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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-12-06 16:20:47 UTC

Update Date

2021-09-14 15:40:10 UTC

HMDB ID

HMDB0059695

Secondary Accession Numbers

HMDB59695

Metabolite Identification

Common Name

alpha-Cedrene

Description

alpha-Cedrene, also known as a-cedrene, 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. Thus, alpha-cedrene is considered to be an isoprenoid lipid molecule. alpha-Cedrene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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

HMDB0059695
     RDKit          3D
alpha-Cedrene
 39 41  0  0  0  0  0  0  0  0999 V2000
   -3.1314    1.8062    0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7191    1.3695   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8878    1.9085   -0.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419    1.4618   -1.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8804    0.4558    0.0103 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1615    0.7429    1.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2680    0.3225    0.9237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0693   -0.9947    0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1217   -2.1781    1.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451   -1.1774   -0.8511 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2945   -0.8782   -0.3973 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2901   -1.8408    0.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -1.1789   -0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3211    0.2620    0.2750 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2434    1.1367   -0.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2789    2.3680    0.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8466    0.9604    0.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3936    2.5013   -0.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2568    2.7144   -1.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6032    0.9570   -2.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492    2.3640   -1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417    0.1809    2.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1685    1.8418    1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8998    0.2332    1.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6410   -1.9967    2.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2080   -2.4442    1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6974   -3.0507    0.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1082   -1.3002   -0.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598   -2.0750   -1.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2292   -0.3193   -1.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355   -1.0553   -1.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474   -1.7833    1.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2043   -2.8587   -0.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6829   -1.1800   -1.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4652   -1.6086    0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5561    0.3319    1.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2808    0.8954   -0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1078    2.2169   -0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1904    0.8887   -1.6106 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
  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
  1 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  1  0            999 V2000
    0.6253    1.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5187    0.4513    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2066    0.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0949   -0.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117   -0.8886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1148   -0.1154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7449    0.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5618    0.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346   -0.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1168   -1.1178    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3274   -1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6023   -2.2653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8181   -2.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5148   -0.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2935   -1.6131    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8393   -0.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  0  0  0  0
  5 15  1  1  0  0  0
  6 16  1  6  0  0  0
 10 16  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0059695

> <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/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12+,13+,15+/m1/s1

> <INCHI_KEY>
IRAQOCYXUMOFCW-OSFYFWSMSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.628158060679286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene

> <ALOGPS_LOGP>
5.18

> <JCHEM_LOGP>
4.101158186333333

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
65.6944

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0059695
     RDKit          3D
alpha-Cedrene
 39 41  0  0  0  0  0  0  0  0999 V2000
   -3.1314    1.8062    0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7191    1.3695   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8878    1.9085   -0.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419    1.4618   -1.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8804    0.4558    0.0103 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1615    0.7429    1.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2680    0.3225    0.9237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0693   -0.9947    0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1217   -2.1781    1.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451   -1.1774   -0.8511 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2945   -0.8782   -0.3973 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2901   -1.8408    0.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -1.1789   -0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3211    0.2620    0.2750 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2434    1.1367   -0.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2789    2.3680    0.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8466    0.9604    0.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3936    2.5013   -0.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2568    2.7144   -1.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6032    0.9570   -2.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492    2.3640   -1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417    0.1809    2.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1685    1.8418    1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8998    0.2332    1.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6410   -1.9967    2.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2080   -2.4442    1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6974   -3.0507    0.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1082   -1.3002   -0.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598   -2.0750   -1.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2292   -0.3193   -1.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355   -1.0553   -1.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474   -1.7833    1.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2043   -2.8587   -0.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6829   -1.1800   -1.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4652   -1.6086    0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5561    0.3319    1.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2808    0.8954   -0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1078    2.2169   -0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1904    0.8887   -1.6106 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
  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
  1 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       1.167   2.349   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.968   0.842   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.386   0.108   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.177  -1.398   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.329  -1.659   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.081  -0.215   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.257   0.951   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.782   0.614   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.105  -0.934   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.951  -2.087   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.478  -2.798   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.991  -4.229   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.527  -3.984   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.561  -1.368   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       0.548  -3.011   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       3.433  -0.996   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11   15                                             
CONECT    6    5    2    7   16                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10    5   12   13                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9                                                            
CONECT   15    5                                                            
CONECT   16    6   10                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0059695
HETATM    1  C1  UNL     1      -3.131   1.806   0.002  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.719   1.370  -0.027  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.888   1.909  -0.885  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.542   1.462  -1.039  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.880   0.456   0.010  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.162   0.743   1.306  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.268   0.323   0.924  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.069  -0.995   0.196  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.122  -2.178   1.121  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.145  -1.177  -0.851  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.294  -0.878  -0.397  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.290  -1.841   0.256  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.596  -1.179  -0.153  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.321   0.262   0.275  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.243   1.137  -0.522  1.00  0.00           C  
HETATM   16  H1  UNL     1      -3.279   2.368   0.970  1.00  0.00           H  
HETATM   17  H2  UNL     1      -3.847   0.960   0.025  1.00  0.00           H  
HETATM   18  H3  UNL     1      -3.394   2.501  -0.799  1.00  0.00           H  
HETATM   19  H4  UNL     1      -1.257   2.714  -1.509  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.603   0.957  -2.032  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.149   2.364  -1.041  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.542   0.181   2.153  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.169   1.842   1.485  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.900   0.233   1.815  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.641  -1.997   2.101  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.208  -2.444   1.279  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.697  -3.051   0.579  1.00  0.00           H  
HETATM   28  H13 UNL     1      -3.108  -1.300  -0.326  1.00  0.00           H  
HETATM   29  H14 UNL     1      -1.960  -2.075  -1.443  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.229  -0.319  -1.541  1.00  0.00           H  
HETATM   31  H16 UNL     1       0.335  -1.055  -1.485  1.00  0.00           H  
HETATM   32  H17 UNL     1       1.247  -1.783   1.360  1.00  0.00           H  
HETATM   33  H18 UNL     1       1.204  -2.859  -0.134  1.00  0.00           H  
HETATM   34  H19 UNL     1       2.683  -1.180  -1.243  1.00  0.00           H  
HETATM   35  H20 UNL     1       3.465  -1.609   0.377  1.00  0.00           H  
HETATM   36  H21 UNL     1       2.556   0.332   1.347  1.00  0.00           H  
HETATM   37  H22 UNL     1       4.281   0.895  -0.206  1.00  0.00           H  
HETATM   38  H23 UNL     1       3.108   2.217  -0.336  1.00  0.00           H  
HETATM   39  H24 UNL     1       3.190   0.889  -1.611  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    7
CONECT    3    4   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

HMDB0059695
     RDKit          3D
alpha-Cedrene
 39 41  0  0  0  0  0  0  0  0999 V2000
   -3.1314    1.8062    0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7191    1.3695   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8878    1.9085   -0.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419    1.4618   -1.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8804    0.4558    0.0103 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1615    0.7429    1.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2680    0.3225    0.9237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0693   -0.9947    0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1217   -2.1781    1.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451   -1.1774   -0.8511 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2945   -0.8782   -0.3973 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2901   -1.8408    0.2558 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -1.1789   -0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3211    0.2620    0.2750 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2434    1.1367   -0.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2789    2.3680    0.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8466    0.9604    0.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3936    2.5013   -0.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2568    2.7144   -1.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6032    0.9570   -2.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492    2.3640   -1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417    0.1809    2.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1685    1.8418    1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8998    0.2332    1.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6410   -1.9967    2.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2080   -2.4442    1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6974   -3.0507    0.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1082   -1.3002   -0.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598   -2.0750   -1.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2292   -0.3193   -1.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355   -1.0553   -1.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474   -1.7833    1.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2043   -2.8587   -0.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6829   -1.1800   -1.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4652   -1.6086    0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5561    0.3319    1.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2808    0.8954   -0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1078    2.2169   -0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1904    0.8887   -1.6106 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
  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
  1 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
(-)-alpha-Cedrene	ChEBI
(1S,2R,5S,7S)-2,6,6,8-Tetramethyltricyclo[5.3.1.0(1,5)]undec-8-ene	ChEBI
[3R-(3alpha,3Abeta,7beta,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene	ChEBI
(-)-a-Cedrene	Generator
(-)-Α-cedrene	Generator
[3R-(3a,3Abeta,7b,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene	Generator
[3R-(3Α,3abeta,7β,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene	Generator
a-Cedrene	Generator
Α-cedrene	Generator
alpha-Cedrene	ChEBI
beta-Cedrene	MeSH
Cedrone	MeSH
Cedrene	MeSH

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.3511

Monoisotopic Molecular Weight

204.187800768

IUPAC Name

(1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene

Traditional Name

(1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene

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/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12+,13+,15+/m1/s1

InChI Key

IRAQOCYXUMOFCW-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

bridged compound (CHEBI:10216 )
sesquiterpene (CHEBI:10216 )
polycyclic olefin (CHEBI:10216 )
Cedrane and isocedrane sesquiterpenoids (LMPR0103690006 )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0059695)

Source

Endogenous

Endogenous (HMDB: HMDB0059695)

Animal

Animal (HMDB: HMDB0059695)

Exogenous

Food

Food (HMDB: HMDB0059695)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)
Ginger (FooDB: FOOD00206)

Oilseed crop

Safflower (FooDB: FOOD00042)

Herb

Fruit

Berry

Highbush blueberry (FooDB: FOOD00191)
Rabbiteye blueberry (FooDB: FOOD00898)

Vegetable

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

Synthetic

Personal care products

Perfume (HMDB: HMDB0059695)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0059695)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0059695)

Lipid metabolism pathway (HMDB: HMDB0059695)

Cellular process

Cell signaling (HMDB: HMDB0059695)

Biochemical process

Lipid transport (HMDB: HMDB0059695)

Role

Biological role

Energy source (HMDB: HMDB0059695)
Irritant (HMDB: HMDB0059695)

Industrial application

Pharmaceutical industry

Antineoplastic agent

Cancer preventive (HMDB: HMDB0059695)

Physical Properties

State

Solid

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
Water Solubility	0.0016 g/L	ALOGPS
logP	5.18	ALOGPS
logP	4.1	ChemAxon
logS	-5.1	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	65.69 m³·mol⁻¹	ChemAxon
Polarizability	25.63 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
DarkChem	[M+H]+	149.651	31661259
DarkChem	[M-H]-	145.007	31661259
DeepCCS	[M-2H]-	189.513	30932474
DeepCCS	[M+Na]+	164.315	30932474
AllCCS	[M+H]+	147.2	32859911
AllCCS	[M+H-H2O]+	143.3	32859911
AllCCS	[M+NH4]+	150.8	32859911
AllCCS	[M+Na]+	151.9	32859911
AllCCS	[M-H]-	158.4	32859911
AllCCS	[M+Na-2H]-	158.7	32859911
AllCCS	[M+HCOO]-	159.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.7 minutes	32390414
Predicted by Siyang on May 30, 2022	19.0679 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.03 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2538.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	663.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	239.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	348.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	467.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	709.7 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	866.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	99.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1495.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	509.7 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	1445.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	555.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	473.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	471.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	602.1 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	8.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Cedrene	[H][C@@]12CC[C@@H](C)[C@]11C[C@@H](C(C)=CC1)C2(C)C	1575.5	Standard polar	33892256
alpha-Cedrene	[H][C@@]12CC[C@@H](C)[C@]11C[C@@H](C(C)=CC1)C2(C)C	1435.8	Standard non polar	33892256
alpha-Cedrene	[H][C@@]12CC[C@@H](C)[C@]11C[C@@H](C(C)=CC1)C2(C)C	1411.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - alpha-Cedrene GC-EI-Q (Non-derivatized)	splash10-014l-8900000000-bf26b564b0b20c1d093a	2020-07-08	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Cedrene GC-MS (Non-derivatized) - 70eV, Positive	splash10-03g1-1900000000-d9586d99c9949bf8088b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Cedrene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - alpha-Cedrene 10V, Positive-QTOF	splash10-0a4i-0190000000-cd7b7bd3ccd75e24c49b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cedrene 20V, Positive-QTOF	splash10-0a4i-0690000000-5c3400f19be2d725de04	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cedrene 40V, Positive-QTOF	splash10-0f9i-9800000000-6baec4093195d46de24a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cedrene 10V, Negative-QTOF	splash10-0udi-0090000000-6589dee75f8602eecab5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cedrene 20V, Negative-QTOF	splash10-0udi-0090000000-1b2a943b4a7f32ee7b6f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cedrene 40V, Negative-QTOF	splash10-0f79-1920000000-80c16a78fccc89798b3d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cedrene 10V, Positive-QTOF	splash10-0a4i-0090000000-bfe3306c5c32cdb9f028	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cedrene 20V, Positive-QTOF	splash10-0w29-0980000000-7697f0bed333d272bce2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cedrene 40V, Positive-QTOF	splash10-0002-3910000000-cd4b988301c3693d423b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cedrene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cedrene 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Cedrene 40V, Negative-QTOF	splash10-0udi-0090000000-19077c1e88a70668273f	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details

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

6431015

PDB ID

Not Available

ChEBI ID

10216

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for alpha-Cedrene (HMDB0059695)

MOL for HMDB0059695 (alpha-Cedrene)

3D MOL for HMDB0059695 (alpha-Cedrene)

3D SDF for HMDB0059695 (alpha-Cedrene)

3D-SDF for HMDB0059695 (alpha-Cedrene)

PDB for HMDB0059695 (alpha-Cedrene)

3D PDB for HMDB0059695 (alpha-Cedrene)

SMILES for HMDB0059695 (alpha-Cedrene)

INCHI for HMDB0059695 (alpha-Cedrene)

Structure for HMDB0059695 (alpha-Cedrene)

3D Structure for HMDB0059695 (alpha-Cedrene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra