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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 20:41:17 UTC

Update Date

2021-09-23 20:41:17 UTC

HMDB ID

HMDB0302788

Secondary Accession Numbers

None

Metabolite Identification

Common Name

beta-Cedrene

Description

≈í¬±-Cedrene also known as Cedrene, belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiterpenoids with a structure based on the cedrane or the isocedrane skeleton. Isocedrane is a rearranged cedrane arising from the migration of a methyl group from the position 6 to the position 4. Sesquiterpenoides 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-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ). 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. ≈í¬±-Cedrene is a tricyclic molecule based on a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. ≈í¬±-Cedrene is a naturally occurring tricyclic sesquiterpene found in the essential oil of cedar. There are two known cedrene isomers, namely ≈í¬±- and ≈í‚â§-cedrene, which differ in the position of a double bond.

Structure

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

HMDB0302788
     RDKit          3D
beta-Cedrene
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.3475   -0.7458    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325   -0.7187    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770   -1.9006   -0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1522   -1.9514    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6217   -0.5349    0.4256 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1712   -0.0274    1.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139    0.4701    0.8799 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7828    1.3196   -0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3263    2.6290    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7839    1.6010   -1.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2360    0.3928   -0.7110 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4715    0.9359   -1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4942   -0.1421   -0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0809   -0.3742    0.5343 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8030   -1.5679    1.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345    0.0833    0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8679   -1.5904   -0.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8245   -2.8036    0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3068   -2.0049   -1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8051   -2.4658   -0.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3077   -2.5015    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3310    0.7381    2.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635   -0.8558    2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0915    1.0219    1.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408    2.5963    1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4091    3.1603   -0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2349    3.3020    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6994    0.8312   -2.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097    2.5747   -1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8020    1.7325   -0.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2520   -0.2650   -1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3907    0.9916   -2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8486    1.8704   -0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2454   -1.0259   -1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5151    0.2131   -1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099    0.5619    1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2888   -1.9954    1.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9557   -2.3450    0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8144   -1.2094    1.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  5  4  1  6
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  7  2  1  0
 11  5  1  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  1
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  6
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  1
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END


  Mrv1652303202019002D          

 16 18  0  0  0  0            999 V2000
    0.5115    0.4450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2037    0.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0936   -0.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7019   -0.8764    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0995   -0.1138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7209    0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5265    0.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6969   -0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4664   -0.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0877   -1.1024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3091   -1.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5802   -2.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8069   -2.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1185   -1.4598    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6198    1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8140   -0.5263    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  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
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  4 14  1  1  0  0  0
  1 15  1  1  0  0  0
  5 16  1  6  0  0  0
 10 16  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0302788

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@@H](C)[C@]11C[C@@H](C(=C)CC1)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h11-13H,1,5-9H2,2-4H3/t11-,12+,13+,15+/m1/s1

> <INCHI_KEY>
DYLPEFGBWGEFBB-OSFYFWSMSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.65960229581147

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,7S)-2,6,6-trimethyl-8-methylidenetricyclo[5.3.1.0^{1,5}]undecane

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
4.159091856666667

> <ALOGPS_LOGS>
-5.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
64.6219

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,7S)-2,6,6-trimethyl-8-methylidenetricyclo[5.3.1.0^{1,5}]undecane

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302788
     RDKit          3D
beta-Cedrene
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.3475   -0.7458    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325   -0.7187    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770   -1.9006   -0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1522   -1.9514    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6217   -0.5349    0.4256 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1712   -0.0274    1.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139    0.4701    0.8799 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7828    1.3196   -0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3263    2.6290    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7839    1.6010   -1.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2360    0.3928   -0.7110 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4715    0.9359   -1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4942   -0.1421   -0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0809   -0.3742    0.5343 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8030   -1.5679    1.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345    0.0833    0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8679   -1.5904   -0.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8245   -2.8036    0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3068   -2.0049   -1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8051   -2.4658   -0.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3077   -2.5015    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3310    0.7381    2.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635   -0.8558    2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0915    1.0219    1.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408    2.5963    1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4091    3.1603   -0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2349    3.3020    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6994    0.8312   -2.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097    2.5747   -1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8020    1.7325   -0.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2520   -0.2650   -1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3907    0.9916   -2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8486    1.8704   -0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2454   -1.0259   -1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5151    0.2131   -1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099    0.5619    1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2888   -1.9954    1.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9557   -2.3450    0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8144   -1.2094    1.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  5  4  1  6
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  7  2  1  0
 11  5  1  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  1
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  6
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  1
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       0.955   0.831   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.380   0.107   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.175  -1.379   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.310  -1.636   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.052  -0.212   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.212   0.938   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.716   0.605   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.034  -0.921   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.471  -1.349   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.897  -2.058   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.444  -2.759   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.950  -4.170   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.506  -3.929   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       0.221  -2.725   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       1.157   2.357   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.386  -0.982   0.000  0.00  0.00           C+0
CONECT    1    2    5   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11   14                                             
CONECT    5    4    1    6   16                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   16                                                  
CONECT   11   10    4   12   13                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    4                                                            
CONECT   15    1                                                            
CONECT   16    5   10                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0302788
HETATM    1  C1  UNL     1       3.348  -0.746   0.048  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.032  -0.719   0.236  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.277  -1.901  -0.223  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.152  -1.951   0.191  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.622  -0.535   0.426  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.171  -0.027   1.604  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.414   0.470   0.880  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.783   1.320  -0.210  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.326   2.629   0.323  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.784   1.601  -1.332  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.236   0.393  -0.711  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.471   0.936  -1.304  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.494  -0.142  -0.906  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.081  -0.374   0.534  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.803  -1.568   1.107  1.00  0.00           C  
HETATM   16  H1  UNL     1       3.934   0.083   0.362  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.868  -1.590  -0.420  1.00  0.00           H  
HETATM   18  H3  UNL     1       1.824  -2.804   0.156  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.307  -2.005  -1.342  1.00  0.00           H  
HETATM   20  H5  UNL     1      -0.805  -2.466  -0.571  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.308  -2.502   1.142  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.331   0.738   2.185  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.463  -0.856   2.266  1.00  0.00           H  
HETATM   24  H9  UNL     1       2.092   1.022   1.527  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.041   2.596   1.374  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.409   3.160  -0.270  1.00  0.00           H  
HETATM   27  H12 UNL     1       1.235   3.302   0.371  1.00  0.00           H  
HETATM   28  H13 UNL     1       1.699   0.831  -2.131  1.00  0.00           H  
HETATM   29  H14 UNL     1       1.510   2.575  -1.836  1.00  0.00           H  
HETATM   30  H15 UNL     1       2.802   1.733  -0.963  1.00  0.00           H  
HETATM   31  H16 UNL     1       0.252  -0.265  -1.492  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.391   0.992  -2.415  1.00  0.00           H  
HETATM   33  H18 UNL     1      -1.849   1.870  -0.917  1.00  0.00           H  
HETATM   34  H19 UNL     1      -2.245  -1.026  -1.515  1.00  0.00           H  
HETATM   35  H20 UNL     1      -3.515   0.213  -1.011  1.00  0.00           H  
HETATM   36  H21 UNL     1      -2.310   0.562   1.089  1.00  0.00           H  
HETATM   37  H22 UNL     1      -2.289  -1.995   1.971  1.00  0.00           H  
HETATM   38  H23 UNL     1      -2.956  -2.345   0.329  1.00  0.00           H  
HETATM   39  H24 UNL     1      -3.814  -1.209   1.448  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3    7
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6   11   14
CONECT    6    7   22   23
CONECT    7    8   24
CONECT    8    9   10   11
CONECT    9   25   26   27
CONECT   10   28   29   30
CONECT   11   12   31
CONECT   12   13   32   33
CONECT   13   14   34   35
CONECT   14   15   36
CONECT   15   37   38   39
END

HMDB0302788
     RDKit          3D
beta-Cedrene
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.3475   -0.7458    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325   -0.7187    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770   -1.9006   -0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1522   -1.9514    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6217   -0.5349    0.4256 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1712   -0.0274    1.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139    0.4701    0.8799 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7828    1.3196   -0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3263    2.6290    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7839    1.6010   -1.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2360    0.3928   -0.7110 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4715    0.9359   -1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4942   -0.1421   -0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0809   -0.3742    0.5343 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8030   -1.5679    1.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345    0.0833    0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8679   -1.5904   -0.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8245   -2.8036    0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3068   -2.0049   -1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8051   -2.4658   -0.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3077   -2.5015    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3310    0.7381    2.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635   -0.8558    2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0915    1.0219    1.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408    2.5963    1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4091    3.1603   -0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2349    3.3020    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6994    0.8312   -2.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097    2.5747   -1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8020    1.7325   -0.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2520   -0.2650   -1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3907    0.9916   -2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8486    1.8704   -0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2454   -1.0259   -1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5151    0.2131   -1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099    0.5619    1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2888   -1.9954    1.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9557   -2.3450    0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8144   -1.2094    1.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  5  4  1  6
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  7  2  1  0
 11  5  1  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  1
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  6
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  1
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
b-Cedrene	Generator
Β-cedrene	Generator
Cedrone	MeSH
alpha-Cedrene	MeSH
Cedrene	MeSH

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.3511

Monoisotopic Molecular Weight

204.187800768

IUPAC Name

(1S,2R,5S,7S)-2,6,6-trimethyl-8-methylidenetricyclo[5.3.1.0^{1,5}]undecane

Traditional Name

(1S,2R,5S,7S)-2,6,6-trimethyl-8-methylidenetricyclo[5.3.1.0^{1,5}]undecane

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@@H](C)[C@]11C[C@@H](C(=C)CC1)C2(C)C

InChI Identifier

InChI=1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h11-13H,1,5-9H2,2-4H3/t11-,12+,13+,15+/m1/s1

InChI Key

DYLPEFGBWGEFBB-OSFYFWSMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Cedrane and isocedrane sesquiterpenoids

Alternative Parents

Substituents

Cedrane 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

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302788)

Food

Herb and spice

Herb

Sweet basil (FooDB: FOOD00119)

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	4.5	ALOGPS
logP	4.16	ChemAxon
logS	-5.2	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	64.62 m³·mol⁻¹	ChemAxon
Polarizability	25.66 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]+	148.347	32859911
AllCCS	[M+H-H2O]+	144.483	32859911
AllCCS	[M+Na]+	152.978	32859911
AllCCS	[M+NH4]+	151.943	32859911
AllCCS	[M-H]-	157.985	32859911
AllCCS	[M+Na-2H]-	158.318	32859911
AllCCS	[M+HCOO]-	158.785	32859911
DeepCCS	[M-2H]-	189.868	30932474
DeepCCS	[M+Na]+	164.704	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	20.5898 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.13 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2548.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	749.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	266.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	406.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	501.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	787.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	963.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	157.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1632.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	516.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1703.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	608.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	539.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	543.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	676.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.7 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Cedrene 10V, Positive-QTOF	splash10-0a4i-0190000000-160394d3d26f706157c6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Cedrene 20V, Positive-QTOF	splash10-0a4i-1790000000-e6f0484b6a92d5df01d2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Cedrene 40V, Positive-QTOF	splash10-0ky0-8900000000-f8464b212174dc736609	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Cedrene 10V, Negative-QTOF	splash10-0udi-0090000000-139f56b646b5d2bd9331	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Cedrene 20V, Negative-QTOF	splash10-0udi-0090000000-93640a2ea4701a286b3c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Cedrene 40V, Negative-QTOF	splash10-000i-1910000000-97e69de92b5437f20d9f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Cedrene 10V, Positive-QTOF	splash10-0a4i-0090000000-bfe3306c5c32cdb9f028	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Cedrene 20V, Positive-QTOF	splash10-0w29-0980000000-0d54002ce2f150d93292	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Cedrene 40V, Positive-QTOF	splash10-0002-3910000000-86af0a94fe4a8ae930dd	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Cedrene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Cedrene 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Cedrene 40V, Negative-QTOF	splash10-0udi-0090000000-fc9228a641e3e70e9650	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

FDB006258

KNApSAcK ID

Not Available

Chemspider ID

9281621

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11106485

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]

Showing metabocard for beta-Cedrene (HMDB0302788)

MOL for HMDB0302788 (beta-Cedrene)

3D MOL for HMDB0302788 (beta-Cedrene)

3D SDF for HMDB0302788 (beta-Cedrene)

3D-SDF for HMDB0302788 (beta-Cedrene)

PDB for HMDB0302788 (beta-Cedrene)

3D PDB for HMDB0302788 (beta-Cedrene)

SMILES for HMDB0302788 (beta-Cedrene)

INCHI for HMDB0302788 (beta-Cedrene)

Structure for HMDB0302788 (beta-Cedrene)

3D Structure for HMDB0302788 (beta-Cedrene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra