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3-Hydroxymethyl Mefenamic Acid

PubChem CID
610738
Structure
3-Hydroxymethyl Mefenamic Acid_small.png
3-Hydroxymethyl Mefenamic Acid_3D_Structure.png
Molecular Formula
Synonyms
  • 3-Hydroxymethyl Mefenamic Acid
  • 5129-20-4
  • Enamic acid (m1)
  • Mefenamic acid (metabolite I)
  • 2-[3-(Hydroxymethyl)-2-methylanilino]benzoic acid
Molecular Weight
257.28 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-11

1 Structures

1.1 2D Structure

Chemical Structure Depiction
3-Hydroxymethyl Mefenamic Acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[3-(hydroxymethyl)-2-methylanilino]benzoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C15H15NO3/c1-10-11(9-17)5-4-8-13(10)16-14-7-3-2-6-12(14)15(18)19/h2-8,16-17H,9H2,1H3,(H,18,19)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CC1=C(C=CC=C1NC2=CC=CC=C2C(=O)O)CO
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H15NO3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

5129-20-4

2.3.2 UNII

2.3.3 DSSTox Substance ID

2.3.4 Nikkaji Number

2.3.5 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
257.28 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.9
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
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
257.10519334 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
257.10519334 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
69.6 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
308
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 Chemical Classes

3.2.1 Drugs

Pharmaceuticals -> Metabolite of Mefenamic acid
S113 | SWISSPHARMA24 | 2024 Swiss Pharmaceutical List with Metabolites | DOI:10.5281/zenodo.10501043

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 2
NIST Number
298742
Library
Main library
Total Peaks
102
m/z Top Peak
209
m/z 2nd Highest
257
m/z 3rd Highest
180
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
JZ-1992-1696-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 LC-MS

1 of 18
View All
Authors
C. Meyer [dtc], B. Beck [dtc,com], J. Hollender [dtc]
Instrument
Exploris 240 Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
15 % (nominal)
Fragmentation Mode
HCD
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
8.513 min
Precursor m/z
258.1125
Precursor Adduct
[M+H]+
Top 5 Peaks

240.1018 999

222.0911 47

210.0913 21

228.1019 5

Thumbnail
Thumbnail
License
CC BY-SA
Reference
Meyer, C., Stravs, M., Hollender, J.. How Wastewater Reflects Human Metabolism - Suspect Screening of Pharmaceutical Metabolites in Wastewater Influent. doi:10.1021/acs.est.4c00968
2 of 18
View All
Authors
C. Meyer [dtc], B. Beck [dtc,com], J. Hollender [dtc]
Instrument
Exploris 240 Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
30 % (nominal)
Fragmentation Mode
HCD
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
8.513 min
Precursor m/z
258.1125
Precursor Adduct
[M+H]+
Top 5 Peaks

240.1018 999

222.0912 839

210.0911 212

196.112 49

195.1038 19

Thumbnail
Thumbnail
License
CC BY-SA
Reference
Meyer, C., Stravs, M., Hollender, J.. How Wastewater Reflects Human Metabolism - Suspect Screening of Pharmaceutical Metabolites in Wastewater Influent. doi:10.1021/acs.est.4c00968

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Metabolism / Metabolites

3-hydroxymethyl mefenamic aci is a known human metabolite of mefenamic acid.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

7.2 Transformations

8 Literature

8.1 Consolidated References

8.2 Chemical Co-Occurrences in Literature

8.3 Chemical-Gene Co-Occurrences in Literature

8.4 Chemical-Disease Co-Occurrences in Literature

9 Patents

9.1 Depositor-Supplied Patent Identifiers

10 Classification

10.1 ChemIDplus

10.2 NORMAN Suspect List Exchange Classification

10.3 EPA DSSTox Classification

10.4 MolGenie Organic Chemistry Ontology

11 Information Sources

  1. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  2. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  3. 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
  4. Japan Chemical Substance Dictionary (Nikkaji)
  5. MassBank Europe
  6. 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
    3-Hydroxymethylmefenamic acid
    http://www.nist.gov/srd/nist1a.cfm
  7. SpectraBase
    2-[3-(Hydroxymethyl)-2-methylanilino]benzoic acid
    https://spectrabase.com/spectrum/1qb0KrtRNzd
  8. 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/
    3-Hydroxymethylmefenamic acid
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  9. Wikidata
    3-hydroxymethyl mefenamic acid
    https://www.wikidata.org/wiki/Q27270702
  10. PubChem
  11. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS