An official website of the United States government

4-Hydroxytolbutamide

PubChem CID
3656
Structure
4-Hydroxytolbutamide_small.png
4-Hydroxytolbutamide_3D_Structure.png
Molecular Formula
Synonyms
  • 4-Hydroxytolbutamide
  • 5719-85-7
  • Hydroxytolbutamide
  • Hydroxy Tolbutamide
  • hydroxymethyltolbutamide
Molecular Weight
286.35 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-25
Description
4-hydroxytolbutamide is a urea that consists of 1-butylurea having a 4-hydroxymethylbenzenesulfonyl group attached at the 3-position. It has a role as a metabolite. It is a sulfonamide, a member of ureas and a member of benzyl alcohols.
4-Hydroxytolbutamide has been reported in Homo sapiens with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
4-Hydroxytolbutamide.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-butyl-3-[4-(hydroxymethyl)phenyl]sulfonylurea
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C12H18N2O4S/c1-2-3-8-13-12(16)14-19(17,18)11-6-4-10(9-15)5-7-11/h4-7,15H,2-3,8-9H2,1H3,(H2,13,14,16)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

SJRHYONYKZIRPM-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCCCNC(=O)NS(=O)(=O)C1=CC=C(C=C1)CO
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C12H18N2O4S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

1185112-19-9

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 HMDB ID

2.3.7 Metabolomics Workbench ID

2.3.8 Nikkaji Number

2.3.9 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 1-butyl-3-(4-hydroxymethylphenyl)sulfonylurea
  • hydroxymethyltolbutamide
  • methylhydroxytolbutamide
  • N-((butylamino)carbonyl)-4-(hydroxymethyl)benzenesulfonamide

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
286.35 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
1.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
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
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
286.09872823 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
286.09872823 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
104 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
19
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
370
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
0
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

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 MS-MS

NIST Number
1221310
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
287.106
Total Peaks
14
m/z Top Peak
188
m/z 2nd Highest
171
m/z 3rd Highest
106.1
Thumbnail
Thumbnail

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Metabolism / Metabolites

4-Hydroxytolbutamide is a known human metabolite of tolbutamide.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

7.2 Human Metabolite Information

7.2.1 Tissue Locations

  • Kidney
  • Liver

7.2.2 Cellular Locations

  • Cytoplasm
  • Extracellular

7.3 Biochemical Reactions

7.4 Transformations

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Springer Nature References

8.4 Wiley References

8.5 Chemical Co-Occurrences in Literature

8.6 Chemical-Gene Co-Occurrences in Literature

8.7 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 Interactions and Pathways

10.1 Chemical-Target Interactions

10.2 Pathways

11 Biological Test Results

11.1 BioAssay Results

12 Taxonomy

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

13 Classification

13.1 MeSH Tree

13.2 ChEBI Ontology

13.3 ChemIDplus

13.4 NORMAN Suspect List Exchange Classification

13.5 EPA DSSTox Classification

13.6 LOTUS Tree

13.7 MolGenie Organic Chemistry Ontology

14 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. 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
  5. 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
  6. ChEBI
  7. 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/
  8. 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
  9. 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
  10. Japan Chemical Substance Dictionary (Nikkaji)
  11. Metabolomics Workbench
  12. 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
  13. 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/
    4-Hydroxytolbutamide
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  14. Springer Nature
  15. Wikidata
  16. Wiley
  17. PubChem
  18. 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
  19. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  20. PATENTSCOPE (WIPO)
CONTENTS