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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-05-18 15:59:05 UTC

Update Date

2023-02-21 17:18:04 UTC

HMDB ID

HMDB0013821

Secondary Accession Numbers

HMDB13821

Metabolite Identification

Common Name

2-Methyl-4-heptanone

Description

2-Methyl-4-heptanone, also known as isobutyl propyl ketone, 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, 2-methyl-4-heptanone is considered to be an oxygenated hydrocarbon. 2-Methyl-4-heptanone has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 2-methyl-4-heptanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Methyl-4-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
2-Methylheptan-4-one	HMDB
Isobutyl N-propyl ketone	HMDB
Isobutyl propyl ketone	HMDB
6-Methyl-4-heptanone	HMDB
2-Methyl-4-heptanone	HMDB

Chemical Formula

C₈H₁₆O

Average Molecular Weight

128.215

Monoisotopic Molecular Weight

128.120115135

IUPAC Name

2-methylheptan-4-one

Traditional Name

4-heptanone, 2-methyl-

CAS Registry Number

626-33-5

SMILES

CCCC(=O)CC(C)C

InChI Identifier

InChI=1S/C8H16O/c1-4-5-8(9)6-7(2)3/h7H,4-6H2,1-3H3

InChI Key

AKRJXOYALOGLHQ-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

Oxygenated hydrocarbons (LMFA12000100 )

Ontology

Not Available

Urine (HMDB: HMDB0013821)

Cellular substructure

Membrane (HMDB: HMDB0013821)

Source

Endogenous

Endogenous (HMDB: HMDB0013821)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	155 °C	Not Available
Water Solubility	1371 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.350 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.98 g/L	ALOGPS
logP	2.39	ALOGPS
logP	2.68	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Basic)	-7.4	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	39.2 m³·mol⁻¹	ChemAxon
Polarizability	16.05 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
DeepCCS	[M+H]+	134.662	30932474
DeepCCS	[M-H]-	132.127	30932474
DeepCCS	[M-2H]-	168.53	30932474
DeepCCS	[M+Na]+	143.717	30932474
AllCCS	[M+H]+	131.5	32859911
AllCCS	[M+H-H2O]+	127.3	32859911
AllCCS	[M+NH4]+	135.4	32859911
AllCCS	[M+Na]+	136.5	32859911
AllCCS	[M-H]-	135.3	32859911
AllCCS	[M+Na-2H]-	138.1	32859911
AllCCS	[M+HCOO]-	141.3	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.	5.04 minutes	32390414
Predicted by Siyang on May 30, 2022	15.9294 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.06 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2093.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	582.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	207.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	367.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	283.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	657.0 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	682.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	100.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1266.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	453.9 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	1395.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	380.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	383.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	425.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	503.8 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	18.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methyl-4-heptanone	CCCC(=O)CC(C)C	1144.5	Standard polar	33892256
2-Methyl-4-heptanone	CCCC(=O)CC(C)C	904.4	Standard non polar	33892256
2-Methyl-4-heptanone	CCCC(=O)CC(C)C	911.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methyl-4-heptanone,1TMS,isomer #1	CCCC(=CC(C)C)O[Si](C)(C)C	1104.0	Semi standard non polar	33892256
2-Methyl-4-heptanone,1TMS,isomer #1	CCCC(=CC(C)C)O[Si](C)(C)C	1086.7	Standard non polar	33892256
2-Methyl-4-heptanone,1TMS,isomer #1	CCCC(=CC(C)C)O[Si](C)(C)C	1095.2	Standard polar	33892256
2-Methyl-4-heptanone,1TMS,isomer #2	CCC=C(CC(C)C)O[Si](C)(C)C	1122.7	Semi standard non polar	33892256
2-Methyl-4-heptanone,1TMS,isomer #2	CCC=C(CC(C)C)O[Si](C)(C)C	1112.7	Standard non polar	33892256
2-Methyl-4-heptanone,1TMS,isomer #2	CCC=C(CC(C)C)O[Si](C)(C)C	1108.0	Standard polar	33892256
2-Methyl-4-heptanone,1TBDMS,isomer #1	CCCC(=CC(C)C)O[Si](C)(C)C(C)(C)C	1316.0	Semi standard non polar	33892256
2-Methyl-4-heptanone,1TBDMS,isomer #1	CCCC(=CC(C)C)O[Si](C)(C)C(C)(C)C	1276.2	Standard non polar	33892256
2-Methyl-4-heptanone,1TBDMS,isomer #1	CCCC(=CC(C)C)O[Si](C)(C)C(C)(C)C	1280.5	Standard polar	33892256
2-Methyl-4-heptanone,1TBDMS,isomer #2	CCC=C(CC(C)C)O[Si](C)(C)C(C)(C)C	1321.0	Semi standard non polar	33892256
2-Methyl-4-heptanone,1TBDMS,isomer #2	CCC=C(CC(C)C)O[Si](C)(C)C(C)(C)C	1313.5	Standard non polar	33892256
2-Methyl-4-heptanone,1TBDMS,isomer #2	CCC=C(CC(C)C)O[Si](C)(C)C(C)(C)C	1288.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-4-heptanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-4-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 - 2-Methyl-4-heptanone 10V, Negative-QTOF	splash10-004i-0900000000-e8448bc978ba2df6edde	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-4-heptanone 20V, Negative-QTOF	splash10-0a6r-8900000000-6e3ab8578213d705098b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-4-heptanone 40V, Negative-QTOF	splash10-00kf-9000000000-12d78d10a7ca3b7b2d0a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-4-heptanone 10V, Positive-QTOF	splash10-0avl-9000000000-d6dcd28512735896e4b7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-4-heptanone 20V, Positive-QTOF	splash10-066u-9000000000-80be91cfd19bca69b8d1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-4-heptanone 40V, Positive-QTOF	splash10-0006-9000000000-91426460659ddc26157a	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, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

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

Membrane (predicted from logP)

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zhang, S., Liu, L...	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

FDB111655

KNApSAcK ID

Not Available

Chemspider ID

62586

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

69378

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1382361

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 2-Methyl-4-heptanone (HMDB0013821)

MOL for HMDB0013821 (2-Methyl-4-heptanone)

3D MOL for HMDB0013821 (2-Methyl-4-heptanone)

3D SDF for HMDB0013821 (2-Methyl-4-heptanone)

3D-SDF for HMDB0013821 (2-Methyl-4-heptanone)

PDB for HMDB0013821 (2-Methyl-4-heptanone)

3D PDB for HMDB0013821 (2-Methyl-4-heptanone)

SMILES for HMDB0013821 (2-Methyl-4-heptanone)

INCHI for HMDB0013821 (2-Methyl-4-heptanone)

Structure for HMDB0013821 (2-Methyl-4-heptanone)

3D Structure for HMDB0013821 (2-Methyl-4-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