co-Occurrences in Literature

11.5 Chemical-Gene Co-Occurrences in Literature

11.6 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 Chemical Co-Occurrences in Patents

12.3 Chemical-Disease Co-Occurrences in Patents

12.4 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Chemical-Target Interactions

14 Biological Test Results

14.1 BioAssay Results

15 Taxonomy

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

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 ChemIDplus

16.4 ChEMBL Target Tree

16.5 UN GHS Classification

16.6 EPA CPDat Classification

16.7 NORMAN Suspect List Exchange Classification

16.8 EPA DSSTox Classification

16.9 LOTUS Tree

16.10 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. 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
    (1E,6E)-1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione
    https://echa.europa.eu/substance-information/-/substanceinfo/100.356.493
    (1E,6E)-1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione (EC: 881-423-5)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/329421
  5. 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
  6. 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
  7. ChEBI
  8. 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/
  9. 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
  10. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  11. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  12. 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
  13. EPA Chemical and Products Database (CPDat)
  14. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  15. Japan Chemical Substance Dictionary (Nikkaji)
  16. KNApSAcK Species-Metabolite Database
  17. Natural Product Activity and Species Source (NPASS)
  18. MassBank Europe
  19. 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
  20. Metabolomics Workbench
  21. 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/
    Bisdemethoxycurcumin
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  22. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  23. Rhea - Annotated Reactions Database
    LICENSE
    Rhea has chosen to apply the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/). This means that you are free to copy, distribute, display and make commercial use of the database in all legislations, provided you credit (cite) Rhea.
    https://www.rhea-db.org/help/license-disclaimer
  24. SpectraBase
  25. Springer Nature
  26. Wikidata
  27. Wikipedia
  28. PubChem
  29. 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
  30. GHS Classification (UNECE)
  31. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS