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Showing NP-Card for (+)-Fenchone (NP0137036)

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Record Information
Version2.0
Created at2022-05-30 16:39:40 UTC
Updated at2022-05-30 16:39:40 UTC
NP-MRD IDNP0137036
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Fenchone
Description(+)-Fenchone, also known as (1R,4S)-fenchone or L-alpha-fenchone, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, (+)-fenchone is considered to be an isoprenoid lipid molecule (+)-Fenchone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (+)-Fenchone is a bitter, camphor, and cedarleaf tasting compound. Outside of the human body, (+)-Fenchone has been detected, but not quantified in, a few different foods, such as fennels, rosemaries, and star anises. This could make (+)-fenchone a potential biomarker for the consumption of these foods. (+)-Fenchone is found in Abies alba, Abies sibirica, Achillea abrotanoides, Ageratum conyzoides, Aloysia triphylla, Alpinia zerumbet, Anethum graveolens, Artemisia annua, Artemisia tridentata, Cannabis sativa, Catha edulis, Centaurea benedicta, Centratherum punctatum, Chaerophyllum macrospermum, Cinnamomum burmannii, Cinnamomum verum, Citrus limon, Cleonia lusitanica, Cymbopogon citratus, Eucalyptus brassiana, Eucalyptus bridgesiana, Ferula ovina, Foeniculum vulgare, Glycyrrhiza glabra, Mesosphaerum suaveolens, Hyssopus seravschanicus, Juniperus communis, Lavandula angustifolia, Lavandula stoechas, Micromeria juliana, Ocimum basilicum, Osbornia octodonta, Picea abies, Pimpinella serbica, Pistacia vera, Pityophthorus pityographus, Plectranthus glabratus, Santolina chamaecyparissus, Sassafras albidum, Satureja thymbra, Sideritis chamaedryfolia, Sideritis tragoriganum, Solanum tuberosum, Stachys aegyptiaca, Syzygium aromaticum, Tetradenia riparia, Thuja occidentalis, Thuja plicata, Thymbra capitata, Thymus pulegioides, Zingiber mioga and Zingiber zerumbet. A carbobicyclic compound that is fenchane in which the hydrogens at position 2 are replaced by an oxo group.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0137036 ((+)-Fenchone)

fenchone
  Mrv1652310031711232D          

 11 12  0  0  0  0            999 V2000
   -0.2822   -0.7752    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
   -0.8125    0.1433    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5082    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    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
Download

3D MOL for NP0137036 ((+)-Fenchone)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
   -2.1526   -1.2078   -0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1352   -0.1121    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8449    1.0576    0.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0593   -0.5524    1.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2125   -1.0007    2.1552 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2232   -0.2985    0.3101 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3839   -1.0141    0.8322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3994    1.1745    0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3253    1.5171   -0.9700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4103    0.2189   -1.1767 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7774   -0.7568   -1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1711   -0.7697   -0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2576   -1.8683    0.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8872   -1.7526   -1.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4168    0.6498    1.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1887    1.8326    1.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6122    1.4127   -0.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0431   -1.7217    1.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8922   -1.6306    0.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1179   -0.3302    1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3684    1.3558   -0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2774    1.7874    0.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3038    2.3495   -0.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7896    1.7966   -1.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648    0.1327   -2.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630   -1.7934   -1.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561   -0.4763   -1.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2 10  1  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  1  1
  6 11  1  0
  6  4  1  0
  4  5  2  0
  4  2  1  0
 11 10  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
 10 25  1  6
  9 23  1  0
  9 24  1  0
  8 21  1  0
  8 22  1  0
  7 18  1  0
  7 19  1  0
  7 20  1  0
 11 26  1  0
 11 27  1  0
M  END
Download

3D SDF for NP0137036 ((+)-Fenchone)

fenchone
  Mrv1652310031711232D          

 11 12  0  0  0  0            999 V2000
   -0.2822   -0.7752    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
   -0.8125    0.1433    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5082    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    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0137036

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C2CCC(C)(C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3

> <INCHI_KEY>
LHXDLQBQYFFVNW-UHFFFAOYSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.2334

> <EXACT_MASS>
152.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
17.854032062009345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3,3-trimethylbicyclo[2.2.1]heptan-2-one

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
3.0649199539999996

> <ALOGPS_LOGS>
-2.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.5937409427587745

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
44.543800000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fenchone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0137036 ((+)-Fenchone)

