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Cholesterol sulfate

PubChem CID
65076
Structure
Cholesterol sulfate_small.png
Cholesterol sulfate_3D_Structure.png
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.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Cholesterol sulfate.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(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)

2.1.2 InChI

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)

2.1.3 InChIKey

BHYOQNUELFTYRT-DPAQBDIFSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

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)

2.2 Molecular Formula

C27H46O4S
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 DrugBank ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 KEGG ID

2.3.9 Lipid Maps ID (LM_ID)

2.3.10 Metabolomics Workbench ID

2.3.11 Nikkaji Number

2.3.12 Pharos Ligand ID

2.3.13 Wikidata

2.3.14 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 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

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

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)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Collision Cross Section

237.01 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

3.3 Chemical Classes

3.3.1 Drugs

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

3.3.2 Lipids

Lipids -> Sterol Lipids [ST] -> Steroid conjugates [ST05] -> Sulfates [ST0502]

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
1.06:9.82, 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
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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
1.50:27.23:0.18, 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
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4.3 Mass Spectrometry

4.3.1 LC-MS

1 of 3
View All
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

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Thumbnail
2 of 3
View All
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

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6 Chemical Vendors

7 Drug and Medication Information

7.1 Biomarker Information

8 Food Additives and Ingredients

8.1 Associated Foods

9 Pharmacology and Biochemistry

9.1 MeSH Pharmacological Classification

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.)

9.2 Human Metabolite Information

9.2.1 Tissue Locations

  • Adrenal Gland
  • Epidermis
  • Platelet

9.2.2 Cellular Locations

  • Cytoplasm
  • Endoplasmic reticulum
  • Extracellular
  • Membrane

10 Associated Disorders and Diseases

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Chemical Co-Occurrences in Literature

11.5 Chemical-Gene Co-Occurrences in Literature

11.6 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Protein Bound 3D Structures

13.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

13.2 Chemical-Target Interactions

14 Biological Test Results

14.1 BioAssay Results

15 Taxonomy

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

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 LIPID MAPS Classification

16.4 KEGG: Lipid

16.5 ChemIDplus

16.6 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

16.7 ChEMBL Target Tree

16.8 NORMAN Suspect List Exchange Classification

16.9 CCSBase Classification

16.10 EPA DSSTox Classification

16.11 LOTUS Tree

16.12 MolGenie Organic Chemistry Ontology

17 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. 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
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. 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
  6. 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
  7. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  8. ChEBI
  9. 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/
  10. 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
  11. 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
  12. 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
  13. 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
  14. 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
  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. KNApSAcK Species-Metabolite Database
  18. Natural Product Activity and Species Source (NPASS)
  19. West Coast Metabolomics Center-UC Davis
    Cholesterol 3-sulfate
  20. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  21. MarkerDB
    LICENSE
    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
  22. 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
  23. Metabolomics Workbench
  24. 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/
    Cholesterol Sulfate
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  25. Pharos
    LICENSE
    Data 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/about
  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. Wikidata
  30. Wikipedia
  31. PubChem
  32. 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
    Serine Proteinase Inhibitors
    https://www.ncbi.nlm.nih.gov/mesh/68015842
  33. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  34. PATENTSCOPE (WIPO)
  35. NCBI
CONTENTS