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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:40:16 UTC

Update Date

2022-03-07 02:52:47 UTC

HMDB ID

HMDB0030992

Secondary Accession Numbers

HMDB30992

Metabolite Identification

Common Name

5-Butyltetrahydro-2-oxo-3-furancarboxylic acid

Description

5-Butyltetrahydro-2-oxo-3-furancarboxylic acid, also known as 2-carboxy-4-octanolide or 5-butyl-2-oxooxolane-3-carboxylate, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Based on a literature review a significant number of articles have been published on 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.608   6.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.267  -1.375   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.109  -2.943   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    6                                                       
CONECT    5    6    7                                                       
CONECT    6    4    5   13                                                  
CONECT    7    5    8    9                                                  
CONECT    8    7   10   11                                                  
CONECT    9    7   12   13                                                  
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    6    9                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0030992
HETATM    1  C1  UNL     1       3.513   0.436   0.361  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.532  -0.277   1.275  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.475  -0.958   0.413  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.798   0.111  -0.372  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.273  -0.346  -1.298  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.363  -1.030  -0.554  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.119   0.154   0.045  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.571   0.002  -0.158  1.00  0.00           C  
HETATM    9  O1  UNL     1      -4.018  -0.995  -0.751  1.00  0.00           O  
HETATM   10  O2  UNL     1      -4.429   0.967   0.310  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.668   1.316  -0.745  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.918   2.515  -0.514  1.00  0.00           O  
HETATM   13  O4  UNL     1      -0.916   0.837  -1.791  1.00  0.00           O  
HETATM   14  H1  UNL     1       3.520  -0.040  -0.639  1.00  0.00           H  
HETATM   15  H2  UNL     1       3.224   1.516   0.219  1.00  0.00           H  
HETATM   16  H3  UNL     1       4.528   0.394   0.795  1.00  0.00           H  
HETATM   17  H4  UNL     1       3.012  -0.967   1.969  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.980   0.505   1.856  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.756  -1.489   1.061  1.00  0.00           H  
HETATM   20  H7  UNL     1       1.941  -1.719  -0.236  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.426   0.898   0.337  1.00  0.00           H  
HETATM   22  H9  UNL     1       1.590   0.619  -0.992  1.00  0.00           H  
HETATM   23  H10 UNL     1       0.153  -0.935  -2.126  1.00  0.00           H  
HETATM   24  H11 UNL     1      -2.072  -1.581  -1.222  1.00  0.00           H  
HETATM   25  H12 UNL     1      -1.016  -1.744   0.204  1.00  0.00           H  
HETATM   26  H13 UNL     1      -1.873   0.253   1.127  1.00  0.00           H  
HETATM   27  H14 UNL     1      -4.212   1.557   1.123  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17   18
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6   13   23
CONECT    6    7   24   25
CONECT    7    8   11   26
CONECT    8    9    9   10
CONECT   10   27
CONECT   11   12   12   13
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-Butyltetrahydro-2-oxo-3-furancarboxylate	Generator
2-Carboxy-4-octanolide	HMDB
5-Butyl-2-oxooxolane-3-carboxylate	HMDB

Chemical Formula

C₉H₁₄O₄

Average Molecular Weight

186.2051

Monoisotopic Molecular Weight

186.089208936

IUPAC Name

5-butyl-2-oxooxolane-3-carboxylic acid

Traditional Name

5-butyl-2-oxooxolane-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCCCC1CC(C(O)=O)C(=O)O1

InChI Identifier

InChI=1S/C9H14O4/c1-2-3-4-6-5-7(8(10)11)9(12)13-6/h6-7H,2-5H2,1H3,(H,10,11)

InChI Key

XCIYLBHMPNYNTF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

1,3-dicarbonyl compound
Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030992)
Cytoplasm (HMDB: HMDB0030992)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030992)

Source

Endogenous

Endogenous (HMDB: HMDB0030992)

Animal

Animal (HMDB: HMDB0030992)

Exogenous

Food

Food (HMDB: HMDB0030992)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	48 - 50 °C	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
Water Solubility	8.23 g/L	ALOGPS
logP	1.69	ALOGPS
logP	1.71	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	4.16	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	44.74 m³·mol⁻¹	ChemAxon
Polarizability	19.06 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
DarkChem	[M+H]+	142.904	31661259
DarkChem	[M-H]-	139.544	31661259
DeepCCS	[M+H]+	146.367	30932474
DeepCCS	[M-H]-	142.391	30932474
DeepCCS	[M-2H]-	179.952	30932474
DeepCCS	[M+Na]+	155.361	30932474
AllCCS	[M+H]+	142.6	32859911
AllCCS	[M+H-H2O]+	138.5	32859911
AllCCS	[M+NH4]+	146.5	32859911
AllCCS	[M+Na]+	147.6	32859911
AllCCS	[M-H]-	142.7	32859911
AllCCS	[M+Na-2H]-	143.7	32859911
AllCCS	[M+HCOO]-	144.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Butyltetrahydro-2-oxo-3-furancarboxylic acid	CCCCC1CC(C(O)=O)C(=O)O1	2639.5	Standard polar	33892256
5-Butyltetrahydro-2-oxo-3-furancarboxylic acid	CCCCC1CC(C(O)=O)C(=O)O1	1517.9	Standard non polar	33892256
5-Butyltetrahydro-2-oxo-3-furancarboxylic acid	CCCCC1CC(C(O)=O)C(=O)O1	1649.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Butyltetrahydro-2-oxo-3-furancarboxylic acid,1TMS,isomer #1	CCCCC1CC(C(=O)O[Si](C)(C)C)C(=O)O1	1580.2	Semi standard non polar	33892256
5-Butyltetrahydro-2-oxo-3-furancarboxylic acid,1TBDMS,isomer #1	CCCCC1CC(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1	1828.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-795c58abe357852605d7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0076-9200000000-1f607d7f41756a71a70b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid 10V, Positive-QTOF	splash10-000l-3900000000-de2e9d5a7b637e2bf65e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid 20V, Positive-QTOF	splash10-00ko-7900000000-74bf73781478761f7eee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid 40V, Positive-QTOF	splash10-0536-9000000000-d615e0f2913ebae70ae0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid 10V, Negative-QTOF	splash10-000f-1900000000-2ddd014ab7ef3cddf5d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid 20V, Negative-QTOF	splash10-0006-3900000000-7e07f77fab8acfad702c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid 40V, Negative-QTOF	splash10-006w-9100000000-26fb4797c2af865021f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid 10V, Positive-QTOF	splash10-000i-1900000000-78604aee13474093d7ed	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid 20V, Positive-QTOF	splash10-00kr-8900000000-59b743cb5f1e6b0fa986	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid 40V, Positive-QTOF	splash10-05ru-9000000000-7eb9d29b3ffdd42fa8fe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid 10V, Negative-QTOF	splash10-000i-0900000000-4c98e1b2c7bbae6459df	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid 20V, Negative-QTOF	splash10-000f-2900000000-1911fa2b70f922e569c8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid 40V, Negative-QTOF	splash10-0pbd-9100000000-2c967f8980a80dd46999	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB002980

KNApSAcK ID

Not Available

Chemspider ID

35013303

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751118

PDB ID

Not Available

ChEBI ID

173888

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 5-Butyltetrahydro-2-oxo-3-furancarboxylic acid (HMDB0030992)

MOL for HMDB0030992 (5-Butyltetrahydro-2-oxo-3-furancarboxylic acid)

3D MOL for HMDB0030992 (5-Butyltetrahydro-2-oxo-3-furancarboxylic acid)

3D SDF for HMDB0030992 (5-Butyltetrahydro-2-oxo-3-furancarboxylic acid)

3D-SDF for HMDB0030992 (5-Butyltetrahydro-2-oxo-3-furancarboxylic acid)

PDB for HMDB0030992 (5-Butyltetrahydro-2-oxo-3-furancarboxylic acid)

3D PDB for HMDB0030992 (5-Butyltetrahydro-2-oxo-3-furancarboxylic acid)

SMILES for HMDB0030992 (5-Butyltetrahydro-2-oxo-3-furancarboxylic acid)

INCHI for HMDB0030992 (5-Butyltetrahydro-2-oxo-3-furancarboxylic acid)

Structure for HMDB0030992 (5-Butyltetrahydro-2-oxo-3-furancarboxylic acid)

3D Structure for HMDB0030992 (5-Butyltetrahydro-2-oxo-3-furancarboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra