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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:11:42 UTC

Update Date

2022-03-07 02:54:47 UTC

HMDB ID

HMDB0036129

Secondary Accession Numbers

HMDB36129

Metabolite Identification

Common Name

Verbenol

Description

Verbenol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Based on a literature review a significant number of articles have been published on Verbenol.

Structure

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

COMPND    HMDB0036129
HETATM    1  C1  UNL     1       2.174  -1.830  -0.135  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.266  -0.676  -0.068  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.487   0.447  -0.734  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.517   1.602  -0.637  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.233   2.641  -0.038  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.581   1.218   0.337  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.050   0.590   1.561  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.040  -0.730   0.767  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.157  -0.163   0.037  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.419  -0.378   0.801  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.261  -0.491  -1.409  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.092  -1.700   0.495  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.687  -2.768   0.177  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.555  -2.003  -1.166  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.362   0.546  -1.352  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.131   1.868  -1.631  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.052   2.869  -0.517  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.326   1.989   0.520  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.597   0.554   2.452  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.076   0.979   1.746  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.121  -1.623   1.364  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.008  -1.203   0.315  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.048   0.526   0.702  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.223  -0.669   1.839  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.045  -1.249  -1.597  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.328  -0.790  -1.888  1.00  0.00           H  
HETATM   27  H16 UNL     1      -1.607   0.441  -1.942  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3    8
CONECT    3    4   15
CONECT    4    5    6   16
CONECT    5   17
CONECT    6    7    9   18
CONECT    7    8   19   20
CONECT    8    9   21
CONECT    9   10   11
CONECT   10   22   23   24
CONECT   11   25   26   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+)-Verbenol	HMDB
(e)-Verbenol	HMDB
(S)-cis-Verbenol	HMDB
2-Pinen-4-ol (8ci)	HMDB
4,6,6-Trimethyl-bicyclo(3.1.1)hept-3-en-2-ol	HMDB
4,6,6-Trimethyl-bicyclo[3,1,1]hept-3-en-2-ol	HMDB
4,6,6-Trimethyl-bicyclo[3.1.1]hept-3-en-2-ol	HMDB
4,6,6-trimethylbicyclo(3.1.1)Hept-3-en-2-ol	HMDB
4,6,6-trimethylbicyclo[3.1.1]Hept-3-en-2-ol	HMDB
4,6,6-trimethylbicyclo[3.1.1]Hept-3-en-2-ol, 9ci	HMDB
4-Hydroxy-2,6,6-trimethylbicyclo(3.1.1)hept-2-ene	HMDB
Berbenol	HMDB
bicyclo(3.1.1)Hept-3-en-2-ol, 4,6,6-trimethyl- (9ci)	HMDB
D-Verbenol	HMDB
FEMA 3594	HMDB
PINEN-4-O1	HMDB
Pinen-4-ol	HMDB
trans-Verbenol	HMDB
Verbenol, (1S-(1alpha,2beta,5alpha))-isomer	MeSH, HMDB
Verbenol, (1alpha,2alpha,5alpha)-isomer	MeSH, HMDB
Verbenol, (1R-(1alpha,2beta,5alpha))-isomer	MeSH, HMDB
Verbenol, (1S-(1alpha,2alpha,5alpha))-isomer	MeSH, HMDB
Verbenol, (1R-(1alpha,2alpha,5alpha))-isomer	MeSH, HMDB
Verbenol, (1alpha,2beta,5alpha)-isomer	MeSH, HMDB
Verbenol	MeSH

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.237

Monoisotopic Molecular Weight

152.120115135

IUPAC Name

4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol

Traditional Name

verbenol

CAS Registry Number

473-67-6

SMILES

CC1=CC(O)C2CC1C2(C)C

InChI Identifier

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

InChI Key

WONIGEXYPVIKFS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Pinane monoterpenoid
Bicyclic monoterpenoid
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

an insect hormone (CPD-8833 )
a monoterpenol (CPD-8833 )

Ontology

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036129)

Source

Endogenous

Endogenous (HMDB: HMDB0036129)

Plant

Plant (HMDB: HMDB0036129)

Animal

Animal (HMDB: HMDB0036129)

Exogenous

Food

Food (HMDB: HMDB0036129)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Herb

Exogenous (HMDB: HMDB0036129)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036129)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036129)

Lipid metabolism pathway (HMDB: HMDB0036129)

Cellular process

Cell signaling (HMDB: HMDB0036129)

Biochemical process

Lipid transport (HMDB: HMDB0036129)

Role

Biological role

Energy source (HMDB: HMDB0036129)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036129)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036129)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	63.00 to 67.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	214.00 to 215.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	2.554 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.51 g/L	ALOGPS
logP	2.07	ALOGPS
logP	1.65	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	18.59	ChemAxon
pKa (Strongest Basic)	-1.2	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	0	ChemAxon
Refractivity	46.16 m³·mol⁻¹	ChemAxon
Polarizability	18.1 Å³	ChemAxon
Number of Rings	2	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]+	135.906	31661259
DarkChem	[M-H]-	130.435	31661259
DeepCCS	[M+H]+	135.432	30932474
DeepCCS	[M-H]-	132.629	30932474
DeepCCS	[M-2H]-	168.702	30932474
DeepCCS	[M+Na]+	144.119	30932474
AllCCS	[M+H]+	132.5	32859911
AllCCS	[M+H-H2O]+	128.1	32859911
AllCCS	[M+NH4]+	136.6	32859911
AllCCS	[M+Na]+	137.7	32859911
AllCCS	[M-H]-	135.7	32859911
AllCCS	[M+Na-2H]-	136.9	32859911
AllCCS	[M+HCOO]-	138.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Verbenol	CC1=CC(O)C2CC1C2(C)C	1683.7	Standard polar	33892256
Verbenol	CC1=CC(O)C2CC1C2(C)C	1127.9	Standard non polar	33892256
Verbenol	CC1=CC(O)C2CC1C2(C)C	1130.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Verbenol,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)C2CC1C2(C)C	1250.6	Semi standard non polar	33892256
Verbenol,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)C2CC1C2(C)C	1532.3	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 - Verbenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f7c-6900000000-725a3ffa9a2c27657f75	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Verbenol GC-MS (1 TMS) - 70eV, Positive	splash10-05ic-9220000000-b90f976faa3abdbac445	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Verbenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Verbenol 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 - Verbenol 10V, Positive-QTOF	splash10-0f79-0900000000-6ff630040559510e3f1d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenol 20V, Positive-QTOF	splash10-0f79-0900000000-d77ee423e0f6f183d1df	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenol 40V, Positive-QTOF	splash10-00kr-0900000000-bffee4e8536c2e4722c4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenol 10V, Negative-QTOF	splash10-0udi-0900000000-1384a080edbf08e60385	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenol 20V, Negative-QTOF	splash10-0udi-0900000000-66f689eb5b9ce53ca27c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenol 40V, Negative-QTOF	splash10-0udr-0900000000-f5d698ddd2cc8c2502fb	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenol 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenol 20V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenol 40V, Negative-QTOF	splash10-0udi-0900000000-c8f08741da2f9e0cc3d0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenol 10V, Positive-QTOF	splash10-0udi-0900000000-ed74c9ab4d3b693dc4fd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenol 20V, Positive-QTOF	splash10-0f79-0900000000-4ea2325ddaf644f1dd2d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verbenol 40V, Positive-QTOF	splash10-014r-0900000000-688f35897c40c564f2a9	2021-09-22	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

Cytoplasm
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

FDB014977

KNApSAcK ID

C00053892

Chemspider ID

55074

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Verbenol

METLIN ID

Not Available

PubChem Compound

61126

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036981

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 Verbenol (HMDB0036129)

MOL for HMDB0036129 (Verbenol)

3D MOL for HMDB0036129 (Verbenol)

3D SDF for HMDB0036129 (Verbenol)

3D-SDF for HMDB0036129 (Verbenol)

PDB for HMDB0036129 (Verbenol)

3D PDB for HMDB0036129 (Verbenol)

SMILES for HMDB0036129 (Verbenol)

INCHI for HMDB0036129 (Verbenol)

Structure for HMDB0036129 (Verbenol)

3D Structure for HMDB0036129 (Verbenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra