An official website of the United States government

Hyocholic Acid

PubChem CID
92805
Structure
Hyocholic Acid_small.png
Hyocholic Acid_3D_Structure.png
Molecular Formula
Synonyms
  • Hyocholic acid
  • 547-75-1
  • gamma-Muricholic acid
  • Iocholic acid
  • 3alpha,6alpha,7alpha-Trihydroxy-5beta-cholan-24-oic acid
Molecular Weight
408.6 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-11
Description
Hyocholic acid is a trihydroxy-5beta-cholanic acid in which the three hydroxy substituents are located at the 3alpha-, 6alpha- and 7alpha-positions. It has a role as a mouse metabolite, a human urinary metabolite and a rat metabolite. It is a C24-steroid, a 6alpha-hydroxy steroid, a 7alpha-hydroxy steroid and a member of muricholic acids. It is a conjugate acid of a hyocholate.
Hyocholic acid has been reported in Homo sapiens with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Hyocholic Acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4R)-4-[(3R,5R,6R,7S,8S,9S,10R,13R,14S,17R)-3,6,7-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21-,22+,23-,24-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

DKPMWHFRUGMUKF-KWXDGCAGSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H]([C@@H]([C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C24H40O5
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 KEGG ID

2.3.8 Lipid Maps ID (LM_ID)

2.3.9 Metabolomics Workbench ID

2.3.10 Nikkaji Number

2.3.11 Wikidata

2.3.12 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 3 alpha,6 alpha,7 beta-trihydroxy-5 beta-cholanoic acid
  • 3,6,7-trihydroxy-5-cholanoic acid
  • alpha-muricholic acid
  • beta-muricholic acid
  • hyocholic acid
  • muricholic acid
  • muricholic acid, (3alpha,5alpha,6alpha,7alpha)-isomer
  • muricholic acid, (3alpha,5beta,6alpha,7alpha)-isomer
  • muricholic acid, (3alpha,5beta,6alpha,7beta)-isomer
  • muricholic acid, (3alpha,5beta,6beta,7alpha)-isomer
  • muricholic acid, (3alpha,5beta,6beta,7beta)-isomer
  • muricholic acid, sodium salt
  • omega-muricholic acid
  • trihydroxy-5 alpha-cholanoic acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
408.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
3.9
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
408.28757437 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
408.28757437 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
98 Ų
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
637
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
11
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 Collision Cross Section

206 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

209.2 Ų [M+K-H+HCOO]- [CCS Type: DT; Method: single field calibrated]

200.1 Ų [M+Na-H+Cl]- [CCS Type: DT; Method: single field calibrated]

206.8 Ų [M+Na-H+HCOO]- [CCS Type: DT; Method: single field calibrated]

197.8 Ų [M-H2O+HCOO]- [CCS Type: DT; Method: single field calibrated]

197 Ų [M+Na-2H]- [CCS Type: DT; Method: single field calibrated]

196.4 Ų [M-H2O-H]- [CCS Type: DT; Method: single field calibrated]

199.6 Ų [M+H-H2O]+ [CCS Type: DT; Method: single field calibrated]

218.4 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated]

202.5 Ų [M+HCOO]- [CCS Type: DT; Method: single field calibrated]

203.3 Ų [M+H-2H2O]+ [CCS Type: DT; Method: single field calibrated]

190.1 Ų [M-H]- [CCS Type: DT; Method: single field calibrated]

204.2 Ų [M-H]-
S50 | CCSCOMPEND | The Unified Collision Cross Section (CCS) Compendium | DOI:10.5281/zenodo.2658162

3.3 Chemical Classes

3.3.1 Lipids

Lipids -> Sterol Lipids [ST] -> Bile acids and derivatives [ST04] -> C24 bile acids, alcohols, and derivatives [ST0401]

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

NIST Number
236028
Library
Main library
Total Peaks
372
m/z Top Peak
372
m/z 2nd Highest
55
m/z 3rd Highest
95
Thumbnail
Thumbnail

4.1.2 LC-MS

1 of 11
View All
Authors
BGC, Helmholtz Zentrum Muenchen
Instrument
maXis plus UHR-ToF-MS, Bruker Daltonics
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10
Fragmentation Mode
CID
Column Name
BEH C18 1.7um, 2.1x100mm, Waters
Retention Time
4.512 min
Precursor m/z
409.2949
Precursor Adduct
[M+H]+
Top 5 Peaks

373.2741 999

355.2632 384

374.2771 329

409.2945 189

391.2842 155

Thumbnail
Thumbnail
License
CC BY
2 of 11
View All
Authors
BGC, Helmholtz Zentrum Muenchen
Instrument
maXis plus UHR-ToF-MS, Bruker Daltonics
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20
Fragmentation Mode
CID
Column Name
BEH C18 1.7um, 2.1x100mm, Waters
Retention Time
4.512 min
Precursor m/z
409.2949
Precursor Adduct
[M+H]+
Top 5 Peaks

355.2638 999

373.2741 438

356.2672 301

337.253 136

374.2774 124

Thumbnail
Thumbnail
License
CC BY

4.1.3 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[2M+H]+
Precursor m/z
817.582
Instrument
qTof
Ionization Mode
positive
Top 5 Peaks

355.261963 100

373.272522 86.13

356.265015 33.12

374.275757 28.59

337.250977 15.13

Thumbnail
Thumbnail
2 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-2H2O+H]+
Precursor m/z
373.274
Instrument
qTof
Ionization Mode
positive
Top 5 Peaks

355.261688 100

159.115952 66.70

161.131393 45.66

147.115738 44.64

199.146957 34.94

Thumbnail
Thumbnail

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Metabolism / Metabolites

Hyocholic acid has known human metabolites that include hyocholic acid 24-O-glucuronide and hyocholic acid 6-O-glucuronide.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

7.2 Transformations

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Springer Nature References

8.4 Chemical Co-Occurrences in Literature

8.5 Chemical-Gene Co-Occurrences in Literature

8.6 Chemical-Disease Co-Occurrences in Literature

9 Patents

9.1 Depositor-Supplied Patent Identifiers

9.2 WIPO PATENTSCOPE

9.3 Chemical Co-Occurrences in Patents

9.4 Chemical-Disease Co-Occurrences in Patents

9.5 Chemical-Gene Co-Occurrences in Patents

10 Biological Test Results

10.1 BioAssay Results

11 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

12 Classification

12.1 MeSH Tree

12.2 ChEBI Ontology

12.3 LIPID MAPS Classification

12.4 KEGG: Lipid

12.5 ChemIDplus

12.6 ChEMBL Target Tree

12.7 NORMAN Suspect List Exchange Classification

12.8 CCSBase Classification

12.9 EPA DSSTox Classification

12.10 LOTUS Tree

12.11 MolGenie Organic Chemistry Ontology

13 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. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  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. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  7. 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/
    hyocholic acid
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  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. Japan Chemical Substance Dictionary (Nikkaji)
  12. 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
  13. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  14. Natural Product Activity and Species Source (NPASS)
  15. MassBank Europe
  16. 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
  17. Metabolomics Workbench
  18. 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
  19. Springer Nature
  20. Wikidata
  21. Wikipedia
  22. PubChem
  23. 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
  24. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  25. PATENTSCOPE (WIPO)
  26. NCBI
CONTENTS