16alpha-Hydroxyestrone
PubChem CID
115116
Structure
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).
Chemical Structure Depiction
(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)
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)
WPOCIZJTELRQMF-QFXBJFAPSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
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)
C18H22O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- 16 alpha-hydroxyestrone
- 16 beta-hydroxyestrone
- 16-alpha-hydroxyestrone
- 16-hydroxyestrone
- 16alpha-Hydroxyestrone
- 566-76-7
- 16alpha-hydroxy estrone
- 16|A-Hydroxyestrone
- 1,3,5[10]-ESTRATRIENE-3,16ALPHA-DIOL-17-ONE
- 16a-Hydroxyestrone
- (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
- 16a-Hydroxy Estrone
- 1.16a-Hydroxyestrone
- 16.alpha.-Hydroxyestrone
- 3,16alpha-dihydroxy-1,3,5(10)-estratrien-17-one
- CHEBI:776
- JY611949JU
- 3,16alpha-Dihydroxyestra-1,3,5(10)-trien-17-one
- (8R,9S,13S,14S,16R)-3,16-Dihydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one
- C05300
- Estra-1,3,5(10)-trien-17-one, 3,16-dihydroxy-, (16.alpha.)-
- (9beta,13alpha,16beta)-3,16-dihydroxyestra-1,3,5(10)-trien-17-one
- 16 alpha-hydroxyestrone
- 16alpha-OHE1
- Hydroxyestrone-16alpha
- 16.alpha.-hydroxy Estrone
- UNII-JY611949JU
- CCRIS 7200
- (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
- 3,16a-dihydroxy-estra-1,3,5(10)-trien-17-one
- 16.alpha.Ho-oe
- 16 alpha OHE
- 16??-Hydroxyestrone
- 16?-Hydroxy Estrone
- 3,16-Dihydroxyestra-1,3,5(10)-trien-17-one #
- Estrone, 16alpha-hydroxy-
- 16 alpha -Hydroxy Estrone
- Estra-1,3,5(10)-triene-3,16a-diol-17-one
- 16.ALPHA.-OHE1
- SCHEMBL193937
- HYDROXYESTRONE [WHO-DD]
- CHEMBL1233720
- GTPL12965
- DTXSID901047947
- Estra-1,3,5(10)-trien-17-one, 3,16-dihydroxy-, (16alpha)-
- LMST02010041
- AKOS027378621
- MS-24094
- HY-113344
- J130.683I
- CS-0061863
- 3,16a-Dihydroxy-1,3,5(10)-estratrien-17-one
- estra-1,3,5(10)-triene-3,16alpha-diol-17-one
- Q27067422
- 3,16.alpha.-Dihydroxyestra-1,3,5(10)-trien-17-one
- 88B6090E-294B-4358-B2CE-BF627E048AD0
- Estra-1,3,5(10)-trien-17-one, 3,16.alpha.-dihydroxy-
- 3,16.ALPHA.-DIHYDROXY-1,3,5(10)-ESTRATRIEN-17-ONE
- ESTRA-1,3,5(10)-TRIENE-3,16.ALPHA.-DIOL-17-ONE
- (16.ALPHA.)-3,16-DIHYDROXYESTRA-1(10),2,4-TRIEN-17-ONE
- (16R)-3,16.ALPHA.-DIHYDROXY-1,3,5(10)-ESTRATRIEN-17-ONE
- 3,16alpha-Dihydroxyestra-1,3,5(10)-trien-17-one (16alpha-Hydroxyestrone)
- (8R,13S,14S,16R)-3,16-dihydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one
- (8R,13S,16R)-3,16-Dihydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one
- 16alpha-Hydroxyestrone, 100 mug/mL in methanol, certified reference material, ampule of 1 mL
- J2Z
Property Name
Property Value
Reference
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)
Solid
Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198
Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C18 steroids (estrogens) and derivatives [ST0201]
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
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
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
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
MoNA ID
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
MoNA ID
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
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Stereo Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Stereo Count
Same Parent, Isotope Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
16-Hydroxyestrone (annotation moved to)
- Extracellular
- Membrane
Disease
References
Disease
Perillyl alcohol administration for cancer treatment
References
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=WPOCIZJTELRQMF-QFXBJFAPSA-N
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/16α-Hydroxyestronehttps://commonchemistry.cas.org/detail?cas_rn=566-76-7
- ChemIDplus16alpha-Hydroxyestronehttps://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000566767ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSTox16alpha-Hydroxyestronehttps://comptox.epa.gov/dashboard/DTXSID901047947CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless 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#linking16.ALPHA.-HYDROXYESTRONEhttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/JY611949JU
- Human Metabolome Database (HMDB)LICENSEHMDB 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/citing16a-Hydroxyestronehttp://www.hmdb.ca/metabolites/HMDB0000335HMDB0000335_cms_31127https://hmdb.ca/metabolites/HMDB0000335#spectra
- ChEBI16alpha-hydroxyestronehttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:776
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/16alpha-Hydroxyestronehttps://www.wikidata.org/wiki/Q27067422LOTUS Treehttps://lotus.naturalproducts.net/
- NCI Thesaurus (NCIt)LICENSEUnless 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-reuseNCI Thesaurushttps://ncit.nci.nih.gov
- ChEMBLLICENSEAccess 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.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- FooDBLICENSEFooDB 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/about16alpha-Hydroxyestronehttps://foodb.ca/compounds/FDB021959
- MassBank of North America (MoNA)LICENSEThe content of the MoNA database is licensed under CC BY 4.0.https://mona.fiehnlab.ucdavis.edu/documentation/license
- NIST Mass Spectrometry Data CenterLICENSEData covered by the Standard Reference Data Act of 1968 as amended.https://www.nist.gov/srd/public-lawEstra-1,3,5(10)-trien-17-one, 3,16-dihydroxy-, (16.alpha.)-http://www.nist.gov/srd/nist1a.cfm
- SpectraBaseESTRA-1,3,5(10)-TRIENE-3,16.ALPHA.-DIOL-17-ONEhttps://spectrabase.com/spectrum/A2LjiPMeVlw3,16.ALPHA.-DIHYDROXY-ESTRA-1,3,5(10)-TRIENE-17-ONEhttps://spectrabase.com/spectrum/5gSSkZ3KWGf1,3,5(10)-estratrien-3,16α-diol-17-onehttps://spectrabase.com/spectrum/34ZCxHiatzl1,3,5(10)-estratrien-3,16α-diol-17-onehttps://spectrabase.com/spectrum/FjPI6gWtneJ
- IUPHAR/BPS Guide to PHARMACOLOGYLICENSEThe 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#license16α-hydroxyestronehttps://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=12965Guide to Pharmacology Target Classificationhttps://www.guidetopharmacology.org/targets.jsp
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlCompounds with biological roleshttp://www.genome.jp/kegg-bin/get_htext?br08001.keg
- LIPID MAPSLipid Classificationhttps://www.lipidmaps.org/
- Natural Product Activity and Species Source (NPASS)16Alpha-Hydroxyestronehttps://bidd.group/NPASS/compound.php?compoundID=NPC262936
- Metabolomics Workbench16alpha-hydroxyestronehttps://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=35299
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/
- Protein Data Bank in Europe (PDBe)
- RCSB Protein Data Bank (RCSB PDB)LICENSEData 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
- Rhea - Annotated Reactions DatabaseLICENSERhea 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
- Springer Nature
- SpringerMaterials(8R,13S,16R)-3,16-Dihydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-onehttps://materials.springer.com/substanceprofile/docs/smsid_fsoqohmxyfeovdih
- Wikidata16α-hydroxyestronehttps://www.wikidata.org/wiki/Q27067422
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks 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.html16-hydroxyestronehttps://www.ncbi.nlm.nih.gov/mesh/67026702
- GHS Classification (UNECE)GHS Classification Treehttp://www.unece.org/trans/danger/publi/ghs/ghs_welcome_e.html
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 388468277https://pubchem.ncbi.nlm.nih.gov/substance/388468277
CONTENTS