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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:44:15 UTC

Update Date

2022-03-07 02:54:58 UTC

HMDB ID

HMDB0036579

Secondary Accession Numbers

HMDB36579

Metabolite Identification

Common Name

Carotol

Description

Carotol is found in carrot. Carotol is a constituent of Daucus carota (carrot) Carotol was first isolated by scientists Asahina and Tsukamoto in 1925. It is one of the primary components found in carrot seed oil comprising approximately 40% of this essential oil. This sesquiterpene alcohol is thought to be formed in carrot seeds (Daucus carota L., Umbelliferae) during the vegetation period. Additionally, studies have shown that carotol may be involved in allelopathic interactions expressing activity as a antifungal, herbicidal and insecticidal agent. It has been proposed that there is a direct cyclisation of farnesyl pyrophosphate (FPP) to the carotol (carotane backbone). This type of cyclisation is unconventional for the typical chemistry of sesquiterpenes. The only other proposed mechanism requires a complex ten-membered ring with a methyl migration. This later reaction, regardless of how plausible it may appear to be on paper, is energetically undesired and through the diligent work of M. Soucek and coworkers it was shown that the cyclization from FPP to carotol is the most probable biosynthesis route.

Structure

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

HMDB0036579
     RDKit          3D
Carotol
 42 43  0  0  0  0  0  0  0  0999 V2000
    3.5704    1.7384    0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5767    0.6317    0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7638   -0.3027   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9504   -1.4951   -0.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4931   -1.3384   -0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1003   -2.0934    0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2506   -1.9785   -1.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5970   -1.3340   -1.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2766    0.1351   -1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4846    0.7470   -0.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0350    0.2087    0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3990    2.2596   -0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0070    0.0807   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9534    0.7403   -1.1527 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0964    0.8046    0.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4646    0.6615    1.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5881    1.3014    0.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3929    2.2863    1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5259    2.3674   -0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6564   -0.1204   -0.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3572   -2.3324    0.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537   -1.7765   -1.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4340   -1.5500    1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0349   -2.4972    1.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5000   -3.0168    0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3024   -3.0708   -1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2327   -1.6274   -2.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1107   -1.4439   -2.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2502   -1.7665   -0.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2093    0.6014   -2.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2934    0.5976   -1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1371    0.0418    0.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6285   -0.7625    1.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9439    0.9936    1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5775    2.6731   -0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3272    2.7532   -0.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3191    2.5164    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6340    0.8210   -2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0115    1.8869    0.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6058    0.4820    1.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145    1.4678    2.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5409   -0.2906    2.2180 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
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16  2  1  0
 13  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END


  Mrv0541 05061309122D          

 16 17  0  0  0  0            999 V2000
    0.8611   -1.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2201   -2.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603    1.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680   -1.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603   -1.4297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14  4  1  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036579

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1CCC2(C)CC=C(C)CCC12O

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-11(2)13-7-9-14(4)8-5-12(3)6-10-15(13,14)16/h5,11,13,16H,6-10H2,1-4H3

> <INCHI_KEY>
XZYQCFABZDVOPN-UHFFFAOYSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.3663

> <EXACT_MASS>
222.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.505297290574735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-3a-ol

> <ALOGPS_LOGP>
4.65

> <JCHEM_LOGP>
3.785609167666667

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.26190218001724463

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
69.12599999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carotol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036579
     RDKit          3D
Carotol
 42 43  0  0  0  0  0  0  0  0999 V2000
    3.5704    1.7384    0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5767    0.6317    0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7638   -0.3027   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9504   -1.4951   -0.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4931   -1.3384   -0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1003   -2.0934    0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2506   -1.9785   -1.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5970   -1.3340   -1.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2766    0.1351   -1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4846    0.7470   -0.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0350    0.2087    0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3990    2.2596   -0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0070    0.0807   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9534    0.7403   -1.1527 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0964    0.8046    0.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4646    0.6615    1.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5881    1.3014    0.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3929    2.2863    1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5259    2.3674   -0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6564   -0.1204   -0.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3572   -2.3324    0.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537   -1.7765   -1.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4340   -1.5500    1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0349   -2.4972    1.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5000   -3.0168    0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3024   -3.0708   -1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2327   -1.6274   -2.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1107   -1.4439   -2.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2502   -1.7665   -0.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2093    0.6014   -2.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2934    0.5976   -1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1371    0.0418    0.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6285   -0.7625    1.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9439    0.9936    1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5775    2.6731   -0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3272    2.7532   -0.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3191    2.5164    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6340    0.8210   -2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0115    1.8869    0.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6058    0.4820    1.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145    1.4678    2.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5409   -0.2906    2.2180 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
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16  2  1  0
 13  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  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       1.607  -3.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.144  -4.238   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.968  -0.384   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.779   1.902   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.760  -1.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.114  -3.094   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590  -1.629   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.779  -2.669   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   14                                                            
CONECT    5    8   12                                                       
CONECT    6   10   12                                                       
CONECT    7    9   13                                                       
CONECT    8    5   14                                                       
CONECT    9    7   14                                                       
CONECT   10    6   15                                                       
CONECT   11    1    2   13                                                  
CONECT   12    3    5    6                                                  
CONECT   13    7   11   15                                                  
CONECT   14    4    8    9   15                                             
CONECT   15   10   13   14   16                                             
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0036579
HETATM    1  C1  UNL     1       3.570   1.738   0.731  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.577   0.632   0.652  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.764  -0.303  -0.277  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.950  -1.495  -0.578  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.493  -1.338  -0.271  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.100  -2.093   0.939  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.251  -1.978  -1.454  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.597  -1.334  -1.323  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.277   0.135  -1.021  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.485   0.747  -0.435  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.035   0.209   0.815  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.399   2.260  -0.347  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.007   0.081  -0.330  1.00  0.00           C  
HETATM   14  O1  UNL     1       0.953   0.740  -1.153  1.00  0.00           O  
HETATM   15  C14 UNL     1       0.096   0.805   0.982  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.465   0.661   1.613  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.588   1.301   0.804  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.393   2.286   1.669  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.526   2.367  -0.172  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.656  -0.120  -0.876  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.357  -2.332   0.039  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.154  -1.776  -1.638  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.434  -1.550   1.710  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.035  -2.497   1.424  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.500  -3.017   0.714  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.302  -3.071  -1.352  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.233  -1.627  -2.381  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.111  -1.444  -2.306  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.250  -1.766  -0.571  1.00  0.00           H  
HETATM   30  H14 UNL     1      -1.209   0.601  -2.045  1.00  0.00           H  
HETATM   31  H15 UNL     1      -3.293   0.598  -1.224  1.00  0.00           H  
HETATM   32  H16 UNL     1      -4.137   0.042   0.754  1.00  0.00           H  
HETATM   33  H17 UNL     1      -2.629  -0.762   1.153  1.00  0.00           H  
HETATM   34  H18 UNL     1      -2.944   0.994   1.625  1.00  0.00           H  
HETATM   35  H19 UNL     1      -1.578   2.673  -0.955  1.00  0.00           H  
HETATM   36  H20 UNL     1      -3.327   2.753  -0.701  1.00  0.00           H  
HETATM   37  H21 UNL     1      -2.319   2.516   0.728  1.00  0.00           H  
HETATM   38  H22 UNL     1       0.634   0.821  -2.068  1.00  0.00           H  
HETATM   39  H23 UNL     1      -0.011   1.887   0.771  1.00  0.00           H  
HETATM   40  H24 UNL     1      -0.606   0.482   1.744  1.00  0.00           H  
HETATM   41  H25 UNL     1       1.615   1.468   2.392  1.00  0.00           H  
HETATM   42  H26 UNL     1       1.541  -0.291   2.218  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3   16
CONECT    3    4   20
CONECT    4    5   21   22
CONECT    5    6    7   13
CONECT    6   23   24   25
CONECT    7    8   26   27
CONECT    8    9   28   29
CONECT    9   10   13   30
CONECT   10   11   12   31
CONECT   11   32   33   34
CONECT   12   35   36   37
CONECT   13   14   15
CONECT   14   38
CONECT   15   16   39   40
CONECT   16   41   42
END

HMDB0036579
     RDKit          3D
Carotol
 42 43  0  0  0  0  0  0  0  0999 V2000
    3.5704    1.7384    0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5767    0.6317    0.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7638   -0.3027   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9504   -1.4951   -0.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4931   -1.3384   -0.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1003   -2.0934    0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2506   -1.9785   -1.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5970   -1.3340   -1.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2766    0.1351   -1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4846    0.7470   -0.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0350    0.2087    0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3990    2.2596   -0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0070    0.0807   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9534    0.7403   -1.1527 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0964    0.8046    0.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4646    0.6615    1.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5881    1.3014    0.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3929    2.2863    1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5259    2.3674   -0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6564   -0.1204   -0.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3572   -2.3324    0.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537   -1.7765   -1.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4340   -1.5500    1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0349   -2.4972    1.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5000   -3.0168    0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3024   -3.0708   -1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2327   -1.6274   -2.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1107   -1.4439   -2.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2502   -1.7665   -0.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2093    0.6014   -2.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2934    0.5976   -1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1371    0.0418    0.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6285   -0.7625    1.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9439    0.9936    1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5775    2.6731   -0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3272    2.7532   -0.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3191    2.5164    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6340    0.8210   -2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0115    1.8869    0.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6058    0.4820    1.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6145    1.4678    2.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5409   -0.2906    2.2180 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
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16  2  1  0
 13  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Carotol	HMDB
cis-Dauc-8-en-5beta -ol (carotol)	HMDB

Chemical Formula

C₁₅H₂₆O

Average Molecular Weight

222.3663

Monoisotopic Molecular Weight

222.198365454

IUPAC Name

6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-3a-ol

Traditional Name

carotol

CAS Registry Number

465-28-1

SMILES

CC(C)C1CCC2(C)CC=C(C)CCC12O

InChI Identifier

InChI=1S/C15H26O/c1-11(2)13-7-9-14(4)8-5-12(3)6-10-15(13,14)16/h5,11,13,16H,6-10H2,1-4H3

InChI Key

XZYQCFABZDVOPN-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

Daucane sesquiterpenoid
Sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036579)

Source

Endogenous

Endogenous (HMDB: HMDB0036579)

Plant

Plant (HMDB: HMDB0036579)

Animal

Animal (HMDB: HMDB0036579)

Exogenous

Food

Food (HMDB: HMDB0036579)

Parsley (FooDB: FOOD00131)

Exogenous (HMDB: HMDB0036579)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036579)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036579)

Lipid metabolism pathway (HMDB: HMDB0036579)

Cellular process

Cell signaling (HMDB: HMDB0036579)

Biochemical process

Lipid transport (HMDB: HMDB0036579)

Role

Biological role

Energy source (HMDB: HMDB0036579)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036579)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	109.00 °C. @ 1.50 mm Hg	The Good Scents Company Information System
Water Solubility	8.51 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.465 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.08 g/L	ALOGPS
logP	4.65	ALOGPS
logP	3.79	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	0.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.13 m³·mol⁻¹	ChemAxon
Polarizability	27.51 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]+	153.58	31661259
DarkChem	[M-H]-	150.65	31661259
DeepCCS	[M-2H]-	186.105	30932474
DeepCCS	[M+Na]+	161.684	30932474
AllCCS	[M+H]+	153.3	32859911
AllCCS	[M+H-H2O]+	149.5	32859911
AllCCS	[M+NH4]+	156.8	32859911
AllCCS	[M+Na]+	157.8	32859911
AllCCS	[M-H]-	161.9	32859911
AllCCS	[M+Na-2H]-	162.6	32859911
AllCCS	[M+HCOO]-	163.4	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.	6.43 minutes	32390414
Predicted by Siyang on May 30, 2022	17.2235 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.07 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2464.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	519.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	203.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	258.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	230.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	795.3 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	766.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	78.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1392.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	470.4 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	1342.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	534.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	383.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	369.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	589.4 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Carotol	CC(C)C1CCC2(C)CC=C(C)CCC12O	2057.7	Standard polar	33892256
Carotol	CC(C)C1CCC2(C)CC=C(C)CCC12O	1614.5	Standard non polar	33892256
Carotol	CC(C)C1CCC2(C)CC=C(C)CCC12O	1588.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Carotol,1TMS,isomer #1	CC1=CCC2(C)CCC(C(C)C)C2(O[Si](C)(C)C)CC1	1700.3	Semi standard non polar	33892256
Carotol,1TBDMS,isomer #1	CC1=CCC2(C)CCC(C(C)C)C2(O[Si](C)(C)C(C)(C)C)CC1	1950.2	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 - Carotol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udl-3910000000-78f3009388119ba724c3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carotol GC-MS (1 TMS) - 70eV, Positive	splash10-0200-3090000000-3adcde312055f37d2461	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carotol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carotol 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 - Carotol 10V, Positive-QTOF	splash10-0ab9-0190000000-010a0378a3d865b1ef1f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carotol 20V, Positive-QTOF	splash10-05ai-8790000000-043981cd1e8aad9f50d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carotol 40V, Positive-QTOF	splash10-05o9-9500000000-11dacc05a509cf2d394d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carotol 10V, Negative-QTOF	splash10-00di-0090000000-c229abad4ae29b356be0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carotol 20V, Negative-QTOF	splash10-00di-0190000000-df9ec002da314b33f3c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carotol 40V, Negative-QTOF	splash10-0k9i-2920000000-0ece9f40f0637b7b5de4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carotol 10V, Positive-QTOF	splash10-00di-0190000000-d9db26ad9ef6f66807a2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carotol 20V, Positive-QTOF	splash10-007c-7910000000-914b81f58b5c346b0489	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carotol 40V, Positive-QTOF	splash10-0a4u-9400000000-700ae1733923d3b829e7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carotol 10V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carotol 20V, Negative-QTOF	splash10-00di-0090000000-caa5a644e1dcbfa0bac5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carotol 40V, Negative-QTOF	splash10-0079-0920000000-754708042fa30dc4ff14	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carotol

METLIN ID

Not Available

PubChem Compound

287687

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1014541

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 Carotol (HMDB0036579)

MOL for HMDB0036579 (Carotol)

3D MOL for HMDB0036579 (Carotol)

3D SDF for HMDB0036579 (Carotol)

3D-SDF for HMDB0036579 (Carotol)

PDB for HMDB0036579 (Carotol)

3D PDB for HMDB0036579 (Carotol)

SMILES for HMDB0036579 (Carotol)

INCHI for HMDB0036579 (Carotol)

Structure for HMDB0036579 (Carotol)

3D Structure for HMDB0036579 (Carotol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra