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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:12:09 UTC

Update Date

2021-09-26 22:56:43 UTC

HMDB ID

HMDB0247190

Secondary Accession Numbers

None

Metabolite Identification

Common Name

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

Description

N-(2-oxooxolan-3-yl)butanimidic acid belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. Based on a literature review very few articles have been published on N-(2-oxooxolan-3-yl)butanimidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-[(3s)-2-oxotetrahydrofuran-3-yl]butanamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    7                                                       
CONECT    4    5    6                                                       
CONECT    5    4   12                                                       
CONECT    6    4    8    9                                                  
CONECT    7    3    9   10                                                  
CONECT    8    6   11   12                                                  
CONECT    9    6    7                                                       
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    5    8                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
N-(2-Oxooxolan-3-yl)butanimidate	Generator
BHL-Serine	MeSH
BHL CPD	MeSH
C(4)-HSL	MeSH
N-Butanoyl-L-homoserine lactone	MeSH
N-Butyryl-L-homoserine lactone	MeSH
C4-HSL	MeSH
PAI-2 CPD	MeSH
Plasminogen activator inhibitor 2	MeSH
N-Butyrylhomoserine lactone	MeSH
Serpin b2	MeSH
Type 2 plasminogen activator inhibitor	MeSH
PAI-2	MeSH

Chemical Formula

C₈H₁₃NO₃

Average Molecular Weight

171.1937

Monoisotopic Molecular Weight

171.089543287

IUPAC Name

N-(2-oxooxolan-3-yl)butanimidic acid

Traditional Name

Hsl

CAS Registry Number

Not Available

SMILES

CCCC(O)=NC1CCOC1=O

InChI Identifier

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

InChI Key

VFFNZZXXTGXBOG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
Acyl-homoserine lactone
Fatty amide
Gamma butyrolactone
Fatty acyl
N-acyl-amine
Tetrahydrofuran
Carboxamide group
Carboxylic acid ester
Lactone
Secondary carboxylic acid amide
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Fatty acyl homoserine lactones (LMFA08030002 )
an acyl-homoserine lactone (CPD-10784 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.76	ALOGPS
logP	0.88	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	7.45	ChemAxon
pKa (Strongest Basic)	1.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	58.89 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	42.61 m³·mol⁻¹	ChemAxon
Polarizability	17.58 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	134.247	30932474
DeepCCS	[M-H]-	130.416	30932474
DeepCCS	[M-2H]-	167.431	30932474
DeepCCS	[M+Na]+	142.883	30932474
AllCCS	[M+H]+	138.6	32859911
AllCCS	[M+H-H2O]+	134.5	32859911
AllCCS	[M+NH4]+	142.4	32859911
AllCCS	[M+Na]+	143.5	32859911
AllCCS	[M-H]-	137.5	32859911
AllCCS	[M+Na-2H]-	138.7	32859911
AllCCS	[M+HCOO]-	140.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide	CCCC(O)=NC1CCOC1=O	2375.1	Standard polar	33892256
N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide	CCCC(O)=NC1CCOC1=O	1491.4	Standard non polar	33892256
N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide	CCCC(O)=NC1CCOC1=O	1549.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide GC-MS (Non-derivatized)	splash10-00di-9500000000-4a7e6c83b313a1da727f	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide GC-MS (1 TMS)	splash10-00e9-3900000000-9d7551152f8bdd3ed1ae	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-9300000000-0e2e21cf9e828a428a6d	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide 40V, Positive-QTOF	splash10-00di-9000000000-1cdedf48fbd42e5d2c34	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide 20V, Positive-QTOF	splash10-00di-9200000000-c2a7ee8cb0fb4b131464	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide 10V, Positive-QTOF	splash10-00di-9700000000-43634cb172ae189315e9	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide 10V, Positive-QTOF	splash10-0uk9-3900000000-e816c290903db83f013d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide 20V, Positive-QTOF	splash10-0k96-9200000000-e1a4cc9b176f9d9a9d30	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide 40V, Positive-QTOF	splash10-0006-9000000000-070b690f0c0195a185ff	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide 10V, Negative-QTOF	splash10-00di-1900000000-ef9d9d63696bd19052f7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide 20V, Negative-QTOF	splash10-0fdn-9700000000-527fbed17063a0e94df6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide 40V, Negative-QTOF	splash10-0006-9100000000-d6fb762415c43b56f6dc	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

391651

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide (HMDB0247190)

MOL for HMDB0247190 (N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide)

3D MOL for HMDB0247190 (N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide)

3D SDF for HMDB0247190 (N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide)

3D-SDF for HMDB0247190 (N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide)

PDB for HMDB0247190 (N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide)

3D PDB for HMDB0247190 (N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide)

SMILES for HMDB0247190 (N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide)

INCHI for HMDB0247190 (N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide)

Structure for HMDB0247190 (N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide)

3D Structure for HMDB0247190 (N-[(3s)-2-Oxotetrahydrofuran-3-Yl]butanamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra