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Showing NP-Card for (+/-)-alpha-Thujene (NP0334990)

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Record Information
Version2.0
Created at2024-09-10 23:23:30 UTC
Updated at2024-09-10 23:23:31 UTC
NP-MRD IDNP0334990
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+/-)-alpha-Thujene
Description(-)-3-Thujene, also known as alpha-thujen or origanene, 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 (-)-3-Thujene is a green, herb, and woody tasting compound. Outside of the human body, (-)-3-Thujene is found, on average, in the highest concentration within a few different foods, such as cardamoms, sweet bay, and common sages and in a lower concentration in winter savories, cumins, and limes (-)-3-Thujene has also been detected, but not quantified in, several different foods, such as common thymes, nutmegs, white cabbages, corianders, and spearmints. This could make (-)-3-thujene a potential biomarker for the consumption of these foods. A thujene that has a bicyclohex-2-ene skeleton which is substituted at positions 2 and 5 by methyl and isopropyl groups, respectively.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334990 ((+/-)-alpha-Thujene)


  Mrv1652310121719422D          

 10 11  0  0  1  0            999 V2000
    0.7846   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0397    1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  5  1  0  0  0  0
  2  8  1  0  0  0  0
  1  3  1  0  0  0  0
  4  3  2  0  0  0  0
  6  4  1  0  0  0  0
 10  2  1  0  0  0  0
 10  4  1  0  0  0  0
 10  5  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
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3D MOL for NP0334990 ((+/-)-alpha-Thujene)

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3D SDF for NP0334990 ((+/-)-alpha-Thujene)

  Mrv1652310121719422D          

 10 11  0  0  1  0            999 V2000
    0.7846   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0397    1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  5  1  0  0  0  0
  2  8  1  0  0  0  0
  1  3  1  0  0  0  0
  4  3  2  0  0  0  0
  6  4  1  0  0  0  0
 10  2  1  0  0  0  0
 10  4  1  0  0  0  0
 10  5  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334990

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C12CC1C(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

> <INCHI_KEY>
KQAZVFVOEIRWHN-UHFFFAOYSA-N

> <FORMULA>
C10H16

> <MOLECULAR_WEIGHT>
136.234

> <EXACT_MASS>
136.125200512

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.360951786414848

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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 NP0334990 ((+/-)-alpha-Thujene)
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PDB for NP0334990 ((+/-)-alpha-Thujene)
HEADER    PROTEIN                                 12-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-OCT-17         0                                  
HETATM    1  C   UNK     0       1.465  -1.246   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.370   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.465   1.246   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.941   2.711   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    5    8   10                                             
CONECT    3    1    4                                                       
CONECT    4    3    6   10                                                  
CONECT    5    2   10                                                       
CONECT    6    4                                                            
CONECT    7    8                                                            
CONECT    8    2    7    9                                                  
CONECT    9    8                                                            
CONECT   10    2    4    5                                                  
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0334990 ((+/-)-alpha-Thujene)
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SMILES for NP0334990 ((+/-)-alpha-Thujene)
CC(C)C12CC1C(C)=CC2
Download
INCHI for NP0334990 ((+/-)-alpha-Thujene)
InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h4,7,9H,5-6H2,1-3H3
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View in JSmol
Synonyms
ValueSource
2-Methyl-5-(1-methylethyl)-bicyclo[3.1.0]hex-2-eneChEBI
5-Isopropyl-2-methylbicyclo[3.1.0]hex-2-eneChEBI
alpha-ThuieneChEBI
alpha-ThujenChEBI
OriganeneChEBI
a-ThuieneGenerator
Α-thuieneGenerator
a-ThujenGenerator
Α-thujenGenerator
(-)-alpha-ThujeneHMDB
(1R,5S)-2-Methyl-5-(propan-2-yl)bicyclo[3.1.0]hex-2-eneHMDB
(1R,5S)-5-Isopropyl-2-methylbicyclo[3.1.0]hex-2-eneHMDB
(1R,5S)-Thuj-2-eneHMDB
alpha-ThujeneHMDB
a-ThujeneGenerator
Α-thujeneGenerator
(+/-)-a-thujeneGenerator
(+/-)-α-thujeneGenerator
Chemical FormulaC10H16
Average Mass136.2340 Da
Monoisotopic Mass136.12520 Da
IUPAC Name2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hex-2-ene
Traditional Nameα-thujene
CAS Registry NumberNot Available
SMILES
CC(C)C12CC1C(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
InChI KeyKQAZVFVOEIRWHN-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Polarizability17.36 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036116  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001413  
KNApSAcK IDC00000184  
Chemspider ID16878  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThujene  
METLIN IDNot Available
PubChem Compound17868  
PDB IDNot Available
ChEBI ID50031  
Good Scents IDNot Available
References
General References