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Showing metabocard for Terpinolene oxide (HMDB0037009)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:15:08 UTC
Update Date2023-02-21 17:25:32 UTC
HMDB IDHMDB0037009
Secondary Accession Numbers
  • HMDB37009
Metabolite Identification
Common NameTerpinolene oxide
DescriptionTerpinolene oxide belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review a significant number of articles have been published on Terpinolene oxide.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0037009 (Terpinolene oxide)

  Mrv0541 05061309302D          

 11 12  0  0  0  0            999 V2000
    3.1895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822   -0.7752    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
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    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
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
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3D MOL for HMDB0037009 (Terpinolene oxide)

HMDB0037009
     RDKit          3D
Terpinolene oxide
 27 28  0  0  0  0  0  0  0  0999 V2000
    3.7489   -0.0001   -0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3076   -0.0673    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657    0.9951    0.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2158    0.8231    0.8064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5439    0.1756   -0.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1800   -1.0055   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4871   -1.3002   -0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082    0.9434   -1.2486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0037    0.2968   -0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6100    1.2843    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9294   -0.7899   -0.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3019    0.4466    0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8783    0.6477   -1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1368   -1.0251   -0.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1460    1.9308    0.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    0.1286    1.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2094    1.7752    1.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097   -0.8417   -1.9306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4151   -1.9516   -0.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0741   -1.9477   -0.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3033   -1.8491    0.7552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6641    1.4508    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1267    2.2740    0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6964    0.8701    1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4810   -0.5401   -1.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4443   -1.7615   -0.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6825   -0.9623    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  7  2  1  0
  9  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
 10 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
M  END
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3D SDF for HMDB0037009 (Terpinolene oxide)

  Mrv0541 05061309302D          

 11 12  0  0  0  0            999 V2000
    3.1895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822   -0.7752    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
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    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
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037009

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CCC2(CC1)OC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-8-4-6-10(7-5-8)9(2,3)11-10/h4H,5-7H2,1-3H3

> <INCHI_KEY>
RTLTXXDTPFWZLO-UHFFFAOYSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.2334

> <EXACT_MASS>
152.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.38913237436464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,2,6-trimethyl-1-oxaspiro[2.5]oct-5-ene

> <ALOGPS_LOGP>
2.92

> <JCHEM_LOGP>
2.254655045

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.248530636712766

> <JCHEM_POLAR_SURFACE_AREA>
12.53

> <JCHEM_REFRACTIVITY>
46.402899999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2,6-trimethyl-1-oxaspiro[2.5]oct-5-ene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0037009 (Terpinolene oxide)

HMDB0037009
     RDKit          3D
Terpinolene oxide
 27 28  0  0  0  0  0  0  0  0999 V2000
    3.7489   -0.0001   -0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3076   -0.0673    0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657    0.9951    0.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2158    0.8231    0.8064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5439    0.1756   -0.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1800   -1.0055   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4871   -1.3002   -0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082    0.9434   -1.2486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0037    0.2968   -0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6100    1.2843    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9294   -0.7899   -0.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3019    0.4466    0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8783    0.6477   -1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1368   -1.0251   -0.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1460    1.9308    0.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    0.1286    1.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2094    1.7752    1.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097   -0.8417   -1.9306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4151   -1.9516   -0.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0741   -1.9477   -0.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3033   -1.8491    0.7552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6641    1.4508    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1267    2.2740    0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6964    0.8701    1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4810   -0.5401   -1.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4443   -1.7615   -0.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6825   -0.9623    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  7  2  1  0
  9  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
 10 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
M  END
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PDB for HMDB0037009 (Terpinolene oxide)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.954   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.527  -1.447   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       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4    6    8                                                       
CONECT    5    7    8                                                       
CONECT    6    4   10                                                       
CONECT    7    5   10                                                       
CONECT    8    1    4    5                                                  
CONECT    9    2    3   10   11                                             
CONECT   10    6    7    9   11                                             
CONECT   11    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for HMDB0037009 (Terpinolene oxide)

COMPND    HMDB0037009
HETATM    1  C1  UNL     1       3.749  -0.000  -0.306  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.308  -0.067   0.021  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.666   0.995   0.510  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.216   0.823   0.806  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.544   0.176  -0.303  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.180  -1.005  -0.837  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.487  -1.300  -0.169  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.208   0.943  -1.249  1.00  0.00           O  
HETATM    9  C8  UNL     1      -2.004   0.297  -0.283  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.610   1.284   0.705  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.929  -0.790  -0.728  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.302   0.447   0.553  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.878   0.648  -1.198  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.137  -1.025  -0.470  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.146   1.931   0.689  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.159   0.129   1.692  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.209   1.775   1.151  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.410  -0.842  -1.931  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.415  -1.952  -0.823  1.00  0.00           H  
HETATM   20  H9  UNL     1       2.074  -1.948  -0.878  1.00  0.00           H  
HETATM   21  H10 UNL     1       1.303  -1.849   0.755  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.664   1.451   0.338  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.127   2.274   0.663  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.696   0.870   1.709  1.00  0.00           H  
HETATM   25  H14 UNL     1      -3.481  -0.540  -1.663  1.00  0.00           H  
HETATM   26  H15 UNL     1      -2.444  -1.761  -0.906  1.00  0.00           H  
HETATM   27  H16 UNL     1      -3.682  -0.962   0.078  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3    7
CONECT    3    4   15
CONECT    4    5   16   17
CONECT    5    6    8    9
CONECT    6    7   18   19
CONECT    7   20   21
CONECT    8    9
CONECT    9   10   11
CONECT   10   22   23   24
CONECT   11   25   26   27
END
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SMILES for HMDB0037009 (Terpinolene oxide)

CC1=CCC2(CC1)OC2(C)C
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INCHI for HMDB0037009 (Terpinolene oxide)

InChI=1S/C10H16O/c1-8-4-6-10(7-5-8)9(2,3)11-10/h4H,5-7H2,1-3H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2,2,6-Trimethyl-1-oxaspiro(2.5)oct-5-eneHMDB
4,8-Terpinolene epoxideHMDB
Arginine N-acetylasparaginateHMDB
Terpinolene monoxideHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name2,2,6-trimethyl-1-oxaspiro[2.5]oct-5-ene
Traditional Name2,2,6-trimethyl-1-oxaspiro[2.5]oct-5-ene
CAS Registry Number4584-23-0
SMILES
CC1=CCC2(CC1)OC2(C)C
InChI Identifier
InChI=1S/C10H16O/c1-8-4-6-10(7-5-8)9(2,3)11-10/h4H,5-7H2,1-3H3
InChI KeyRTLTXXDTPFWZLO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point197.00 to 198.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility94.44 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.247 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015984
KNApSAcK IDC00010838
Chemspider ID96568
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound107303
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1378041
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.