Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Show more...Show more...Show more...Show more...Show more...Show more...

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 19:02:21 UTC

Update Date

2023-02-21 17:24:03 UTC

HMDB ID

HMDB0034235

Secondary Accession Numbers

HMDB34235

Metabolite Identification

Common Name

2-Pentanone

Description

2-Pentanone, also known as ethyl acetone or fema 2842, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 2-Pentanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, 2-pentanone is considered to be an oxygenated hydrocarbon lipid molecule. 2-Pentanone is a sweet, alcohol, and banana tasting compound. 2-Pentanone is found, on average, in the highest concentration within milk (cow). 2-Pentanone has also been detected, but not quantified, in several different foods, such as fats and oils, corns, apples, evergreen blackberries, and fruits. This could make 2-pentanone a potential biomarker for the consumption of these foods. 2-Pentanone, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, nonalcoholic fatty liver disease, and crohn's disease; 2-pentanone has also been linked to the inborn metabolic disorder celiac disease.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Methyl propyl ketone	ChEBI
Ethyl acetone	HMDB
Ethylacetone	HMDB
FEMA 2842	HMDB
Methyl N-propyl ketone	HMDB
Methyl-N-propyl ketone	HMDB
Methyl-propyl-cetone	HMDB
Methylpropyl ketone	HMDB
Metylopropyloketon	HMDB
MPK	HMDB
N-C3H7COCH3	HMDB
N-Propyl methyl ketone	HMDB
PENTAN-2-one	HMDB
Pentanone	HMDB
Pentanone-2	HMDB
Propyl methyl ketone	HMDB
2-Pentanone	ChEBI

Chemical Formula

C₅H₁₀O

Average Molecular Weight

86.1323

Monoisotopic Molecular Weight

86.073164942

IUPAC Name

pentan-2-one

Traditional Name

2-pentanone

CAS Registry Number

107-87-9

SMILES

CCCC(C)=O

InChI Identifier

InChI=1S/C5H10O/c1-3-4-5(2)6/h3-4H2,1-2H3

InChI Key

XNLICIUVMPYHGG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

methyl ketone (CHEBI:16472 )
pentanone (CHEBI:16472 )
Oxygenated hydrocarbons (C01949 )
Oxygenated hydrocarbons (LMFA12000003 )
a small molecule (PENTAN-2-ONE )

Ontology

Sweet

Urine (PMID: 24023812)
Feces (PMID: 17314143)

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Cellular substructure

Extracellular (HMDB: HMDB0034235)
Cytoplasm (HMDB: HMDB0034235)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034235)

Source

Exogenous

Exogenous (HMDB: HMDB0034235)

Food

Food (HMDB: HMDB0034235)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)

Tropical fruit

Banana (FooDB: FOOD00208)
Pineapple (FooDB: FOOD00012)

Fruits (FooDB: FOOD00871)

Berry

Evergreen blackberry (FooDB: FOOD00901)
Blackberry (FooDB: FOOD00906)

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Root vegetable

Carrot (FooDB: FOOD00245)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0034235)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0034235)

Biological role

Nutrient (HMDB: HMDB0034235)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-76.9 °C	Not Available
Boiling Point	100.00 to 110.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	43 mg/mL at 25 °C	Not Available
LogP	0.91	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	29.5 g/L	ALOGPS
logP	0.87	ALOGPS
logP	1.25	ChemAxon
logS	-0.47	ALOGPS
pKa (Strongest Acidic)	19.65	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	25.42 m³·mol⁻¹	ChemAxon
Polarizability	10.26 Å³	ChemAxon
Number of Rings	0	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]+	116.602	31661259
DarkChem	[M-H]-	111.073	31661259
DeepCCS	[M+H]+	129.058	30932474
DeepCCS	[M-H]-	127.162	30932474
DeepCCS	[M-2H]-	162.594	30932474
DeepCCS	[M+Na]+	137.001	30932474
AllCCS	[M+H]+	121.9	32859911
AllCCS	[M+H-H2O]+	117.4	32859911
AllCCS	[M+NH4]+	126.1	32859911
AllCCS	[M+Na]+	127.4	32859911
AllCCS	[M-H]-	130.0	32859911
AllCCS	[M+Na-2H]-	134.6	32859911
AllCCS	[M+HCOO]-	139.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Pentanone	CCCC(C)=O	950.2	Standard polar	33892256
2-Pentanone	CCCC(C)=O	649.5	Standard non polar	33892256
2-Pentanone	CCCC(C)=O	671.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Pentanone,1TMS,isomer #1	CCC=C(C)O[Si](C)(C)C	932.6	Semi standard non polar	33892256
2-Pentanone,1TMS,isomer #1	CCC=C(C)O[Si](C)(C)C	874.3	Standard non polar	33892256
2-Pentanone,1TMS,isomer #2	C=C(CCC)O[Si](C)(C)C	868.0	Semi standard non polar	33892256
2-Pentanone,1TMS,isomer #2	C=C(CCC)O[Si](C)(C)C	878.6	Standard non polar	33892256
2-Pentanone,1TBDMS,isomer #1	CCC=C(C)O[Si](C)(C)C(C)(C)C	1128.1	Semi standard non polar	33892256
2-Pentanone,1TBDMS,isomer #1	CCC=C(C)O[Si](C)(C)C(C)(C)C	1092.9	Standard non polar	33892256
2-Pentanone,1TBDMS,isomer #2	C=C(CCC)O[Si](C)(C)C(C)(C)C	1065.4	Semi standard non polar	33892256
2-Pentanone,1TBDMS,isomer #2	C=C(CCC)O[Si](C)(C)C(C)(C)C	1085.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Pentanone EI-B (Non-derivatized)	splash10-0006-9000000000-cd084d7fb390ed239f79	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Pentanone EI-B (Non-derivatized)	splash10-0006-9000000000-a8e31a9aba1a3bc1fe5a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Pentanone EI-B (Non-derivatized)	splash10-0006-9000000000-9d6ab400df7dd4c12a37	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Pentanone EI-B (Non-derivatized)	splash10-0006-9000000000-b4ba5ddb582a624253c0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Pentanone EI-B (Non-derivatized)	splash10-0006-9000000000-cd084d7fb390ed239f79	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Pentanone EI-B (Non-derivatized)	splash10-0006-9000000000-a8e31a9aba1a3bc1fe5a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Pentanone EI-B (Non-derivatized)	splash10-0006-9000000000-9d6ab400df7dd4c12a37	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Pentanone EI-B (Non-derivatized)	splash10-0006-9000000000-b4ba5ddb582a624253c0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Pentanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-88e909b639cb48d4866d	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Pentanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Pentanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-801a958c8ff6cf1a07ac	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanone 10V, Negative-QTOF	splash10-000i-9000000000-0c79c8c6b9ee4aa2a2cd	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanone 20V, Negative-QTOF	splash10-000i-9000000000-dbac0805a7ae1a0fc0e6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanone 40V, Negative-QTOF	splash10-00kf-9000000000-996ef95b676dd2597c22	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanone 10V, Negative-QTOF	splash10-000i-9000000000-2091e44a102d8284a813	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanone 20V, Negative-QTOF	splash10-000l-9000000000-d95b6779e7356054e2c3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanone 40V, Negative-QTOF	splash10-0a4l-9000000000-46c08aba8255f2290666	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanone 10V, Positive-QTOF	splash10-00kr-9000000000-1c38ed487f1bcb4aeee8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanone 20V, Positive-QTOF	splash10-014r-9000000000-3f64843cdd14d5d31f06	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanone 40V, Positive-QTOF	splash10-00kf-9000000000-c73f068d1777d33c5140	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanone 10V, Positive-QTOF	splash10-014l-9000000000-434302e45aaefa9c6cdb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanone 20V, Positive-QTOF	splash10-0006-9000000000-3d025173fd6728c786c6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Pentanone 40V, Positive-QTOF	splash10-0006-9000000000-4de45b52e8c77166cc36	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)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected and Quantified	8750.105 nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	26416813	details
Feces	Detected and Quantified	13243.193 nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	26416813	details
Feces	Detected and Quantified	13359.293 nmol/g wet feces	Adult (>18 years old)	Not Specified	Normal	26416813	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20055983	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	21494609	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Both	Normal	21386183	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21386183	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Not Specified	Normal	21970810	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19167006	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26806034	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative Colitis	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Not Specified	Treated celiac disease	21970810	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohns disease	26806034	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	26806034	details

Associated Disorders and Diseases

Disease References

Ulcerative colitis
Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ] Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Celiac disease
Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Nonalcoholic fatty liver disease
Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Crohn's disease
Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]