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N-Butyrylhomoserine lactone

PubChem CID
443433
Structure
N-Butyrylhomoserine lactone_small.png
N-Butyrylhomoserine lactone_3D_Structure.png
Molecular Formula
Synonyms
  • 98426-48-3
  • N-Butanoyl-DL-homoserine lactone
  • N-Butyrylhomoserine lactone
  • N-Butyryl-DL-homoserine lactone
  • N-(2-oxooxolan-3-yl)butanamide
Molecular Weight
171.19 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-18
Description
N-butanoyl-lhomoserine lactone is a N-acyl-amino acid.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
N-Butyrylhomoserine lactone.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
butanoyl-DL-Hsl
Sequence
X
HELM
PEPTIDE1{[CCCC(=O)NC1CCOC1=O]}$$$$
IUPAC
N-butanoyl-DL-homoserine lactone

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

N-(2-oxooxolan-3-yl)butanamide
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

3.1.2 InChI

InChI=1S/C8H13NO3/c1-2-3-7(10)9-6-4-5-12-8(6)11/h6H,2-5H2,1H3,(H,9,10)
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.3 InChIKey

VFFNZZXXTGXBOG-UHFFFAOYSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

3.1.4 SMILES

CCCC(=O)NC1CCOC1=O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C8H13NO3
Computed by PubChem 2.1 (PubChem release 2019.06.18)

3.3 Other Identifiers

3.3.1 ChEBI ID

3.3.2 HMDB ID

3.3.3 Metabolomics Workbench ID

3.3.4 Nikkaji Number

3.3.5 Wikidata

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • BHL-serine
  • C(4)-HSL
  • C4-HSL
  • N-butanoyl-L-homoserine lactone
  • N-butyryl-L-homoserine lactone
  • N-butyrylhomoserine lactone

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
171.19 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
0.5
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
171.08954328 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
171.08954328 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
55.4 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
12
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
191
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
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 2019.01.04)

4.2 Experimental Properties

4.2.1 Kovats Retention Index

Semi-standard non-polar
1530

4.3 Chemical Classes

other linear non-peptide (AHLs)
S75 | CyanoMetDB | Comprehensive database of secondary metabolites from cyanobacteria | DOI:10.5281/zenodo.4551528 | DOI:10.1016/S0031-9422(00)89364-4

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 13C NMR Spectra

Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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5.2 Mass Spectrometry

5.2.1 GC-MS

1 of 4
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Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

71.0 1

143.0 0.56

83.0 0.27

85.0 0.16

72.0 0.15

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Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

130.0 1

71.0 0.83

125.0 0.76

153.0 0.69

156.0 0.66

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5.2.2 MS-MS

1 of 5
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

71.0481 100

85.0286 38.11

145.9884 9.12

84.08 7.82

57.0319 6.84

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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

71.0483 100

102.0546 24.48

84.0439 4.71

85.0281 3.33

154.0856 2.45

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5.2.3 LC-MS

1 of 6
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Authors
BGC, Helmholtz Zentrum Muenchen
Instrument
maXis plus UHR-ToF-MS, Bruker Daltonics
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10
Fragmentation Mode
CID
Column Name
BEH C18 1.7um, 2.1x100mm, Waters
Retention Time
2.223 min
Precursor m/z
172.0968
Precursor Adduct
[M+H]+
Top 5 Peaks

71.0482 999

102.0548 459

172.0962 415

74.0594 161

154.0855 68

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License
CC BY
2 of 6
View All
Authors
BGC, Helmholtz Zentrum Muenchen
Instrument
maXis plus UHR-ToF-MS, Bruker Daltonics
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20
Fragmentation Mode
CID
Column Name
BEH C18 1.7um, 2.1x100mm, Waters
Retention Time
2.223 min
Precursor m/z
172.0968
Precursor Adduct
[M+H]+
Top 5 Peaks

71.0483 999

102.0546 244

84.0439 47

85.0281 33

154.0856 24

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License
CC BY

5.2.4 Other MS

1 of 3
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MS Category
Experimental
MS Type
Other
Precursor Type
M-H2O+H
Precursor m/z
154.086
Instrument
Orbitrap
Ionization Mode
positive
Retention Time
CCS:
Top 5 Peaks

85.028076 100

126.091019 9.95

70.064835 5.91

57.033157 4.12

154.085953 3.15

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2 of 3
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MS Category
Experimental
MS Type
Other
Precursor Type
M+H
Precursor m/z
172.097
Instrument
Orbitrap
Ionization Mode
positive
Retention Time
CCS:
Top 5 Peaks

102.054718 100

154.086075 47.67

74.059822 16.15

144.1017 12.16

144.065445 4.32

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7 Chemical Vendors

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Springer Nature References

8.4 Chemical Co-Occurrences in Literature

8.5 Chemical-Gene Co-Occurrences in Literature

8.6 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

11 Taxonomy

12 Classification

12.1 MeSH Tree

12.2 ChEBI Ontology

12.3 NORMAN Suspect List Exchange Classification

12.4 MolGenie Organic Chemistry Ontology

13 Information Sources

  1. ChEBI
  2. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  3. 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
    N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide
    http://www.hmdb.ca/metabolites/HMDB0247190
  4. 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
    N-Butyryl-DL-homoserine lactone
    http://www.nist.gov/srd/nist1a.cfm
  5. Japan Chemical Substance Dictionary (Nikkaji)
  6. MassBank Europe
  7. 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
  8. Metabolomics Workbench
  9. 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/
  10. SpectraBase
    (+).alpha.(S)-Butyramido.gamma.-butyrolactone
    https://spectrabase.com/spectrum/Btdi4xc6PvM
  11. Springer Nature
  12. Therapeutic Target Database (TTD)
  13. Wikidata
    N-(2-oxooxolan-3-yl)butanimidic acid
    https://www.wikidata.org/wiki/Q105285247
  14. PubChem
  15. 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
  16. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  17. PATENTSCOPE (WIPO)
CONTENTS