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Showing NP-Card for Verbenol (NP0048460)

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Record Information
Version2.0
Created at2022-03-17 20:56:49 UTC
Updated at2022-03-17 20:56:49 UTC
NP-MRD IDNP0048460
Secondary Accession NumbersNone
Natural Product Identification
Common NameVerbenol
DescriptionVerbenol, also known as (e)-verbenol or fema 3594, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. These compounds have been found to be active components of insect pheromones and essential oils. For the cis isomer, the two methyl groups (-CH3) are on the same side of the carbon ring as the hydroxy group (-OH), and for the trans isomer, they are on the opposite sides. Verbenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Verbenol is a fresh, ozone, and pine tasting compound. Outside of the human body, Verbenol is found, on average, in the highest concentration within hyssops. Verbenol has also been detected, but not quantified in, a few different foods, such as rosemaries, spearmints, and wild celeries. This could make verbenol a potential biomarker for the consumption of these foods. Verbenol (2-pine-4-ol) is a group of stereoisomeric bicyclic monoterpene alcohols. Typically, verbenol and related cyclic monoterpenes are available as non‐racemic mixtures of their enantiomers. Four stereoisomers of verbenol are known. There are methods to increase enantiomeric excess (optical purity) of verbenol and to isolate individual enantiomers. Verbenol is found in Anthemis aciphylla, Anthemis aciphylla BOISS.var.discoidea BOISS, Artemisia judaica, Artemisia rutifolia, Asparagus racemosus , Cedrus libani , Centaurea atropurpurea, Centaurea sessilis, Chrysanthemum indicum, Citrus aurantiifolia, Commiphora gurreh, Curcuma mangga , Cymbopogon citratus , Cyperus rotundus, Dendroctonus ponderosae, Espeletiopsis guacharaca, Ferula hermonis , Ips cembrae, Lippia javanica , Mosla chinensis, Picea abies, Pinus ponder, Tanacetum macrophyllum, Tanacetum parthenium, Tarchonanthus camphoratus , Tetradenia riparia , Thymus cilicicus, Thymus vulgaris, Tipuana tipu, Xylopia parviflora and Xylopia sericea . Again, there are enantiomers of each form that exhibit optical activity, that is, turn the plane of linearly polarized light as it passes through the substance or solution.Trans-Verbenol is a mountain pine beetle pheromone that attracts insects to a tree.Cis-Verbenol is an aggregation pheromone of Ips typographus and Dendroctonus ponderosae Hopkins.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048460 (Verbenol)

Verbenol
  Mrv1572001071617232D          

 11 12  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  4  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  3  1  0  0  0  0
  7  5  1  0  0  0  0
  1  6  1  0  0  0  0
  6  5  2  0  0  0  0
  3 10  1  0  0  0  0
  2 10  1  0  0  0  0
  1 11  1  0  0  0  0
M  END
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3D MOL for NP0048460 (Verbenol)

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3D SDF for NP0048460 (Verbenol)
Verbenol
  Mrv1572001071617232D          

 11 12  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  4  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  3  1  0  0  0  0
  7  5  1  0  0  0  0
  1  6  1  0  0  0  0
  6  5  2  0  0  0  0
  3 10  1  0  0  0  0
  2 10  1  0  0  0  0
  1 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048460

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.237

> <EXACT_MASS>
152.120115135

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.104736529546866

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
1.648804109333334

> <ALOGPS_LOGS>
-1.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.58834245842004

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2292590086870732

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
46.1608

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
verbenol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048460 (Verbenol)
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PDB for NP0048460 (Verbenol)
HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Verbenol                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.104  -2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.874  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6   11                                                  
CONECT    2    1    4   10                                                  
CONECT    3    4    5   10                                                  
CONECT    4    3    2    8    9                                             
CONECT    5    3    7    6                                                  
CONECT    6    1    5                                                       
CONECT    7    5                                                            
CONECT    8    4                                                            
CONECT    9    4                                                            
CONECT   10    3    2                                                       
CONECT   11    1                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0048460 (Verbenol)
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SMILES for NP0048460 (Verbenol)
CC1=CC(O)C2CC1C2(C)C
Download
INCHI for NP0048460 (Verbenol)
InChI=1S/C10H16O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-9,11H,5H2,1-3H3
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View in JSmol
Synonyms
ValueSource
(+)-VerbenolHMDB
(e)-VerbenolHMDB
(S)-cis-VerbenolHMDB
2-Pinen-4-ol (8ci)HMDB
4,6,6-Trimethyl-bicyclo(3.1.1)hept-3-en-2-olHMDB
4,6,6-Trimethyl-bicyclo[3,1,1]hept-3-en-2-olHMDB
4,6,6-Trimethyl-bicyclo[3.1.1]hept-3-en-2-olHMDB
4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-olHMDB
4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-olHMDB
4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-ol, 9ciHMDB
4-Hydroxy-2,6,6-trimethylbicyclo(3.1.1)hept-2-eneHMDB
BerbenolHMDB
Bicyclo(3.1.1)hept-3-en-2-ol, 4,6,6-trimethyl- (9ci)HMDB
D-VerbenolHMDB
FEMA 3594HMDB
PINEN-4-O1HMDB
Pinen-4-olHMDB
trans-VerbenolHMDB
Verbenol, (1S-(1alpha,2beta,5alpha))-isomerHMDB
Verbenol, (1alpha,2alpha,5alpha)-isomerHMDB
Verbenol, (1R-(1alpha,2beta,5alpha))-isomerHMDB
Verbenol, (1S-(1alpha,2alpha,5alpha))-isomerHMDB
Verbenol, (1R-(1alpha,2alpha,5alpha))-isomerHMDB
Verbenol, (1alpha,2beta,5alpha)-isomerHMDB
VerbenolMeSH
Chemical FormulaC10H16O
Average Mass152.2370 Da
Monoisotopic Mass152.12012 Da
IUPAC Name4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol
Traditional Nameverbenol
CAS Registry Number473-67-6
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 KeyWONIGEXYPVIKFS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anthemis aciphyllaLOTUS Database
Anthemis aciphylla BOISS.var.discoidea BOISSPlant
Apium graveolensFooDB
Artemisia judaicaLOTUS Database
Artemisia rutifoliaLOTUS Database
Asparagus racemosusPlant
Cedrus libaniPlant
Centaurea atropurpureaPlant
Centaurea sessilisPlant
Chrysanthemum indicumLOTUS Database
Citrus aurantiifoliaLOTUS Database
Commiphora gurrehLOTUS Database
Curcuma manggaPlant
Cymbopogon citratusPlant
Cyperus rotundusLOTUS Database
Dendroctonus ponderosaeAnimalia
Espeletiopsis guacharacaLOTUS Database
Ferula hermonisPlant
Hyssopus officinalis L.FooDB
Ips cembraeLOTUS Database
Lippia javanicaPlant
Mentha spicataFooDB
Mosla chinensisLOTUS Database
Picea abiesLOTUS Database
Pinus ponderPlant
Salvia rosmarinusFooDB
Tanacetum macrophyllumPlant
Tanacetum partheniumLOTUS Database
Tarchonanthus camphoratusPlant
Tetradenia ripariaPlant
Thymus cilicicusLOTUS Database
Thymus vulgarisLOTUS Database
Tipuana tipuPlant
Xylopia parvifloraPlant
Xylopia sericeaPlant
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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentBicyclic monoterpenoids  
Alternative Parents
Substituents
  • Pinane monoterpenoid
    • 

  • Bicyclic monoterpenoid
    • 

  • Secondary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.07ALOGPS
logP1.65ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)18.59ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.16 m³·mol⁻¹ChemAxon
Polarizability18.1 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036129  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014977  
KNApSAcK IDNot Available
Chemspider ID55074  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVerbenol  
METLIN IDNot Available
PubChem Compound61126  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References