Download
PDB for NP0137036 ((+)-Fenchone)
HEADER    PROTEIN                                 03-OCT-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: fenchone                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-OCT-17         0                                  
HETATM    1  C   UNK     0      -0.527  -1.447   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.517   0.267   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.949   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   10                                             
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7    4                                                       
CONECT   10    7    2   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

Download
3D PDB for NP0137036 ((+)-Fenchone)
Download
SMILES for NP0137036 ((+)-Fenchone)
CC1(C)C2CCC(C)(C2)C1=O
Download
INCHI for NP0137036 ((+)-Fenchone)
InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3
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View in JSmol
Synonyms
ValueSource
1,3,3-Trimethyl-2-norbornanoneChEBI
1,3,3-Trimethyl-2-norcamphanoneChEBI
1,3,3-Trimethylbicyclo[2.2.1]heptan-2-oneChEBI
(1R,4S)-(+)-FenchoneHMDB
(1R,4S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-oneHMDB
(1R,4S)-Fenchan-2-oneHMDB
(1R,4S)-FenchoneHMDB
L-alpha-FenchoneHMDB
L-FenchoneHMDB
Fenchone, (1S)-isomerHMDB
Fenchone, (+-)-isomerHMDB
Fenchone, (1R)-isomerHMDB
(+)-FenchoneKEGG
Chemical FormulaC10H16O
Average Mass152.2334 Da
Monoisotopic Mass152.12012 Da
IUPAC Name1,3,3-trimethylbicyclo[2.2.1]heptan-2-one
Traditional Namefenchone
CAS Registry NumberNot Available
SMILES
CC1(C)C2CCC(C)(C2)C1=O
InChI Identifier
InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3
InChI KeyLHXDLQBQYFFVNW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abies albaLOTUS Database
Abies sibiricaLOTUS Database
Achillea abrotanoidesLOTUS Database
Ageratum conyzoidesLOTUS Database
Aloysia triphyllaLOTUS Database
Alpinia zerumbetLOTUS Database
Anethum graveolensLOTUS Database
Artemisia annuaLOTUS Database
Artemisia tridentataLOTUS Database
Cannabis sativaLOTUS Database
Catha edulisLOTUS Database
Centaurea benedictaLOTUS Database
Centratherum punctatumLOTUS Database
Chaerophyllum macrospermumLOTUS Database
Cinnamomum burmanniLOTUS Database
Cinnamomum verumLOTUS Database
Citrus limonLOTUS Database
Cleonia lusitanicaLOTUS Database
Cymbopogon citratusLOTUS Database
Eucalyptus brassianaLOTUS Database
Eucalyptus bridgesianaLOTUS Database
Ferula ovinaLOTUS Database
Foeniculum vulgareLOTUS Database
Glycyrrhiza glabraLOTUS Database
Hyptis suaveolensLOTUS Database
Hyssopus seravschanicusLOTUS Database
Juniperus communisLOTUS Database
Lavandula angustifoliaLOTUS Database
Lavandula stoechasLOTUS Database
Micromeria julianaLOTUS Database
Ocimum basilicumLOTUS Database
Osbornia octodontaLOTUS Database
Picea abiesLOTUS Database
Pimpinella serbicaLOTUS Database
Pistacia veraLOTUS Database
Pityophthorus pityographusLOTUS Database
Plectranthus glabratusLOTUS Database
Santolina chamaecyparissusLOTUS Database
Sassafras albidumLOTUS Database
Satureja thymbraLOTUS Database
Sideritis chamaedrifoliaLOTUS Database
Sideritis tragoriganumLOTUS Database
Solanum tuberosumLOTUS Database
Stachys aegyptiacaLOTUS Database
Syzygium aromaticumLOTUS Database
Tetradenia ripariaLOTUS Database
Thuja occidentalisLOTUS Database
Thuja plicataLOTUS Database
Thymbra capitataLOTUS Database
Thymus pulegioidesLOTUS Database
Zingiber miogaLOTUS Database
Zingiber zerumbetLOTUS Database
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
  • Fenchane monoterpenoid
    • 

  • Bicyclic monoterpenoid
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP2.54ALOGPS
logP3.06ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-7.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.54 m³·mol⁻¹ChemAxon
Polarizability17.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034985  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014535  
KNApSAcK IDC00011027  
Chemspider ID13869  
KEGG Compound IDC11387  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFenchone  
METLIN IDNot Available
PubChem Compound14525  
PDB IDNot Available
ChEBI ID4999  
Good Scents IDNot Available
References
General References