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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:54:30 UTC

Update Date

2023-02-21 17:24:30 UTC

HMDB ID

HMDB0034974

Secondary Accession Numbers

HMDB34974

Metabolite Identification

Common Name

(R)-Carvotanacetone

Description

(R)-Carvotanacetone 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. Based on a literature review a significant number of articles have been published on (R)-Carvotanacetone.

Structure

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

COMPND    HMDB0034974
HETATM    1  C1  UNL     1       3.729   0.232  -0.710  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.327  -0.035  -0.267  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.590  -0.929  -0.891  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.192  -1.251  -0.513  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.456   0.000   0.007  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.867  -0.214   0.476  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.379   1.139   0.969  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.793  -0.733  -0.555  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.320   0.581   1.174  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.761   0.691   0.860  1.00  0.00           C  
HETATM   11  O1  UNL     1       2.497   1.417   1.574  1.00  0.00           O  
HETATM   12  H1  UNL     1       4.262  -0.710  -0.948  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.301   0.713   0.127  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.768   0.958  -1.550  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.057  -1.444  -1.725  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.324  -1.551  -1.447  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.129  -2.037   0.265  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.421   0.762  -0.799  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.897  -0.882   1.362  1.00  0.00           H  
HETATM   20  H9  UNL     1      -3.484   1.021   1.058  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.114   1.943   0.252  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.980   1.355   1.967  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.334  -1.189  -1.430  1.00  0.00           H  
HETATM   24  H13 UNL     1      -3.450   0.099  -0.937  1.00  0.00           H  
HETATM   25  H14 UNL     1      -3.526  -1.486  -0.142  1.00  0.00           H  
HETATM   26  H15 UNL     1       0.159  -0.069   2.039  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.067   1.619   1.312  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3   10
CONECT    3    4   15
CONECT    4    5   16   17
CONECT    5    6    9   18
CONECT    6    7    8   19
CONECT    7   20   21   22
CONECT    8   23   24   25
CONECT    9   10   26   27
CONECT   10   11   11
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Carvotanacetone	HMDB
Androcur	HMDB
Cyprostat	HMDB
Cyprosterone acetate	HMDB
Cyproteron acetate	HMDB
Cyproteron-R acetate	HMDB
Cyproterone 17-O-acetate	HMDB
Cyproterone 17alpha-acetate	HMDB
Cyproterone acetate	HMDB
Cyproteroneacetate	HMDB
Carvone, (S)-isomer	MeSH
Limonen-6-one	MeSH
Carvone	MeSH
(RS)-5-Isopropenyl-2-methylcyclohex-2-en-1-one	MeSH
2-Methyl-5-isopropenyl-2-cyclohexenone	MeSH
5-Isopropyl-2-methyl-2-cyclohexen-1-one	MeSH
Carvone, (R)-isomer	MeSH
2-Methyl-5-(1-methylethenyl)-2-cyclohexene-1-one	MeSH

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

2-methyl-5-(propan-2-yl)cyclohex-2-en-1-one

Traditional Name

5-isopropyl-2-methylcyclohex-2-en-1-one

CAS Registry Number

33375-08-5

SMILES

CC(C)C1CC=C(C)C(=O)C1

InChI Identifier

InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,7,9H,5-6H2,1-3H3

InChI Key

WPGPCDVQHXOMQP-UHFFFAOYSA-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
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034974)

Source

Endogenous

Endogenous (HMDB: HMDB0034974)

Plant

Plant (HMDB: HMDB0034974)

Animal

Animal (HMDB: HMDB0034974)

Exogenous

Food

Food (HMDB: HMDB0034974)

Herb and spice

Spice

Pepper (Spice) (FooDB: FOOD00139)

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034974)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034974)

Lipid metabolism pathway (HMDB: HMDB0034974)

Cellular process

Cell signaling (HMDB: HMDB0034974)

Biochemical process

Lipid transport (HMDB: HMDB0034974)

Role

Biological role

Energy source (HMDB: HMDB0034974)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034974)

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
Water Solubility	1.36 g/L	ALOGPS
logP	2.75	ALOGPS
logP	2.9	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	-4.6	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	47.4 m³·mol⁻¹	ChemAxon
Polarizability	18.4 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
DarkChem	[M+H]+	134.684	31661259
DarkChem	[M-H]-	132.081	31661259
DeepCCS	[M+H]+	140.003	30932474
DeepCCS	[M-H]-	136.257	30932474
DeepCCS	[M-2H]-	173.712	30932474
DeepCCS	[M+Na]+	149.149	30932474
AllCCS	[M+H]+	132.2	32859911
AllCCS	[M+H-H2O]+	127.7	32859911
AllCCS	[M+NH4]+	136.3	32859911
AllCCS	[M+Na]+	137.5	32859911
AllCCS	[M-H]-	137.9	32859911
AllCCS	[M+Na-2H]-	139.5	32859911
AllCCS	[M+HCOO]-	141.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Carvotanacetone	CC(C)C1CC=C(C)C(=O)C1	1662.2	Standard polar	33892256
(R)-Carvotanacetone	CC(C)C1CC=C(C)C(=O)C1	1243.1	Standard non polar	33892256
(R)-Carvotanacetone	CC(C)C1CC=C(C)C(=O)C1	1247.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Carvotanacetone,1TMS,isomer #1	CC1=CCC(C(C)C)C=C1O[Si](C)(C)C	1375.5	Semi standard non polar	33892256
(R)-Carvotanacetone,1TMS,isomer #1	CC1=CCC(C(C)C)C=C1O[Si](C)(C)C	1288.2	Standard non polar	33892256
(R)-Carvotanacetone,1TBDMS,isomer #1	CC1=CCC(C(C)C)C=C1O[Si](C)(C)C(C)(C)C	1606.6	Semi standard non polar	33892256
(R)-Carvotanacetone,1TBDMS,isomer #1	CC1=CCC(C(C)C)C=C1O[Si](C)(C)C(C)(C)C	1485.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Carvotanacetone GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9300000000-2f8475f123b9e8cdea64	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Carvotanacetone 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 - (R)-Carvotanacetone 10V, Positive-QTOF	splash10-0udi-0900000000-cb7d76cf6095237c0f17	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Carvotanacetone 20V, Positive-QTOF	splash10-0udi-9800000000-60c503e1ff2723928a46	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Carvotanacetone 40V, Positive-QTOF	splash10-100r-9000000000-375dcdd5898f683b6be0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Carvotanacetone 10V, Negative-QTOF	splash10-0udi-0900000000-f82c83439c41b1415211	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Carvotanacetone 20V, Negative-QTOF	splash10-0udi-0900000000-ad15e054514d8515c995	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Carvotanacetone 40V, Negative-QTOF	splash10-0f7c-9800000000-ec4477331d3c1cefd448	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Carvotanacetone 10V, Positive-QTOF	splash10-0w29-3900000000-3979614d67936e2eab40	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Carvotanacetone 20V, Positive-QTOF	splash10-055f-9200000000-8dd2756f6e2ca7142cf0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Carvotanacetone 40V, Positive-QTOF	splash10-0006-9000000000-0a06a9c60be1f46855b3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Carvotanacetone 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Carvotanacetone 20V, Negative-QTOF	splash10-0udi-0900000000-6bf96790df77f609bfa8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Carvotanacetone 40V, Negative-QTOF	splash10-0gbm-9700000000-806e27bdb4cfeeb5926e	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

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

FDB014523

KNApSAcK ID

C00052126

Chemspider ID

454694

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

521267

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (R)-Carvotanacetone (HMDB0034974)

MOL for HMDB0034974 ((R)-Carvotanacetone)

3D MOL for HMDB0034974 ((R)-Carvotanacetone)

3D SDF for HMDB0034974 ((R)-Carvotanacetone)

3D-SDF for HMDB0034974 ((R)-Carvotanacetone)

PDB for HMDB0034974 ((R)-Carvotanacetone)

3D PDB for HMDB0034974 ((R)-Carvotanacetone)

SMILES for HMDB0034974 ((R)-Carvotanacetone)

INCHI for HMDB0034974 ((R)-Carvotanacetone)

Structure for HMDB0034974 ((R)-Carvotanacetone)

3D Structure for HMDB0034974 ((R)-Carvotanacetone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra