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Alpha-Naphthoflavone

PubChem CID
11790
Structure
Alpha-Naphthoflavone_small.png
Alpha-Naphthoflavone_3D_Structure.png
Alpha-Naphthoflavone__Crystal_Structure.png
Molecular Formula
Synonyms
  • alpha-Naphthoflavone
  • 7,8-Benzoflavone
  • 604-59-1
  • 2-Phenyl-4H-benzo[h]chromen-4-one
  • 2-phenylbenzo[h]chromen-4-one
Molecular Weight
272.3 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-18
Description
Alpha-naphthoflavone is an extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14). It has a role as an EC 1.14.14.14 (aromatase) inhibitor, an aryl hydrocarbon receptor antagonist and an aryl hydrocarbon receptor agonist. It is an organic heterotricyclic compound, an extended flavonoid and a naphtho-gamma-pyrone.
alpha-Naphthoflavone has been reported in Rhaponticum repens with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Alpha-Naphthoflavone.png

1.2 3D Conformer

1.3 Crystal Structures

COD Number
Associated Article
Panneerselvam, K.; Soriano-García, M.. α-Naphthoflavone. Acta Crystallographica Section C 1995;51(7):1418-1420. DOI: 10.1107/S0108270195000680
Crystal Structure Depiction
Crystal Structure Depiction
Hermann-Mauguin space group symbol
P b c a
Hall space group symbol
-P 2ac 2ab
Space group number
61
a
14.788 Å
b
7.470 Å
c
24.188 Å
α
90.00 °
β
90.00 °
γ
90.00 °
Z
8
Z'
1
Residual factor
0.0500
Weighted residual factor
0.1034

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-phenylbenzo[h]chromen-4-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C19H12O2/c20-17-12-18(14-7-2-1-3-8-14)21-19-15-9-5-4-6-13(15)10-11-16(17)19/h1-12H
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C4=CC=CC=C4C=C3
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C19H12O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DrugBank 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 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 7,8-benzoflavone
  • alpha-naphthoflavone

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
272.3 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
4.8
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
272.083729621 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
272.083729621 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
26.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
21
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
433
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 Experimental Properties

3.2.1 Physical Description

Solid; [Sigma-Aldrich MSDS]

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Other Uses -> Biochemical Research

3.4.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

3.4.2 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 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian A-60
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
N1801
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
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 6
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

170.0 99.99

272.0 97.50

114.0 55.80

273.0 21.30

122.0 14.20

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Notes
instrument=JEOL JMS-06-H
2 of 6
View All
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
JEOL JMS-06-H
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

170 99.99

272 97.50

114 55.80

273 21.30

122 14.20

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License
CC BY-NC-SA

4.2.2 MS-MS

1 of 6
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

273.0923 100

194.9573 7.30

143.0453 6.98

Thumbnail
Thumbnail
2 of 6
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

273.0881 100

164.9459 9.27

Thumbnail
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4.2.3 LC-MS

1 of 7
View All
Authors
Cuthbertson DJ, Johnson SR, Lange BM, Institute of Biological Chemistry, Washington State University
Instrument
Agilent 1200 RRLC; Agilent 6520 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Collision Energy
10 ev
Column Name
Agilent C8 Cartridge Column 2.1X30mm 3.5 micron (guard); Agilent SB-Aq 2.1x50mm 1.8 micron (analytical)
Retention Time
10.364
Precursor m/z
273.091
Precursor Adduct
[M+H]+
Top 5 Peaks

273.0923 999

194.9573 73

143.0453 70

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License
CC BY-SA
2 of 7
View All
Authors
Cuthbertson DJ, Johnson SR, Lange BM, Institute of Biological Chemistry, Washington State University
Instrument
Agilent 1200 RRLC; Agilent 6520 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Collision Energy
20 ev
Column Name
Agilent C8 Cartridge Column 2.1X30mm 3.5 micron (guard); Agilent SB-Aq 2.1x50mm 1.8 micron (analytical)
Retention Time
10.364
Precursor m/z
273.091
Precursor Adduct
[M+H]+
Top 5 Peaks

273.0881 999

164.9459 93

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Thumbnail
License
CC BY-SA

4.2.4 Other MS

Authors
TAKATORI M, DEPT. OF CHEMISTRY, FAC. OF EDUC., FUKUSHIMA UNIV.
Instrument
JEOL JMS-06-H
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 75 eV
Top 5 Peaks

170 999

272 975

114 558

273 213

122 142

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License
CC BY-NC-SA

4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
Mull
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
N1801
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3.2 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Film (MeCl2) (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Indofine Chemical Company, Inc.
Catalog Number
B-003
Lot Number
206160
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Sample
Aldrich
Catalog Number
N1801
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.3 Vapor Phase IR Spectra

Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4 Raman Spectra

1 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Indofine Chemical Company, Inc.
Catalog Number
B-003
Lot Number
0206160
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories
Source of Sample
Sigma-Aldrich Company Llc.
Catalog Number
N5757
Lot Number
071M1471V
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Use and Manufacturing

7.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
4H-Naphtho[1,2-b]pyran-4-one, 2-phenyl-: INACTIVE

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 Hazards Summary

Causes lung changes, liver changes, thyroid hypofunction, and multiple enzyme effects in acute intraperitoneal studies of rats; [RTECS] May cause irritation; [Sigma-Aldrich MSDS]

9 Associated Disorders and Diseases

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Thieme References

10.5 Wiley References

10.6 Chemical Co-Occurrences in Literature

10.7 Chemical-Gene Co-Occurrences in Literature

10.8 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Interactions and Pathways

12.1 Protein Bound 3D Structures

12.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Conformer

12.2 Chemical-Target Interactions

13 Biological Test Results

13.1 BioAssay Results

14 Taxonomy

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

15 Classification

15.1 MeSH Tree

15.2 ChEBI Ontology

15.3 ChemIDplus

15.4 ChEMBL Target Tree

15.5 NORMAN Suspect List Exchange Classification

15.6 EPA DSSTox Classification

15.7 EPA TSCA and CDR Classification

15.8 LOTUS Tree

15.9 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. BindingDB
    LICENSE
    All data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).
    https://www.bindingdb.org/rwd/bind/info.jsp
  2. 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
  3. 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
  4. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  5. Therapeutic Target Database (TTD)
  6. 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/
  7. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  8. 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
  9. EPA Chemicals under the TSCA
    4H-Naphtho[1,2-b]pyran-4-one, 2-phenyl-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  10. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  11. 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
  12. FDA Global Substance Registration System (GSRS)
    LICENSE
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  13. ChEBI
  14. 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/
  15. 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
  16. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  17. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  18. 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
  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. 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
  21. SpectraBase
    2-PHENYL-4H-NAPHTHO[1,2-b]PYRAN-4-ONE
    https://spectrabase.com/spectrum/AI216JmIx2h
    2-Phenyl-4H-naphtho(1,2-B)pyran-4-one
    https://spectrabase.com/spectrum/nk2oTe7cun
    2-PHENYL-4H-NAPHTHO[1,2-b]PYRAN-4-ONE
    https://spectrabase.com/spectrum/L3EdLCmUJ9f
    4H-NAPHTHO/1,2-B/PYRAN-4-ONE, 2-PHENYL-,
    https://spectrabase.com/spectrum/9faj5BDCFoq
    2-Phenyl-4H-benzo[h]chromen-4-one
    https://spectrabase.com/spectrum/J5usYOBWVGV
  22. Japan Chemical Substance Dictionary (Nikkaji)
  23. MassBank Europe
  24. Metabolomics Workbench
  25. 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/
    Alpha-Naphthoflavone
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  26. Protein Data Bank in Europe (PDBe)
  27. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  28. Springer Nature
  29. SpringerMaterials
  30. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  31. Wikidata
    2-phenyl-4H-benzo[h]chromen-4-one
    https://www.wikidata.org/wiki/Q4734915
  32. Wiley
  33. PubChem
  34. Medical Subject Headings (MeSH)
    LICENSE
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    https://www.nlm.nih.gov/copyright.html
  35. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  36. PATENTSCOPE (WIPO)
CONTENTS