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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 00:15:50 UTC

Update Date

2021-09-24 00:15:50 UTC

HMDB ID

HMDB0303216

Secondary Accession Numbers

None

Metabolite Identification

Common Name

cis-Dihydrocarvone

Description

Cis-dihydrocarvone, also known as (2r,5s)-2-methyl-5-isopropenylcyclohexanone or (1r,4s)-menth-8-en-2-one, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, cis-dihydrocarvone is considered to be an isoprenoid lipid molecule. Cis-dihydrocarvone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Cis-dihydrocarvone is a herbal and warm tasting compound and can be found in a number of food items such as dill, spearmint, wild celery, and common oregano, which makes cis-dihydrocarvone a potential biomarker for the consumption of these food products.

Structure

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

COMPND    HMDB0303216
HETATM    1  C1  UNL     1      -2.419   0.290  -1.314  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.148   0.001  -0.055  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.203   0.180   0.970  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.787  -0.496   0.290  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.062  -0.643  -0.945  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.438  -1.171  -0.540  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.154  -0.136   0.287  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.262   0.507  -0.539  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.170   0.879   0.718  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.401   2.062   0.627  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.127   0.436   1.275  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.411   0.652  -1.560  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.669   0.166  -2.064  1.00  0.00           H  
HETATM   14  H3  UNL     1      -4.184   0.111   0.485  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.181  -0.651   1.732  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.137   1.148   1.487  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.834  -1.499   0.769  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.370  -1.349  -1.657  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.241   0.356  -1.385  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.223  -2.077   0.094  1.00  0.00           H  
HETATM   21  H10 UNL     1       2.031  -1.471  -1.423  1.00  0.00           H  
HETATM   22  H11 UNL     1       2.625  -0.607   1.196  1.00  0.00           H  
HETATM   23  H12 UNL     1       4.255   0.159  -0.189  1.00  0.00           H  
HETATM   24  H13 UNL     1       3.059   0.288  -1.596  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.233   1.622  -0.426  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.772   1.305   1.522  1.00  0.00           H  
HETATM   27  H16 UNL     1       0.090  -0.064   2.243  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    4
CONECT    3   14   15   16
CONECT    4    5   11   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8    9   22
CONECT    8   23   24   25
CONECT    9   10   10   11
CONECT   11   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1R,4S)-Iso-dihydrocarvone	ChEBI
(1R,4S)-Isodihydrocarvone	ChEBI
(2R,5S)-2-Methyl-5-isopropenylcyclohexanone	ChEBI
(2R,5S)-5-Isopropenyl-2-methylcyclohexanone	ChEBI

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

(2R,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one

Traditional Name

(-)-isodihydrocarvone

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@H](CC1=O)C(C)=C

InChI Identifier

InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-9H,1,4-6H2,2-3H3/t8-,9+/m1/s1

InChI Key

AZOCECCLWFDTAP-BDAKNGLRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

dihydrocarvone (CHEBI:155 )
Menthane monoterpenoids (C11412 )
Menthane monoterpenoids (LMPR0102090037 )

Ontology

Exogenous (HMDB: HMDB0303216)

Food

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)
Caraway (FooDB: FOOD00043)

Herb

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	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	2.39	ALOGPS
logP	2.7	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	46.3 m³·mol⁻¹	ChemAxon
Polarizability	17.9 Å³	ChemAxon
Number of Rings	1	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
AllCCS	[M+H]+	132.692	32859911
AllCCS	[M+H-H2O]+	128.231	32859911
AllCCS	[M+Na]+	138.052	32859911
AllCCS	[M+NH4]+	136.852	32859911
AllCCS	[M-H]-	137.05	32859911
AllCCS	[M+Na-2H]-	138.593	32859911
AllCCS	[M+HCOO]-	140.358	32859911
DeepCCS	[M+H]+	142.393	30932474
DeepCCS	[M-H]-	139.997	30932474
DeepCCS	[M-2H]-	174.121	30932474
DeepCCS	[M+Na]+	148.78	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cis-Dihydrocarvone,1TMS,isomer #1	C=C(C)[C@H]1CCC(C)=C(O[Si](C)(C)C)C1	1368.3	Semi standard non polar	33892256
cis-Dihydrocarvone,1TMS,isomer #1	C=C(C)[C@H]1CCC(C)=C(O[Si](C)(C)C)C1	1353.2	Standard non polar	33892256
cis-Dihydrocarvone,1TMS,isomer #1	C=C(C)[C@H]1CCC(C)=C(O[Si](C)(C)C)C1	1576.7	Standard polar	33892256
cis-Dihydrocarvone,1TMS,isomer #2	C=C(C)[C@@H]1C=C(O[Si](C)(C)C)[C@H](C)CC1	1305.4	Semi standard non polar	33892256
cis-Dihydrocarvone,1TMS,isomer #2	C=C(C)[C@@H]1C=C(O[Si](C)(C)C)[C@H](C)CC1	1353.4	Standard non polar	33892256
cis-Dihydrocarvone,1TMS,isomer #2	C=C(C)[C@@H]1C=C(O[Si](C)(C)C)[C@H](C)CC1	1591.2	Standard polar	33892256
cis-Dihydrocarvone,1TBDMS,isomer #1	C=C(C)[C@H]1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1	1603.3	Semi standard non polar	33892256
cis-Dihydrocarvone,1TBDMS,isomer #1	C=C(C)[C@H]1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1	1528.8	Standard non polar	33892256
cis-Dihydrocarvone,1TBDMS,isomer #1	C=C(C)[C@H]1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1	1741.4	Standard polar	33892256
cis-Dihydrocarvone,1TBDMS,isomer #2	C=C(C)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@H](C)CC1	1540.5	Semi standard non polar	33892256
cis-Dihydrocarvone,1TBDMS,isomer #2	C=C(C)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@H](C)CC1	1504.4	Standard non polar	33892256
cis-Dihydrocarvone,1TBDMS,isomer #2	C=C(C)[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@H](C)CC1	1747.7	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 - cis-Dihydrocarvone 10V, Positive-QTOF	splash10-0udi-0900000000-aac90d2e594a64ffc23b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Dihydrocarvone 20V, Positive-QTOF	splash10-0zfr-9600000000-07ad24338c7e47056fd3	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Dihydrocarvone 40V, Positive-QTOF	splash10-0le9-9000000000-a10b5ec9782fd22e6d6a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Dihydrocarvone 10V, Negative-QTOF	splash10-0udi-0900000000-9820037a1b10b33bdc1f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Dihydrocarvone 20V, Negative-QTOF	splash10-0udi-0900000000-ab126e3fddd65ad137c4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Dihydrocarvone 40V, Negative-QTOF	splash10-05mx-9500000000-380342ffa7a1fd0a2134	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Dihydrocarvone 10V, Positive-QTOF	splash10-0gws-7900000000-b08efab8959a09a26216	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Dihydrocarvone 20V, Positive-QTOF	splash10-000x-9200000000-13ccbe770389182b9c06	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Dihydrocarvone 40V, Positive-QTOF	splash10-0006-9000000000-4b6afc70d0efd7f97f15	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Dihydrocarvone 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Dihydrocarvone 20V, Negative-QTOF	splash10-0udi-1900000000-6d20364e296745592a69	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Dihydrocarvone 40V, Negative-QTOF	splash10-00kn-6900000000-23186e60d8ffad674527	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

FDB009286

KNApSAcK ID

Not Available

Chemspider ID

391453

KEGG Compound ID

C11412

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443181

PDB ID

Not Available

ChEBI ID

155

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 cis-Dihydrocarvone (HMDB0303216)

MOL for HMDB0303216 (cis-Dihydrocarvone)

3D MOL for HMDB0303216 (cis-Dihydrocarvone)

3D SDF for HMDB0303216 (cis-Dihydrocarvone)

3D-SDF for HMDB0303216 (cis-Dihydrocarvone)

PDB for HMDB0303216 (cis-Dihydrocarvone)

3D PDB for HMDB0303216 (cis-Dihydrocarvone)

SMILES for HMDB0303216 (cis-Dihydrocarvone)

INCHI for HMDB0303216 (cis-Dihydrocarvone)

Structure for HMDB0303216 (cis-Dihydrocarvone)

3D Structure for HMDB0303216 (cis-Dihydrocarvone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra