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2-Aminobutyric acid

PubChem CID
6657
Structure
2-Aminobutyric acid_small.png
2-Aminobutyric acid_3D_Structure.png
Molecular Formula
Synonyms
  • DL-2-Aminobutyric acid
  • 2835-81-6
  • 2-Aminobutyric acid
  • 2-Aminobutanoic acid
  • H-DL-ABU-OH
Molecular Weight
103.12 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-11
Description
Alpha-aminobutyric acid is an alpha-amino acid that is butyric acid bearing a single amino substituent located at position 2. It has a role as a human metabolite. It is a monocarboxylic acid and a non-proteinogenic alpha-amino acid. It is functionally related to a butyric acid. It is a conjugate acid of an alpha-aminobutyrate.
2-Aminobutyric acid has been reported in Euphorbia prostrata, Ascochyta medicaginicola, and other organisms with data available.
Alpha-Aminobutyric Acid is an alpha-amino acid that is a derivative of alanine with a side chain that is one carbon longer than the alanine side chain. It is synthesized through the transamination of oxobutyrate and is utilized in the biosynthesis of nonribosomal peptides.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
2-Aminobutyric acid.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
H-DL-Abu-OH
Sequence
X
HELM
PEPTIDE1{[CCC(C(=O)O)N]}$$$$
IUPAC
2-aminobutyric acid

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

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

3.1.2 InChI

InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

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

3.1.4 SMILES

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

3.2 Molecular Formula

C4H9NO2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

2835-81-6
1492-24-6
80-60-4

3.3.2 Deprecated CAS

80-60-4

3.3.3 European Community (EC) Number

3.3.4 UNII

3.3.5 ChEBI ID

3.3.6 ChEMBL ID

3.3.7 DrugBank ID

3.3.8 DSSTox Substance ID

3.3.9 HMDB ID

3.3.10 NCI Thesaurus Code

3.3.11 Nikkaji Number

3.3.12 NSC Number

3.3.13 Wikidata

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • (2S)-2-aminobutanoic acid
  • 2-aminobutanoic acid
  • 2-aminobutyric acid
  • alpha-aminobutyric acid
  • alpha-aminobutyric acid, (+-)-isomer
  • alpha-aminobutyric acid, (R)-isomer
  • alpha-aminobutyric acid, (S)-isomer
  • butyrine
  • butyrine, (+-)-isomer
  • butyrine, (R)-isomer
  • butyrine, (S)-isomer
  • homoalanine
  • L-2-aminobutyric acid
  • l-homoalanine

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
103.12 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-2.5
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
3
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
103.063328530 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
103.063328530 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
63.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
7
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
72.1
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
1
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)

4.2 Experimental Properties

4.2.1 Physical Description

White solid; [Acros Organics MSDS]

4.2.2 Dissociation Constants

4.3 Chemical Classes

Biological Agents -> Amino Acids and Derivatives

4.3.1 Drugs

Pharmaceuticals -> Antiepileptics
S57 | GREEKPHARMA | Suspect Pharmaceuticals from the National Organization of Medicine, Greece | DOI:10.5281/zenodo.3248883

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 1H NMR Spectra

1 of 3
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Spectra ID
Instrument Type
JEOL
Frequency
400 MHz
Solvent
D2O
Shifts [ppm]:Intensity
1.92:129.00, 3.72:254.00, 1.94:42.00, 1.86:48.00, 1.92:121.00, 3.72:221.00, 1.88:135.00, 1.94:38.00, 1.87:41.00, 1.90:164.00, 0.98:1000.00, 1.93:50.00, 1.89:115.00, 3.73:169.00, 1.93:51.00, 1.91:120.00, 1.00:490.00, 1.90:166.00, 0.96:443.00, 1.90:144.00, 3.70:174.00
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Instrument Name
BRUKER AC-300
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1991-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.1.2 13C NMR Spectra

1 of 3
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Spectra ID
Instrument Type
Varian
Frequency
25.16 MHz
Solvent
D2O
Shifts [ppm]:Intensity
56.70:881.00, 24.53:1000.00, 175.61:721.00, 9.43:836.00
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Source of Sample
The Dow Chemical Company, MIdland, Michigan
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.2 Mass Spectrometry

5.2.1 GC-MS

1 of 6
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Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

142.0 1

103.0 0.98

76.0 0.51

114.0 0.42

160.0 0.37

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NIST Number
230247
Library
Main library
Total Peaks
74
m/z Top Peak
58
m/z 2nd Highest
28
m/z 3rd Highest
41
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5.2.2 MS-MS

1 of 6
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

43.04158 100

41.03788 37.40

58.06516 33.30

42.0338 27.30

39.02293 7.70

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Spectra ID
Ionization Mode
Negative
Top 5 Peaks

102.05646 100

59.02249 3.70

60.99391 3

56.06445 1.90

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5.2.3 LC-MS

1 of 30
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Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
NEGATIVE
Collision Energy
10 V
Precursor m/z
102
Precursor Adduct
[M-H]-
Top 5 Peaks

102.1 999

100.8 1

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License
CC BY-NC-SA
2 of 30
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Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
NEGATIVE
Collision Energy
20 V
Precursor m/z
102
Precursor Adduct
[M-H]-
Top 5 Peaks

102.1 999

56 14

44.6 6

60 5

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License
CC BY-NC-SA

5.2.4 Other MS

1 of 2
MS Category
Experimental
MS Type
Other
Precursor Type
[M-H]-
Precursor m/z
102.0561
Ionization
ESI
Ionization Mode
negative
Collision Energy
30.0,50.0,70.0
Retention Time
7.82613
Top 5 Peaks
102.0563 100
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2 of 2
MS Category
Experimental
MS Type
Other
Precursor Type
[M+H]+
Precursor m/z
104.0706
Ionization
ESI
Ionization Mode
positive
Collision Energy
30.0,50.0,70.0
Retention Time
7.74143
Top 5 Peaks

58.0650 100

104.0705 3.20

41.0384 1.90

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5.3 IR Spectra

5.3.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
MCB MANUFACTURING CHEMISTS, NORWOOD, OHIO
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bruker IFS 85 A
Technique
KBr-Pellet
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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5.3.2 ATR-IR Spectra

1 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Spectrochem Pvt. Ltd.
Catalog Number
101247
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Sample
Aldrich
Catalog Number
162663
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.4 Raman Spectra

1 of 2
Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories
Source of Sample
Spectrochem Pvt. Ltd., India
Catalog Number
101247
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Catalog Number
162663
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
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7 Chemical Vendors

8 Use and Manufacturing

8.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
Butanoic acid, 2-amino-: INACTIVE

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

1 of 2
View All
Note
Pictograms displayed are for 98.3% (57 of 58) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 1.7% (1 of 58) of reports.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements
H319 (98.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
Precautionary Statement Codes

P264+P265, P280, P305+P351+P338, and P337+P317

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

ECHA C&L Notifications Summary

Aggregated GHS information provided per 58 reports by companies from 4 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 1 of 58 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 3 notifications provided by 57 of 58 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Eye Irrit. 2 (98.3%)
Eye Irrit. 2 (100%)

9.1.3 Hazards Summary

May cause irritation; [Acros Organics MSDS]

9.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Butanoic acid, 2-amino-, (.+-.)-
New Zealand EPA Inventory of Chemical Status
Butanoic acid, 2-amino-: Does not have an individual approval but may be used under an appropriate group standard

9.3 Other Safety Information

Chemical Assessment
Evaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia

10 Associated Disorders and Diseases

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Thieme References

11.5 Chemical Co-Occurrences in Literature

11.6 Chemical-Gene Co-Occurrences in Literature

11.7 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Protein Bound 3D Structures

13.2 Chemical-Target Interactions

14 Biological Test Results

14.1 BioAssay Results

15 Taxonomy

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

16 Classification

16.1 MeSH Tree

16.2 NCI Thesaurus Tree

16.3 ChEBI Ontology

16.4 ChemIDplus

16.5 UN GHS Classification

16.6 NORMAN Suspect List Exchange Classification

16.7 EPA DSSTox Classification

16.8 EPA TSCA and CDR Classification

16.9 LOTUS Tree

16.10 EPA Substance Registry Services Tree

16.11 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
    LICENSE
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    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DTP/NCI
    LICENSE
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    https://www.cancer.gov/policies/copyright-reuse
  5. EPA Chemicals under the TSCA
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  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
  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. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  10. ChEBI
  11. 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/
  12. NCI Thesaurus (NCIt)
    LICENSE
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    https://www.cancer.gov/policies/copyright-reuse
  13. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  14. 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
  15. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  16. Therapeutic Target Database (TTD)
  17. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
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    https://haz-map.com/About
    DL-alpha-Amino-n-butyric acid
    https://haz-map.com/Agents/13949
  18. 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
  19. 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
    Butanoic acid, 2-amino-, (S)-
    http://www.nist.gov/srd/nist1a.cfm
  20. SpectraBase
  21. IUPAC Digitized pKa Dataset
  22. Japan Chemical Substance Dictionary (Nikkaji)
  23. Natural Product Activity and Species Source (NPASS)
  24. MassBank Europe
  25. 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
  26. 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/
    Aminobutyric acid
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  27. Springer Nature
  28. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  29. Wikidata
  30. PubChem
  31. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  32. GHS Classification (UNECE)
  33. EPA Substance Registry Services
  34. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  35. PATENTSCOPE (WIPO)
CONTENTS