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Glycolithocholic acid

PubChem CID
115245
Structure
Glycolithocholic acid_small.png
Glycolithocholic acid_3D_Structure.png
Molecular Formula
Synonyms
  • Glycolithocholic acid
  • Lithocholylglycine
  • 474-74-8
  • Lithocholic acid glycine conjugate
  • Glycolithocholate
Molecular Weight
433.6 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-18
Description
Glycolithocholic acid is the glycine conjugate of lithocholic acid. It is a bile acid glycine conjugate and a N-acylglycine. It is functionally related to a lithocholic acid. It is a conjugate acid of a glycolithocholate.
Glycolithocholic acid has been reported in Homo sapiens and Bos taurus with data available.
See also: Glycolithocholate (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Glycolithocholic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C26H43NO4/c1-16(4-9-23(29)27-15-24(30)31)20-7-8-21-19-6-5-17-14-18(28)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22,28H,4-15H2,1-3H3,(H,27,29)(H,30,31)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

XBSQTYHEGZTYJE-OETIFKLTSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

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

2.2 Molecular Formula

C26H43NO4
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Lipid Maps ID (LM_ID)

2.3.11 Metabolomics Workbench ID

2.3.12 Nikkaji Number

2.3.13 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 3a-Hydroxy-5b-cholanic acid glycine ester
  • glycolithocholate
  • glycolithocholic acid
  • glycolithocholic acid, monosodium salt
  • lithocholylglycine

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
433.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
5.6
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
433.31920885 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
433.31920885 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
86.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
31
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
695
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
9
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

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

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

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

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

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

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

205.49 Ų [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

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

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

3.3 Chemical Classes

3.3.1 Lipids

Lipids -> Sterol Lipids [ST] -> Steroid conjugates [ST05] -> Glycine conjugates [ST0503]

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 LC-MS

1 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS1
Instrument
JMS-T100LP, JEOL
Instrument Type
LC-ESI-TOF
Ionization
ESI
Ionization Mode
negative
Top 5 Peaks

432.31 100

433.30 32

74.02 9

865.62 7

61.98 6

Thumbnail
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License
CC BY
2 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS1
Instrument
JMS-T100LP, JEOL
Instrument Type
LC-ESI-TOF
Ionization
ESI
Ionization Mode
negative
Top 5 Peaks

432.30 100

74.02 73

433.30 30

388.31 10

865.61 10

Thumbnail
Thumbnail
License
CC BY

4.1.2 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
Precursor Type
M-H
Precursor m/z
432.312
Instrument
Orbitrap
Ionization Mode
negative
Retention Time
CCS:
Top 5 Peaks

388.322083 100

433.315918 12.87

432.311737 10.50

414.300934 3.87

388.424042 2.61

Thumbnail
Thumbnail
2 of 3
View All
MS Category
Experimental
MS Type
Other
Precursor Type
2M-2H+Na
Precursor m/z
887.613
Instrument
Orbitrap
Ionization Mode
negative
Retention Time
CCS:
Top 5 Peaks

432.311249 100

663.929565 3.26

674.687195 3.25

663.739685 3.20

432.245758 2.63

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4.2 IR Spectra

4.2.1 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Calbiochem, EMD Chemicals, Inc., an Affiliate of Merck KGaA, Darmstadt, Germany
Catalog Number
36217
Lot Number
410126
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Calbiochem, EMD Chemicals, Inc., an Affiliate of Merck KGaA, Darmstadt, Germany
Catalog Number
36217
Lot Number
410126
Copyright
Copyright © 2013-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Tissue Locations

  • Gall Bladder
  • Intestine
  • Kidney
  • Liver

8.1.2 Cellular Locations

Extracellular

8.1.3 Metabolite Pathways

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Precautionary Statement Codes

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

9.1.2 Hazard Classes and Categories

Skin Irrit. 2 (100%)

Eye Irrit. 2 (100%)

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Chemical Co-Occurrences in Literature

10.5 Chemical-Gene Co-Occurrences in Literature

10.6 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Interactions and Pathways

12.1 Chemical-Target Interactions

12.2 Pathways

13 Biological Test Results

13.1 BioAssay Results

14 Taxonomy

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

15 Classification

15.1 MeSH Tree

15.2 ChEBI Ontology

15.3 LIPID MAPS Classification

15.4 KEGG: Lipid

15.5 ChemIDplus

15.6 ChEMBL Target Tree

15.7 UN GHS Classification

15.8 CCSBase Classification

15.9 EPA DSSTox Classification

15.10 LOTUS Tree

15.11 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. BindingDB
    LICENSE
    All data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).
    https://www.bindingdb.org/rwd/bind/info.jsp
  2. 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
  3. 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
  4. 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/
  5. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. 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
    2-[[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid
    https://echa.europa.eu/substance-information/-/substanceinfo/100.406.061
    2-[[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid (EC: 976-051-6)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/364947
  8. 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
  9. 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
    Lithocholic acid glycine conjugate
    http://www.hmdb.ca/metabolites/HMDB0000698
  10. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  11. ChEBI
  12. 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/
  13. 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
  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
    Lithocholic acid glycine conjugate
    https://foodb.ca/compounds/FDB022187
  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. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  18. Natural Product Activity and Species Source (NPASS)
  19. 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
  20. Metabolomics Workbench
  21. SpectraBase
  22. Springer Nature
  23. Wikidata
  24. PubChem
  25. 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
  26. GHS Classification (UNECE)
  27. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  28. PATENTSCOPE (WIPO)
CONTENTS