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16alpha-Hydroxyestrone

PubChem CID
115116
Structure
16alpha-Hydroxyestrone_small.png
16alpha-Hydroxyestrone_3D_Structure.png
Molecular Formula
Synonyms
  • 16alpha-Hydroxyestrone
  • 566-76-7
  • 16alpha-hydroxy estrone
  • 16|A-Hydroxyestrone
  • 1,3,5[10]-ESTRATRIENE-3,16ALPHA-DIOL-17-ONE
Molecular Weight
286.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-18
Description
16alpha-hydroxyestrone is the 16alpha-hydroxy derivative of estrone; a minor estrogen metabolite. It has a role as a mouse metabolite, a human blood serum metabolite, an estrogen and a human urinary metabolite. It is a 16alpha-hydroxy steroid, a secondary alpha-hydroxy ketone, a 3-hydroxy steroid and a 17-oxo steroid. It is functionally related to an estrone.
16alpha-Hydroxyestrone has been reported in Homo sapiens with data available.
16alpha-Hydroxyestrone is a metabolite formed during the catabolism of estrone by the liver through the hydroxylation of the carbon at position 16 by cytochrome P450 (CYP) family enzymes, including CYP3A4 and 3A5, with potential carcinogenic activity. With increased estrogenic activity compared to the parent compound, 16alpha-hydroxyestrone (16alpha-OHE1) increases the expression of ER-responsive genes, which leads to increased proliferation of susceptible tumor cells. The ratio between the two estrogen metabolites, 2-hydroxyestrone (2-OHE1), a weak estrogen and metabolite from the 2-hydroxylation pathway, and 16alpha-OHE1, a metabolite from the 16-hydroxylation pathway, may be used to assess the risk of certain cancers; a higher ratio of 2-OHE1:16alpha-OHE1 correlates with decreased cancer risk.
See also: 16-Hydroxyestrone (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
16alpha-Hydroxyestrone.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(8R,9S,13S,14S,16R)-3,16-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

WPOCIZJTELRQMF-QFXBJFAPSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H](C2=O)O)CCC4=C3C=CC(=C4)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C18H22O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 HMDB ID

2.3.7 KEGG ID

2.3.8 Lipid Maps ID (LM_ID)

2.3.9 Metabolomics Workbench ID

2.3.10 NCI Thesaurus Code

2.3.11 Nikkaji Number

2.3.12 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 16 alpha-hydroxyestrone
  • 16 beta-hydroxyestrone
  • 16-alpha-hydroxyestrone
  • 16-hydroxyestrone

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
286.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
2.6
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
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
286.15689456 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
286.15689456 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
57.5 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
448
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
5
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

3.3 SpringerMaterials Properties

3.4 Chemical Classes

3.4.1 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

3.4.2 Lipids

Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C18 steroids (estrogens) and derivatives [ST0201]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
100%_DMSO
pH
7.00
Shifts [ppm]:Intensity
1.95:3.18, 1.49:1.86, 1.29:3.67, 1.65:2.59, 1.38:4.04, 2.78:0.92, 1.40:4.64, 1.34:4.80, 1.84:3.40, 2.73:6.20, 1.83:2.05, 6.45:17.30, 6.50:9.62, 1.31:4.96, 1.28:1.37, 2.15:4.66, 1.35:3.88, 2.30:2.32, 6.45:15.77, 7.04:13.32, 2.79:0.92, 4.23:7.09, 2.15:4.47, 1.38:3.32, 0.87:100.00, 4.25:6.87, 1.27:1.11, 1.47:4.74, 1.73:7.87, 2.30:2.26, 1.33:3.69, 2.13:2.32, 1.67:3.42, 1.43:3.72, 2.29:3.67, 1.87:1.75, 1.67:2.86, 4.24:7.55, 6.51:8.33, 2.70:0.92, 1.75:6.17, 2.31:3.02, 1.68:5.18, 1.32:4.34, 6.52:8.44, 2.77:0.86, 1.69:1.81, 1.85:3.94, 1.47:5.01, 1.30:3.72, 2.74:8.44, 1.99:2.48, 1.74:4.34, 4.22:6.15, 1.97:6.82, 1.42:2.29, 1.49:1.91, 1.33:3.05, 6.52:9.60, 2.75:3.88, 1.85:2.64, 2.00:2.53, 7.05:12.40, 2.28:1.64, 1.66:3.72, 2.31:3.91, 1.44:2.43, 2.17:2.24, 1.86:3.61, 1.45:4.64, 1.86:3.85, 2.29:3.32, 1.87:3.37, 2.14:2.80, 1.98:6.93, 1.70:12.13, 2.76:3.94, 1.37:3.02, 1.96:3.96, 1.45:5.28, 1.75:2.96, 2.71:1.13, 2.73:8.60, 1.36:3.88, 2.17:2.35, 1.72:10.67, 1.41:5.04, 1.68:4.45, 1.84:3.67, 1.39:4.07, 1.71:2.45
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4.2 2D NMR Spectra

4.2.1 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
100%_DMSO
pH
7.00
Shifts [ppm] (F2:F1):Intensity
1.97:31.22:0.15, 7.04:125.84:0.50, 2.30:25.24:0.15, 1.70:31.21:0.26, 1.30:25.90:0.14, 1.40:31.21:0.18, 2.74:28.89:0.65, 1.69:46.82:0.10, 2.15:43.17:0.34, 1.85:25.90:0.18, 4.23:70.06:0.57, 0.87:13.95:0.23, 1.34:25.24:0.06, 6.51:112.54:0.53, 1.46:37.68:0.15, 1.73:31.22:0.49, 6.45:114.87:1.00
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4.3 Mass Spectrometry

4.3.1 GC-MS

1 of 7
View All
Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

184.0 1

89.0 0.88

285.0 0.37

115.0 0.35

100.0 0.32

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2 of 7
View All
Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

89.0 1

184.0 0.71

115.0 0.30

285.0 0.28

128.0 0.25

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4.3.2 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
Precursor Type
[M+H]+
Precursor m/z
287.164171
Instrument
Agilent 6560
Ionization Mode
positive
Collision Energy
40
Retention Time
7.852433
Top 5 Peaks

157.06505 100

105.06999 42.39

151.33533 19.10

107.04488 19.10

285.78772 16.87

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2 of 3
View All
MS Category
Experimental
MS Type
Other
Precursor Type
[M+H]+
Precursor m/z
287.164171
Instrument
Agilent 6560
Ionization Mode
positive
Collision Energy
40
Retention Time
7.8435
Top 5 Peaks

157.06438 100

133.06459 48.18

147.07899 31.57

105.06965 30.88

179.08513 29.40

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4.4 IR Spectra

4.4.1 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Steraloids Inc.
Catalog Number
E1250-000
Lot Number
B0796
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Steraloids Inc.
Catalog Number
E1250-000
Lot Number
B0796
Copyright
Copyright © 2013-2024 John Wiley & Sons, Inc. All Rights Reserved.
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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

  • Extracellular
  • Membrane

8.1.2 Metabolite Pathways

8.2 Biochemical Reactions

9 Associated Disorders and Diseases

Disease
Perillyl alcohol administration for cancer treatment
References

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Chemical Co-Occurrences in Literature

10.5 Chemical-Gene Co-Occurrences in Literature

10.6 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 Structure Code
PDBe Conformer

12.2 Chemical-Target Interactions

12.3 Pathways

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 NCI Thesaurus Tree

15.3 ChEBI Ontology

15.4 LIPID MAPS Classification

15.5 KEGG: Metabolite

15.6 KEGG: Lipid

15.7 ChemIDplus

15.8 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

15.9 ChEMBL Target Tree

15.10 UN GHS Classification

15.11 EPA DSSTox Classification

15.12 LOTUS Tree

15.13 MolGenie Organic Chemistry Ontology

16 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. 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
  5. 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
  6. ChEBI
  7. 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/
  8. NCI Thesaurus (NCIt)
    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. 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. 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
  11. 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
  12. 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
    Estra-1,3,5(10)-trien-17-one, 3,16-dihydroxy-, (16.alpha.)-
    http://www.nist.gov/srd/nist1a.cfm
  13. SpectraBase
    ESTRA-1,3,5(10)-TRIENE-3,16.ALPHA.-DIOL-17-ONE
    https://spectrabase.com/spectrum/A2LjiPMeVlw
    3,16.ALPHA.-DIHYDROXY-ESTRA-1,3,5(10)-TRIENE-17-ONE
    https://spectrabase.com/spectrum/5gSSkZ3KWGf
    1,3,5(10)-estratrien-3,16α-diol-17-one
    https://spectrabase.com/spectrum/34ZCxHiatzl
    1,3,5(10)-estratrien-3,16α-diol-17-one
    https://spectrabase.com/spectrum/FjPI6gWtneJ
  14. IUPHAR/BPS Guide to PHARMACOLOGY
    LICENSE
    The Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)
    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  15. Japan Chemical Substance Dictionary (Nikkaji)
  16. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  17. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  18. Natural Product Activity and Species Source (NPASS)
  19. Metabolomics Workbench
  20. 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/
  21. Protein Data Bank in Europe (PDBe)
  22. 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
  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. Springer Nature
  25. SpringerMaterials
    (8R,13S,16R)-3,16-Dihydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one
    https://materials.springer.com/substanceprofile/docs/smsid_fsoqohmxyfeovdih
  26. Wikidata
  27. PubChem
  28. 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
  29. GHS Classification (UNECE)
  30. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  31. PATENTSCOPE (WIPO)
CONTENTS