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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:43:54 UTC

Update Date

2023-02-21 17:20:46 UTC

HMDB ID

HMDB0031531

Secondary Accession Numbers

HMDB31531

Metabolite Identification

Common Name

Dihydro-5-pentyl-2(3H)-furanone

Description

Dihydro-5-pentyl-2(3H)-furanone, also known as g-nonanolide, 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. Thus, dihydro-5-pentyl-2(3H)-furanone is considered to be a fatty ester. Based on a literature review very few articles have been published on Dihydro-5-pentyl-2(3H)-furanone.

Structure

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

COMPND    HMDB0031531
HETATM    1  C1  UNL     1      -3.435   0.724  -0.074  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.975  -0.704  -0.290  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.456  -0.804  -0.256  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.945  -0.343   1.064  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.527  -0.389   1.244  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.322   0.440   0.280  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.809   0.280   0.607  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.430   0.566  -0.741  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.463  -0.054  -1.666  1.00  0.00           C  
HETATM   10  O1  UNL     1       2.750  -0.518  -2.816  1.00  0.00           O  
HETATM   11  O2  UNL     1       1.235  -0.029  -1.054  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.399   1.012   0.995  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.889   1.425  -0.735  1.00  0.00           H  
HETATM   14  H3  UNL     1      -4.501   0.758  -0.384  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.381  -1.312   0.537  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.362  -1.011  -1.281  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.168  -1.818  -0.529  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.087  -0.122  -1.077  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.272   0.715   1.250  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.395  -0.998   1.847  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.745   0.021   2.267  1.00  0.00           H  
HETATM   22  H11 UNL     1       0.940  -1.425   1.266  1.00  0.00           H  
HETATM   23  H12 UNL     1       1.045   1.507   0.369  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.980  -0.770   0.841  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.125   0.992   1.389  1.00  0.00           H  
HETATM   26  H15 UNL     1       4.454   0.205  -0.841  1.00  0.00           H  
HETATM   27  H16 UNL     1       3.440   1.653  -0.964  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7   11   23
CONECT    7    8   24   25
CONECT    8    9   26   27
CONECT    9   10   10   11
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
g-Nonanolide	HMDB
Γ-nonanolide	HMDB

Chemical Formula

C₉H₁₆O₂

Average Molecular Weight

156.2221

Monoisotopic Molecular Weight

156.115029756

IUPAC Name

5-pentyloxolan-2-one

Traditional Name

5-pentyloxolan-2-one

CAS Registry Number

57084-16-9

SMILES

CCCCCC1CCC(=O)O1

InChI Identifier

InChI=1S/C9H16O2/c1-2-3-4-5-8-6-7-9(10)11-8/h8H,2-7H2,1H3

InChI Key

OALYTRUKMRCXNH-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

Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Lactones (LMFA07040021 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0031531)
Extracellular (HMDB: HMDB0031531)

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0031531)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031531)

Source

Endogenous

Endogenous (HMDB: HMDB0031531)

Plant

Exogenous

Food

Food (HMDB: HMDB0031531)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031531)

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
Water Solubility	0.58 g/L	ALOGPS
logP	2.41	ALOGPS
logP	2.42	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	43.05 m³·mol⁻¹	ChemAxon
Polarizability	18.33 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	137.164	31661259
DarkChem	[M-H]-	132.848	31661259
DeepCCS	[M+H]+	140.147	30932474
DeepCCS	[M-H]-	137.19	30932474
DeepCCS	[M-2H]-	174.329	30932474
DeepCCS	[M+Na]+	149.277	30932474
AllCCS	[M+H]+	136.9	32859911
AllCCS	[M+H-H2O]+	132.6	32859911
AllCCS	[M+NH4]+	141.0	32859911
AllCCS	[M+Na]+	142.2	32859911
AllCCS	[M-H]-	139.5	32859911
AllCCS	[M+Na-2H]-	140.9	32859911
AllCCS	[M+HCOO]-	142.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.51 minutes	32390414
Predicted by Siyang on May 30, 2022	16.3229 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.74 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2254.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	546.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	211.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	360.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	374.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	689.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	705.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	96.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1422.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	446.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1457.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	491.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	399.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	569.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	544.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	51.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydro-5-pentyl-2(3H)-furanone	CCCCCC1CCC(=O)O1	2050.2	Standard polar	33892256
Dihydro-5-pentyl-2(3H)-furanone	CCCCCC1CCC(=O)O1	1293.0	Standard non polar	33892256
Dihydro-5-pentyl-2(3H)-furanone	CCCCCC1CCC(=O)O1	1383.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Dihydro-5-pentyl-2(3H)-furanone EI-B (Non-derivatized)	splash10-000i-9000000000-b49a9ba5068e6a6f37e2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dihydro-5-pentyl-2(3H)-furanone EI-B (Non-derivatized)	splash10-000i-9000000000-b49a9ba5068e6a6f37e2	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydro-5-pentyl-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9100000000-af0a79e6fed6da9b90e5	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydro-5-pentyl-2(3H)-furanone 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 - Dihydro-5-pentyl-2(3H)-furanone 10V, Positive-QTOF	splash10-0a4i-3900000000-744435374457def1ad43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-pentyl-2(3H)-furanone 20V, Positive-QTOF	splash10-0a4j-9400000000-138d9d1b3adff2cc8bc2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-pentyl-2(3H)-furanone 40V, Positive-QTOF	splash10-052f-9000000000-2aef2660fd27b623a33a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-pentyl-2(3H)-furanone 10V, Negative-QTOF	splash10-0a4i-0900000000-8a84aa8e2a9449a5fa56	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-pentyl-2(3H)-furanone 20V, Negative-QTOF	splash10-0bt9-2900000000-f3ab54e2cccc6f3c6d41	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-pentyl-2(3H)-furanone 40V, Negative-QTOF	splash10-0006-9200000000-582e8883da5af41a1b0e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-pentyl-2(3H)-furanone 10V, Positive-QTOF	splash10-0596-9200000000-f9386d8ee820b5a6d62d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-pentyl-2(3H)-furanone 20V, Positive-QTOF	splash10-052f-9100000000-db15bac3d76d44b01087	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-pentyl-2(3H)-furanone 40V, Positive-QTOF	splash10-0006-9000000000-fb82163f045c302c5a5a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-pentyl-2(3H)-furanone 10V, Negative-QTOF	splash10-0a4i-0900000000-376389ca50b091133eac	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-pentyl-2(3H)-furanone 20V, Negative-QTOF	splash10-0a4i-1900000000-046e7beacadfb7f2d9db	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-pentyl-2(3H)-furanone 40V, Negative-QTOF	splash10-0006-9200000000-4575218cc7d74da5620e	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	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
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20809147	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	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

FDB008138

KNApSAcK ID

C00001318

Chemspider ID

7424

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7710

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

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

Showing metabocard for Dihydro-5-pentyl-2(3H)-furanone (HMDB0031531)

MOL for HMDB0031531 (Dihydro-5-pentyl-2(3H)-furanone)

3D MOL for HMDB0031531 (Dihydro-5-pentyl-2(3H)-furanone)

3D SDF for HMDB0031531 (Dihydro-5-pentyl-2(3H)-furanone)

3D-SDF for HMDB0031531 (Dihydro-5-pentyl-2(3H)-furanone)

PDB for HMDB0031531 (Dihydro-5-pentyl-2(3H)-furanone)

3D PDB for HMDB0031531 (Dihydro-5-pentyl-2(3H)-furanone)

SMILES for HMDB0031531 (Dihydro-5-pentyl-2(3H)-furanone)

INCHI for HMDB0031531 (Dihydro-5-pentyl-2(3H)-furanone)

Structure for HMDB0031531 (Dihydro-5-pentyl-2(3H)-furanone)

3D Structure for HMDB0031531 (Dihydro-5-pentyl-2(3H)-furanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra