An official website of the United States government

2-Butenedioic acid

PubChem CID
723
Structure
2-Butenedioic acid_small.png
2-Butenedioic acid_3D_Structure.png
Molecular Formula
Synonyms
  • 2-Butenedioic acid
  • Butenedioic acid
  • 2-aButenedioic acid
  • 1,2-Ethenedicarboxylic
  • NCIOpen2_003792
Molecular Weight
116.07 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-18
Description
2-Butenedioic acid has been reported in Phomopsis velata, Inula grandis, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
2-Butenedioic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

but-2-enedioic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

C(=CC(=O)O)C(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C4H4O4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

6915-18-0

2.3.2 DSSTox Substance ID

2.3.3 HMDB ID

2.3.4 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • (E)-2-butenedioic acid
  • 2-butenedioic acid
  • ammonium fumarate
  • fumarate dianion
  • fumarate(2-)
  • fumaric acid
  • Furamag
  • mafusol
  • magnesium fumarate
  • sodium fumarate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
116.07 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-0.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
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
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
116.01095860 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
116.01095860 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
74.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
8
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
119
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
1
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 SpringerMaterials Properties

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 2
Source of Spectrum
SRH-2022-4046-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
SRH-2022-4047-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 MS-MS

Spectra ID
Ionization Mode
Negative
Top 5 Peaks

71.01202 100

114.99653 23.26

73.02469 20.93

Thumbnail
Thumbnail

4.1.3 LC-MS

Authors
Tetsuya Mori, Center for Sustainable Resource Science, RIKEN
Instrument
LC, Waters Acquity UPLC System; MS, Waters Xevo G2 Q-Tof
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
6V
Column Name
Acquity bridged ethyl hybrid C18 (1.7 um, 2.1 mm * 100 mm, Waters)
Retention Time
1.66
Precursor m/z
115.0023
Precursor Adduct
[M-H]-
Top 5 Peaks

71.01202 999

114.99653 232

73.02469 209

115.00888 209

Thumbnail
Thumbnail
License
CC BY-NC-SA
Reference
Tsugawa H., Nakabayashi R., Mori T., Yamada Y., Takahashi M., Rai A., Sugiyama R., Yamamoto H., Nakaya T., Yamazaki M., Kooke R., Bac-Molenaar JA., Oztolan-Erol N., Keurentjes JJB., Arita M., Saito K. (2019) "A cheminformatics approach to characterize metabolomes in stable-isotope-labeled organisms" Nature Methods 16(4):295-298. [doi:10.1038/s41592-019-0358-2]

6 Chemical Vendors

7 Literature

7.1 Consolidated References

7.2 NLM Curated PubMed Citations

7.3 Springer Nature References

7.4 Chemical Co-Occurrences in Literature

7.5 Chemical-Gene Co-Occurrences in Literature

7.6 Chemical-Disease Co-Occurrences in Literature

8 Patents

8.1 Depositor-Supplied Patent Identifiers

8.2 WIPO PATENTSCOPE

8.3 Chemical Co-Occurrences in Patents

8.4 Chemical-Disease Co-Occurrences in Patents

8.5 Chemical-Gene Co-Occurrences in Patents

9 Biological Test Results

9.1 BioAssay Results

10 Taxonomy

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

11 Classification

11.1 MeSH Tree

11.2 NORMAN Suspect List Exchange Classification

11.3 EPA DSSTox Classification

11.4 LOTUS Tree

11.5 MolGenie Organic Chemistry Ontology

12 Information Sources

  1. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  2. 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/
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. 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
  5. MassBank Europe
  6. SpectraBase
  7. Springer Nature
  8. SpringerMaterials
  9. Wikidata
  10. PubChem
  11. 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
  12. 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/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  13. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  14. PATENTSCOPE (WIPO)
CONTENTS