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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:16:32 UTC

Update Date

2023-02-21 17:27:07 UTC

HMDB ID

HMDB0039736

Secondary Accession Numbers

HMDB39736

Metabolite Identification

Common Name

6-Hydroxy-4,6-dimethyl-3-hepten-2-one

Description

6-Hydroxy-4,6-dimethyl-3-hepten-2-one belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). 6-Hydroxy-4,6-dimethyl-3-hepten-2-one has been detected, but not quantified in, several different foods, such as yellow bell peppers (Capsicum annuum), orange bell peppers (Capsicum annuum), herbs and spices, italian sweet red peppers (Capsicum annuum), and red bell peppers (Capsicum annuum). This could make 6-hydroxy-4,6-dimethyl-3-hepten-2-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 6-Hydroxy-4,6-dimethyl-3-hepten-2-one.

Structure

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

COMPND    HMDB0039736
HETATM    1  C1  UNL     1       3.481  -1.407   0.802  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.090  -0.897   0.857  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.276  -1.570   1.500  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.757   0.319   0.182  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.592   0.916   0.122  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.541   2.199  -0.673  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.601   0.420   0.767  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.733   0.114  -0.214  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.236  -0.938  -1.178  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.921  -0.476   0.515  1.00  0.00           C  
HETATM   11  O2  UNL     1      -2.130   1.277  -0.829  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.495  -2.521   0.625  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.983  -0.975  -0.087  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.018  -1.150   1.756  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.578   0.841  -0.369  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.336   2.807  -0.363  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.504   2.733  -0.557  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.438   1.959  -1.749  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.045   1.252   1.419  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.526  -0.441   1.421  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.005  -1.286  -1.872  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.921  -1.816  -0.569  1.00  0.00           H  
HETATM   23  H12 UNL     1      -0.344  -0.590  -1.725  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.534  -1.199   1.251  1.00  0.00           H  
HETATM   25  H14 UNL     1      -3.524  -1.074  -0.213  1.00  0.00           H  
HETATM   26  H15 UNL     1      -3.559   0.315   0.957  1.00  0.00           H  
HETATM   27  H16 UNL     1      -2.339   1.186  -1.779  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3    4
CONECT    4    5    5   15
CONECT    5    6    7
CONECT    6   16   17   18
CONECT    7    8   19   20
CONECT    8    9   10   11
CONECT    9   21   22   23
CONECT   10   24   25   26
CONECT   11   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₉H₁₆O₂

Average Molecular Weight

156.2221

Monoisotopic Molecular Weight

156.115029756

IUPAC Name

(3Z)-6-hydroxy-4,6-dimethylhept-3-en-2-one

Traditional Name

(3Z)-6-hydroxy-4,6-dimethylhept-3-en-2-one

CAS Registry Number

83348-17-8

SMILES

CC(=O)\C=C(\C)CC(C)(C)O

InChI Identifier

InChI=1S/C9H16O2/c1-7(5-8(2)10)6-9(3,4)11/h5,11H,6H2,1-4H3/b7-5-

InChI Key

OAHJSCYHJQJALB-ALCCZGGFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Alpha,beta-unsaturated ketone
Tertiary alcohol
Enone
Acryloyl-group
Ketone
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039736)
Cytoplasm (HMDB: HMDB0039736)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039736)

Source

Exogenous

Exogenous (HMDB: HMDB0039736)

Food

Food (HMDB: HMDB0039736)

Vegetable

Fruit vegetable

Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Orange bell pepper (FooDB: FOOD00879)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0039736)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039736)

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	19130 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.51 g/L	ALOGPS
logP	0.88	ALOGPS
logP	1.2	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	18.78	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.38 m³·mol⁻¹	ChemAxon
Polarizability	17.85 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]+	140.241	30932474
DeepCCS	[M-H]-	137.605	30932474
DeepCCS	[M-2H]-	173.317	30932474
DeepCCS	[M+Na]+	148.201	30932474
AllCCS	[M+H]+	136.0	32859911
AllCCS	[M+H-H2O]+	132.0	32859911
AllCCS	[M+NH4]+	139.7	32859911
AllCCS	[M+Na]+	140.8	32859911
AllCCS	[M-H]-	137.0	32859911
AllCCS	[M+Na-2H]-	139.1	32859911
AllCCS	[M+HCOO]-	141.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Hydroxy-4,6-dimethyl-3-hepten-2-one	CC(=O)\C=C(\C)CC(C)(C)O	1819.7	Standard polar	33892256
6-Hydroxy-4,6-dimethyl-3-hepten-2-one	CC(=O)\C=C(\C)CC(C)(C)O	1146.6	Standard non polar	33892256
6-Hydroxy-4,6-dimethyl-3-hepten-2-one	CC(=O)\C=C(\C)CC(C)(C)O	1202.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Hydroxy-4,6-dimethyl-3-hepten-2-one,1TMS,isomer #1	CC(=O)/C=C(/C)CC(C)(C)O[Si](C)(C)C	1335.9	Semi standard non polar	33892256
6-Hydroxy-4,6-dimethyl-3-hepten-2-one,1TMS,isomer #2	C=C(/C=C(/C)CC(C)(C)O)O[Si](C)(C)C	1308.2	Semi standard non polar	33892256
6-Hydroxy-4,6-dimethyl-3-hepten-2-one,2TMS,isomer #1	C=C(/C=C(/C)CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C	1438.2	Semi standard non polar	33892256
6-Hydroxy-4,6-dimethyl-3-hepten-2-one,2TMS,isomer #1	C=C(/C=C(/C)CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C	1458.0	Standard non polar	33892256
6-Hydroxy-4,6-dimethyl-3-hepten-2-one,1TBDMS,isomer #1	CC(=O)/C=C(/C)CC(C)(C)O[Si](C)(C)C(C)(C)C	1561.0	Semi standard non polar	33892256
6-Hydroxy-4,6-dimethyl-3-hepten-2-one,1TBDMS,isomer #2	C=C(/C=C(/C)CC(C)(C)O)O[Si](C)(C)C(C)(C)C	1541.2	Semi standard non polar	33892256
6-Hydroxy-4,6-dimethyl-3-hepten-2-one,2TBDMS,isomer #1	C=C(/C=C(/C)CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1896.5	Semi standard non polar	33892256
6-Hydroxy-4,6-dimethyl-3-hepten-2-one,2TBDMS,isomer #1	C=C(/C=C(/C)CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1907.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxy-4,6-dimethyl-3-hepten-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-000w-9500000000-906bf53a3511271d11c0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxy-4,6-dimethyl-3-hepten-2-one GC-MS (1 TMS) - 70eV, Positive	splash10-0089-8920000000-3903b3cdb48b20db07f5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxy-4,6-dimethyl-3-hepten-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxy-4,6-dimethyl-3-hepten-2-one 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 - 6-Hydroxy-4,6-dimethyl-3-hepten-2-one 10V, Positive-QTOF	splash10-0079-1900000000-2f2c76355712b2d6c053	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-4,6-dimethyl-3-hepten-2-one 20V, Positive-QTOF	splash10-00dr-4900000000-2969385ae1cdaf935aa0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-4,6-dimethyl-3-hepten-2-one 40V, Positive-QTOF	splash10-0089-9300000000-b636bb3669252dd42b5f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-4,6-dimethyl-3-hepten-2-one 10V, Negative-QTOF	splash10-0a4i-0900000000-28a4eafdf0e4b6193028	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-4,6-dimethyl-3-hepten-2-one 20V, Negative-QTOF	splash10-0a4s-5900000000-b5547de257e5703944dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-4,6-dimethyl-3-hepten-2-one 40V, Negative-QTOF	splash10-007a-7900000000-0bea3395c6d6651fedf6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-4,6-dimethyl-3-hepten-2-one 10V, Positive-QTOF	splash10-000t-9300000000-95653efec6e2e61d6669	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-4,6-dimethyl-3-hepten-2-one 20V, Positive-QTOF	splash10-001i-9000000000-fcff8650b5c4d9a09940	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-4,6-dimethyl-3-hepten-2-one 40V, Positive-QTOF	splash10-005c-9000000000-2ca25e1d1d27df3ea81a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-4,6-dimethyl-3-hepten-2-one 10V, Negative-QTOF	splash10-0a4j-4900000000-9d5539b3c9167c1e08a5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-4,6-dimethyl-3-hepten-2-one 20V, Negative-QTOF	splash10-01ot-9700000000-378b57ac255b080ebf77	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxy-4,6-dimethyl-3-hepten-2-one 40V, Negative-QTOF	splash10-03di-9100000000-d04ad656f4461541003b	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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+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

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB019378

KNApSAcK ID

Not Available

Chemspider ID

9789953

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11615204

PDB ID

Not Available

ChEBI ID

171763

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1879891

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 6-Hydroxy-4,6-dimethyl-3-hepten-2-one (HMDB0039736)

MOL for HMDB0039736 (6-Hydroxy-4,6-dimethyl-3-hepten-2-one)

3D MOL for HMDB0039736 (6-Hydroxy-4,6-dimethyl-3-hepten-2-one)

3D SDF for HMDB0039736 (6-Hydroxy-4,6-dimethyl-3-hepten-2-one)

3D-SDF for HMDB0039736 (6-Hydroxy-4,6-dimethyl-3-hepten-2-one)

PDB for HMDB0039736 (6-Hydroxy-4,6-dimethyl-3-hepten-2-one)

3D PDB for HMDB0039736 (6-Hydroxy-4,6-dimethyl-3-hepten-2-one)

SMILES for HMDB0039736 (6-Hydroxy-4,6-dimethyl-3-hepten-2-one)

INCHI for HMDB0039736 (6-Hydroxy-4,6-dimethyl-3-hepten-2-one)

Structure for HMDB0039736 (6-Hydroxy-4,6-dimethyl-3-hepten-2-one)

3D Structure for HMDB0039736 (6-Hydroxy-4,6-dimethyl-3-hepten-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra