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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:43:45 UTC

Update Date

2023-02-21 17:24:52 UTC

HMDB ID

HMDB0035714

Secondary Accession Numbers

HMDB35714

Metabolite Identification

Common Name

Epoxyartemisia ketone

Description

Epoxyartemisia 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. Epoxyartemisia ketone has been detected, but not quantified in, mugworts (Artemisia vulgaris). This could make epoxyartemisia ketone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Epoxyartemisia ketone.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       3.882  -4.295   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.088  -1.985   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.008  -1.985   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.624   2.649   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.735   2.649   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.548  -3.525   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.548  -0.445   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.215   0.325   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.548  -1.985   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.445   1.659   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.882   0.325   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.325   0.325   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4   10                                                            
CONECT    5   10                                                            
CONECT    6    1    9                                                       
CONECT    7    8    9   11                                                  
CONECT    8    7   10   12                                                  
CONECT    9    2    3    6    7                                             
CONECT   10    4    5    8   12                                             
CONECT   11    7                                                            
CONECT   12    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0035714
HETATM    1  C1  UNL     1       3.222   1.489   0.617  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.362   1.107  -0.308  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.454  -0.054  -0.104  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.356  -0.766  -1.458  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.136  -0.964   0.894  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.111   0.371   0.358  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.105   1.559   0.516  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.993  -0.573   0.640  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.871  -0.317   1.679  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.386  -0.089   0.359  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.645   1.351   0.095  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.331  -1.142  -0.170  1.00  0.00           C  
HETATM   13  H1  UNL     1       3.885   2.324   0.488  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.257   0.934   1.543  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.330   1.666  -1.238  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.342  -1.846  -1.222  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.243  -0.530  -2.086  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.475  -0.417  -2.014  1.00  0.00           H  
HETATM   19  H7  UNL     1       3.226  -0.922   0.693  1.00  0.00           H  
HETATM   20  H8  UNL     1       1.769  -2.007   0.835  1.00  0.00           H  
HETATM   21  H9  UNL     1       1.911  -0.566   1.907  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.773  -1.648   0.489  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.167   1.731  -0.832  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.743   1.483  -0.061  1.00  0.00           H  
HETATM   25  H13 UNL     1      -2.363   2.033   0.914  1.00  0.00           H  
HETATM   26  H14 UNL     1      -3.201  -2.098   0.380  1.00  0.00           H  
HETATM   27  H15 UNL     1      -3.105  -1.282  -1.247  1.00  0.00           H  
HETATM   28  H16 UNL     1      -4.396  -0.827  -0.076  1.00  0.00           H  
CONECT    1    2    2   13   14
CONECT    2    3   15
CONECT    3    4    5    6
CONECT    4   16   17   18
CONECT    5   19   20   21
CONECT    6    7    7    8
CONECT    8    9   10   22
CONECT    9   10
CONECT   10   11   12
CONECT   11   23   24   25
CONECT   12   26   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(3,3-Dimethyloxiranyl)-2,2-dimethyl-3-buten-1-one, 9ci	HMDB
1-(3,3-Dimethyloxiranyl)-2,2-dimethyl-3-buten-1-one-epoxyartemisia ketone	HMDB
5,6-Epoxy-3,3,6-trimethyl-1-hepten-4-one	HMDB

Chemical Formula

C₁₀H₁₆O₂

Average Molecular Weight

168.2328

Monoisotopic Molecular Weight

168.115029756

IUPAC Name

1-(3,3-dimethyloxiran-2-yl)-2,2-dimethylbut-3-en-1-one

Traditional Name

1-(3,3-dimethyloxiran-2-yl)-2,2-dimethylbut-3-en-1-one

CAS Registry Number

79507-83-8

SMILES

CC(C)(C=C)C(=O)C1OC1(C)C

InChI Identifier

InChI=1S/C10H16O2/c1-6-9(2,3)7(11)8-10(4,5)12-8/h6,8H,1H2,2-5H3

InChI Key

VDWHYKNCKVKWIG-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
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0035714)
Cytoplasm (HMDB: HMDB0035714)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035714)

Source

Exogenous

Exogenous (HMDB: HMDB0035714)

Food

Food (HMDB: HMDB0035714)

Herb and spice

Herb

Mugwort (FooDB: FOOD00020)

Endogenous

Plant

Plant (HMDB: HMDB0035714)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035714)

