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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-10-30 10:32:48 UTC

Update Date

2022-03-07 03:17:33 UTC

HMDB ID

HMDB0059608

Secondary Accession Numbers

HMDB59608

Metabolite Identification

Common Name

(+)-trans-Carveol

Description

(+)-trans-Carveol, also known as (1R,5S)-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 (+)-trans-Carveol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

COMPND    HMDB0059608
HETATM    1  C1  UNL     1      -1.875   1.415  -0.423  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.865   0.117  -0.193  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.865  -0.480   0.717  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.841  -0.728  -0.857  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.056  -0.009  -1.911  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.009   0.853  -1.359  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.566   0.494  -0.219  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.647   1.400   0.309  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.234  -0.691   0.570  1.00  0.00           C  
HETATM   10  O1  UNL     1       2.379  -1.506   0.641  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.039  -1.446   0.131  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.620   2.038   0.058  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.184   1.929  -1.071  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.946  -1.590   0.554  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.896  -0.092   0.531  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.654  -0.288   1.786  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.430  -1.526  -1.404  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.740   0.586  -2.534  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.400  -0.802  -2.562  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.297   1.744  -1.900  1.00  0.00           H  
HETATM   21  H10 UNL     1       2.577   2.411  -0.112  1.00  0.00           H  
HETATM   22  H11 UNL     1       2.537   1.446   1.410  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.655   0.979   0.057  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.067  -0.346   1.632  1.00  0.00           H  
HETATM   25  H14 UNL     1       2.734  -1.721  -0.259  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.572  -1.798   0.988  1.00  0.00           H  
HETATM   27  H16 UNL     1       0.401  -2.393  -0.370  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
(1R,5S)-Carveol	ChEBI
(4S,6R)-trans-Carveol	ChEBI
(1R,5S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol	HMDB
(e)-Carveol	HMDB
(±)-trans-carveol	HMDB
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

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

Traditional Name

(+)-trans-carveol

CAS Registry Number

18383-51-2

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+/m0/s1

InChI Key

BAVONGHXFVOKBV-VHSXEESVSA-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:15388 )
Menthane monoterpenoids (C11409 )
Cyclic monoterpenes (C11409 )

Ontology

Not Available

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	Not Available	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	18.07 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
DeepCCS	[M+H]+	141.348	30932474
DeepCCS	[M-H]-	138.953	30932474
DeepCCS	[M-2H]-	173.384	30932474
DeepCCS	[M+Na]+	147.834	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
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	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-trans-Carveol 20V, Positive-QTOF	splash10-0f79-7900000000-f5a0579ac8857d525d07	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-trans-Carveol 40V, Positive-QTOF	splash10-1000-9200000000-7631d4c31e9b10b2e57b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-trans-Carveol 10V, Negative-QTOF	splash10-0udi-0900000000-6165a03d2d9c9e84c43f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-trans-Carveol 20V, Negative-QTOF	splash10-0udi-0900000000-fb53bb25a46fab88d48a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-trans-Carveol 40V, Negative-QTOF	splash10-0f79-6900000000-985654b955f212c9dee9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-trans-Carveol 10V, Positive-QTOF	splash10-000l-7900000000-14152f364bee2002ab86	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-trans-Carveol 20V, Positive-QTOF	splash10-002f-9100000000-c417dcb5d6ff023a5c44	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-trans-Carveol 40V, Positive-QTOF	splash10-0006-9000000000-33b66b0d611b3c8dca5f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-trans-Carveol 10V, Negative-QTOF	splash10-0udi-0900000000-c751b1e6b18ebbd8226b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-trans-Carveol 20V, Negative-QTOF	splash10-0ue9-0900000000-ff7b348d24f4a9fae768	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-trans-Carveol 40V, Negative-QTOF	splash10-0159-5900000000-32379e3babd1cfac9d58	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

FDB004802

KNApSAcK ID

C00010883

Chemspider ID

Not Available

KEGG Compound ID

C11409

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443178

PDB ID

Not Available

ChEBI ID

15388

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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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 (HMDB0059608)

MOL for HMDB0059608 ((+)-trans-Carveol)

3D MOL for HMDB0059608 ((+)-trans-Carveol)

3D SDF for HMDB0059608 ((+)-trans-Carveol)

3D-SDF for HMDB0059608 ((+)-trans-Carveol)

PDB for HMDB0059608 ((+)-trans-Carveol)

3D PDB for HMDB0059608 ((+)-trans-Carveol)

SMILES for HMDB0059608 ((+)-trans-Carveol)

INCHI for HMDB0059608 ((+)-trans-Carveol)

Structure for HMDB0059608 ((+)-trans-Carveol)

3D Structure for HMDB0059608 ((+)-trans-Carveol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions