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

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:43:33 UTC

Update Date

2023-02-21 17:20:36 UTC

HMDB ID

HMDB0031476

Secondary Accession Numbers

HMDB31476

Metabolite Identification

Common Name

2,3-Heptanedione

Description

2,3-Heptanedione, also known as heptane-23-dione or 2,3-dioxoheptane, belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms. Thus, 2,3-heptanedione is considered to be an oxygenated hydrocarbon lipid molecule. 2,3-Heptanedione is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2,3-Heptanedione is a butter, cheese, and oily tasting compound. 2,3-Heptanedione has been detected, but not quantified, in several different foods, such as alcoholic beverages, garden tomato, mushrooms, and pulses. This could make 2,3-heptanedione a potential biomarker for the consumption of these foods.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Heptane-23-dione	ChEMBL, HMDB
2,3-Dioxoheptane	HMDB
Acetyl pentanoyl	HMDB
Acetyl valeryl	HMDB
Benzil-related compound, 47	HMDB
FEMA 2543	HMDB
Valerylacetyl	HMDB

Chemical Formula

C₇H₁₂O₂

Average Molecular Weight

128.169

Monoisotopic Molecular Weight

128.083729628

IUPAC Name

heptane-2,3-dione

Traditional Name

heptane-2,3-dione

CAS Registry Number

96-04-8

SMILES

CCCCC(=O)C(C)=O

InChI Identifier

InChI=1S/C7H12O2/c1-3-4-5-7(9)6(2)8/h3-5H2,1-2H3

InChI Key

FJPGAMCQJNLTJC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-diketones

Alternative Parents

Substituents

Alpha-diketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Oxygenated hydrocarbons (LMFA12000013 )
a small molecule (CPD-9080 )

Ontology

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Excreta

Biofluid or Excreta

Feces (PMID: 17314143)

Cellular substructure

Extracellular (HMDB: HMDB0031476)
Cytoplasm (HMDB: HMDB0031476)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031476)

Source

Endogenous

Endogenous (HMDB: HMDB0031476)

Plant

Plant (HMDB: HMDB0031476)
Fabaceae (HMDB: HMDB0031476)

Exogenous

Food

Food (HMDB: HMDB0031476)

Vegetable

Mushroom

Fruit vegetable

Garden tomato (FooDB: FOOD00171)

Pulse

Pulses (FooDB: FOOD00867)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0031476)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	64.00 °C. @ 18.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	0.188 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.83 g/L	ALOGPS
logP	1.48	ALOGPS
logP	1.99	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	16.22	ChemAxon
pKa (Strongest Basic)	-8.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	35.37 m³·mol⁻¹	ChemAxon
Polarizability	14.32 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]+	129.592	31661259
DarkChem	[M-H]-	125.596	31661259
DeepCCS	[M+H]+	133.086	30932474
DeepCCS	[M-H]-	130.516	30932474
DeepCCS	[M-2H]-	167.099	30932474
DeepCCS	[M+Na]+	141.633	30932474
AllCCS	[M+H]+	130.8	32859911
AllCCS	[M+H-H2O]+	126.6	32859911
AllCCS	[M+NH4]+	134.8	32859911
AllCCS	[M+Na]+	135.9	32859911
AllCCS	[M-H]-	130.6	32859911
AllCCS	[M+Na-2H]-	133.3	32859911
AllCCS	[M+HCOO]-	136.3	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.	4.33 minutes	32390414
Predicted by Siyang on May 30, 2022	13.5044 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.98 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1705.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	470.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	169.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	303.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	231.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	519.1 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	573.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	108.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1127.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	368.9 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	1178.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	349.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	349.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	431.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	417.6 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	30.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3-Heptanedione	CCCCC(=O)C(C)=O	1231.5	Standard polar	33892256
2,3-Heptanedione	CCCCC(=O)C(C)=O	827.7	Standard non polar	33892256
2,3-Heptanedione	CCCCC(=O)C(C)=O	868.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,3-Heptanedione,1TMS,isomer #1	CCCC=C(O[Si](C)(C)C)C(C)=O	1171.5	Semi standard non polar	33892256
2,3-Heptanedione,1TMS,isomer #1	CCCC=C(O[Si](C)(C)C)C(C)=O	1107.2	Standard non polar	33892256
2,3-Heptanedione,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(=O)CCCC	1168.1	Semi standard non polar	33892256
2,3-Heptanedione,1TMS,isomer #2	C=C(O[Si](C)(C)C)C(=O)CCCC	1125.9	Standard non polar	33892256
2,3-Heptanedione,2TMS,isomer #1	C=C(O[Si](C)(C)C)C(=CCCC)O[Si](C)(C)C	1317.2	Semi standard non polar	33892256
2,3-Heptanedione,2TMS,isomer #1	C=C(O[Si](C)(C)C)C(=CCCC)O[Si](C)(C)C	1271.8	Standard non polar	33892256
2,3-Heptanedione,1TBDMS,isomer #1	CCCC=C(O[Si](C)(C)C(C)(C)C)C(C)=O	1409.2	Semi standard non polar	33892256
2,3-Heptanedione,1TBDMS,isomer #1	CCCC=C(O[Si](C)(C)C(C)(C)C)C(C)=O	1318.5	Standard non polar	33892256
2,3-Heptanedione,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(=O)CCCC	1370.6	Semi standard non polar	33892256
2,3-Heptanedione,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C(=O)CCCC	1306.9	Standard non polar	33892256
2,3-Heptanedione,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(=CCCC)O[Si](C)(C)C(C)(C)C	1761.3	Semi standard non polar	33892256
2,3-Heptanedione,2TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(=CCCC)O[Si](C)(C)C(C)(C)C	1662.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Heptanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-8ac8c67781a56a80f63c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Heptanedione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-054o-9000000000-388f37bf3237397b5b75	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 - 2,3-Heptanedione 10V, Positive-QTOF	splash10-01t9-2900000000-efd72e067859f956ab88	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Heptanedione 20V, Positive-QTOF	splash10-0bvl-9500000000-4f9562374cc653a1151b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Heptanedione 40V, Positive-QTOF	splash10-052f-9000000000-17bcc43d964248c37c8e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Heptanedione 10V, Negative-QTOF	splash10-004i-1900000000-970ce84ef1fc4cd15f84	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Heptanedione 20V, Negative-QTOF	splash10-003i-9400000000-320d78373fc8c67bb103	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Heptanedione 40V, Negative-QTOF	splash10-00ko-9100000000-33a158e0fb098b227891	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Heptanedione 10V, Positive-QTOF	splash10-052u-9000000000-93e034289386e5fd1259	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Heptanedione 20V, Positive-QTOF	splash10-052f-9000000000-4592240fd574c6c857d2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Heptanedione 40V, Positive-QTOF	splash10-052f-9000000000-db8f97af0edda748d78a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Heptanedione 10V, Negative-QTOF	splash10-004i-0900000000-28e0e9380275f577d79b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Heptanedione 20V, Negative-QTOF	splash10-0006-9200000000-e14ea248d70670acd323	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Heptanedione 40V, Negative-QTOF	splash10-00kf-9000000000-b6f1af0ba0e6e67151c9	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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, 1000 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

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
Saliva

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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details

Associated Disorders and Diseases

Disease References

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 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008049

KNApSAcK ID

Not Available

Chemspider ID

54944

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60983

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1025601

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 2,3-Heptanedione (HMDB0031476)

MOL for HMDB0031476 (2,3-Heptanedione)

3D MOL for HMDB0031476 (2,3-Heptanedione)

3D SDF for HMDB0031476 (2,3-Heptanedione)

3D-SDF for HMDB0031476 (2,3-Heptanedione)

PDB for HMDB0031476 (2,3-Heptanedione)

3D PDB for HMDB0031476 (2,3-Heptanedione)

SMILES for HMDB0031476 (2,3-Heptanedione)

INCHI for HMDB0031476 (2,3-Heptanedione)

Structure for HMDB0031476 (2,3-Heptanedione)

3D Structure for HMDB0031476 (2,3-Heptanedione)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra