Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 21:48:39 UTC

Update Date

2022-03-07 02:55:00 UTC

HMDB ID

HMDB0036648

Secondary Accession Numbers

HMDB36648

Metabolite Identification

Common Name

7-Isopropyl-1,4-dimethylazulene

Description

7-Isopropyl-1,4-dimethylazulene, also known as 1,4-dimethyl-7-isopropylazulene or 1,4-dimethyl-7-(1-methylethyl)azulene, belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. Thus, 7-isopropyl-1,4-dimethylazulene is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on 7-Isopropyl-1,4-dimethylazulene.

Structure

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

HMDB0036648
     RDKit          3D
7-Isopropyl-1,4-dimethylazulene
 33 34  0  0  0  0  0  0  0  0999 V2000
   -2.6331    2.8028    0.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5422    1.8458    0.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177    2.3953   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8627    1.7656   -0.4674 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2778    0.4588   -0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7362    0.2021   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154   -0.7300   -1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1549   -0.2993    1.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237   -0.6140   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707   -0.6387    0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7686   -1.7396    0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923   -3.1443    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0813   -1.3145    0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1518    0.0553    0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8637    0.5143    0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2545    3.8373    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0683    2.5990    1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3989    2.6809   -0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3054    3.4723   -0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6192    2.3985   -0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2497    1.1798   -0.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504   -0.3582   -1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3921   -1.7668   -0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4494   -0.7581   -2.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9861    0.3221    1.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3401   -0.3453    1.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6217   -1.3179    1.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751   -1.5783   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1911   -3.8250   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7663   -3.4447    0.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7046   -3.3631   -0.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9801   -1.9469    0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0638    0.6547    0.2354 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15  2  1  0
 15 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
M  END


  Mrv0541 05061309162D          

 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  2  0  0  0  0
  8  6  2  0  0  0  0
 10  1  1  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  2  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  2  0  0  0  0
 15  9  1  0  0  0  0
 15 12  2  0  0  0  0
 15 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036648

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=CC2=C(C)C=CC2=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3

> <INCHI_KEY>
FWKQNCXZGNBPFD-UHFFFAOYSA-N

> <FORMULA>
C15H18

> <MOLECULAR_WEIGHT>
198.3034

> <EXACT_MASS>
198.140850576

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
25.033583274767327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-dimethyl-7-(propan-2-yl)azulene

> <ALOGPS_LOGP>
4.99

> <JCHEM_LOGP>
5.234574501999999

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
66.78140000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
azulon

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036648
     RDKit          3D
7-Isopropyl-1,4-dimethylazulene
 33 34  0  0  0  0  0  0  0  0999 V2000
   -2.6331    2.8028    0.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5422    1.8458    0.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177    2.3953   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8627    1.7656   -0.4674 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2778    0.4588   -0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7362    0.2021   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154   -0.7300   -1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1549   -0.2993    1.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237   -0.6140   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707   -0.6387    0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7686   -1.7396    0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923   -3.1443    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0813   -1.3145    0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1518    0.0553    0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8637    0.5143    0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2545    3.8373    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0683    2.5990    1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3989    2.6809   -0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3054    3.4723   -0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6192    2.3985   -0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2497    1.1798   -0.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504   -0.3582   -1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3921   -1.7668   -0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4494   -0.7581   -2.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9861    0.3221    1.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3401   -0.3453    1.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6217   -1.3179    1.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751   -1.5783   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1911   -3.8250   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7663   -3.4447    0.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7046   -3.3631   -0.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9801   -1.9469    0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0638    0.6547    0.2354 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15  2  1  0
 15 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  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    HMDB0036648
HETATM    1  C1  UNL     1      -2.633   2.803   0.390  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.542   1.846   0.064  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.318   2.395  -0.222  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.863   1.766  -0.467  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.278   0.459  -0.240  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.736   0.202  -0.161  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.215  -0.730  -1.241  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.155  -0.299   1.200  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.424  -0.614  -0.082  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.971  -0.639   0.015  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.769  -1.740   0.066  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.292  -3.144   0.028  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.081  -1.314   0.159  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.152   0.055   0.170  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.864   0.514   0.082  1.00  0.00           C  
HETATM   16  H1  UNL     1      -2.254   3.837   0.299  1.00  0.00           H  
HETATM   17  H2  UNL     1      -3.068   2.599   1.383  1.00  0.00           H  
HETATM   18  H3  UNL     1      -3.399   2.681  -0.424  1.00  0.00           H  
HETATM   19  H4  UNL     1      -0.305   3.472  -0.253  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.619   2.399  -0.925  1.00  0.00           H  
HETATM   21  H6  UNL     1       3.250   1.180  -0.312  1.00  0.00           H  
HETATM   22  H7  UNL     1       4.150  -0.358  -1.721  1.00  0.00           H  
HETATM   23  H8  UNL     1       3.392  -1.767  -0.862  1.00  0.00           H  
HETATM   24  H9  UNL     1       2.449  -0.758  -2.043  1.00  0.00           H  
HETATM   25  H10 UNL     1       3.986   0.322   1.639  1.00  0.00           H  
HETATM   26  H11 UNL     1       2.340  -0.345   1.926  1.00  0.00           H  
HETATM   27  H12 UNL     1       3.622  -1.318   1.071  1.00  0.00           H  
HETATM   28  H13 UNL     1       0.875  -1.578  -0.023  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.191  -3.825  -0.032  1.00  0.00           H  
HETATM   30  H15 UNL     1      -0.766  -3.445   0.955  1.00  0.00           H  
HETATM   31  H16 UNL     1      -0.705  -3.363  -0.894  1.00  0.00           H  
HETATM   32  H17 UNL     1      -3.980  -1.947   0.220  1.00  0.00           H  
HETATM   33  H18 UNL     1      -4.064   0.655   0.235  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3   15
CONECT    3    4   19
CONECT    4    5    5   20
CONECT    5    6    9
CONECT    6    7    8   21
CONECT    7   22   23   24
CONECT    8   25   26   27
CONECT    9   10   10   28
CONECT   10   11   15
CONECT   11   12   13   13
CONECT   12   29   30   31
CONECT   13   14   32
CONECT   14   15   15   33
END

HMDB0036648
     RDKit          3D
7-Isopropyl-1,4-dimethylazulene
 33 34  0  0  0  0  0  0  0  0999 V2000
   -2.6331    2.8028    0.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5422    1.8458    0.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177    2.3953   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8627    1.7656   -0.4674 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2778    0.4588   -0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7362    0.2021   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154   -0.7300   -1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1549   -0.2993    1.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237   -0.6140   -0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707   -0.6387    0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7686   -1.7396    0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2923   -3.1443    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0813   -1.3145    0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1518    0.0553    0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8637    0.5143    0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2545    3.8373    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0683    2.5990    1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3989    2.6809   -0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3054    3.4723   -0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6192    2.3985   -0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2497    1.1798   -0.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504   -0.3582   -1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3921   -1.7668   -0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4494   -0.7581   -2.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9861    0.3221    1.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3401   -0.3453    1.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6217   -1.3179    1.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751   -1.5783   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1911   -3.8250   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7663   -3.4447    0.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7046   -3.3631   -0.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9801   -1.9469    0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0638    0.6547    0.2354 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15  2  1  0
 15 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,4-Dimethyl-7-(1-methylethyl)azulene	ChEBI
1,4-Dimethyl-7-isopropylazulene	ChEBI
3,8-Dimethyl-5-(2-propyl)azulene	ChEBI
Guaiazulene	Kegg
Azunol	Kegg
Guajazulene	MeSH
Azulon	MeSH
1, 4-Dimethyl-7-isopropylazulene	HMDB
1,3,5,7,9-Guaiapentaene	HMDB
1,4-Dimethyl-7-(1-methyl)-azulene (azulon)	HMDB
1,4-Dimethyl-7-(1-methylethyl)-azulene	HMDB
1,4-Dimethyl-7-(1-methylethyl)azulene, 9ci	HMDB
1,4-Dimethyl-7-(propan-2-yl)azulene	HMDB
1,4-Dimethyl-7-isopropyl-azulene	HMDB
7-Isopropyl- 1,4-dimethylazulene	HMDB
7-Isopropyl-1,4-dimethyl-azulene	HMDB
AZ-8 beris	HMDB
Azulen-beris	HMDB
Azulene, 7-isopropyl-1,4-dimethyl- (8ci)	HMDB
Azulol	HMDB
Cuteazul	HMDB
Eucazulen	HMDB
Eucazulene	HMDB
Guiazulene	HMDB
Gurjunazulen	HMDB
Hepatoprotectant	HMDB
Kessazulen	HMDB
Kessazulene	HMDB
Purazulen	HMDB
S-Guaiazulene	HMDB
Silazulon	HMDB
Uroazulen	HMDB
Vaumigan	HMDB
Vetivazulen	HMDB
7-Isopropyl-1,4-dimethylazulene	ChEBI

Chemical Formula

C₁₅H₁₈

Average Molecular Weight

198.3034

Monoisotopic Molecular Weight

198.140850576

IUPAC Name

1,4-dimethyl-7-(propan-2-yl)azulene

Traditional Name

azulon

CAS Registry Number

489-84-9

SMILES

CC(C)C1=CC2=C(C)C=CC2=C(C)C=C1

InChI Identifier

InChI=1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3

InChI Key

FWKQNCXZGNBPFD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Guaianes

Alternative Parents

Substituents

Guaiane sesquiterpenoid
Azulene
Aromatic hydrocarbon
Polycyclic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

sesquiterpene (CHEBI:5550 )
Guaiane sesquiterpenoids (C09675 )
Eudesmanes (C09675 )
Guaiane sesquiterpenoids (LMPR0103410006 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036648)

Source

Exogenous

Exogenous (HMDB: HMDB0036648)

Food

Food (HMDB: HMDB0036648)

Fruit

Other fruit

Fig (FooDB: FOOD00081)

Tea

Herb and spice

Herb

German camomile (FooDB: FOOD00107)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Endogenous (HMDB: HMDB0036648)

Plant

Plant (HMDB: HMDB0036648)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036648)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036648)

Lipid metabolism pathway (HMDB: HMDB0036648)

Cellular process

Cell signaling (HMDB: HMDB0036648)

Biochemical process

Lipid transport (HMDB: HMDB0036648)

Role

Biological role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036648)

Anti-allergic agent (HMDB: HMDB0036648)
Antipyretic (HMDB: HMDB0036648)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0036648)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	31.5 °C	Not Available
Boiling Point	152.00 to 154.00 °C. @ 7.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.00066 mg/mL at 25 °C	Not Available
LogP	5.590 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	4.99	ALOGPS
logP	5.23	ChemAxon
logS	-3.2	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	66.78 m³·mol⁻¹	ChemAxon
Polarizability	25.03 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	145.754	31661259
DarkChem	[M-H]-	147.104	31661259
DeepCCS	[M+H]+	154.398	30932474
DeepCCS	[M-H]-	152.04	30932474
DeepCCS	[M-2H]-	185.062	30932474
DeepCCS	[M+Na]+	160.491	30932474
AllCCS	[M+H]+	140.0	32859911
AllCCS	[M+H-H2O]+	135.8	32859911
AllCCS	[M+NH4]+	144.0	32859911
AllCCS	[M+Na]+	145.2	32859911
AllCCS	[M-H]-	149.6	32859911
AllCCS	[M+Na-2H]-	149.7	32859911
AllCCS	[M+HCOO]-	149.8	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.	8.25 minutes	32390414
Predicted by Siyang on May 30, 2022	19.4858 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.84 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2169.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	677.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	259.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	410.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	410.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	799.3 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	835.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	163.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1711.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	707.6 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	1743.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	590.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	469.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	456.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	334.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-Isopropyl-1,4-dimethylazulene	CC(C)C1=CC2=C(C)C=CC2=C(C)C=C1	2388.2	Standard polar	33892256
7-Isopropyl-1,4-dimethylazulene	CC(C)C1=CC2=C(C)C=CC2=C(C)C=C1	1764.9	Standard non polar	33892256
7-Isopropyl-1,4-dimethylazulene	CC(C)C1=CC2=C(C)C=CC2=C(C)C=C1	1774.8	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 - 7-Isopropyl-1,4-dimethylazulene GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-1900000000-be4c0960d06735436fe8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Isopropyl-1,4-dimethylazulene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Isopropyl-1,4-dimethylazulene 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 - 7-Isopropyl-1,4-dimethylazulene 10V, Positive-QTOF	splash10-0002-0900000000-3339d5b27a9967e9c5da	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Isopropyl-1,4-dimethylazulene 20V, Positive-QTOF	splash10-0002-0900000000-44d06797d9da8aaae9dc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Isopropyl-1,4-dimethylazulene 40V, Positive-QTOF	splash10-05o0-1900000000-6fe86a22e14c459ce6d6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Isopropyl-1,4-dimethylazulene 10V, Negative-QTOF	splash10-0002-0900000000-48f7566ceaa93d43c699	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Isopropyl-1,4-dimethylazulene 20V, Negative-QTOF	splash10-0002-0900000000-ee4c5f9ee7e99d6db7ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Isopropyl-1,4-dimethylazulene 40V, Negative-QTOF	splash10-05o1-1900000000-e4e77ed98ea343b05eb3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Isopropyl-1,4-dimethylazulene 10V, Positive-QTOF	splash10-0002-0900000000-5b7ed2802511ed884e20	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Isopropyl-1,4-dimethylazulene 20V, Positive-QTOF	splash10-052b-0900000000-0415b7647d084754c1b7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Isopropyl-1,4-dimethylazulene 40V, Positive-QTOF	splash10-0fc0-3900000000-4121eb3d95203bd3b5ba	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Isopropyl-1,4-dimethylazulene 10V, Negative-QTOF	splash10-0002-0900000000-77af6775e009aeaad051	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Isopropyl-1,4-dimethylazulene 20V, Negative-QTOF	splash10-0002-0900000000-724c6ec495f7c5a30ebc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Isopropyl-1,4-dimethylazulene 40V, Negative-QTOF	splash10-0a4i-0900000000-998e7ebc0a1ed3713a46	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13329

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

3515

PDB ID

Not Available

ChEBI ID

5550

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1248821

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 7-Isopropyl-1,4-dimethylazulene (HMDB0036648)

MOL for HMDB0036648 (7-Isopropyl-1,4-dimethylazulene)

3D MOL for HMDB0036648 (7-Isopropyl-1,4-dimethylazulene)

3D SDF for HMDB0036648 (7-Isopropyl-1,4-dimethylazulene)

3D-SDF for HMDB0036648 (7-Isopropyl-1,4-dimethylazulene)

PDB for HMDB0036648 (7-Isopropyl-1,4-dimethylazulene)

3D PDB for HMDB0036648 (7-Isopropyl-1,4-dimethylazulene)

SMILES for HMDB0036648 (7-Isopropyl-1,4-dimethylazulene)

INCHI for HMDB0036648 (7-Isopropyl-1,4-dimethylazulene)

Structure for HMDB0036648 (7-Isopropyl-1,4-dimethylazulene)

3D Structure for HMDB0036648 (7-Isopropyl-1,4-dimethylazulene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra