An official website of the United States government

3-hydroxy-N-(2-oxooxolan-3-yl)butanamide

PubChem CID
130846
Structure
3-hydroxy-N-(2-oxooxolan-3-yl)butanamide_small.png
3-hydroxy-N-(2-oxooxolan-3-yl)butanamide_3D_Structure.png
Molecular Formula
Synonyms
  • 912545-51-8
  • 3-hydroxy-N-(2-oxooxolan-3-yl)butanamide
  • 126049-72-7
  • HBHSL
  • 3-Hydroxy-butanoyl-DL-homoserine lactone
Molecular Weight
187.19 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-18

1 Structures

1.1 2D Structure

Chemical Structure Depiction
3-hydroxy-N-(2-oxooxolan-3-yl)butanamide.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
deamino-xiThr-DL-Hsl
Sequence
XX
HELM
PEPTIDE1{[*C(=O)CC(C)O |$_R2;;;;;;$|].[*NC1CCOC1=O |$_R1;;;;;;;$|]}$$$$
IUPAC
deamino-threonyl-DL-homoserine lactone

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

3-hydroxy-N-(2-oxooxolan-3-yl)butanamide
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C8H13NO4/c1-5(10)4-7(11)9-6-2-3-13-8(6)12/h5-6,10H,2-4H2,1H3,(H,9,11)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

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

3.1.4 SMILES

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

3.2 Molecular Formula

C8H13NO4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

126049-72-7

3.3.2 DSSTox Substance ID

3.3.3 HMDB ID

3.3.4 Nikkaji Number

3.3.5 Wikidata

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • 3-hydroxy-C4-HSL
  • HBHL, Vibrio harveyi autoinducer
  • HBHSL
  • N-(3-hydroxybutanoyl)homoserine lactone
  • N-(beta-hydroxybutyryl)homoserine lactone
  • N3-HBHL

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
187.19 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-0.1
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
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
187.08445790 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
187.08445790 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
75.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
13
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
216
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
2
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)

5 Spectral Information

5.1 Mass Spectrometry

5.1.1 MS-MS

1 of 6
View All
Spectra ID
Ionization Mode
Negative
Top 5 Peaks

84.0457 100

57.0344 31.01

Thumbnail
Thumbnail
2 of 6
View All
Spectra ID
Ionization Mode
Negative
Top 5 Peaks

84.0457 100

112.0408 51.83

142.0514 17.54

80.0502 5.76

68.0511 3.66

Thumbnail
Thumbnail

5.1.2 LC-MS

1 of 9
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
10
Fragmentation Mode
CID
Column Name
BEH C18 1.7um, 2.1x100mm, Waters
Retention Time
0.913 min
Precursor m/z
188.0917
Precursor Adduct
[M+H]+
Top 5 Peaks

102.0546 999

188.0917 436

87.0435 69

74.0231 21

170.0815 18

Thumbnail
Thumbnail
License
CC BY
2 of 9
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
0.913 min
Precursor m/z
188.0917
Precursor Adduct
[M+H]+
Top 5 Peaks

102.0546 999

74.0593 872

84.0437 199

87.0434 189

69.0331 87

Thumbnail
Thumbnail
License
CC BY

7 Chemical Vendors

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Chemical Co-Occurrences in Literature

8.4 Chemical-Gene Co-Occurrences in Literature

8.5 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 Classification

10.1 MeSH Tree

10.2 ChemIDplus

10.3 EPA DSSTox Classification

11 Information Sources

  1. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  2. EPA DSSTox
    3-Hydroxy-N-(2-oxooxolan-3-yl)butanimidic acid
    https://comptox.epa.gov/dashboard/DTXSID00925385
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  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
    (3R)-3-Hydroxy-N-[(3S)-2-oxooxolan-3-yl]butanamide
    http://www.hmdb.ca/metabolites/HMDB0243607
  4. Japan Chemical Substance Dictionary (Nikkaji)
  5. MassBank Europe
  6. 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
  7. Wikidata
    3-Hydroxy-N-(2-oxooxolan-3-yl)butanimidic acid
    https://www.wikidata.org/wiki/Q82899700
  8. PubChem
  9. 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
    N-(3-hydroxybutanoyl)homoserine lactone
    https://www.ncbi.nlm.nih.gov/mesh/67062185
  10. PATENTSCOPE (WIPO)
CONTENTS