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	208.5 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	0.55 g/L	ALOGPS
logP	2.24	ALOGPS
logP	2.61	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	19.77	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.83 m³·mol⁻¹	ChemAxon
Polarizability	18.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	138.966	31661259
DarkChem	[M-H]-	135.93	31661259
DeepCCS	[M+H]+	141.962	30932474
DeepCCS	[M-H]-	139.567	30932474
DeepCCS	[M-2H]-	174.903	30932474
DeepCCS	[M+Na]+	149.424	30932474
AllCCS	[M+H]+	136.0	32859911
AllCCS	[M+H-H2O]+	132.0	32859911
AllCCS	[M+NH4]+	139.8	32859911
AllCCS	[M+Na]+	140.9	32859911
AllCCS	[M-H]-	139.5	32859911
AllCCS	[M+Na-2H]-	140.9	32859911
AllCCS	[M+HCOO]-	142.4	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.	4.81 minutes	32390414
Predicted by Siyang on May 30, 2022	15.9626 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.32 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2313.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	536.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	198.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	322.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	128.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	640.9 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	793.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	79.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1221.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	446.4 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	1433.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	452.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	394.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	471.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	524.0 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	20.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Epoxyartemisia ketone	CC(C)(C=C)C(=O)C1OC1(C)C	1478.5	Standard polar	33892256
Epoxyartemisia ketone	CC(C)(C=C)C(=O)C1OC1(C)C	1052.1	Standard non polar	33892256
Epoxyartemisia ketone	CC(C)(C=C)C(=O)C1OC1(C)C	1152.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Epoxyartemisia ketone,1TMS,isomer #1	C=CC(C)(C)C(O[Si](C)(C)C)=C1OC1(C)C	1087.7	Semi standard non polar	33892256
Epoxyartemisia ketone,1TMS,isomer #1	C=CC(C)(C)C(O[Si](C)(C)C)=C1OC1(C)C	1191.1	Standard non polar	33892256
Epoxyartemisia ketone,1TBDMS,isomer #1	C=CC(C)(C)C(O[Si](C)(C)C(C)(C)C)=C1OC1(C)C	1312.1	Semi standard non polar	33892256
Epoxyartemisia ketone,1TBDMS,isomer #1	C=CC(C)(C)C(O[Si](C)(C)C(C)(C)C)=C1OC1(C)C	1431.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Epoxyartemisia ketone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ke-9000000000-cd26c5dcb1ac3000fe8a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epoxyartemisia ketone 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 - Epoxyartemisia ketone 10V, Positive-QTOF	splash10-014i-5900000000-b40b704062145dbfff9d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxyartemisia ketone 20V, Positive-QTOF	splash10-014j-9400000000-f1fb5a3d1db634c12dba	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxyartemisia ketone 40V, Positive-QTOF	splash10-014i-9000000000-5f3ea937a4f8ae461b5b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxyartemisia ketone 10V, Negative-QTOF	splash10-014i-1900000000-1b5b1f1551fb23d6f931	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxyartemisia ketone 20V, Negative-QTOF	splash10-014i-6900000000-3019ff3543dbee534477	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxyartemisia ketone 40V, Negative-QTOF	splash10-0ab9-9100000000-c8daabdab7b2874e35b4	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxyartemisia ketone 10V, Positive-QTOF	splash10-014i-8900000000-fd31798f27b86d1cf31b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxyartemisia ketone 20V, Positive-QTOF	splash10-066u-9300000000-04d2341bb05c390d0fd8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxyartemisia ketone 40V, Positive-QTOF	splash10-0006-9000000000-5babdbceb3647bfdfb16	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxyartemisia ketone 10V, Negative-QTOF	splash10-014i-0900000000-cb7592114e600c180aec	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxyartemisia ketone 20V, Negative-QTOF	splash10-014i-4900000000-cdaf73c61af242558465	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epoxyartemisia ketone 40V, Negative-QTOF	splash10-0a4j-9000000000-3fea428da47792728016	2021-09-22	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

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

FDB014437

KNApSAcK ID

C00010386

Chemspider ID

9990744

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11816089

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1851111

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 Epoxyartemisia ketone (HMDB0035714)

MOL for HMDB0035714 (Epoxyartemisia ketone)

3D MOL for HMDB0035714 (Epoxyartemisia ketone)

3D SDF for HMDB0035714 (Epoxyartemisia ketone)

3D-SDF for HMDB0035714 (Epoxyartemisia ketone)

PDB for HMDB0035714 (Epoxyartemisia ketone)

3D PDB for HMDB0035714 (Epoxyartemisia ketone)

SMILES for HMDB0035714 (Epoxyartemisia ketone)

INCHI for HMDB0035714 (Epoxyartemisia ketone)

Structure for HMDB0035714 (Epoxyartemisia ketone)

3D Structure for HMDB0035714 (Epoxyartemisia ketone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra