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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 19:45:42 UTC

Update Date

2021-11-15 21:12:11 UTC

HMDB ID

HMDB0302687

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Longifolene

Description

Longifolene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Longifolene is a sweet, fir needle, and medical tasting compound found in corn, mandarin orange (clementine, tangerine), rosemary, and star anise, which makes longifolene a potential biomarker for the consumption of these food products. Longifolene is the common (or trivial) chemical name of a naturally occurring, oily Liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated, Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) Chemically, longifolene is a tricyclic sesquiterpene. This molecule is chiral, and the enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73¬∞. The other enantiomer (optical rotation -42.73¬∞) is found in small amounts in certain fungi and liverworts.

Structure

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

HMDB0302687
     RDKit          3D
Longifolene
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.5730    0.6703   -2.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0755    0.5903   -0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1383    1.5531   -0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9067    2.2514    0.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0777    1.1672    1.9442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4225   -0.0591    1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7136    0.6288    0.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6993   -0.1797   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1197    0.4876   -1.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9815   -0.2044    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3747   -1.6146   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1610   -1.8166   -1.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0370   -1.8442   -0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3251   -0.4520    0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7911   -0.3789    0.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3289    1.4738   -2.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2537   -0.0893   -2.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3982    2.2038   -0.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8540    2.6594    0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2631    3.0823    1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5178    1.4497    2.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1166    1.0029    2.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1653   -0.8363    1.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1875    1.3104    1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9971   -0.0571   -1.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4664    1.5155   -1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3206    0.5097   -2.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8141   -0.5375    0.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1244    0.7302    1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7892   -0.9963    1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2848   -2.1987    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2460   -2.0521   -0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2395   -2.8559   -1.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033   -1.1230   -2.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9090   -2.3663   -0.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7461   -2.4594    0.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9421   -0.7636    1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772   -1.0303   -0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000    0.6290    0.5257 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
  4  5  1  0
  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
 14  2  1  0
  7  3  1  0
 14  6  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  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  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

longifolene
  Mrv1572001071617122D          

 15 17  0  0  0  0            999 V2000
    1.3621    2.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1300    1.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9621    1.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3598    0.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0071    0.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1690   -0.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200   -0.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5339   -0.5721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4856    0.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0589    1.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6974    0.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1238    0.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6594    0.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4017    2.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1912    2.8447    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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302687

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCCC(C)(C)C3C(CCC13)C2=C

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

> <INCHI_KEY>
PDSNLYSELAIEBU-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.417236290907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.0²,⁹]undecane

> <ALOGPS_LOGP>
4.65

> <JCHEM_LOGP>
4.159091856666667

> <ALOGPS_LOGS>
-5.21

> <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>
1.26e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
longifolene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302687
     RDKit          3D
Longifolene
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.5730    0.6703   -2.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0755    0.5903   -0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1383    1.5531   -0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9067    2.2514    0.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0777    1.1672    1.9442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4225   -0.0591    1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7136    0.6288    0.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6993   -0.1797   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1197    0.4876   -1.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9815   -0.2044    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3747   -1.6146   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1610   -1.8166   -1.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0370   -1.8442   -0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3251   -0.4520    0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7911   -0.3789    0.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3289    1.4738   -2.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2537   -0.0893   -2.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3982    2.2038   -0.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8540    2.6594    0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2631    3.0823    1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5178    1.4497    2.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1166    1.0029    2.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1653   -0.8363    1.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1875    1.3104    1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9971   -0.0571   -1.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4664    1.5155   -1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3206    0.5097   -2.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8141   -0.5375    0.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1244    0.7302    1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7892   -0.9963    1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2848   -2.1987    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2460   -2.0521   -0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2395   -2.8559   -1.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033   -1.1230   -2.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9090   -2.3663   -0.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7461   -2.4594    0.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9421   -0.7636    1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772   -1.0303   -0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000    0.6290    0.5257 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
  4  5  1  0
  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
 14  2  1  0
  7  3  1  0
 14  6  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  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  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: longifolene                                       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       2.543   4.628   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.109   3.163   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.663   2.981   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.405   1.632   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.747   0.220   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.182  -0.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.837  -1.485   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.997  -1.068   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.906   0.865   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.110   2.556   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.302   1.722   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.231   0.598   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.231   1.796   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.750   3.834   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.357   5.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13   14                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   13                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    2    9                                                  
CONECT   14   10    2   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

COMPND    HMDB0302687
HETATM    1  C1  UNL     1      -1.573   0.670  -2.099  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.076   0.590  -0.874  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.138   1.553  -0.256  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.907   2.251   0.873  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.078   1.167   1.944  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.423  -0.059   1.308  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.714   0.629   0.606  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.699  -0.180  -0.064  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.120   0.488  -1.372  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.981  -0.204   0.789  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.375  -1.615  -0.330  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.161  -1.817  -1.184  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.037  -1.844  -0.280  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.325  -0.452   0.163  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.791  -0.379   0.590  1.00  0.00           C  
HETATM   16  H1  UNL     1      -1.329   1.474  -2.777  1.00  0.00           H  
HETATM   17  H2  UNL     1      -2.254  -0.089  -2.455  1.00  0.00           H  
HETATM   18  H3  UNL     1       0.398   2.204  -0.905  1.00  0.00           H  
HETATM   19  H4  UNL     1      -1.854   2.659   0.535  1.00  0.00           H  
HETATM   20  H5  UNL     1      -0.263   3.082   1.246  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.518   1.450   2.875  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.117   1.003   2.213  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.165  -0.836   1.996  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.188   1.310   1.373  1.00  0.00           H  
HETATM   25  H10 UNL     1       2.997  -0.057  -1.786  1.00  0.00           H  
HETATM   26  H11 UNL     1       2.466   1.515  -1.075  1.00  0.00           H  
HETATM   27  H12 UNL     1       1.321   0.510  -2.116  1.00  0.00           H  
HETATM   28  H13 UNL     1       3.814  -0.538   0.171  1.00  0.00           H  
HETATM   29  H14 UNL     1       3.124   0.730   1.329  1.00  0.00           H  
HETATM   30  H15 UNL     1       2.789  -0.996   1.565  1.00  0.00           H  
HETATM   31  H16 UNL     1       1.285  -2.199   0.597  1.00  0.00           H  
HETATM   32  H17 UNL     1       2.246  -2.052  -0.896  1.00  0.00           H  
HETATM   33  H18 UNL     1       0.240  -2.856  -1.622  1.00  0.00           H  
HETATM   34  H19 UNL     1       0.103  -1.123  -2.020  1.00  0.00           H  
HETATM   35  H20 UNL     1      -1.909  -2.366  -0.718  1.00  0.00           H  
HETATM   36  H21 UNL     1      -0.746  -2.459   0.616  1.00  0.00           H  
HETATM   37  H22 UNL     1      -2.942  -0.764   1.614  1.00  0.00           H  
HETATM   38  H23 UNL     1      -3.377  -1.030  -0.099  1.00  0.00           H  
HETATM   39  H24 UNL     1      -3.200   0.629   0.526  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3   14
CONECT    3    4    7   18
CONECT    4    5   19   20
CONECT    5    6   21   22
CONECT    6    7   14   23
CONECT    7    8   24
CONECT    8    9   10   11
CONECT    9   25   26   27
CONECT   10   28   29   30
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   14   35   36
CONECT   14   15
CONECT   15   37   38   39
END

HMDB0302687
     RDKit          3D
Longifolene
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.5730    0.6703   -2.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0755    0.5903   -0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1383    1.5531   -0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9067    2.2514    0.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0777    1.1672    1.9442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4225   -0.0591    1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7136    0.6288    0.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6993   -0.1797   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1197    0.4876   -1.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9815   -0.2044    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3747   -1.6146   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1610   -1.8166   -1.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0370   -1.8442   -0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3251   -0.4520    0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7911   -0.3789    0.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3289    1.4738   -2.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2537   -0.0893   -2.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3982    2.2038   -0.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8540    2.6594    0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2631    3.0823    1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5178    1.4497    2.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1166    1.0029    2.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1653   -0.8363    1.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1875    1.3104    1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9971   -0.0571   -1.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4664    1.5155   -1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3206    0.5097   -2.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8141   -0.5375    0.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1244    0.7302    1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7892   -0.9963    1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2848   -2.1987    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2460   -2.0521   -0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2395   -2.8559   -1.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033   -1.1230   -2.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9090   -2.3663   -0.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7461   -2.4594    0.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9421   -0.7636    1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772   -1.0303   -0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000    0.6290    0.5257 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
  4  5  1  0
  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
 14  2  1  0
  7  3  1  0
 14  6  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  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  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.357

Monoisotopic Molecular Weight

204.187800773

IUPAC Name

3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.0²,⁹]undecane

Traditional Name

longifolene

CAS Registry Number

Not Available

SMILES

CC12CCCC(C)(C)C3C(CCC13)C2=C

InChI Identifier

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

InChI Key

PDSNLYSELAIEBU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Longifolane or isolongifolane sesquiterpenoid
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

sesquiterpene (CHEBI:6530 )
Longifolane sesquiterpenoids (C09699 )
Humulenes (C09699 )
a diterpenoid (CPD-8701 )

Ontology

Milk and milk product

Fermented milk product

Cheese (FooDB: FOOD00617)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Fruit

Citrus

Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Herb and spice

Herb

Rosemary (FooDB: FOOD00159)

Spice

Star anise (FooDB: FOOD00090)

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	4.65	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	25.42 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]+	147.652	32859911
AllCCS	[M+H-H2O]+	143.779	32859911
AllCCS	[M+Na]+	152.294	32859911
AllCCS	[M+NH4]+	151.256	32859911
AllCCS	[M-H]-	156.632	32859911
AllCCS	[M+Na-2H]-	156.964	32859911
AllCCS	[M+HCOO]-	157.428	32859911
DeepCCS	[M-2H]-	186.848	30932474
DeepCCS	[M+Na]+	162.056	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 - Longifolene GC-MS (Non-derivatized) - 70eV, Positive	splash10-01s9-2900000000-035dbcf027d0dfba677b	2017-07-27	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-9800000000-39919bcbac1cbe903234	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longifolene 10V, Positive-QTOF	splash10-0a4i-0090000000-8be5b82f1970df5d0fba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longifolene 20V, Positive-QTOF	splash10-0a4i-1390000000-5b0723496471550d90fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longifolene 40V, Positive-QTOF	splash10-00n0-8900000000-96000d2a703ee43023ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longifolene 10V, Negative-QTOF	splash10-0udi-0090000000-d8dbe2f117875c63d9b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longifolene 20V, Negative-QTOF	splash10-0udi-0090000000-b23a97fc2ece08b93c5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longifolene 40V, Negative-QTOF	splash10-000i-1900000000-023300ca2a969c85df78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longifolene 10V, Positive-QTOF	splash10-0a4i-0190000000-957001643af974296779	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longifolene 20V, Positive-QTOF	splash10-05fr-4940000000-08e8b30216bee8b9d0b7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longifolene 40V, Positive-QTOF	splash10-006x-6900000000-2057ea9054379c9d846d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longifolene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longifolene 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longifolene 40V, Negative-QTOF	splash10-0udi-0090000000-6efb1ac8bbe4b57b1ab9	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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

289151

PDB ID

Not Available

ChEBI ID

6530

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1020031

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Longifolene (HMDB0302687)

MOL for HMDB0302687 (Longifolene)

3D MOL for HMDB0302687 (Longifolene)

3D SDF for HMDB0302687 (Longifolene)

3D-SDF for HMDB0302687 (Longifolene)

PDB for HMDB0302687 (Longifolene)

3D PDB for HMDB0302687 (Longifolene)

SMILES for HMDB0302687 (Longifolene)

INCHI for HMDB0302687 (Longifolene)

Structure for HMDB0302687 (Longifolene)

3D Structure for HMDB0302687 (Longifolene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra