7alpha-Hydroxy-4-cholesten-3-one
PubChem CID
123743
Structure
Molecular Formula
Synonyms
- 3862-25-7
- 7alpha-Hydroxy-4-cholesten-3-one
- 7alpha-Hydroxycholest-4-en-3-one
- 7-hydroxy-4-cholesten-3-one
- (7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Molecular Weight
400.6 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2004-09-16
- Modify:2024-12-28
Description
7alpha-hydroxycholest-4-en-3-one is a cholestanoid consisting of a cholesterol core having an oxo group at the 3-position, a C=C bond at the 4,5-position and an alpha-hydroxy group at the 7-position. It has a role as a human metabolite and a mouse metabolite. It is a 7alpha-hydroxy steroid, a cholestanoid and a 3-oxo-Delta(4) steroid.
7alpha-Hydroxy-4-cholesten-3-one has been reported in Homo sapiens and Trypanosoma brucei with data available.
Chemical Structure Depiction
(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24-,25+,26+,27-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
IOIZWEJGGCZDOL-RQDYSCIWSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](CC4=CC(=O)CC[C@]34C)O)C
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)
C27H44O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- 7 alpha-hydroxy-4-cholesten-3-one
- 7-hydroxy-4-cholesten-3-one
- 7alpha-hydroxy-4-cholesten-3-one
- cholest-4-en-7 alpha-ol-3-one
- 3862-25-7
- 7alpha-Hydroxy-4-cholesten-3-one
- 7alpha-Hydroxycholest-4-en-3-one
- 7-hydroxy-4-cholesten-3-one
- (7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
- Cholest-4-en-7alpha-ol-3-one
- 7 alpha-3ox-C
- 4-cholesten-7alpha-ol-3-one
- 7-alpha-hydroxy-4-cholesten-3-one
- (7R,8S,9S,10R,13R,14S,17R)-7-Hydroxy-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
- 7?-HYDROXY-4-CHOLESTEN-3-ONE
- 7-Hydroxycholest-4-en-3-one
- 4-Cholesten-7-alpha-ol-3-one
- 7|A-Hydroxy-4-cholesten-3-one
- 7 alpha-hydroxy-4-cholesten-3-one
- BIDD:PXR0048
- SCHEMBL178019
- CHEMBL4285345
- 7-a-hydroxy-4-cholesten-3-one
- 7-a-hydroxycholest-4-en-3-one
- CHEBI:17899
- DTXSID10191938
- GLXC-26103
- 7-alpha-hydroxycholest-4-en-3-one
- LMST04030123
- 7 alpha -Hydroxy-4-cholesten-3-one
- AKOS027320761
- HY-113259R
- 7a-Hydroxy-4-cholesten-3-one-12alpha
- (7alpha)-7-Hydroxycholest-4-en-3-one
- MS-26816
- PD080599
- 7|A-Hydroxy-4-cholesten-3-one (Standard)
- HY-113259
- CS-0059449
- NS00122290
- C05455
- Cholest-4-en-3-one, 7-hydroxy-, (7alpha)-
- G12798
- Q4644247
- 7alpha-Hydroxy-4-cholesten-3-one, >=95.0% (HPLC)
- (7R,8S,9S,10R,13R,17R)-7-hydroxy-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
400.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
7.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
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
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
400.334130642 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
400.334130642 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
37.3Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
29
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
663
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
8
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
Lipids -> Sterol Lipids [ST] -> Bile acids and derivatives [ST04] -> C27 bile acids, alcohols, and derivatives [ST0403]
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[2M+H]+
Precursor m/z
801.676
Instrument
qToF
Ionization Mode
positive
Top 5 Peaks
401.340637 100
402.343872 29.28
383.330017 14.16
384.334137 4.61
403.346649 4.49
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+Na]+
Precursor m/z
423.323
Instrument
qToF
Ionization Mode
positive
Top 5 Peaks
423.324860 100
442.334595 51.94
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
Similar Compounds (2D)
Similar Conformers (3D)
Same Count
Liver
Extracellular
Disease
References
Disease
Alcoholism
References
Disease
Crohn's disease
References
Disease
Irritable bowel syndrome
References
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=IOIZWEJGGCZDOL-RQDYSCIWSA-N
WormJam Metabolites Local CSV for MetFrag | DOI:10.5281/zenodo.3403364
WormJam: A consensus C. elegans Metabolic Reconstruction and Metabolomics Community and Workshop Series, Worm, 6:2, e1373939, DOI:10.1080/21624054.2017.1373939
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/4.0/7α-Hydroxy-4-cholesten-3-onehttps://commonchemistry.cas.org/detail?cas_rn=3862-25-7
- ChemIDplus7alpha-Hydroxy-4-cholesten-3-onehttps://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0003862257ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSTox7alpha-Hydroxy-4-cholesten-3-onehttps://comptox.epa.gov/dashboard/DTXSID10191938CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- 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/citing7a-Hydroxy-cholestene-3-onehttp://www.hmdb.ca/metabolites/HMDB0001993
- ChEBI7alpha-hydroxycholest-4-en-3-onehttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17899
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/7alpha-Hydroxy-4-cholesten-3-onehttps://www.wikidata.org/wiki/Q4644247LOTUS Treehttps://lotus.naturalproducts.net/
- 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.html
- Comparative Toxicogenomics Database (CTD)LICENSEIt 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.jsp7 alpha-hydroxy-4-cholesten-3-onehttps://ctdbase.org/detail.go?type=chem&acc=C002656
- ECI Group, LCSB, University of Luxembourg7alpha-hydroxycholest-4-en-3-one
- Natural Product Activity and Species Source (NPASS)
- 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/about7a-Hydroxy-cholestene-3-onehttps://foodb.ca/compounds/FDB022786
- 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.html
- LIPID MAPSLipid Classificationhttps://www.lipidmaps.org/
- 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
- Metabolomics Workbench7alpha-Hydroxy-4-cholesten-3-onehttps://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=36794
- 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
- Thieme ChemistryLICENSEThe 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/
- Wikidata7alpha-hydroxycholest-4-en-3-onehttps://www.wikidata.org/wiki/Q4644247
- 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.html7 alpha-hydroxy-4-cholesten-3-onehttps://www.ncbi.nlm.nih.gov/mesh/67002656
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/NORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 403681377https://pubchem.ncbi.nlm.nih.gov/substance/403681377
CONTENTS