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Showing NP-Card for alpha-Thujene (NP0044932)

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Record Information
Version2.0
Created at2022-03-10 18:51:21 UTC
Updated at2022-03-10 22:18:13 UTC
NP-MRD IDNP0044932
Secondary Accession NumbersNone
Natural Product Identification
Common Namealpha-Thujene
Description(-)-3-Thujene, also known as alpha-Thujene, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (-)-3-Thujene is possibly neutral. It has a green, herb, and woody taste and contributes pungency to the flavor of some herbs such as summer savory. (-)-3-Thujene is found in highest concentrations in cardamoms, sweet bay, and common sages and in lower concentrations in allspices, dills, and cumins. (-)-3-Thujene has also been detected in caraway, corianders, cornmints, spearmints, and pepper (c. Annuum). This could make (-)-3-thujene a potential biomarker for the consumption of these foods. (-)-3-Thujene was isolated from Indian olibanum tree (Boswellia serrata), Eucalyptus species, juniper, and cannabis plants (PMID:6991645 ).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0044932 (alpha-Thujene)


  Mrv1652309272007282D          

 10 11  0  0  0  0            999 V2000
 9995.8400 9998.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2526 9996.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5075 9997.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7375 9996.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3881 9997.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.7750 9997.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.2165 9998.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6191 9997.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4276 9996.8328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.1726 9997.6173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  9 10  1  0  0  0  0
  9  8  1  1  0  0  0
  1 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9  2  1  0  0  0  0
 10  8  1  1  0  0  0
M  END
Download

3D MOL for NP0044932 (alpha-Thujene)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -3.2150   -0.1426   -1.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9312   -0.3482   -0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6182   -1.4063    0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2361   -1.2637    0.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2389    0.1018    0.5844 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6948    0.3009    0.3507 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4207   -0.9602   -0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0029    1.3459   -0.6879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5504    1.2974    0.9742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8017    0.6143   -0.3347 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0936   -0.1720   -2.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6067    0.8802   -0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9918   -0.8690   -0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2308   -2.2717    0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3927   -2.0048    0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1975   -1.4646    2.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1514    0.6457    1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1156   -1.3264   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3949   -1.7292    0.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5057   -0.6709   -0.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5895    1.1003   -1.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7551    2.3766   -0.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1273    1.3491   -0.8023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3103    1.2239    1.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0756    2.2867    0.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5304    1.1067   -1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  5  6  1  0
  5  9  1  1
  9 10  1  0
 10  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
 10  5  1  0
  4  5  1  0
  7 18  1  0
  7 19  1  0
  7 20  1  0
  6 17  1  1
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  6
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
M  END
Download

3D SDF for NP0044932 (alpha-Thujene)


  Mrv1652309272007282D          

 10 11  0  0  0  0            999 V2000
 9995.8400 9998.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2526 9996.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5075 9997.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7375 9996.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3881 9997.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.7750 9997.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.2165 9998.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6191 9997.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4276 9996.8328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.1726 9997.6173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  9 10  1  0  0  0  0
  9  8  1  1  0  0  0
  1 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9  2  1  0  0  0  0
 10  8  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044932

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@]12C[C@@H]1C(C)=CC2

> <INCHI_IDENTIFIER>
InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h4,7,9H,5-6H2,1-3H3/t9-,10-/m1/s1

> <INCHI_KEY>
KQAZVFVOEIRWHN-NXEZZACHSA-N

> <FORMULA>
C10H16

> <MOLECULAR_WEIGHT>
136.238

> <EXACT_MASS>
136.125200515

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.32463035023257

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hex-2-ene

> <ALOGPS_LOGP>
4.07

> <JCHEM_LOGP>
2.801661446333333

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
44.7223

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-α-thujene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0044932 (alpha-Thujene)

Download
PDB for NP0044932 (alpha-Thujene)
HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8658.9018663.124   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8659.6728660.755   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8660.1478662.219   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8660.5778659.509   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8656.1918662.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8655.0478661.665   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8655.8718664.201   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8656.6228661.072   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8658.1328660.755   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8657.6568662.219   0.000  0.00  0.00           C+0
CONECT    1    3   10                                                       
CONECT    2    3    4    9                                                  
CONECT    3    1    2                                                       
CONECT    4    2                                                            
CONECT    5    6    7   10                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    9   10                                                       
CONECT    9   10    8    2                                                  
CONECT   10    9    1    5    8                                             
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0044932 (alpha-Thujene)
Download
SMILES for NP0044932 (alpha-Thujene)
CC(C)[C@@]12C[C@@H]1C(C)=CC2
Download
INCHI for NP0044932 (alpha-Thujene)
InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h4,7,9H,5-6H2,1-3H3/t9-,10-/m1/s1
Download
View in JSmol
Synonyms
ValueSource
(1R,5S)-5-Isopropyl-2-methylbicyclo[3.1.0]hex-2-eneChEBI
(-)-a-ThujeneGenerator
(-)-Α-thujeneGenerator
(1R,5R)-(-)-3-ThujenePhytoBank
(-)-alpha-ThujenePhytoBank
3-ThujenePhytoBank
2-Methyl-5-(1-methylethyl)bicyclo[3.1.0]hex-2-enePhytoBank
(±)-alpha-ThujenePhytoBank
(±)-α-ThujenePhytoBank
alpha-ThujenePhytoBank
2-Methyl-5-isopropylbicyclo[3.1.0]-2-hexenePhytoBank
OriganenePhytoBank
Chemical FormulaC10H16
Average Mass136.2380 Da
Monoisotopic Mass136.12520 Da
IUPAC Name(1R)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hex-2-ene
Traditional Name(-)-α-thujene
CAS Registry Number3917-48-4
SMILES
CC(C)[C@@]12C[C@@H]1C(C)=CC2
InChI Identifier
InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h4,7,9H,5-6H2,1-3H3/t9-,10-/m1/s1
InChI KeyKQAZVFVOEIRWHN-NXEZZACHSA-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
Acorus calanus L.Plant
Alphinia galanga-
Anethum foeniculumPlant
Arabidopsis thalianaPlant
Atalantia guillauminiiPlant
Baeckea frutescens-
Boswellia serrataPlant
Cannabis sativaNULL
      Not Available
Cinnamomum camphoraPlant
Citrus aurantiifoliaPlant
Citrus aurantiumPlant
Citrus hystrixPlant
Citrus limonPlant
Citrus maximaPlant
Citrus paradisiPlant
Citrus reticulataPlant
Citrus X sinensis (L.) Osbeck (pro. sp.)Plant
Curcuma manggaPlant
Espeletia timotensisLOTUS Database
Eucalyptus spp.Plant
Houttuynia cordataPlant
Juglans regiaLOTUS Database
Lavandula angustifoliaPlant
Lavandula dentataPlant
Lippia chevalieriPlant
Marjorana hortensis-
Melaleuca leucadendra L.Plant
Monodora myristicaPlant
Myrtus communisPlant
Nigella sativa LPlant
Origanum vulgarePlant
Petroselinum crispumPlant
Pinus halepensisPlant
Pinus sibiricaPlant
Piper nigrum L.Plant
Polygonum minusPlant
Salvia rosmarinusPlant
Tanacetum macrophyllumPlant
Teucrium leucocladumLOTUS Database
Teucrium poliumLOTUS Database
Thuja occidentalisPlant
Thymus broussonetiiLOTUS Database
Thymus broussonettiPlant
Thymus capitatusPlant
Thymus eriocalyxPlant
Thymus maroccanusPlant
Thymus praecosPlant
Thymus vulgarisPlant
Thymus X-porlockPlant
Turnera diffusaPlant
Valeriana jatamansiPlant
Valeriana officinalisPlant
Vitex agnus-castusLOTUS Database
Xylopia aethiopicaPlant
Xylopia parvifloraPlant
Zanthoxylum armatumPlant
Zingiber montanumPlant
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
  • Bicyclic monoterpenoid
    • 

  • Thujane monoterpenoid
    • 

  • Branched unsaturated hydrocarbon
    • 

  • Polycyclic hydrocarbon
    • 

  • Cyclic olefin
    • 

  • Unsaturated aliphatic hydrocarbon
    • 

  • Unsaturated hydrocarbon
    • 

  • Olefin
    • 

  • Hydrocarbon
    • 

  • 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
logP4.07ALOGPS
logP2.8ChemAxon
logS-2.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.72 m³·mol⁻¹ChemAxon
Polarizability17.32 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound637518  
PDB IDNot Available
ChEBI ID50033  
Good Scents IDNot Available
References
General References