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N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide

PubChem CID
10130163
Structure
N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide_small.png
N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide_3D_Structure.png
Molecular Formula
Synonyms
  • 67605-85-0
  • (S)-N-(2-Oxotetrahydrofuran-3-yl)butyramide
  • N-Butyryl-L-homoserine lactone
  • N-butanoyl-L-homoserine lactone
  • N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide
Molecular Weight
171.19 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2006-10-25
  • Modify:
    2025-01-11
Description
(+)-a(S)-butyr-amido-r-butyrolactone is a N-acyl-amino acid.
N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide has been reported in Lyngbya majuscula with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
butanoyl-Hsl
Sequence
X
HELM
PEPTIDE1{[CCCC(=O)N[C@H]1CCOC1=O]}$$$$
IUPAC
N-butanoyl-L-homoserine lactone

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

N-[(3S)-2-oxooxolan-3-yl]butanamide
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

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)/t6-/m0/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

3.1.3 InChIKey

VFFNZZXXTGXBOG-LURJTMIESA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

3.1.4 SMILES

CCCC(=O)N[C@H]1CCOC1=O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C8H13NO3
Computed by PubChem 2.2 (PubChem release 2024.11.20)

3.3 Other Identifiers

3.3.1 CAS

67605-85-0

3.3.2 ChEBI ID

3.3.3 ChEMBL ID

3.3.4 DSSTox Substance ID

3.3.5 KEGG ID

3.3.6 Lipid Maps ID (LM_ID)

3.3.7 Metabolomics Workbench ID

3.3.8 Nikkaji Number

3.3.9 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 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
0.5
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
171.08954328 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
171.08954328 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
55.4 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
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 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
1
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)

4.2 Chemical Classes

4.2.1 Lipids

Fatty Acyls [FA] -> Fatty amides [FA08] -> Fatty acyl homoserine lactones [FA0803]

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 13C NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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5.2 Mass Spectrometry

5.2.1 GC-MS

1 of 2
Instrument Name
Shimadzu GC-17A
Source of Spectrum
US7642285B2
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
CBC-6-2205-2205_1
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.2.2 MS-MS

NIST Number
1213780
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
172.0968
Total Peaks
7
m/z Top Peak
102.2
m/z 2nd Highest
154.1
m/z 3rd Highest
144.1
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7 Chemical Vendors

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Thieme 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 Protein Bound 3D Structures

10.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

10.2 Chemical-Target Interactions

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 LIPID MAPS Classification

13.4 KEGG: Lipid

13.5 ChemIDplus

13.6 ChEMBL Target Tree

13.7 EPA DSSTox Classification

13.8 The Natural Products Atlas Classification

13.9 LOTUS Tree

13.10 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. ChEBI
  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/
    N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide
    https://www.wikidata.org/wiki/Q27461123
  3. 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
  4. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  5. EPA DSSTox
    N-[(3S)-2-oxooxolan-3-yl]butanamide
    https://comptox.epa.gov/dashboard/DTXSID30435962
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. 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
  7. Japan Chemical Substance Dictionary (Nikkaji)
  8. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  9. KNApSAcK Species-Metabolite Database
  10. The Natural Products Atlas
    LICENSE
    The Natural Products Atlas is licensed under a Creative Commons Attribution 4.0 International License.
    https://www.npatlas.org/terms
    The Natural Products Atlas Classification
    https://www.npatlas.org/
  11. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  12. Metabolomics Workbench
  13. 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-L-homoserine lactone
    http://www.nist.gov/srd/nist1a.cfm
  14. Protein Data Bank in Europe (PDBe)
  15. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  16. SpectraBase
    N-butanoyl-L-homoserine lactone
    https://spectrabase.com/spectrum/3wlYieALsf4
    N-Butyryl-L-homoserine lactone
    https://spectrabase.com/spectrum/CPALsXqhO6v
  17. 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/
  18. Wikidata
    N-[(3S)-2-oxotetrahydrofuran-3-yl]butanamide
    https://www.wikidata.org/wiki/Q27461123
  19. PubChem
  20. 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
  21. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  22. PATENTSCOPE (WIPO)
  23. NCBI
CONTENTS