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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 16:12:31 UTC

Update Date

2021-09-23 16:12:31 UTC

HMDB ID

HMDB0302236

Secondary Accession Numbers

None

Metabolite Identification

Common Name

D-(+)-dihydrocarvone

Description

(1r,4r)-dihydrocarvone, also known as (2r,5r)-2-methyl-5-isopropenylcyclohexanone, 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, (1r,4r)-dihydrocarvone is considered to be an isoprenoid lipid molecule (1r,4r)-dihydrocarvone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (1r,4r)-dihydrocarvone is a herbal and minty tasting compound found in spearmint, which makes (1r,4r)-dihydrocarvone a potential biomarker for the consumption of this food product.

Structure

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

COMPND    HMDB0302236
HETATM    1  C1  UNL     1      -1.928  -2.107  -1.274  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.641  -0.825  -1.115  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.545   0.152  -1.797  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.490  -0.450  -0.305  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.805   0.459   0.853  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.392   0.522   1.747  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.671   0.844   1.051  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.843   0.151   1.714  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.702   0.522  -0.373  1.00  0.00           C  
HETATM   10  O1  UNL     1       2.771   0.391  -0.929  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.470   0.339  -1.208  1.00  0.00           C  
HETATM   12  H1  UNL     1      -1.304  -2.843  -0.801  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.785  -2.453  -1.875  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.458   1.113  -1.249  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.604  -0.161  -1.746  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.226   0.345  -2.840  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.011  -1.338   0.097  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.077   1.481   0.537  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.652   0.056   1.463  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.208   1.285   2.532  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.480  -0.448   2.278  1.00  0.00           H  
HETATM   22  H11 UNL     1       1.871   1.944   1.154  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.655   0.082   0.965  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.557  -0.913   1.960  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.189   0.690   2.618  1.00  0.00           H  
HETATM   26  H15 UNL     1       0.022   1.344  -1.318  1.00  0.00           H  
HETATM   27  H16 UNL     1       0.675  -0.180  -2.141  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,4R)-Dihydrocarvone	ChEBI
(2R,5R)-2-Methyl-5-isopropenylcyclohexanone	ChEBI
(2R,5R)-5-Isopropenyl-2-methylcyclohexanone	ChEBI
(2R-trans)-2-Methyl-5-(1-methylvinyl)cyclohexan-1-one	ChEBI
D-Dihydrocarvone	ChEBI

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

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

Traditional Name

(+)-dihydrocarvone

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-RKDXNWHRSA-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:154 )
Menthane monoterpenoids (C11398 )
Menthane monoterpenoids (LMPR0102090033 )

Ontology

Not Available

Exogenous (HMDB: HMDB0302236)

Food

Herb and spice

Herb

Dill (FooDB: FOOD00013)

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	18.26 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]+	142.424	30932474
DeepCCS	[M-H]-	140.028	30932474
DeepCCS	[M-2H]-	174.291	30932474
DeepCCS	[M+Na]+	148.871	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	15.0159 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.98 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1738.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	345.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	149.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	188.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	107.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	405.9 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	485.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	989.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	323.4 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	1101.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	287.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	335.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	392.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	367.6 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	67.3 seconds	40023050

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
D-(+)-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
D-(+)-dihydrocarvone,1TMS,isomer #1	C=C(C)[C@@H]1CCC(C)=C(O[Si](C)(C)C)C1	1353.2	Standard non polar	33892256
D-(+)-dihydrocarvone,1TMS,isomer #1	C=C(C)[C@@H]1CCC(C)=C(O[Si](C)(C)C)C1	1576.7	Standard polar	33892256
D-(+)-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
D-(+)-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
D-(+)-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
D-(+)-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
D-(+)-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
D-(+)-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
D-(+)-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
D-(+)-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
D-(+)-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

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
MS	Mass Spectrum (Electron Ionization)	splash10-066r-9200000000-f04be1ac2888052faf10	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 10V, Positive-QTOF	splash10-0udi-1900000000-8861ba576d835c24c4e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 20V, Positive-QTOF	splash10-0zfr-9700000000-7b7dfb5b5671e2efed19	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 40V, Positive-QTOF	splash10-100r-9000000000-02b93dd813cef6744911	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 10V, Negative-QTOF	splash10-0udi-0900000000-3bdcde43911faafba8b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 20V, Negative-QTOF	splash10-0udi-0900000000-66279fba8a75e05ec84b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 40V, Negative-QTOF	splash10-05n3-9500000000-02a124dc8509d82c4bb8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 10V, Positive-QTOF	splash10-0gws-7900000000-b08efab8959a09a26216	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 20V, Positive-QTOF	splash10-000x-9200000000-13ccbe770389182b9c06	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 40V, Positive-QTOF	splash10-0006-9000000000-4b6afc70d0efd7f97f15	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-(+)-dihydrocarvone 20V, Negative-QTOF	splash10-0udi-1900000000-6d20364e296745592a69	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-(+)-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

FDB003846

KNApSAcK ID

Not Available

Chemspider ID

20869

KEGG Compound ID

C11398

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22227

PDB ID

Not Available

ChEBI ID

154

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1106571

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for D-(+)-dihydrocarvone (HMDB0302236)

MOL for HMDB0302236 (D-(+)-dihydrocarvone)

3D MOL for HMDB0302236 (D-(+)-dihydrocarvone)

3D SDF for HMDB0302236 (D-(+)-dihydrocarvone)

3D-SDF for HMDB0302236 (D-(+)-dihydrocarvone)

PDB for HMDB0302236 (D-(+)-dihydrocarvone)

3D PDB for HMDB0302236 (D-(+)-dihydrocarvone)

SMILES for HMDB0302236 (D-(+)-dihydrocarvone)

INCHI for HMDB0302236 (D-(+)-dihydrocarvone)

Structure for HMDB0302236 (D-(+)-dihydrocarvone)

3D Structure for HMDB0302236 (D-(+)-dihydrocarvone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra