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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:09:08 UTC

Update Date

2022-03-07 02:54:46 UTC

HMDB ID

HMDB0036083

Secondary Accession Numbers

HMDB36083

Metabolite Identification

Common Name

Carveol

Description

Carveol, also known as fema 2247, 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 Carveol.

Structure

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

COMPND    HMDB0243509
HETATM    1  C1  UNL     1      -1.918   1.482   0.628  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.876   0.192   0.399  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.786  -0.696   1.163  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.952  -0.397  -0.596  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.249   0.641  -1.437  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.880   1.203  -0.645  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.700   0.315  -0.105  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.859   0.742   0.704  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.451  -1.132  -0.318  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.726  -1.519  -1.631  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.004  -1.382   0.039  1.00  0.00           C  
HETATM   12  H1  UNL     1      -1.281   2.218   0.111  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.638   1.848   1.388  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.200  -0.169   2.047  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.668  -1.015   0.540  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.255  -1.595   1.557  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.537  -1.011  -1.356  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.122   0.201  -2.396  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.009   1.420  -1.707  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.001   2.274  -0.537  1.00  0.00           H  
HETATM   21  H10 UNL     1       3.132   0.012   1.492  1.00  0.00           H  
HETATM   22  H11 UNL     1       3.773   0.912   0.100  1.00  0.00           H  
HETATM   23  H12 UNL     1       2.644   1.701   1.262  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.069  -1.768   0.333  1.00  0.00           H  
HETATM   25  H14 UNL     1       2.328  -0.827  -2.013  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.072  -1.216   1.149  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.247  -2.432  -0.172  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    7   20
CONECT    7    8    9
CONECT    8   21   22   23
CONECT    9   10   11   24
CONECT   10   25
CONECT   11   26   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-Isopropenyl-2-methyl-2-cyclohexen-1-ol	ChEBI
p-Mentha-1,8-dien-6-ol	ChEBI
p-Mentha-6,8-dien-2-ol	ChEBI
1-Methyl-4-isopropenyl-6-cyclohexen-2-ol	HMDB
2-Methyl-5(1-methylethenyl)cyclohex-2-ene-1-ol	HMDB
2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol	HMDB
2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol	HMDB
2-Methyl-5-isopropenyl-2-cyclohexen-1-ol	HMDB
2-Methyl-5-[1-methylethenyl]-2-cyclohexen-1-ol	HMDB
5-Isopropenyl-2-methylcyclohex-2-en-1-ol	HMDB
6,8-p-Menthadien-2-ol	HMDB
FEMA 2247	HMDB
p-Mentha-1(6),8-dien-2-ol	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.237

Monoisotopic Molecular Weight

152.120115135

IUPAC Name

2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol

Traditional Name

carveol

CAS Registry Number

99-48-9

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/h4,9-11H,1,5-6H2,2-3H3

InChI Key

BAVONGHXFVOKBV-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
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

limonene monoterpenoid (CHEBI:23046 )
a carveol (CPD-260 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0036083)
Membrane (HMDB: HMDB0036083)

Source

Exogenous

Exogenous (HMDB: HMDB0036083)

Dill (FooDB: FOOD00013)
Parsley (FooDB: FOOD00131)
Peppermint (FooDB: FOOD00113)

Herbs and Spices (FooDB: FOOD00866)

Fruit

Citrus

Lemon (FooDB: FOOD00054)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Berry

Rabbiteye blueberry (FooDB: FOOD00898)

Tea

Vegetable

Leaf vegetable

Rocket salad (ssp.) (FooDB: FOOD00077)
Green vegetables (FooDB: FOOD00872)

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

Endogenous

Endogenous (HMDB: HMDB0036083)

Process

Not Available

Role

Industrial application

Central nervous system stimulant (HMDB: HMDB0036083)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	226.00 to 227.00 °C. @ 751.00 mm Hg	The Good Scents Company Information System
Water Solubility	519.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.12	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.82 g/L	ALOGPS
logP	2.41	ALOGPS
logP	1.99	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	18.21	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48 m³·mol⁻¹	ChemAxon
Polarizability	18.34 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]+	134.407	31661259
DarkChem	[M-H]-	130.38	31661259
DeepCCS	[M+H]+	138.324	30932474
DeepCCS	[M-H]-	135.773	30932474
DeepCCS	[M-2H]-	172.029	30932474
DeepCCS	[M+Na]+	147.344	30932474
AllCCS	[M+H]+	133.6	32859911
AllCCS	[M+H-H2O]+	129.1	32859911
AllCCS	[M+NH4]+	137.7	32859911
AllCCS	[M+Na]+	138.9	32859911
AllCCS	[M-H]-	136.2	32859911
AllCCS	[M+Na-2H]-	137.7	32859911
AllCCS	[M+HCOO]-	139.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.54 minutes	32390414
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.58 minutes	32390414
Predicted by Siyang on May 30, 2022	11.5572 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.5 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Carveol	CC(=C)C1CC=C(C)C(O)C1	1862.7	Standard polar	33892256
Carveol	CC(=C)C1CC=C(C)C(O)C1	1199.6	Standard non polar	33892256
Carveol	CC(=C)C1CC=C(C)C(O)C1	1208.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Carveol,1TMS,isomer #1	C=C(C)C1CC=C(C)C(O[Si](C)(C)C)C1	1286.6	Semi standard non polar	33892256
Carveol,1TBDMS,isomer #1	C=C(C)C1CC=C(C)C(O[Si](C)(C)C(C)(C)C)C1	1523.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Carveol EI-B (Non-derivatized)	splash10-001i-9300000000-c0df06475a23b1847e64	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Carveol EI-B (Non-derivatized)	splash10-0a5c-9400000000-20e9d5aa724b146ecbe0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Carveol EI-B (Non-derivatized)	splash10-001i-9300000000-c0df06475a23b1847e64	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Carveol EI-B (Non-derivatized)	splash10-0a5c-9400000000-20e9d5aa724b146ecbe0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carveol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gc9-9200000000-d270baae0672bddf4630	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carveol GC-MS (1 TMS) - 70eV, Positive	splash10-059l-9420000000-c8fe9a59dae7a88e5d86	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carveol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carveol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carveol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00kf-9600000000-b8936fad384c0f501d3a	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 - Carveol 10V, Positive-QTOF	splash10-0f79-1900000000-6cbdaa00e43b6a5f1466	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carveol 20V, Positive-QTOF	splash10-0f79-7900000000-b55dc6268bf1d9facfab	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carveol 40V, Positive-QTOF	splash10-1000-9200000000-82efaa1d3034c0a127ad	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carveol 10V, Negative-QTOF	splash10-0udi-0900000000-63662b96265d54ab95ac	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carveol 20V, Negative-QTOF	splash10-0udi-0900000000-fb53bb25a46fab88d48a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carveol 40V, Negative-QTOF	splash10-0frl-6900000000-b30096dc2484f9341f67	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carveol 10V, Negative-QTOF	splash10-0udi-0900000000-c751b1e6b18ebbd8226b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carveol 20V, Negative-QTOF	splash10-0ue9-0900000000-ff7b348d24f4a9fae768	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carveol 40V, Negative-QTOF	splash10-0159-5900000000-32379e3babd1cfac9d58	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carveol 10V, Positive-QTOF	splash10-000l-7900000000-14152f364bee2002ab86	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carveol 20V, Positive-QTOF	splash10-002f-9100000000-c417dcb5d6ff023a5c44	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carveol 40V, Positive-QTOF	splash10-0006-9000000000-33b66b0d611b3c8dca5f	2021-09-23	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

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

FDB014919

KNApSAcK ID

C00010883

Chemspider ID

7160

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carveol

METLIN ID

Not Available

PubChem Compound

7438

PDB ID

Not Available

ChEBI ID

23046

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1005281

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 Carveol (HMDB0036083)

MOL for HMDB0036083 (Carveol)

3D MOL for HMDB0036083 (Carveol)

3D SDF for HMDB0036083 (Carveol)

3D-SDF for HMDB0036083 (Carveol)

PDB for HMDB0036083 (Carveol)

3D PDB for HMDB0036083 (Carveol)

SMILES for HMDB0036083 (Carveol)

INCHI for HMDB0036083 (Carveol)

Structure for HMDB0036083 (Carveol)

3D Structure for HMDB0036083 (Carveol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra