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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:43:35 UTC

Update Date

2023-02-21 17:20:37 UTC

HMDB ID

HMDB0031482

Secondary Accession Numbers

HMDB31482

Metabolite Identification

Common Name

3-Heptanone

Description

3-Heptanone, also known as aethylbutylketon, 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. Thus, 3-heptanone is considered to be an oxygenated hydrocarbon. 3-Heptanone is a fatty, fruity, and green tasting compound. 3-Heptanone has been detected, but not quantified in, a few different foods, such as corns (Zea mays), spearmints (Mentha spicata), and sweet cherries (Prunus avium). This could make 3-heptanone a potential biomarker for the consumption of these foods. 3-Heptanone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 3-Heptanone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Aethylbutylketon	ChEBI
Butyl ethyl ketone	ChEBI
Ethyl N-butyl ketone	ChEBI
Ethyl-N-butyl ketone	ChEBI
Ethylbutylcetone	ChEBI
N-Butyl ethyl ketone	ChEBI
Alkaline potassium sodium tartrate	HMDB
Eptan-3-one	HMDB
Ethyl butyl ketone	HMDB
Ethyl butyl ketone 3-heptanone	HMDB
Ethylbutylketon	HMDB
Etilbutilchetone	HMDB
Fehling'S reagent II for sugars	HMDB
FEMA 2545	HMDB
Heptan-3-ON	HMDB
Heptan-3-one	HMDB
N-C4H9COC2H5	HMDB
N-Heptan-3-one	HMDB
3-Heptanone	ChEBI

Chemical Formula

C₇H₁₄O

Average Molecular Weight

114.1855

Monoisotopic Molecular Weight

114.10446507

IUPAC Name

heptan-3-one

Traditional Name

3-heptanone

CAS Registry Number

106-35-4

SMILES

CCCCC(=O)CC

InChI Identifier

InChI=1S/C7H14O/c1-3-5-6-7(8)4-2/h3-6H2,1-2H3

InChI Key

NGAZZOYFWWSOGK-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

dialkyl ketone (CHEBI:50139 )
Oxygenated hydrocarbons (LMFA12000047 )

Ontology

Feces (PMID: 17314143)

Cellular substructure

Extracellular (HMDB: HMDB0031482)
Cytoplasm (HMDB: HMDB0031482)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031482)

Source

Endogenous

Endogenous (HMDB: HMDB0031482)

Plant

Plant (HMDB: HMDB0031482)

Exogenous

Food

Food (HMDB: HMDB0031482)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Herb and spice

Herb

Spearmint (FooDB: FOOD00112)

Fruit

Drupe

Sweet cherry (FooDB: FOOD00145)

Exogenous (HMDB: HMDB0031482)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031482)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-39 °C	Not Available
Boiling Point	146.00 to 148.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	4.3 mg/mL at 20 °C	Not Available
LogP	1.996 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.96 g/L	ALOGPS
logP	2.09	ALOGPS
logP	2.4	ChemAxon
logS	-1.5	ALOGPS
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	4	ChemAxon
Refractivity	34.65 m³·mol⁻¹	ChemAxon
Polarizability	14.27 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]+	124.612	31661259
DarkChem	[M-H]-	121.993	31661259
DeepCCS	[M+H]+	131.285	30932474
DeepCCS	[M-H]-	128.608	30932474
DeepCCS	[M-2H]-	165.018	30932474
DeepCCS	[M+Na]+	139.564	30932474
AllCCS	[M+H]+	129.4	32859911
AllCCS	[M+H-H2O]+	125.1	32859911
AllCCS	[M+NH4]+	133.4	32859911
AllCCS	[M+Na]+	134.6	32859911
AllCCS	[M-H]-	132.8	32859911
AllCCS	[M+Na-2H]-	136.0	32859911
AllCCS	[M+HCOO]-	139.6	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.	4.59 minutes	32390414
Predicted by Siyang on May 30, 2022	15.071 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.93 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1948.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	537.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	198.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	358.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	321.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	613.6 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	624.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1274.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	419.2 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	1304.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	384.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	378.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	467.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	487.5 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	28.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Heptanone	CCCCC(=O)CC	1148.6	Standard polar	33892256
3-Heptanone	CCCCC(=O)CC	853.7	Standard non polar	33892256
3-Heptanone	CCCCC(=O)CC	869.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Heptanone,1TMS,isomer #1	CC=C(CCCC)O[Si](C)(C)C	1062.3	Semi standard non polar	33892256
3-Heptanone,1TMS,isomer #1	CC=C(CCCC)O[Si](C)(C)C	1053.7	Standard non polar	33892256
3-Heptanone,1TMS,isomer #2	CCCC=C(CC)O[Si](C)(C)C	1083.2	Semi standard non polar	33892256
3-Heptanone,1TMS,isomer #2	CCCC=C(CC)O[Si](C)(C)C	1055.6	Standard non polar	33892256
3-Heptanone,1TBDMS,isomer #1	CC=C(CCCC)O[Si](C)(C)C(C)(C)C	1279.8	Semi standard non polar	33892256
3-Heptanone,1TBDMS,isomer #1	CC=C(CCCC)O[Si](C)(C)C(C)(C)C	1241.8	Standard non polar	33892256
3-Heptanone,1TBDMS,isomer #2	CCCC=C(CC)O[Si](C)(C)C(C)(C)C	1291.9	Semi standard non polar	33892256
3-Heptanone,1TBDMS,isomer #2	CCCC=C(CC)O[Si](C)(C)C(C)(C)C	1257.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Heptanone EI-B (Non-derivatized)	splash10-056r-9000000000-4e65dc079db33fe23a4b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Heptanone EI-B (Non-derivatized)	splash10-0a6r-9000000000-40ada3eeb51322d0129f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Heptanone EI-B (Non-derivatized)	splash10-0a6r-9000000000-884a26b430e5a2b0ca43	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Heptanone EI-B (Non-derivatized)	splash10-0ab9-9100000000-0bdca1841d57cf5f49f6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Heptanone EI-B (Non-derivatized)	splash10-056r-9000000000-4e65dc079db33fe23a4b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Heptanone EI-B (Non-derivatized)	splash10-0a6r-9000000000-40ada3eeb51322d0129f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Heptanone EI-B (Non-derivatized)	splash10-0a6r-9000000000-884a26b430e5a2b0ca43	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Heptanone EI-B (Non-derivatized)	splash10-0ab9-9100000000-0bdca1841d57cf5f49f6	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Heptanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-a320b93f9115562ce5f6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Heptanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Heptanone 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 - 3-Heptanone 10V, Positive-QTOF	splash10-014i-3900000000-cc0299b1fd1f8d3066fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptanone 20V, Positive-QTOF	splash10-066u-9300000000-6831d09e5cd8fc71f518	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptanone 40V, Positive-QTOF	splash10-0a4l-9000000000-b0923efd762ce51af5db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptanone 10V, Negative-QTOF	splash10-03di-1900000000-ed06430f7e365b62957c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptanone 20V, Negative-QTOF	splash10-03di-9800000000-86d6d6228d505357fc8f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptanone 40V, Negative-QTOF	splash10-0aou-9000000000-b6800cb34f7041dc1399	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptanone 10V, Positive-QTOF	splash10-0a4i-9000000000-e5f9eee19c5507170ec7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptanone 20V, Positive-QTOF	splash10-0a4i-9000000000-7b0a60d669f2350c1b68	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptanone 40V, Positive-QTOF	splash10-0a4i-9000000000-4e5af4aed079f320ab94	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptanone 10V, Negative-QTOF	splash10-03di-1900000000-9a528a431b2e9c020507	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptanone 20V, Negative-QTOF	splash10-0bu0-9300000000-8beb1e276bd09d17aee2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Heptanone 40V, Negative-QTOF	splash10-0a4i-9000000000-57385ebe4566be6e6e97	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)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	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	Ulcerative Colitis	17314143	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 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008058

KNApSAcK ID

C00011627

Chemspider ID

7514

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3-Heptanone

METLIN ID

Not Available

PubChem Compound

7802

PDB ID

Not Available

ChEBI ID

50139

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1025651

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 3-Heptanone (HMDB0031482)

MOL for HMDB0031482 (3-Heptanone)

3D MOL for HMDB0031482 (3-Heptanone)

3D SDF for HMDB0031482 (3-Heptanone)

3D-SDF for HMDB0031482 (3-Heptanone)

PDB for HMDB0031482 (3-Heptanone)

3D PDB for HMDB0031482 (3-Heptanone)

SMILES for HMDB0031482 (3-Heptanone)

INCHI for HMDB0031482 (3-Heptanone)

Structure for HMDB0031482 (3-Heptanone)

3D Structure for HMDB0031482 (3-Heptanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra