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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-12 21:15:59 UTC

Update Date

2023-02-21 17:16:41 UTC

HMDB ID

HMDB0003450

Secondary Accession Numbers

HMDB0006410
HMDB03450
HMDB06410

Metabolite Identification

Common Name

(-)-trans-Carveol

Description

(-)-trans-Carveol, also known as (1S,5R)-carveol, 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. Thus, (-)-trans-carveol is considered to be an isoprenoid lipid molecule (-)-trans-Carveol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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

COMPND    HMDB0003450
HETATM    1  C1  UNL     1      -2.867   0.963  -0.245  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.112  -0.093  -0.144  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.725  -1.459  -0.259  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.660  -0.026   0.078  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.267  -0.689   1.411  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.196  -0.893   1.300  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.920  -0.007   0.674  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.390  -0.245   0.581  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.410   1.230   0.039  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.670   1.133  -1.333  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.101   1.373   0.173  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.468   1.951  -0.169  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.935   0.853  -0.412  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.640  -1.549   0.358  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.951  -1.680  -1.335  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.025  -2.248   0.082  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.121  -0.528  -0.757  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.409   0.062   2.243  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.830  -1.600   1.601  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.631  -1.768   1.737  1.00  0.00           H  
HETATM   21  H10 UNL     1       3.558  -1.321   0.517  1.00  0.00           H  
HETATM   22  H11 UNL     1       3.820   0.249  -0.316  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.836   0.121   1.531  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.884   2.142   0.408  1.00  0.00           H  
HETATM   25  H14 UNL     1       1.639   0.184  -1.575  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.507   2.043  -0.614  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.337   1.804   1.154  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
(-)-(4R,6S)-trans-Carveol	ChEBI
(1S,5R)-Carveol	ChEBI
Carveol	HMDB
(-)-(4R,6S)-Carveol	HMDB
(1S,5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol	HMDB
(e)-Carveol	HMDB
(±)-trans-carveol	HMDB
trans-(-)-Carveol	HMDB
trans-5-(1-Methylethenyl)-2-methyl-2-cyclohexenol	HMDB
trans-Carveol	HMDB
trans-Mentha-1,8-dien-6-ol	HMDB
(-)-trans-Carveol	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

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

Traditional Name

(-)-trans-carveol

CAS Registry Number

2102-58-1

SMILES

CC(=C)[C@@H]1CC=C(C)[C@@H](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/t9-,10+/m1/s1

InChI Key

BAVONGHXFVOKBV-ZJUUUORDSA-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

carveol (CHEBI:15389 )
Menthane monoterpenoids (C00964 )
Cyclic monoterpenes (C00964 )
Menthane monoterpenoids (LMPR0102090005 )

Ontology

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003450)

Source

Endogenous

Endogenous (HMDB: HMDB0003450)

Plant

Plant (HMDB: HMDB0003450)

Animal

Animal (HMDB: HMDB0003450)

Exogenous

Food

Food (HMDB: HMDB0003450)

Herb and spice

Herb

Dill (FooDB: FOOD00013)
Spearmint (FooDB: FOOD00112)

Spice

Caraway (FooDB: FOOD00043)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Exogenous (HMDB: HMDB0003450)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0003450)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0003450)

Lipid metabolism pathway (HMDB: HMDB0003450)

Cellular process

Cell signaling (HMDB: HMDB0003450)

Biochemical process

Lipid transport (HMDB: HMDB0003450)

Role

Biological role

Energy source (HMDB: HMDB0003450)

Industrial application

Personal care product

Cosmetic (HMDB: HMDB0003450)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0003450)

Physical Properties

State

Solid

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	3.12	GRIFFIN,S ET AL. (1999)

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 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]+	138.082	31661259
DarkChem	[M-H]-	133.768	31661259
DeepCCS	[M+H]+	142.664	30932474
DeepCCS	[M-H]-	140.269	30932474
DeepCCS	[M-2H]-	174.24	30932474
DeepCCS	[M+Na]+	148.743	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 Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-trans-Carveol	CC(=C)[C@@H]1CC=C(C)[C@@H](O)C1	1803.9	Standard polar	33892256
(-)-trans-Carveol	CC(=C)[C@@H]1CC=C(C)[C@@H](O)C1	1198.7	Standard non polar	33892256
(-)-trans-Carveol	CC(=C)[C@@H]1CC=C(C)[C@@H](O)C1	1214.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-trans-Carveol,1TMS,isomer #1	C=C(C)[C@@H]1CC=C(C)[C@@H](O[Si](C)(C)C)C1	1295.1	Semi standard non polar	33892256
(-)-trans-Carveol,1TBDMS,isomer #1	C=C(C)[C@@H]1CC=C(C)[C@@H](O[Si](C)(C)C(C)(C)C)C1	1538.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (-)-trans-Carveol EI-B (Non-derivatized)	splash10-05nf-9700000000-a75055e28480ba00b820	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (-)-trans-Carveol EI-B (Non-derivatized)	splash10-0a5c-9300000000-0497c064b7fcb0223af5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (-)-trans-Carveol EI-B (Non-derivatized)	splash10-05nf-9700000000-a75055e28480ba00b820	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (-)-trans-Carveol EI-B (Non-derivatized)	splash10-0a5c-9300000000-0497c064b7fcb0223af5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (-)-trans-Carveol EI-B (Non-derivatized)	splash10-05nf-9700000000-a75055e28480ba00b820	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (-)-trans-Carveol EI-B (Non-derivatized)	splash10-0a5c-9300000000-0497c064b7fcb0223af5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (-)-trans-Carveol EI-B (Non-derivatized)	splash10-05nf-9700000000-a75055e28480ba00b820	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (-)-trans-Carveol EI-B (Non-derivatized)	splash10-0a5c-9300000000-0497c064b7fcb0223af5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-trans-Carveol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0040-9300000000-900d20824e13ff7b371a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-trans-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 - (-)-trans-Carveol 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 - (-)-trans-Carveol 10V, Positive-QTOF	splash10-0f79-1900000000-6cbdaa00e43b6a5f1466	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-trans-Carveol 20V, Positive-QTOF	splash10-0f79-7900000000-b55dc6268bf1d9facfab	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-trans-Carveol 40V, Positive-QTOF	splash10-1000-9200000000-82efaa1d3034c0a127ad	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-trans-Carveol 10V, Negative-QTOF	splash10-0udi-0900000000-63662b96265d54ab95ac	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-trans-Carveol 20V, Negative-QTOF	splash10-0udi-0900000000-fb53bb25a46fab88d48a	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-trans-Carveol 40V, Negative-QTOF	splash10-0frl-6900000000-b30096dc2484f9341f67	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-trans-Carveol 10V, Negative-QTOF	splash10-0udi-0900000000-c751b1e6b18ebbd8226b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-trans-Carveol 20V, Negative-QTOF	splash10-0ue9-0900000000-ff7b348d24f4a9fae768	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-trans-Carveol 40V, Negative-QTOF	splash10-0159-5900000000-32379e3babd1cfac9d58	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-trans-Carveol 10V, Positive-QTOF	splash10-000l-7900000000-14152f364bee2002ab86	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-trans-Carveol 20V, Positive-QTOF	splash10-002f-9100000000-c417dcb5d6ff023a5c44	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-trans-Carveol 40V, Positive-QTOF	splash10-0006-9000000000-33b66b0d611b3c8dca5f	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15389

Food Biomarker Ontology

Not Available

VMH ID

CARVEOL

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Wouter, Adrian Duetz; Witholt, Bernard; Jourdat, Catherine. Process for the preparation of trans-carveol. Eur. Pat. Appl. (2002), 12 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

Reactions

(+)-Limonene + NADPH + Oxygen → (-)-trans-Carveol + NADP + Water	details

Enzyme Details

2. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

Reactions

(+)-Limonene + NADPH + Oxygen → (-)-trans-Carveol + NADP + Water	details

Showing metabocard for (-)-trans-Carveol (HMDB0003450)

MOL for HMDB0003450 ((-)-trans-Carveol)

3D MOL for HMDB0003450 ((-)-trans-Carveol)

3D SDF for HMDB0003450 ((-)-trans-Carveol)

3D-SDF for HMDB0003450 ((-)-trans-Carveol)

PDB for HMDB0003450 ((-)-trans-Carveol)

3D PDB for HMDB0003450 ((-)-trans-Carveol)

SMILES for HMDB0003450 ((-)-trans-Carveol)

INCHI for HMDB0003450 ((-)-trans-Carveol)

Structure for HMDB0003450 ((-)-trans-Carveol)

3D Structure for HMDB0003450 ((-)-trans-Carveol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions