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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:04:04 UTC

Update Date

2022-03-07 02:54:44 UTC

HMDB ID

HMDB0036003

Secondary Accession Numbers

HMDB36003

Metabolite Identification

Common Name

alpha-Guaiene

Description

alpha-Guaiene, also known as a-guaiene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on alpha-Guaiene.

Structure

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

HMDB0036003
     RDKit          3D
alpha-Guaiene
 39 40  0  0  0  0  0  0  0  0999 V2000
    3.0648    1.6690   -0.9052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984    0.6526   -0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1371    0.0154    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575    0.1191    0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5330   -1.3219   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4688   -2.0119    0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8786   -1.9379   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781   -2.9382    0.7180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4709   -0.6112   -0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8730    0.5617   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5102    0.8988   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9035    1.5865    0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5272    2.9597   -0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1112    1.0283   -0.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9710   -0.4493   -0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0629    2.0360   -1.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    2.1867   -1.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6498   -0.5964   -0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8285   -0.5761    1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8130    0.8367    0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4867    0.1467    1.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5424   -1.7316   -0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2282   -1.3009   -1.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7584   -3.0787    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4469   -1.6003    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7920   -2.3408   -1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -3.6665    1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4698   -3.4380    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3967   -2.3154    1.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6780    1.9748   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450    0.8516   -1.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0841    1.5447    1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4487    3.5381   -0.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9488    2.9556   -1.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0072    3.4700    0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9355    1.1302   -1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0572    1.4557   -0.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4321   -0.6206    0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3951   -1.0822   -0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 11  4  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
M  END


  Mrv0541 05061308502D          

 15 16  0  0  0  0            999 V2000
    3.4036    3.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208    3.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2027    0.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7017    3.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    1.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    1.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863    2.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7050    3.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863    0.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    2.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    2.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    2.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  5  1  0  0  0  0
 12  4  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036003

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2=C1CC(CCC2C)C(C)=C

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

> <INCHI_KEY>
ADIDQIZBYUABQK-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
26.360783338568886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-dimethyl-7-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydroazulene

> <ALOGPS_LOGP>
5.80

> <JCHEM_LOGP>
4.462623543333334

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
67.2593

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
guaiene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036003
     RDKit          3D
alpha-Guaiene
 39 40  0  0  0  0  0  0  0  0999 V2000
    3.0648    1.6690   -0.9052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984    0.6526   -0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1371    0.0154    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575    0.1191    0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5330   -1.3219   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4688   -2.0119    0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8786   -1.9379   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781   -2.9382    0.7180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4709   -0.6112   -0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8730    0.5617   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5102    0.8988   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9035    1.5865    0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5272    2.9597   -0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1112    1.0283   -0.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9710   -0.4493   -0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0629    2.0360   -1.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    2.1867   -1.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6498   -0.5964   -0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8285   -0.5761    1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8130    0.8367    0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4867    0.1467    1.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5424   -1.7316   -0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2282   -1.3009   -1.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7584   -3.0787    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4469   -1.6003    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7920   -2.3408   -1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -3.6665    1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4698   -3.4380    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3967   -2.3154    1.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6780    1.9748   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450    0.8516   -1.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0841    1.5447    1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4487    3.5381   -0.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9488    2.9556   -1.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0072    3.4700    0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9355    1.1302   -1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0572    1.4557   -0.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4321   -0.6206    0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3951   -1.0822   -0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 11  4  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.353   7.387   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.439   5.724   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.112   0.130   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.310   6.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.956   1.975   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.881   3.362   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.624   3.362   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.786   2.116   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.454   5.092   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.916   5.954   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.454   1.632   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.786   4.608   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.956   4.750   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.250   2.592   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.250   4.132   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5    7   11                                                       
CONECT    6    8   12                                                       
CONECT    7    5   13                                                       
CONECT    8    6   14                                                       
CONECT    9   13   15                                                       
CONECT   10    1    2   13                                                  
CONECT   11    3    5   14                                                  
CONECT   12    4    6   15                                                  
CONECT   13    7    9   10                                                  
CONECT   14    8   11   15                                                  
CONECT   15    9   12   14                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0036003
HETATM    1  C1  UNL     1       3.065   1.669  -0.905  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.898   0.653  -0.084  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.137   0.015   0.509  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.557   0.119   0.275  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.533  -1.322  -0.218  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.469  -2.012   0.609  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.879  -1.938  -0.012  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.778  -2.938   0.718  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.471  -0.611  -0.093  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.873   0.562  -0.113  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.510   0.899  -0.416  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.903   1.587   0.251  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.527   2.960  -0.213  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.111   1.028  -0.476  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.971  -0.449  -0.170  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.063   2.036  -1.147  1.00  0.00           H  
HETATM   17  H2  UNL     1       2.261   2.187  -1.376  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.650  -0.596  -0.255  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.829  -0.576   1.372  1.00  0.00           H  
HETATM   20  H5  UNL     1       4.813   0.837   0.819  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.487   0.147   1.386  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.542  -1.732  -0.055  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.228  -1.301  -1.285  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.758  -3.079   0.697  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.447  -1.600   1.647  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.792  -2.341  -1.064  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.190  -3.666   1.303  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.470  -3.438   0.041  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.397  -2.315   1.422  1.00  0.00           H  
HETATM   30  H15 UNL     1       0.678   1.975  -0.148  1.00  0.00           H  
HETATM   31  H16 UNL     1       0.745   0.852  -1.522  1.00  0.00           H  
HETATM   32  H17 UNL     1      -2.084   1.545   1.326  1.00  0.00           H  
HETATM   33  H18 UNL     1      -2.449   3.538  -0.408  1.00  0.00           H  
HETATM   34  H19 UNL     1      -0.949   2.956  -1.152  1.00  0.00           H  
HETATM   35  H20 UNL     1      -1.007   3.470   0.625  1.00  0.00           H  
HETATM   36  H21 UNL     1      -2.935   1.130  -1.580  1.00  0.00           H  
HETATM   37  H22 UNL     1      -4.057   1.456  -0.151  1.00  0.00           H  
HETATM   38  H23 UNL     1      -3.432  -0.621   0.809  1.00  0.00           H  
HETATM   39  H24 UNL     1      -3.395  -1.082  -0.965  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3    4
CONECT    3   18   19   20
CONECT    4    5   11   21
CONECT    5    6   22   23
CONECT    6    7   24   25
CONECT    7    8    9   26
CONECT    8   27   28   29
CONECT    9   10   10   15
CONECT   10   11   12
CONECT   11   30   31
CONECT   12   13   14   32
CONECT   13   33   34   35
CONECT   14   15   36   37
CONECT   15   38   39
END

HMDB0036003
     RDKit          3D
alpha-Guaiene
 39 40  0  0  0  0  0  0  0  0999 V2000
    3.0648    1.6690   -0.9052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984    0.6526   -0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1371    0.0154    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575    0.1191    0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5330   -1.3219   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4688   -2.0119    0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8786   -1.9379   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781   -2.9382    0.7180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4709   -0.6112   -0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8730    0.5617   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5102    0.8988   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9035    1.5865    0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5272    2.9597   -0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1112    1.0283   -0.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9710   -0.4493   -0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0629    2.0360   -1.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    2.1867   -1.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6498   -0.5964   -0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8285   -0.5761    1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8130    0.8367    0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4867    0.1467    1.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5424   -1.7316   -0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2282   -1.3009   -1.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7584   -3.0787    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4469   -1.6003    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7920   -2.3408   -1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -3.6665    1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4698   -3.4380    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3967   -2.3154    1.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6780    1.9748   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450    0.8516   -1.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0841    1.5447    1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4487    3.5381   -0.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9488    2.9556   -1.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0072    3.4700    0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9355    1.1302   -1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0572    1.4557   -0.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4321   -0.6206    0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3951   -1.0822   -0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 11  4  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-Guaiene	Generator
Α-guaiene	Generator
7-Isopropenyl-1,4-dimethyl-1,2,3,4,5,6,7,8-octahydroazulene	HMDB
alpha-Guajene	HMDB

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.3511

Monoisotopic Molecular Weight

204.187800768

IUPAC Name

1,4-dimethyl-7-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydroazulene

Traditional Name

guaiene

CAS Registry Number

3691-12-1

SMILES

CC1CCC2=C1CC(CCC2C)C(C)=C

InChI Identifier

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

InChI Key

ADIDQIZBYUABQK-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

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

a sesquiterpenoid (CPD-8749 )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036003)

Source

Endogenous

Endogenous (HMDB: HMDB0036003)

Plant

Plant (HMDB: HMDB0036003)

Animal

Animal (HMDB: HMDB0036003)

Exogenous

Food

Food (HMDB: HMDB0036003)

Herb and spice

Spice

Pepper (Spice) (FooDB: FOOD00139)

Herb

Sweet basil (FooDB: FOOD00119)
Sweet bay (FooDB: FOOD00097)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Root vegetable

Burdock (FooDB: FOOD00017)

Exogenous (HMDB: HMDB0036003)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036003)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036003)

Lipid metabolism pathway (HMDB: HMDB0036003)

Cellular process

Cell signaling (HMDB: HMDB0036003)

Biochemical process

Lipid transport (HMDB: HMDB0036003)

Role

Biological role

Energy source (HMDB: HMDB0036003)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036003)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	281.00 to 282.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.021 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.602 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.023 g/L	ALOGPS
logP	5.8	ALOGPS
logP	4.46	ChemAxon
logS	-3.9	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.26 m³·mol⁻¹	ChemAxon
Polarizability	26.36 Å³	ChemAxon
Number of Rings	2	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]+	149.503	31661259
DarkChem	[M-H]-	144.393	31661259
DeepCCS	[M+H]+	150.154	30932474
DeepCCS	[M-H]-	147.156	30932474
DeepCCS	[M-2H]-	183.44	30932474
DeepCCS	[M+Na]+	158.977	30932474
AllCCS	[M+H]+	148.0	32859911
AllCCS	[M+H-H2O]+	144.0	32859911
AllCCS	[M+NH4]+	151.7	32859911
AllCCS	[M+Na]+	152.7	32859911
AllCCS	[M-H]-	156.5	32859911
AllCCS	[M+Na-2H]-	157.1	32859911
AllCCS	[M+HCOO]-	157.8	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.	7.51 minutes	32390414
Predicted by Siyang on May 30, 2022	22.4179 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.74 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2681.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	845.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	310.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	495.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	418.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	896.2 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	1003.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	296.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1767.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	636.6 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	1797.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	638.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	525.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	606.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	783.8 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	9.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Guaiene	CC1CCC2=C1CC(CCC2C)C(C)=C	1656.2	Standard polar	33892256
alpha-Guaiene	CC1CCC2=C1CC(CCC2C)C(C)=C	1451.9	Standard non polar	33892256
alpha-Guaiene	CC1CCC2=C1CC(CCC2C)C(C)=C	1438.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Guaiene GC-MS (Non-derivatized) - 70eV, Positive	splash10-01w0-2900000000-53ce55d6a02afdfebb56	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Guaiene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Guaiene 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-Guaiene 10V, Positive-QTOF	splash10-0a4i-0390000000-ca6fe668203bbe8ab5fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Guaiene 20V, Positive-QTOF	splash10-0bt9-2950000000-1a2ba6895a66bed19ab9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Guaiene 40V, Positive-QTOF	splash10-0f9j-5900000000-2f78480fe60f51a83de9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Guaiene 10V, Negative-QTOF	splash10-0udi-0090000000-85d9f5a453c9140a140c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Guaiene 20V, Negative-QTOF	splash10-0udi-0190000000-49a48b52de1914c108cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Guaiene 40V, Negative-QTOF	splash10-000i-2900000000-50b55803c93cfd4d7c3c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Guaiene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Guaiene 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Guaiene 40V, Negative-QTOF	splash10-000i-0920000000-a7c0eb9904c1602a8df1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Guaiene 10V, Positive-QTOF	splash10-0ab9-1940000000-35b45f7d19ec7bab53ed	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Guaiene 20V, Positive-QTOF	splash10-0ab9-3930000000-a79edbe5406e60236644	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Guaiene 40V, Positive-QTOF	splash10-004l-9300000000-8d8f036e2ad20d12485e	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

FDB014813

KNApSAcK ID

C00020377

Chemspider ID

96423

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

107152

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1054351

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for alpha-Guaiene (HMDB0036003)

MOL for HMDB0036003 (alpha-Guaiene)

3D MOL for HMDB0036003 (alpha-Guaiene)

3D SDF for HMDB0036003 (alpha-Guaiene)

3D-SDF for HMDB0036003 (alpha-Guaiene)

PDB for HMDB0036003 (alpha-Guaiene)

3D PDB for HMDB0036003 (alpha-Guaiene)

SMILES for HMDB0036003 (alpha-Guaiene)

INCHI for HMDB0036003 (alpha-Guaiene)

Structure for HMDB0036003 (alpha-Guaiene)

3D Structure for HMDB0036003 (alpha-Guaiene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra