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Showing NP-Card for Nopol (NP0045508)

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Record Information
Version2.0
Created at2022-03-17 19:21:10 UTC
Updated at2022-03-17 19:21:10 UTC
NP-MRD IDNP0045508
Secondary Accession NumbersNone
Natural Product Identification
Common NameNopol
Description(-)-Nopol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other (-)-Nopol is an extremely weak basic (essentially neutral) compound (based on its pKa) (-)-Nopol is a sweet, balsamic, and citrus tasting compound. Outside of the human body, (-)-Nopol is found, on average, in the highest concentration within rosemaries (-)-Nopol has also been detected, but not quantified in, carrots and wild carrots. This could make (-)-nopol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0045508 (Nopol)


  Mrv0541 02241219092D          

 12 13  0  0  0  0            999 V2000
   -0.7148   -0.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148   -1.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7148   -1.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7148   -0.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471   -0.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070   -1.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6510    1.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6510    1.7639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
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3D MOL for NP0045508 (Nopol)

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3D SDF for NP0045508 (Nopol)

  Mrv0541 02241219092D          

 12 13  0  0  0  0            999 V2000
   -0.7148   -0.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148   -1.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7148   -1.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7148   -0.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471   -0.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070   -1.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6510    1.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6510    1.7639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C2CC1C(CCO)=CC2

> <INCHI_IDENTIFIER>
InChI=1S/C11H18O/c1-11(2)9-4-3-8(5-6-12)10(11)7-9/h3,9-10,12H,4-7H2,1-2H3

> <INCHI_KEY>
ROKSAUSPJGWCSM-UHFFFAOYSA-N

> <FORMULA>
C11H18O

> <MOLECULAR_WEIGHT>
166.26

> <EXACT_MASS>
166.135765198

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
20.17461742428023

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl}ethan-1-ol

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
1.8095514946666666

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.989000185661215

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9288113187917846

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
51.252

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl}ethanol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0045508 (Nopol)
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PDB for NP0045508 (Nopol)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.334  -0.981   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.524   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.293   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.524   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.981   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.213   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -1.762   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.189   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.021  -1.762   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.946  -2.311   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.215   1.891   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.215   3.293   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    8                                                  
CONECT    7    1    3    9   10                                             
CONECT    8    6   11                                                       
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    8   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0045508 (Nopol)
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SMILES for NP0045508 (Nopol)
CC1(C)C2CC1C(CCO)=CC2
Download
INCHI for NP0045508 (Nopol)
InChI=1S/C11H18O/c1-11(2)9-4-3-8(5-6-12)10(11)7-9/h3,9-10,12H,4-7H2,1-2H3
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View in JSmol
Synonyms
ValueSource
NopolMeSH
Chemical FormulaC11H18O
Average Mass166.2600 Da
Monoisotopic Mass166.13577 Da
IUPAC Name2-{6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl}ethan-1-ol
Traditional Name2-{6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl}ethanol
CAS Registry Number128-50-7
SMILES
CC1(C)C2CC1C(CCO)=CC2
InChI Identifier
InChI=1S/C11H18O/c1-11(2)9-4-3-8(5-6-12)10(11)7-9/h3,9-10,12H,4-7H2,1-2H3
InChI KeyROKSAUSPJGWCSM-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
    • David M. Alabran, Howard R. Moskowitz, and Ahmed F. Mabrouk. Carrot-Root Oil Components and Their...
Salvia rosmarinusFooDB
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
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP3.22ALOGPS
logP1.81ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)16.99ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity51.25 m³·mol⁻¹ChemAxon
Polarizability20.17 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0030002  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001291  
KNApSAcK IDNot Available
Chemspider ID29138  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound31408  
PDB IDNot Available
ChEBI ID525644  
Good Scents IDNot Available
References
General References