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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:44:49 UTC

Update Date

2023-02-21 17:21:10 UTC

HMDB ID

HMDB0031681

Secondary Accession Numbers

HMDB31681

Metabolite Identification

Common Name

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

Description

Dihydro-5-propyl-2(3H)-furanone 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-propyl-2(3H)-furanone is considered to be a fatty ester. Dihydro-5-propyl-2(3H)-furanone is a sweet, caramel, and coconut tasting compound. Dihydro-5-propyl-2(3H)-furanone has been detected, but not quantified in, asparagus (Asparagus officinalis) and peaches (Prunus persica). This could make dihydro-5-propyl-2(3H)-furanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dihydro-5-propyl-2(3H)-furanone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+/-)-4-heptanolide	HMDB
(+/-)-dihydro-5-propyl-2(3H)-furanone	HMDB
(+/-)-gamma-propyl-gamma-butyrolactone	HMDB
1,4-Heptanolide	HMDB
4-Hydroxyheptanoic acid, gamma-lactone	HMDB
4-Propyl-4-hydroxybutanoic acid lactone	HMDB
5-Propyl-tetrahydro-furan-2-one	HMDB
gamma-Heptalactone	HMDB
gamma-Heptanolactone	HMDB
gamma-Propiobutyrolactone	HMDB
gamma-Propyl-gamma-butyrolactone	HMDB
Heptan-4-olide	HMDB
Heptanolide-4,1	HMDB
4-Propyl-g-butyrolactone	Generator
4-Propyl-γ-butyrolactone	Generator

Chemical Formula

C₇H₁₂O₂

Average Molecular Weight

128.169

Monoisotopic Molecular Weight

128.083729628

IUPAC Name

5-propyloxolan-2-one

Traditional Name

5-propyloxolan-2-one

CAS Registry Number

57129-71-2

SMILES

CCCC1CCC(=O)O1

InChI Identifier

InChI=1S/C7H12O2/c1-2-3-6-4-5-7(8)9-6/h6H,2-5H2,1H3

InChI Key

VLSVVMPLPMNWBH-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 (LMFA07040012 )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0031681)
Extracellular (HMDB: HMDB0031681)

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0031681)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0031681)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031681)

Source

Exogenous

Exogenous (HMDB: HMDB0031681)

Food

Food (HMDB: HMDB0031681)

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Fruit

Drupe

Peach (FooDB: FOOD00149)

Endogenous

Plant

Plant (HMDB: HMDB0031681)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0031681)

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	6.81 g/L	ALOGPS
logP	1.42	ALOGPS
logP	1.53	ChemAxon
logS	-1.3	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	2	ChemAxon
Refractivity	33.85 m³·mol⁻¹	ChemAxon
Polarizability	14.17 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]+	127.07	31661259
DarkChem	[M-H]-	121.296	31661259
DeepCCS	[M+H]+	132.994	30932474
DeepCCS	[M-H]-	130.641	30932474
DeepCCS	[M-2H]-	166.949	30932474
DeepCCS	[M+Na]+	141.482	30932474
AllCCS	[M+H]+	128.5	32859911
AllCCS	[M+H-H2O]+	123.8	32859911
AllCCS	[M+NH4]+	132.8	32859911
AllCCS	[M+Na]+	134.1	32859911
AllCCS	[M-H]-	129.8	32859911
AllCCS	[M+Na-2H]-	131.9	32859911
AllCCS	[M+HCOO]-	134.2	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.	4.01 minutes	32390414
Predicted by Siyang on May 30, 2022	14.2049 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.47 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1942.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	492.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	188.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	334.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	326.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	575.0 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	624.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	102.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1174.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	393.4 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	1274.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	395.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	361.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	524.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	485.4 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	79.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydro-5-propyl-2(3H)-furanone	CCCC1CCC(=O)O1	1802.2	Standard polar	33892256
Dihydro-5-propyl-2(3H)-furanone	CCCC1CCC(=O)O1	1085.7	Standard non polar	33892256
Dihydro-5-propyl-2(3H)-furanone	CCCC1CCC(=O)O1	1159.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Dihydro-5-propyl-2(3H)-furanone EI-B (Non-derivatized)	splash10-000i-9000000000-c224bc120cc60670620f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dihydro-5-propyl-2(3H)-furanone EI-B (Non-derivatized)	splash10-000i-9000000000-c224bc120cc60670620f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydro-5-propyl-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-056u-9000000000-d65f08c5431130e748ca	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydro-5-propyl-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydro-5-propyl-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-propyl-2(3H)-furanone 10V, Positive-QTOF	splash10-004i-4900000000-98642a6f9598537ab510	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 20V, Positive-QTOF	splash10-05r9-9300000000-d38e27aabefbd271fd0a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 40V, Positive-QTOF	splash10-00kf-9000000000-ebcb66a25ad3f79fa256	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 10V, Negative-QTOF	splash10-004i-3900000000-705e0da057c614b37de1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 20V, Negative-QTOF	splash10-0059-9700000000-dc33ef926913eed12375	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 40V, Negative-QTOF	splash10-0006-9000000000-f99153eb643bf57c921d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 10V, Positive-QTOF	splash10-05o3-9100000000-c0ea09b5a63622fe42f6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 20V, Positive-QTOF	splash10-0a4i-9000000000-548b7b2060383993efa4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 40V, Positive-QTOF	splash10-0a4l-9000000000-bf344b6b6e2f603abaab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 10V, Negative-QTOF	splash10-004i-0900000000-3a7b7e53b32e365081f9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 20V, Negative-QTOF	splash10-004i-9700000000-30794976276fa018bbe4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydro-5-propyl-2(3H)-furanone 40V, Negative-QTOF	splash10-052f-9000000000-3e450e442b08ba75cbd5	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

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

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

Feces
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)	Not Specified	Normal	24421258	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20809147	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details

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

FDB008341

KNApSAcK ID

Not Available

Chemspider ID

7456

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7742

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-propyl-2(3H)-furanone (HMDB0031681)

MOL for HMDB0031681 (Dihydro-5-propyl-2(3H)-furanone)

3D MOL for HMDB0031681 (Dihydro-5-propyl-2(3H)-furanone)

3D SDF for HMDB0031681 (Dihydro-5-propyl-2(3H)-furanone)

3D-SDF for HMDB0031681 (Dihydro-5-propyl-2(3H)-furanone)

PDB for HMDB0031681 (Dihydro-5-propyl-2(3H)-furanone)

3D PDB for HMDB0031681 (Dihydro-5-propyl-2(3H)-furanone)

SMILES for HMDB0031681 (Dihydro-5-propyl-2(3H)-furanone)

INCHI for HMDB0031681 (Dihydro-5-propyl-2(3H)-furanone)

Structure for HMDB0031681 (Dihydro-5-propyl-2(3H)-furanone)

3D Structure for HMDB0031681 (Dihydro-5-propyl-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