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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:17:15 UTC

Update Date

2023-02-21 17:25:33 UTC

HMDB ID

HMDB0037044

Secondary Accession Numbers

HMDB37044

Metabolite Identification

Common Name

Rotundifolone

Description

Rotundifolone 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. Rotundifolone is a herbal and minty tasting compound. Rotundifolone is found, on average, in the highest concentration within spearmints (Mentha spicata) and cornmints (Mentha arvensis). Rotundifolone has also been detected, but not quantified in, herbs and spices. This could make rotundifolone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Rotundifolone.

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       8.891   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.558  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.787   2.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.224   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.890   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.558  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.224   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.890  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.557   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.557   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.890  -2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.223   0.770   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6                                                            
CONECT    3   10                                                            
CONECT    4    5    7                                                       
CONECT    5    4   10                                                       
CONECT    6    1    2    7                                                  
CONECT    7    4    6    8                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10   12                                                  
CONECT   10    3    5    9   12                                             
CONECT   11    8                                                            
CONECT   12    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2-Epoxy-P-menth-4(8)-en-3-one	HMDB
2,3-Epoxy-6-isopropylidene-3-methylcyclohexanone	HMDB
6-Methyl-3-(1-methylethylidene)-7-oxabicyclo[4.1.0]heptan-2-one, 9ci	HMDB
Piperitenone oxide	HMDB

Chemical Formula

C₁₀H₁₄O₂

Average Molecular Weight

166.217

Monoisotopic Molecular Weight

166.099379692

IUPAC Name

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

Traditional Name

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

CAS Registry Number

5945-46-0

SMILES

CC(C)=C1CCC2(C)OC2C1=O

InChI Identifier

InChI=1S/C10H14O2/c1-6(2)7-4-5-10(3)9(12-10)8(7)11/h9H,4-5H2,1-3H3

InChI Key

AKASWINDKIEEBO-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

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037044)

Source

Endogenous

Endogenous (HMDB: HMDB0037044)

Plant

Plant (HMDB: HMDB0037044)

Exogenous

Food

Food (HMDB: HMDB0037044)

Herb and spice

Herb

Spearmint (FooDB: FOOD00112)
Cornmint (FooDB: FOOD00111)

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0037044)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	27.5 °C	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
Water Solubility	8.95 g/L	ALOGPS
logP	1.61	ALOGPS
logP	2.07	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	-4.2	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	0	ChemAxon
Refractivity	46.56 m³·mol⁻¹	ChemAxon
Polarizability	18.49 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
DarkChem	[M+H]+	138.117	31661259
DarkChem	[M-H]-	134.663	31661259
DeepCCS	[M+H]+	137.28	30932474
DeepCCS	[M-H]-	133.453	30932474
DeepCCS	[M-2H]-	170.889	30932474
DeepCCS	[M+Na]+	146.427	30932474
AllCCS	[M+H]+	135.6	32859911
AllCCS	[M+H-H2O]+	131.3	32859911
AllCCS	[M+NH4]+	139.7	32859911
AllCCS	[M+Na]+	140.8	32859911
AllCCS	[M-H]-	139.6	32859911
AllCCS	[M+Na-2H]-	140.5	32859911
AllCCS	[M+HCOO]-	141.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rotundifolone	CC(C)=C1CCC2(C)OC2C1=O	1809.7	Standard polar	33892256
Rotundifolone	CC(C)=C1CCC2(C)OC2C1=O	1290.3	Standard non polar	33892256
Rotundifolone	CC(C)=C1CCC2(C)OC2C1=O	1360.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rotundifolone,1TMS,isomer #1	CC(C)=C1CCC2(C)OC2=C1O[Si](C)(C)C	1387.1	Semi standard non polar	33892256
Rotundifolone,1TMS,isomer #1	CC(C)=C1CCC2(C)OC2=C1O[Si](C)(C)C	1331.6	Standard non polar	33892256
Rotundifolone,1TBDMS,isomer #1	CC(C)=C1CCC2(C)OC2=C1O[Si](C)(C)C(C)(C)C	1649.7	Semi standard non polar	33892256
Rotundifolone,1TBDMS,isomer #1	CC(C)=C1CCC2(C)OC2=C1O[Si](C)(C)C(C)(C)C	1546.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Rotundifolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00o4-9300000000-28ac35eefccb97ecf8f7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rotundifolone 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 - Rotundifolone 10V, Positive-QTOF	splash10-014i-0900000000-0d2244bb050ca70a3c49	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundifolone 20V, Positive-QTOF	splash10-014i-4900000000-a49b13c97830692f36f0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundifolone 40V, Positive-QTOF	splash10-067i-9100000000-5d3ca3ad1a2c8d254117	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundifolone 10V, Negative-QTOF	splash10-014i-0900000000-ab194c3e028cf03581b8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundifolone 20V, Negative-QTOF	splash10-014i-1900000000-a1934865dd6aa8ca0d4a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundifolone 40V, Negative-QTOF	splash10-0a59-9600000000-37561a809cd7b097631e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundifolone 10V, Negative-QTOF	splash10-014i-0900000000-349584a3f625d5b5807f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundifolone 20V, Negative-QTOF	splash10-014i-0900000000-d1252c53df5aa0366a66	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundifolone 40V, Negative-QTOF	splash10-014i-9300000000-442ba93afe2056decf39	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundifolone 10V, Positive-QTOF	splash10-014i-1900000000-d8e5853d91f1eb90687c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundifolone 20V, Positive-QTOF	splash10-00kf-9300000000-0dfe3b6fd9baf52e4fd7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundifolone 40V, Positive-QTOF	splash10-014l-9100000000-6c52be035dfdc4e36ed2	2021-09-24	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]+)	2023-02-04	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
Membrane

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

FDB016026

KNApSAcK ID

C00003058

Chemspider ID

55800

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61942

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Rotundifolone (HMDB0037044)

MOL for HMDB0037044 (Rotundifolone)

3D MOL for HMDB0037044 (Rotundifolone)

3D SDF for HMDB0037044 (Rotundifolone)

3D-SDF for HMDB0037044 (Rotundifolone)

PDB for HMDB0037044 (Rotundifolone)

3D PDB for HMDB0037044 (Rotundifolone)

SMILES for HMDB0037044 (Rotundifolone)

INCHI for HMDB0037044 (Rotundifolone)

Structure for HMDB0037044 (Rotundifolone)

3D Structure for HMDB0037044 (Rotundifolone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra