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Showing metabocard for 3,7-Dimethyl-1,6-octadien-3-ol (HMDB0036100)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:10:02 UTC
Update Date2023-02-21 17:25:04 UTC
HMDB IDHMDB0036100
Secondary Accession Numbers
  • HMDB36100
Metabolite Identification
Common Name3,7-Dimethyl-1,6-octadien-3-ol
Description3,7-Dimethyl-1,6-octadien-3-ol, also known simply as linalool is a naturally occurring terpene alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Linalool has a role as a plant metabolite, a volatile oil component, an antimicrobial agent and a fragrance. There are two stereoisomers of Linalool – (S)-linalool and (R)-linalool. Linalool is used as a scent in 60% to 80% of perfumed hygiene products and cleaning agents including soaps, detergents, shampoos, and lotions. Linalool is also used by pest professionals as a flea, fruit fly, and cockroach insecticide. Linalool is found in more than 200 different species of plants, including many flowers and spice plants. (S)-linalool is found, for example, as a major constituent of the essential oils of coriander (Coriandrum sativum L.), cymbopogon (Cymbopogon martini var. martinii), and sweet orange (Citrus sinensis) flowers. (R)-linalool is present in lavender (Lavandula officinalis), bay laurel (Laurus nobilis), and sweet basil (Ocimum basilicum), among others. Linalool is also found in plants from the Lamiaceae family (mint and other herbs), Lauraceae (laurels, cinnamon, rosewood), Cinnamomum tamala, Solidago Meyen, Artemisia vulgaris (mugwort), Humulus lupulus. Linalool is also one of several monoterpenes that are found in cannabis plants (PMID:6991645 ). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita. Like the majority of monoterpenes, linalool starts with the condensation of dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP) to form geranyl pyrophosphate (GPP) (PMID:7640522 ). Linalool is then synthesized with the aid of linalool synthase (LIS) (PMID:12572612 ). Linalool has a citrus, floral, rose, woody aroma and a citrus, orange, waxy taste. Linalool is found in a few different foods and spices, such as spearmints, corianders, common thymes, limes, grapes, lemons, grapefruit, oranges, pineapples, blackcurrants, basil, and common oregano. This could make, Linalool a potential biomarker for the consumption of these foods. Linalool is also synthesized, de novo, by yeast (C. cerevisiae) and may contribute to the floral tones found in some wines (PMID:15668008 ).
Structure
Data?1677000304
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0036100 (3,7-Dimethyl-1,6-octadien-3-ol)

linalool
  Mrv1652305261923582D          

 11 10  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -3.5724    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
  2  4  2  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
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
Download

3D MOL for HMDB0036100 (3,7-Dimethyl-1,6-octadien-3-ol)

HMDB0036100
     RDKit          3D
3,7-Dimethyl-1,6-octadien-3-ol
 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.2027   -1.7246   -0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2186   -0.4212   -0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9945    0.2779    0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0911    1.7790   -0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7984    0.0256    1.4264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7627   -0.1872   -0.7025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3987    0.6348   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6750    0.2801   -0.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6803   -0.1930   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9584   -0.5465   -0.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5379   -0.3716    1.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3122   -2.3330   -0.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0968   -2.2795   -0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1291    0.1394   -0.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7467    2.0736   -1.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1868    2.0244   -0.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5272    2.2952    0.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4427    0.5004    1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5856   -1.2592   -0.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8675    0.0858   -1.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4363    0.4024    0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1394    1.6940   -0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7716    0.4100   -1.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7862   -0.5513   -0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1802    0.1043   -1.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8244   -1.5972   -1.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3694    0.6107    1.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7161   -1.0891    1.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4889   -0.7840    1.7810 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
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  4 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
M  END
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3D SDF for HMDB0036100 (3,7-Dimethyl-1,6-octadien-3-ol)

linalool
  Mrv1652305261923582D          

 11 10  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -3.5724    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
  2  4  2  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
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036100

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCCC(C)(O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3

> <INCHI_KEY>
CDOSHBSSFJOMGT-UHFFFAOYSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.253

> <EXACT_MASS>
154.1357652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.313446170105586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,7-dimethylocta-1,6-dien-3-ol

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
2.647492452666667

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.459388377759243

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2856635235681075

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
50.2066

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
linalool, (+-)-

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0036100 (3,7-Dimethyl-1,6-octadien-3-ol)

HMDB0036100
     RDKit          3D
3,7-Dimethyl-1,6-octadien-3-ol
 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.2027   -1.7246   -0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2186   -0.4212   -0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9945    0.2779    0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0911    1.7790   -0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7984    0.0256    1.4264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7627   -0.1872   -0.7025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3987    0.6348   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6750    0.2801   -0.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6803   -0.1930   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9584   -0.5465   -0.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5379   -0.3716    1.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3122   -2.3330   -0.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0968   -2.2795   -0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1291    0.1394   -0.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7467    2.0736   -1.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1868    2.0244   -0.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5272    2.2952    0.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4427    0.5004    1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5856   -1.2592   -0.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8675    0.0858   -1.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4363    0.4024    0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1394    1.6940   -0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7716    0.4100   -1.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7862   -0.5513   -0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1802    0.1043   -1.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8244   -1.5972   -1.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3694    0.6107    1.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7161   -1.0891    1.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4889   -0.7840    1.7810 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
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  4 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
M  END
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PDB for HMDB0036100 (3,7-Dimethyl-1,6-octadien-3-ol)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: linalool                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770  -4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.104  -3.231   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.564  -4.771   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.540  -5.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.770  -6.668   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for HMDB0036100 (3,7-Dimethyl-1,6-octadien-3-ol)

COMPND    HMDB0036100
HETATM    1  C1  UNL     1      -3.203  -1.725  -0.564  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.219  -0.421  -0.346  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.995   0.278   0.073  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.091   1.779  -0.144  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.798   0.026   1.426  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.763  -0.187  -0.703  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.399   0.635  -0.142  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.675   0.280  -0.816  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.680  -0.193  -0.109  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.958  -0.547  -0.794  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.538  -0.372   1.360  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.312  -2.333  -0.449  1.00  0.00           H  
HETATM   13  H2  UNL     1      -4.097  -2.280  -0.878  1.00  0.00           H  
HETATM   14  H3  UNL     1      -4.129   0.139  -0.474  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.747   2.074  -1.151  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.187   2.024  -0.084  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.527   2.295   0.671  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.443   0.500   1.986  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.586  -1.259  -0.614  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.868   0.086  -1.771  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.436   0.402   0.942  1.00  0.00           H  
HETATM   22  H11 UNL     1       0.139   1.694  -0.341  1.00  0.00           H  
HETATM   23  H12 UNL     1       1.772   0.410  -1.868  1.00  0.00           H  
HETATM   24  H13 UNL     1       4.786  -0.551  -0.048  1.00  0.00           H  
HETATM   25  H14 UNL     1       4.180   0.104  -1.648  1.00  0.00           H  
HETATM   26  H15 UNL     1       3.824  -1.597  -1.166  1.00  0.00           H  
HETATM   27  H16 UNL     1       2.369   0.611   1.875  1.00  0.00           H  
HETATM   28  H17 UNL     1       1.716  -1.089   1.554  1.00  0.00           H  
HETATM   29  H18 UNL     1       3.489  -0.784   1.781  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3   14
CONECT    3    4    5    6
CONECT    4   15   16   17
CONECT    5   18
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9    9   23
CONECT    9   10   11
CONECT   10   24   25   26
CONECT   11   27   28   29
END
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SMILES for HMDB0036100 (3,7-Dimethyl-1,6-octadien-3-ol)

CC(C)=CCCC(C)(O)C=C
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INCHI for HMDB0036100 (3,7-Dimethyl-1,6-octadien-3-ol)

InChI=1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2,6-Dimethylocta-2,7-dien-6-olChEBI
3,7-Dimethylocta-1,6-dien-3-olChEBI
beta-LinaloolChEBI
Linalyl alcoholChEBI
(RS)-LinaloolKegg
b-LinaloolGenerator
Β-linaloolGenerator
7-Methyl-3-methyleneocta-4,6-dien-2-olMeSH
Allo-ocimenolMeSH
Linalool, (+-)-isomerMeSH
Linalool, (R)-isomerMeSH
Linalool, (S)-isomerMeSH
Linalool, titanium (4+) saltMeSH
MuguolMeSH
2,6-Dimethyl-2,7-octadien-6-olHMDB
2,6-Dimethyl-2,7-octadiene-6-olHMDB
3,7-Dimethyl-1, 6-octadien-3-olHMDB
FEMA 2635HMDB
LinalolHMDB
LinaloolHMDB
Linalool bHMDB
LinanoolHMDB
LinoloolHMDB
3,7-Dimethyl-1,6-octadien-3-olMeSH
Chemical FormulaC10H18O
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
IUPAC Name3,7-dimethylocta-1,6-dien-3-ol
Traditional Namelinalool, (+-)-
CAS Registry Number78-70-6
SMILES
CC(C)=CCCC(C)(O)C=C
InChI Identifier
InChI=1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3
InChI KeyCDOSHBSSFJOMGT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point194.00 to 197.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1.59 mg/mL at 25 °CNot Available
LogP2.97Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.48 g/LALOGPS
logP2.68ALOGPS
logP2.65ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)18.46ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.21 m³·mol⁻¹ChemAxon
Polarizability19.31 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.71231661259
DarkChem[M-H]-134.49831661259
DeepCCS[M+H]+138.16430932474
DeepCCS[M-H]-134.33630932474
DeepCCS[M-2H]-171.78530932474
DeepCCS[M+Na]+147.32330932474
AllCCS[M+H]+137.032859911
AllCCS[M+H-H2O]+132.932859911
AllCCS[M+NH4]+140.832859911
AllCCS[M+Na]+141.932859911
AllCCS[M-H]-136.332859911
AllCCS[M+Na-2H]-138.332859911
AllCCS[M+HCOO]-140.632859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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. 4.96 minutes32390414
Predicted by Siyang on May 30, 20229.7986 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.79 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid31.1 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1955.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid257.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid134.1 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid161.7 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid59.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid355.5 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid378.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)88.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid849.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid305.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid663.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid276.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid254.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate305.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA322.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water9.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,7-Dimethyl-1,6-octadien-3-olCC(C)=CCCC(C)(O)C=C1537.2Standard polar33892256
3,7-Dimethyl-1,6-octadien-3-olCC(C)=CCCC(C)(O)C=C1078.2Standard non polar33892256
3,7-Dimethyl-1,6-octadien-3-olCC(C)=CCCC(C)(O)C=C1098.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,7-Dimethyl-1,6-octadien-3-ol,1TMS,isomer #1C=CC(C)(CCC=C(C)C)O[Si](C)(C)C1221.7Semi standard non polar33892256
3,7-Dimethyl-1,6-octadien-3-ol,1TBDMS,isomer #1C=CC(C)(CCC=C(C)C)O[Si](C)(C)C(C)(C)C1445.1Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis		 details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014940
KNApSAcK IDC00003047
Chemspider ID13849981
KEGG Compound IDC03985
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLinalool
METLIN IDNot Available
PubChem Compound6549
PDB IDNot Available
ChEBI ID17580
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1007872
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  6. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  7. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.