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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 11:40:01 UTC

Update Date

2021-09-24 11:40:01 UTC

HMDB ID

HMDB0304686

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Gurjunene-alpha

Description

Alpha-Gurjunene or (-)-Alpha-Gurjunene, belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpenoid as it synthesized via isoprene units. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-Gurjunene is a neutral, hydrophobic molecule that is insoluble in water. It exists as a colorless clear Liquid and has a woody, balsamic odor. It is used as a perfuming agent. Alpha-gurjunene is found in many plants, essential oils and foods including allspice, bay leaf, carrot seeds, eucalyptus, guava, parsley, black papper, sage and tea tree oil.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0304686
     RDKit          3D
Gurjunene-alpha
 39 41  0  0  0  0  0  0  0  0999 V2000
    0.1475    2.9472    0.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7108    1.8659    0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231    0.5747    0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8346    0.0383    0.7246 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2816   -1.2460    0.2604 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6753   -1.9230   -0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310   -2.3594   -0.8160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6821   -1.5497   -0.0229 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6293   -1.7527    1.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5325   -0.1265   -0.4656 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7141    0.7367   -0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532    2.1105   -0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0822    0.0271   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181    0.4945   -1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4198    0.2215    0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1703    3.7694   -0.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2790    3.3240    1.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901    2.6203    0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0079    0.2823    1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8288   -1.8995    0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070   -1.3256   -1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2824   -2.8548   -1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1480   -2.4432   -1.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7994   -3.4248   -0.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7223   -1.8600   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5552   -2.8468    1.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8976   -1.1624    1.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6384   -1.4565    1.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3320   -0.1443   -1.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1696    0.6625    0.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4844    0.6726   -1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5713    2.8458    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9832    2.3776   -1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9840    0.7061   -1.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5484   -0.2351   -2.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5968    1.4399   -1.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334    0.3725    1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8427    1.1550    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1055   -0.6343    0.4129 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
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 13 15  1  0
 12  2  1  0
 10  3  1  0
 13  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  1
  5 20  1  1
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  6
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  6
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

Gurjunene-alpha
  Mrv1652304022019452D          
  Mrv0541 01091316492D          
 15 17  0  0  1  0            999 V2000
    3.7157   -0.7019    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3976   -1.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590   -0.3440    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9723   -0.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426    0.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7888    0.4604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3032    1.1054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2203   -1.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9327   -1.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1282    1.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2672   -0.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9717    0.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501   -0.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9452    1.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1918   -1.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  2  9  1  0  0  0  0
  3  5  1  1  0  0  0
  4  6  1  0  0  0  0
  4 11  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  6  0  0  0
  7 10  1  0  0  0  0
  7 14  1  6  0  0  0
 11 13  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0304686

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1CC[C@@H]2[C@H](C3=C(C)CC[C@H]13)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h9,11-12,14H,5-8H2,1-4H3/t9-,11-,12-,14-/m1/s1

> <INCHI_KEY>
SPCXZDDGSGTVAW-XIDUGBJDSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.219109896104246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1aR,4R,4aR,7bS)-1,1,4,7-tetramethyl-1H,1aH,2H,3H,4H,4aH,5H,6H,7bH-cyclopropa[e]azulene

> <ALOGPS_LOGP>
4.45

> <JCHEM_LOGP>
4.044472338

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
65.5013

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-α-gurjunene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0304686
     RDKit          3D
Gurjunene-alpha
 39 41  0  0  0  0  0  0  0  0999 V2000
    0.1475    2.9472    0.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7108    1.8659    0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231    0.5747    0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8346    0.0383    0.7246 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2816   -1.2460    0.2604 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6753   -1.9230   -0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310   -2.3594   -0.8160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6821   -1.5497   -0.0229 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6293   -1.7527    1.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5325   -0.1265   -0.4656 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7141    0.7367   -0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532    2.1105   -0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0822    0.0271   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181    0.4945   -1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4198    0.2215    0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1703    3.7694   -0.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2790    3.3240    1.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901    2.6203    0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0079    0.2823    1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8288   -1.8995    0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070   -1.3256   -1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2824   -2.8548   -1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1480   -2.4432   -1.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7994   -3.4248   -0.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7223   -1.8600   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5552   -2.8468    1.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8976   -1.1624    1.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6384   -1.4565    1.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3320   -0.1443   -1.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1696    0.6625    0.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4844    0.6726   -1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5713    2.8458    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9832    2.3776   -1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9840    0.7061   -1.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5484   -0.2351   -2.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5968    1.4399   -1.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334    0.3725    1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8427    1.1550    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1055   -0.6343    0.4129 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
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 13 15  1  0
 12  2  1  0
 10  3  1  0
 13  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  1
  5 20  1  1
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  6
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  6
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Gurjunene-alpha                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0       6.936  -1.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.209  -2.179   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.323  -0.642   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.548  -0.642   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.666   0.859   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.206   0.859   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.166   2.063   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.745  -2.294   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.341  -3.451   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.706   2.063   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.232  -1.424   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.681   0.993   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -0.416   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.498   3.451   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.091  -2.958   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    3    8    9                                             
CONECT    3    1    2    5                                                  
CONECT    4    1    6   11                                                  
CONECT    5    3   10                                                       
CONECT    6    4    7   12                                                  
CONECT    7    6   10   14                                                  
CONECT    8    2                                                            
CONECT    9    2                                                            
CONECT   10    5    7                                                       
CONECT   11    4   13   15                                                  
CONECT   12    6   13                                                       
CONECT   13   11   12                                                       
CONECT   14    7                                                            
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

COMPND    HMDB0304686
HETATM    1  C1  UNL     1       0.148   2.947   0.746  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.711   1.866   0.189  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.423   0.575   0.171  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.835   0.038   0.725  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.282  -1.246   0.260  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.675  -1.923  -0.884  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.731  -2.359  -0.816  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.682  -1.550  -0.023  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.629  -1.753   1.452  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.532  -0.126  -0.466  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.714   0.737  -0.240  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.053   2.110  -0.441  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.082   0.027  -0.091  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.018   0.495  -1.531  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.420   0.221   0.555  1.00  0.00           C  
HETATM   16  H1  UNL     1       0.170   3.769  -0.014  1.00  0.00           H  
HETATM   17  H2  UNL     1      -0.279   3.324   1.689  1.00  0.00           H  
HETATM   18  H3  UNL     1       1.190   2.620   0.875  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.008   0.282   1.795  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.829  -1.900   0.979  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.807  -1.326  -1.814  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.282  -2.855  -1.109  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.148  -2.443  -1.863  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.799  -3.425  -0.439  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.722  -1.860  -0.348  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.555  -2.847   1.641  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.898  -1.162   1.995  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.638  -1.457   1.865  1.00  0.00           H  
HETATM   29  H14 UNL     1      -1.332  -0.144  -1.570  1.00  0.00           H  
HETATM   30  H15 UNL     1      -3.170   0.663   0.755  1.00  0.00           H  
HETATM   31  H16 UNL     1      -3.484   0.673  -1.051  1.00  0.00           H  
HETATM   32  H17 UNL     1      -2.571   2.846   0.197  1.00  0.00           H  
HETATM   33  H18 UNL     1      -1.983   2.378  -1.494  1.00  0.00           H  
HETATM   34  H19 UNL     1       0.984   0.706  -1.866  1.00  0.00           H  
HETATM   35  H20 UNL     1       2.548  -0.235  -2.177  1.00  0.00           H  
HETATM   36  H21 UNL     1       2.597   1.440  -1.574  1.00  0.00           H  
HETATM   37  H22 UNL     1       3.233   0.373   1.657  1.00  0.00           H  
HETATM   38  H23 UNL     1       3.843   1.155   0.182  1.00  0.00           H  
HETATM   39  H24 UNL     1       4.105  -0.634   0.413  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3   12
CONECT    3    4   10
CONECT    4    5   13   19
CONECT    5    6   13   20
CONECT    6    7   21   22
CONECT    7    8   23   24
CONECT    8    9   10   25
CONECT    9   26   27   28
CONECT   10   11   29
CONECT   11   12   30   31
CONECT   12   32   33
CONECT   13   14   15
CONECT   14   34   35   36
CONECT   15   37   38   39
END

HMDB0304686
     RDKit          3D
Gurjunene-alpha
 39 41  0  0  0  0  0  0  0  0999 V2000
    0.1475    2.9472    0.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7108    1.8659    0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231    0.5747    0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8346    0.0383    0.7246 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2816   -1.2460    0.2604 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6753   -1.9230   -0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310   -2.3594   -0.8160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6821   -1.5497   -0.0229 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6293   -1.7527    1.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5325   -0.1265   -0.4656 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7141    0.7367   -0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532    2.1105   -0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0822    0.0271   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181    0.4945   -1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4198    0.2215    0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1703    3.7694   -0.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2790    3.3240    1.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901    2.6203    0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0079    0.2823    1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8288   -1.8995    0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070   -1.3256   -1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2824   -2.8548   -1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1480   -2.4432   -1.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7994   -3.4248   -0.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7223   -1.8600   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5552   -2.8468    1.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8976   -1.1624    1.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6384   -1.4565    1.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3320   -0.1443   -1.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1696    0.6625    0.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4844    0.6726   -1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5713    2.8458    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9832    2.3776   -1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9840    0.7061   -1.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5484   -0.2351   -2.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5968    1.4399   -1.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334    0.3725    1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8427    1.1550    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1055   -0.6343    0.4129 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
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 13 15  1  0
 12  2  1  0
 10  3  1  0
 13  4  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  1
  5 20  1  1
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  6
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  6
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-a-Gurjunene	Generator
(-)-Α-gurjunene	Generator
a-Gurjunene	Generator
Α-gurjunene	Generator

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.357

Monoisotopic Molecular Weight

204.187800773

IUPAC Name

(1aR,4R,4aR,7bS)-1,1,4,7-tetramethyl-1H,1aH,2H,3H,4H,4aH,5H,6H,7bH-cyclopropa[e]azulene

Traditional Name

(-)-α-gurjunene

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@H]2[C@H](C3=C(C)CC[C@H]13)C2(C)C

InChI Identifier

InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h9,11-12,14H,5-8H2,1-4H3/t9-,11-,12-,14-/m1/s1

InChI Key

SPCXZDDGSGTVAW-XIDUGBJDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

5,10-cycloaromadendrane sesquiterpenoids

Alternative Parents

Substituents

5,10-cycloaromadendrane sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

carbotricyclic compound (CHEBI:61699 )
sesquiterpene (CHEBI:61699 )

Ontology

Not Available

Milk and milk product

Fermented milk product

Cheese (FooDB: FOOD00617)

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.45	ALOGPS
logP	4.04	ChemAxon
logS	-4.2	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.5 m³·mol⁻¹	ChemAxon
Polarizability	26.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	147.117	32859911
AllCCS	[M+H-H2O]+	143.195	32859911
AllCCS	[M+Na]+	151.817	32859911
AllCCS	[M+NH4]+	150.766	32859911
AllCCS	[M-H]-	158.441	32859911
AllCCS	[M+Na-2H]-	158.714	32859911
AllCCS	[M+HCOO]-	159.116	32859911
DeepCCS	[M-2H]-	196.367	30932474
DeepCCS	[M+Na]+	171.501	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Gurjunene-alpha GC-MS (Non-derivatized) - 70eV, Positive	splash10-03fr-1900000000-a9f60ba2e6d644daa013	2017-07-27	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gurjunene-alpha 10V, Positive-QTOF	splash10-0a4i-0290000000-345ad3b09da9e2a50762	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gurjunene-alpha 20V, Positive-QTOF	splash10-0a4i-3970000000-b3966925656c14a82f16	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gurjunene-alpha 40V, Positive-QTOF	splash10-1170-8900000000-df99e2c36d98b0db95e2	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gurjunene-alpha 10V, Negative-QTOF	splash10-0udi-0090000000-1b060cde85b4f43a1531	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gurjunene-alpha 20V, Negative-QTOF	splash10-0udi-0190000000-07f1ef066e7c398c1e83	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gurjunene-alpha 40V, Negative-QTOF	splash10-009i-2900000000-67a968fed51e1a89291d	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gurjunene-alpha 10V, Positive-QTOF	splash10-0a4i-4290000000-9bfe83bd2ec7aa800c45	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gurjunene-alpha 20V, Positive-QTOF	splash10-0a4i-7920000000-b84f94c3b0eeef942277	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gurjunene-alpha 40V, Positive-QTOF	splash10-056r-9200000000-079173ace0ae9daa444b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gurjunene-alpha 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gurjunene-alpha 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gurjunene-alpha 40V, Negative-QTOF	splash10-0udi-0090000000-f72e0de45a6955aeac7c	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15560276

PDB ID

Not Available

ChEBI ID

61699

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1025401

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Gurjunene-alpha (HMDB0304686)

MOL for HMDB0304686 (Gurjunene-alpha)

3D MOL for HMDB0304686 (Gurjunene-alpha)

3D SDF for HMDB0304686 (Gurjunene-alpha)

3D-SDF for HMDB0304686 (Gurjunene-alpha)

PDB for HMDB0304686 (Gurjunene-alpha)

3D PDB for HMDB0304686 (Gurjunene-alpha)

SMILES for HMDB0304686 (Gurjunene-alpha)

INCHI for HMDB0304686 (Gurjunene-alpha)

Structure for HMDB0304686 (Gurjunene-alpha)

3D Structure for HMDB0304686 (Gurjunene-alpha)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra