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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:24:45 UTC

Update Date

2023-02-21 17:27:15 UTC

HMDB ID

HMDB0039874

Secondary Accession Numbers

HMDB39874

Metabolite Identification

Common Name

Furfuryl isovalerate

Description

Furfuryl isovalerate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review a small amount of articles have been published on Furfuryl isovalerate.

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       7.196   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.530   4.977   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.636   2.149   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.605   3.294   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.866   0.816   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.863   2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.864   3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.530   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.198   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.197   3.437   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.197   4.977   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      15.359   1.136   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      12.531   2.667   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    4    5                                                       
CONECT    4    3    9                                                       
CONECT    5    3   12                                                       
CONECT    6    8   10                                                       
CONECT    7    9   13                                                       
CONECT    8    1    2    6                                                  
CONECT    9    4    7   12                                                  
CONECT   10    6   11   13                                                  
CONECT   11   10                                                            
CONECT   12    5    9                                                       
CONECT   13    7   10                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0039874
HETATM    1  C1  UNL     1      -3.658   0.361   0.782  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.199  -0.022   0.538  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.142  -1.478   0.199  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.709   0.830  -0.594  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.306   0.585  -0.965  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.107  -0.553  -1.304  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.682   1.586  -0.971  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.025   1.330  -1.336  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.667   0.315  -0.492  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.263   0.529   0.720  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.729  -0.690   1.155  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.376  -1.569   0.156  1.00  0.00           C  
HETATM   13  O3  UNL     1       2.756  -0.940  -0.789  1.00  0.00           O  
HETATM   14  H1  UNL     1      -4.262  -0.533   1.092  1.00  0.00           H  
HETATM   15  H2  UNL     1      -4.116   0.785  -0.138  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.718   1.122   1.584  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.644   0.173   1.486  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.710  -2.072   0.961  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.126  -1.893   0.143  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.636  -1.613  -0.806  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.933   1.900  -0.424  1.00  0.00           H  
HETATM   22  H9  UNL     1      -2.330   0.537  -1.494  1.00  0.00           H  
HETATM   23  H10 UNL     1       2.101   1.030  -2.399  1.00  0.00           H  
HETATM   24  H11 UNL     1       2.539   2.335  -1.274  1.00  0.00           H  
HETATM   25  H12 UNL     1       3.371   1.469   1.279  1.00  0.00           H  
HETATM   26  H13 UNL     1       4.265  -0.887   2.096  1.00  0.00           H  
HETATM   27  H14 UNL     1       3.609  -2.636   0.201  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    4   17
CONECT    3   18   19   20
CONECT    4    5   21   22
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   23   24
CONECT    9   10   10   13
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   13   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Furfuryl isovaleric acid	Generator
2-Furanylmethyl 3-methylbutanoate	HMDB
2-Furanylmethyl isovalerate	HMDB
3-Methylbutyric acid, 2-furanylmethyl ester	HMDB
Butanoic acid, 3-methyl-, 2-furanmethyl ester	HMDB
Butanoic acid, 3-methyl-, 2-furanylmethyl ester	HMDB
FEMA 3283	HMDB
Furfuryl 3-methylbutanoate	HMDB
Isovaleric acid, furfuryl ester	HMDB

Chemical Formula

C₁₀H₁₄O₃

Average Molecular Weight

182.2164

Monoisotopic Molecular Weight

182.094294314

IUPAC Name

furan-2-ylmethyl 3-methylbutanoate

Traditional Name

furan-2-ylmethyl 3-methylbutanoate

CAS Registry Number

13678-60-9

SMILES

CC(C)CC(=O)OCC1=CC=CO1

InChI Identifier

InChI=1S/C10H14O3/c1-8(2)6-10(11)13-7-9-4-3-5-12-9/h3-5,8H,6-7H2,1-2H3

InChI Key

FKGUIBCHHSHJNQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Heteroaromatic compound
Furan
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0039874)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039874)

Source

Endogenous

Endogenous (HMDB: HMDB0039874)

Plant

Coffea (HMDB: HMDB0039874)

Animal

Animal (HMDB: HMDB0039874)

Exogenous

Food

Food (HMDB: HMDB0039874)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0039874)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0039874)

Lipid metabolism pathway (HMDB: HMDB0039874)

Cellular process

Cell signaling (HMDB: HMDB0039874)

Biochemical process

Lipid transport (HMDB: HMDB0039874)

Role

Biological role

Energy source (HMDB: HMDB0039874)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039874)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0039874)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	97.00 to 98.00 °C. @ 11.00 mm Hg	The Good Scents Company Information System
Water Solubility	197.6 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.475 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.42 g/L	ALOGPS
logP	2.6	ALOGPS
logP	2.14	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	48.19 m³·mol⁻¹	ChemAxon
Polarizability	19.64 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.885	31661259
DarkChem	[M-H]-	139.201	31661259
DeepCCS	[M+H]+	146.013	30932474
DeepCCS	[M-H]-	143.632	30932474
DeepCCS	[M-2H]-	179.751	30932474
DeepCCS	[M+Na]+	154.967	30932474
AllCCS	[M+H]+	139.6	32859911
AllCCS	[M+H-H2O]+	135.6	32859911
AllCCS	[M+NH4]+	143.4	32859911
AllCCS	[M+Na]+	144.5	32859911
AllCCS	[M-H]-	142.2	32859911
AllCCS	[M+Na-2H]-	143.2	32859911
AllCCS	[M+HCOO]-	144.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Furfuryl isovalerate	CC(C)CC(=O)OCC1=CC=CO1	1687.1	Standard polar	33892256
Furfuryl isovalerate	CC(C)CC(=O)OCC1=CC=CO1	1233.5	Standard non polar	33892256
Furfuryl isovalerate	CC(C)CC(=O)OCC1=CC=CO1	1243.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Furfuryl isovalerate EI-B (Non-derivatized)	splash10-001i-9000000000-53a8460f17b1f9b4430b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Furfuryl isovalerate EI-B (Non-derivatized)	splash10-001i-9000000000-53a8460f17b1f9b4430b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Furfuryl isovalerate GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-cd449e090f4a0e879e32	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Furfuryl isovalerate 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 - Furfuryl isovalerate 10V, Positive-QTOF	splash10-001i-5900000000-29b955d513c0bea74710	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl isovalerate 20V, Positive-QTOF	splash10-0006-9100000000-eedcfbd2c08dd5ffc0b4	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl isovalerate 40V, Positive-QTOF	splash10-052f-9000000000-d552fed89a0c5e62ec6a	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl isovalerate 10V, Negative-QTOF	splash10-001i-7900000000-25218e0e865f0918974c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl isovalerate 20V, Negative-QTOF	splash10-001i-9300000000-07a0917219b9ed21775b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl isovalerate 40V, Negative-QTOF	splash10-015c-9000000000-f57a58fd5aef87aca150	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl isovalerate 10V, Negative-QTOF	splash10-001j-9500000000-c40d9dcc0cfffb0828b9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl isovalerate 20V, Negative-QTOF	splash10-015a-9000000000-a97ec1d299422d80316c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl isovalerate 40V, Negative-QTOF	splash10-014i-9000000000-e301d9ad6b9fd66f0a12	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl isovalerate 10V, Positive-QTOF	splash10-0006-9000000000-ccb90d883a002cc5b26d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl isovalerate 20V, Positive-QTOF	splash10-001m-9000000000-ab7f862f822f4fd10d7f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl isovalerate 40V, Positive-QTOF	splash10-001j-9000000000-022f46cf7ef5654a60b1	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

FDB019533

KNApSAcK ID

Not Available

Chemspider ID

55563

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61658

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1024341

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Furfuryl isovalerate (HMDB0039874)

MOL for HMDB0039874 (Furfuryl isovalerate)

3D MOL for HMDB0039874 (Furfuryl isovalerate)

3D SDF for HMDB0039874 (Furfuryl isovalerate)

3D-SDF for HMDB0039874 (Furfuryl isovalerate)

PDB for HMDB0039874 (Furfuryl isovalerate)

3D PDB for HMDB0039874 (Furfuryl isovalerate)

SMILES for HMDB0039874 (Furfuryl isovalerate)

INCHI for HMDB0039874 (Furfuryl isovalerate)

Structure for HMDB0039874 (Furfuryl isovalerate)

3D Structure for HMDB0039874 (Furfuryl isovalerate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra