Cholesterol sulfate
PubChem CID
65076
Structure
Molecular Formula
Synonyms
- Cholesterol sulfate
- Cholesteryl sulfate
- 1256-86-6
- Cholesterol 3-sulfate
- cholesterol sulphate
Molecular Weight
466.7 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-06-01
- Modify:2025-01-18
Description
Cholesterol sulfate is a steroid sulfate that is cholesterol substituted by a sulfoxy group at position 3. It has a role as a human metabolite. It is functionally related to a cholesterol. It is a conjugate acid of a cholesterol sulfate(1-).
Component of human seminal plasma & spermatozoa.
Cholesterol sulfate has been reported in Homo sapiens, Gorgonocephalus eucnemis, and other organisms with data available.
Chemical Structure Depiction
[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C27H46O4S/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30)/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
BHYOQNUELFTYRT-DPAQBDIFSA-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]2CC=C4[C@@]3(CC[C@@H](C4)OS(=O)(=O)O)C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C27H46O4S
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- cholesterol sulfate
- cholesteryl sulfate
- cholesteryl sulfate, 3H-labeled, (3beta)-isomer
- cholesteryl sulfate, ammonium salt, (3beta)-isomer
- cholesteryl sulfate, potassium salt, (3beta)-isomer
- cholesteryl sulfate, sodium salt, (3beta)-isomer
- cholesteryl sulfate, sodium salt, 26-(14)C-labeled
- Cholesterol sulfate
- Cholesteryl sulfate
- 1256-86-6
- Cholesterol 3-sulfate
- cholesterol sulphate
- CHOLEST-5-EN-3-YL HYDROGEN SULFATE
- CCRIS 7559
- Cholest-5-en-3beta-ol sulfate
- CHOLESTEROL-SULFATE
- cholesteryl sulphate
- Cholesterol hydrogen sulfate
- Cholest-5-en-3-ol (3beta)-, hydrogen sulfate
- Cholesterol 3-sulphate
- cholest-5-en-3beta-yl hydrogen sulfate
- Chol-sulf
- 5-Cholesten-3b-yl sulfate
- Cholesterol hydrogen sulphate
- UNII-KU576NT9O9
- Cholest-5-en-3b-ol sulfate
- [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
- CHEBI:41321
- 5-Cholesten-3b-yl sulphate
- Cholest-5-en-3b-ol sulphate
- KU576NT9O9
- Y5-Cholesten-3beta-yl sulfate
- DTXSID401016822
- Cholest-5-en-3-ol (3.beta.)-, hydrogen sulfate
- CHOLESTEROL, HYDROGEN SULFATE
- CMC_13400
- 5-CHOLESTEN-3.BETA.-YL SULFATE
- Cholesterol, hydrogen sulfate (7CI,8CI)
- cholesteryl 3-sulfate
- cholest-5-en-3-ol, hydrogen sulfate, (3beta)-
- Cholest-5-en-3-ol (3beta)-, hydrogen sulfate (9CI)
- Cholesteryl sulfate sodium salt
- C3S
- 5-Cholesten-3beta-ol sulfate sodium salt
- Cholesterol sulfic acid
- NSC628320
- cholesterol sulfuric acid
- Cholesteryl sulfuric acid
- Cholesterol sulphuric acid
- Cholesteryl sulphuric acid
- bmse000961
- Cholesterol 3-sulfuric acid
- Cholesterol 3-sulphuric acid
- C9523_SIGMA
- SCHEMBL161397
- Cholest-5-en-3I2-ol sulfate
- GTPL2738
- Cholest-5-en-3I2-ol sulphate
- CHEMBL1231592
- Cholest-5-en-3beta-ol sulphate
- HMDB00653
- BHYOQNUELFTYRT-DPAQBDIFSA-N
- Cholesterol hydrogen sulfuric acid
- Cholest-5-en-3b-ol sulfuric acid
- Cholesterol hydrogen sulphuric acid
- DTXCID001475012
- Cholest-5-en-3b-ol sulphuric acid
- Cholest-5-en-3I2-ol sulfuric acid
- Cholest-5-en-3beta-ol sulfuric acid
- Cholest-5-en-3I2-ol sulphuric acid
- LMST05020016
- 5-CHOLESTEN-3BETA-YL SULFATE
- CHOLEST-5-en-3-yl hydrogen sulphate
- Cholest-5-en-3beta-ol sulphuric acid
- DB01990
- [(3S,8S,9S,10R,13R,14S,17R)-17-[(1R)-1,5-dimethylhexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
- CHOLEST-5-EN-3.BETA.-OL SULFATE
- CHOLEST-5-en-3-yl hydrogen sulfuric acid
- CHOLEST-5-en-3-yl hydrogen sulphuric acid
- NS00120400
- C18043
- Q27075985
- (3alpha,8alpha,17alpha)-cholest-5-en-3-yl hydrogen sulfate
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
466.7 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
8.2
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
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
466.31168112 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
466.31168112 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
72 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
32
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
812
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
237.01 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
Lipids -> Sterol Lipids [ST] -> Steroid conjugates [ST05] -> Sulfates [ST0502]
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
100%_DMSO
pH
7.00
Shifts [ppm]:Intensity
1.06:9.82, 1.89:4.47, 1.42:6.10, 1.93:3.62, 1.32:9.03, 2.35:4.54, 0.87:3.38, 1.47:4.85, 1.56:1.47, 0.91:4.77, 1.48:9.64, 2.16:2.80, 1.06:5.15, 0.99:8.39, 1.90:2.81, 1.41:5.99, 3.82:2.97, 1.34:4.99, 1.43:1.84, 1.35:6.13, 1.23:3.62, 1.31:10.54, 1.12:7.44, 1.55:1.95, 1.77:5.76, 1.95:5.52, 1.25:1.45, 1.10:9.85, 1.11:6.21, 1.13:8.48, 0.92:3.97, 1.43:2.07, 1.05:6.57, 1.12:8.12, 0.89:46.22, 3.80:1.93, 1.82:1.19, 1.85:3.41, 2.38:4.17, 1.40:11.23, 0.65:97.61, 1.38:8.87, 0.84:76.42, 1.52:6.05, 1.53:6.95, 1.89:3.83, 1.14:10.14, 0.96:4.86, 3.85:3.89, 1.75:1.57, 1.01:7.91, 0.84:75.04, 1.89:4.96, 1.19:1.84, 0.90:45.62, 5.28:8.59, 3.83:8.20, 2.35:5.00, 1.86:3.48, 1.54:3.47, 3.84:4.63, 2.36:4.62, 1.26:1.24, 1.14:8.94, 2.37:3.89, 1.96:3.42, 1.04:4.54, 1.22:2.52, 1.77:9.04, 1.94:2.40, 1.78:6.67, 0.97:9.90, 1.16:4.81, 1.44:1.61, 1.02:2.56, 2.38:3.99, 0.99:13.03, 1.22:4.57, 1.03:4.82, 1.92:2.46, 1.51:11.46, 0.85:78.83, 2.13:5.02, 2.15:2.87, 1.08:11.70, 1.90:4.24, 1.29:2.20, 1.20:2.00, 1.95:3.57, 1.88:4.05, 3.81:4.12, 0.88:3.82, 1.97:2.81, 5.28:9.45, 2.38:4.33, 1.34:4.54, 1.36:4.98, 1.12:7.56, 2.12:2.39, 1.29:1.46, 1.34:5.09, 1.37:7.78, 1.17:3.56, 1.28:0.91, 1.86:4.09, 1.79:6.20, 1.76:2.40, 0.85:76.89, 1.39:7.51, 1.56:1.93, 1.55:3.62, 1.97:5.19, 1.91:2.32, 1.78:4.56, 1.50:13.35, 1.92:3.52, 1.86:4.05, 1.32:8.29, 1.88:3.49, 2.11:2.35, 5.28:9.75, 1.91:2.01, 1.80:7.37, 0.96:6.99, 1.87:2.64, 2.36:4.97, 3.82:4.53, 1.94:3.19, 1.49:10.14, 1.48:6.72, 3.86:1.89, 0.95:100.00, 3.84:2.80, 1.93:2.33
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
1.50:27.23:0.18, 1.93:31.21:0.14, 1.23:27.55:0.10, 1.10:38.84:0.23, 1.55:23.59:0.14, 2.38:39.15:0.19, 1.35:35.17:0.21, 0.97:36.68:0.09, 1.97:39.15:0.16, 0.90:18.39:0.43, 1.08:55.43:0.18, 1.32:35.51:0.14, 0.99:35.51:0.12, 0.84:22.37:1.00, 1.80:36.86:0.15, 1.14:39.15:0.18, 0.90:49.46:0.18, 1.14:22.91:0.10, 2.14:39.15:0.16, 1.04:23.57:0.06, 0.94:18.92:0.61, 1.79:27.55:0.13, 1.39:31.19:0.18, 1.52:31.19:0.12, 0.65:11.53:0.34, 1.48:20.41:0.15, 1.42:28.54:0.12, 1.88:28.55:0.16, 5.28:120.84:0.36, 3.83:75.03:0.23, 1.32:22.91:0.13, 0.99:55.92:0.10, 1.40:20.41:0.11
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Instrument Type
Quattro_QQQ
Ionization Mode
negative
Top 5 Peaks
465.72 100
465.48 96.93
466.5 10.36
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Instrument Type
Quattro_QQQ
Ionization Mode
negative
Top 5 Peaks
465.66 100
465.48 93.36
466.5 11.51
467.58 1.54
97.02 1.42
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)
Anticarcinogenic Agents
Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved. (See all compounds classified as Anticarcinogenic Agents.)
Serine Proteinase Inhibitors
Exogenous or endogenous compounds which inhibit SERINE ENDOPEPTIDASES. (See all compounds classified as Serine Proteinase Inhibitors.)
- Adrenal Gland
- Epidermis
- Platelet
- Cytoplasm
- Endoplasmic reticulum
- Extracellular
- Membrane
Disease
References
Disease
Cirrhosis
References
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=BHYOQNUELFTYRT-DPAQBDIFSA-N
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
A metabolome atlas of the aging mouse brain. Nat Commun. 2021 Oct 15;12(1):6021. DOI:10.1038/s41467-021-26310-y. PMID:34654818; PMCID:PMC8519999.
The Metabolome Atlas of the Aging Mouse Brain: https://mouse.atlas.metabolomics.us
A metabolome atlas of the aging mouse brain. Nat Commun. 2021 Oct 15;12(1):6021. DOI:10.1038/s41467-021-26310-y. PMID:34654818; PMCID:PMC8519999.
The Metabolome Atlas of the Aging Mouse Brain: https://mouse.atlas.metabolomics.us
- 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/Cholesterol sulfatehttps://commonchemistry.cas.org/detail?cas_rn=1256-86-6
- ChemIDplusCholesteryl sulfatehttps://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0001256866ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_useCholesterol sulfatehttps://www.drugbank.ca/drugs/DB01990
- EPA DSSToxCholesteryl sulfatehttps://comptox.epa.gov/dashboard/DTXSID401016822CompTox 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#linkingCHOLESTERYL SULFATEhttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/KU576NT9O9
- 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/citingCholesterol sulfatehttp://www.hmdb.ca/metabolites/HMDB0000653HMDB0000653_nmr_one_1457https://hmdb.ca/metabolites/HMDB0000653#spectra
- CCSbaseCCSbase Classificationhttps://ccsbase.net/
- ChEBICholesterol sulfatehttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:41321
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/Cholesterol sulfatehttps://www.wikidata.org/wiki/Q27075985LOTUS 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.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- 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.jspcholesteryl sulfatehttps://ctdbase.org/detail.go?type=chem&acc=C007045
- Drug Gene Interaction database (DGIdb)LICENSEThe 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
- 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#licensecholesterol sulphatehttps://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=2738Guide to Pharmacology Target Classificationhttps://www.guidetopharmacology.org/targets.jsp
- 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/aboutCholesterol sulfatehttps://foodb.ca/compounds/FDB022164
- 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
- KNApSAcK Species-Metabolite Database
- Natural Product Activity and Species Source (NPASS)
- West Coast Metabolomics Center-UC DavisCholesterol 3-sulfate
- LIPID MAPSLipid Classificationhttps://www.lipidmaps.org/
- MarkerDBLICENSEThis work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.https://markerdb.ca/Cholesterol sulfatehttps://markerdb.ca/chemicals/345
- 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 WorkbenchCholesterol sulfatehttps://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=36958
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/Cholesterol SulfateNORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
- PharosLICENSEData 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/aboutCholesterol sulfatehttps://pharos.nih.gov/ligands/6TRBLVMKJDVM
- 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
- Springer Nature
- Wikidatacholesteryl sulfatehttps://www.wikidata.org/wiki/Q27075985
- WikipediaTaraxasterolhttps://en.wikipedia.org/wiki/TaraxasterolCholesterol sulfatehttps://en.wikipedia.org/wiki/Cholesterol_sulfate
- 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.htmlcholesteryl sulfatehttps://www.ncbi.nlm.nih.gov/mesh/67007045Anticarcinogenic Agentshttps://www.ncbi.nlm.nih.gov/mesh/68016588Serine Proteinase Inhibitorshttps://www.ncbi.nlm.nih.gov/mesh/68015842
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 388568118https://pubchem.ncbi.nlm.nih.gov/substance/388568118
- NCBI
CONTENTS