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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 20:20:25 UTC

Update Date

2021-09-23 20:20:25 UTC

HMDB ID

HMDB0302746

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Piperitone oxide

Description

Piperitone oxide is a member of the class of compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. Piperitone oxide is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Piperitone oxide can be found in cornmint, orange mint, peppermint, and spearmint, which makes piperitone oxide a potential biomarker for the consumption of these food products.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334   0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770   2.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3    5                                                       
CONECT    5    4    3    6    7                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    2   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

COMPND    HMDB0302746
HETATM    1  C1  UNL     1      -2.594   1.279   0.511  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.954  -0.037   0.119  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.876  -0.717  -0.850  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.602   0.266  -0.474  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.131  -0.982  -0.903  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.591  -0.623  -1.079  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.224  -0.409   0.276  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.691  -0.178   0.322  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.533  -0.950   1.328  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.392   0.427   1.183  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.198   0.991   0.533  1.00  0.00           C  
HETATM   12  O2  UNL     1      -0.162   2.116   0.831  1.00  0.00           O  
HETATM   13  H1  UNL     1      -3.705   1.217   0.476  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.330   1.592   1.527  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.268   2.093  -0.182  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.832  -0.615   1.059  1.00  0.00           H  
HETATM   17  H5  UNL     1      -3.617   0.003  -1.274  1.00  0.00           H  
HETATM   18  H6  UNL     1      -3.392  -1.559  -0.318  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.366  -1.175  -1.712  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.741   0.921  -1.355  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.219  -1.387  -1.863  1.00  0.00           H  
HETATM   22  H10 UNL     1       0.020  -1.764  -0.131  1.00  0.00           H  
HETATM   23  H11 UNL     1       2.083  -1.535  -1.509  1.00  0.00           H  
HETATM   24  H12 UNL     1       1.650   0.244  -1.736  1.00  0.00           H  
HETATM   25  H13 UNL     1       3.986   0.302  -0.654  1.00  0.00           H  
HETATM   26  H14 UNL     1       4.309  -1.070   0.421  1.00  0.00           H  
HETATM   27  H15 UNL     1       3.971   0.542   1.115  1.00  0.00           H  
HETATM   28  H16 UNL     1       1.879   1.007   1.963  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    4   16
CONECT    3   17   18   19
CONECT    4    5   11   20
CONECT    5    6   21   22
CONECT    6    7   23   24
CONECT    7    8    9   10
CONECT    8   25   26   27
CONECT    9   10
CONECT   10   11   28
CONECT   11   12   12
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₁₆O₂

Average Molecular Weight

168.2328

Monoisotopic Molecular Weight

168.115029756

IUPAC Name

6-methyl-3-(propan-2-yl)-7-oxabicyclo[4.1.0]heptan-2-one

Traditional Name

3-isopropyl-6-methyl-7-oxabicyclo[4.1.0]heptan-2-one

CAS Registry Number

Not Available

SMILES

CC(C)C1CCC2(C)OC2C1=O

InChI Identifier

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

InChI Key

IAFONZHDZMCORS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Ketone
Oxacycle
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.96	ALOGPS
logP	2.26	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	19.7	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	1	ChemAxon
Refractivity	45.95 m³·mol⁻¹	ChemAxon
Polarizability	19.05 Å³	ChemAxon
Number of Rings	2	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
AllCCS	[M+H]+	136.718	32859911
AllCCS	[M+H-H2O]+	132.444	32859911
AllCCS	[M+Na]+	141.848	32859911
AllCCS	[M+NH4]+	140.7	32859911
AllCCS	[M-H]-	141.885	32859911
AllCCS	[M+Na-2H]-	142.835	32859911
AllCCS	[M+HCOO]-	143.959	32859911
DeepCCS	[M+H]+	138.728	30932474
DeepCCS	[M-H]-	134.943	30932474
DeepCCS	[M-2H]-	172.361	30932474
DeepCCS	[M+Na]+	147.759	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Piperitone oxide,1TMS,isomer #1	CC(C)C1=C(O[Si](C)(C)C)C2OC2(C)CC1	1321.7	Semi standard non polar	33892256
Piperitone oxide,1TMS,isomer #1	CC(C)C1=C(O[Si](C)(C)C)C2OC2(C)CC1	1359.1	Standard non polar	33892256
Piperitone oxide,1TMS,isomer #1	CC(C)C1=C(O[Si](C)(C)C)C2OC2(C)CC1	1465.2	Standard polar	33892256
Piperitone oxide,1TMS,isomer #2	CC(C)C1CCC2(C)OC2=C1O[Si](C)(C)C	1286.8	Semi standard non polar	33892256
Piperitone oxide,1TMS,isomer #2	CC(C)C1CCC2(C)OC2=C1O[Si](C)(C)C	1321.1	Standard non polar	33892256
Piperitone oxide,1TMS,isomer #2	CC(C)C1CCC2(C)OC2=C1O[Si](C)(C)C	1481.4	Standard polar	33892256
Piperitone oxide,1TBDMS,isomer #1	CC(C)C1=C(O[Si](C)(C)C(C)(C)C)C2OC2(C)CC1	1567.1	Semi standard non polar	33892256
Piperitone oxide,1TBDMS,isomer #1	CC(C)C1=C(O[Si](C)(C)C(C)(C)C)C2OC2(C)CC1	1559.1	Standard non polar	33892256
Piperitone oxide,1TBDMS,isomer #1	CC(C)C1=C(O[Si](C)(C)C(C)(C)C)C2OC2(C)CC1	1622.7	Standard polar	33892256
Piperitone oxide,1TBDMS,isomer #2	CC(C)C1CCC2(C)OC2=C1O[Si](C)(C)C(C)(C)C	1517.0	Semi standard non polar	33892256
Piperitone oxide,1TBDMS,isomer #2	CC(C)C1CCC2(C)OC2=C1O[Si](C)(C)C(C)(C)C	1556.7	Standard non polar	33892256
Piperitone oxide,1TBDMS,isomer #2	CC(C)C1CCC2(C)OC2=C1O[Si](C)(C)C(C)(C)C	1635.8	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone oxide 10V, Positive-QTOF	splash10-014i-0900000000-84e0f2ba3b8d0ef89bdb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone oxide 20V, Positive-QTOF	splash10-016r-5900000000-666ddf592e8faee26e09	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone oxide 40V, Positive-QTOF	splash10-0a4l-9000000000-2ec3894aee3c7ba610cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone oxide 10V, Negative-QTOF	splash10-014i-0900000000-0a9d9075eb6dbb60f519	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone oxide 20V, Negative-QTOF	splash10-014i-0900000000-08c625b6d7e7d8d1af9b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone oxide 40V, Negative-QTOF	splash10-0api-9300000000-5ecba8f5f51171dc7974	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone oxide 10V, Positive-QTOF	splash10-0gb9-2900000000-3078baf052e17b19f699	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone oxide 20V, Positive-QTOF	splash10-014u-9400000000-c8f059a4a1c43a374eb6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone oxide 40V, Positive-QTOF	splash10-052f-9100000000-8f6d53758a34361baeb1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone oxide 10V, Negative-QTOF	splash10-014i-0900000000-cb7592114e600c180aec	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone oxide 20V, Negative-QTOF	splash10-014i-0900000000-91cd3438271379b18821	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperitone oxide 40V, Negative-QTOF	splash10-014j-9500000000-52659251260bf3b93032	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB006036

KNApSAcK ID

Not Available

Chemspider ID

83951

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Piperitone oxide (HMDB0302746)

MOL for HMDB0302746 (Piperitone oxide)

3D MOL for HMDB0302746 (Piperitone oxide)

3D SDF for HMDB0302746 (Piperitone oxide)

3D-SDF for HMDB0302746 (Piperitone oxide)

PDB for HMDB0302746 (Piperitone oxide)

3D PDB for HMDB0302746 (Piperitone oxide)

SMILES for HMDB0302746 (Piperitone oxide)

INCHI for HMDB0302746 (Piperitone oxide)

Structure for HMDB0302746 (Piperitone oxide)

3D Structure for HMDB0302746 (Piperitone oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra