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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:37:15 UTC

Update Date

2022-03-07 02:54:13 UTC

HMDB ID

HMDB0034718

Secondary Accession Numbers

HMDB34718

Metabolite Identification

Common Name

Isospathulenol

Description

Isospathulenol belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Based on a literature review a significant number of articles have been published on Isospathulenol.

Structure

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

HMDB0034718
     RDKit          3D
Isospathulenol
 40 42  0  0  0  0  0  0  0  0999 V2000
   -1.4517    3.1620   -0.6738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6000    2.0006   -0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845    0.7972   -0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3689    0.4787   -1.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271   -0.7990   -0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6835   -1.1776    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5958   -2.6621    0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8844   -0.4815    1.6185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5166   -0.5849   -0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285   -0.3862    0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6775    0.3098   -0.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8880    1.6812   -0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6614    2.3619    0.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0389   -0.9219    0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1277   -0.7582    1.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1626   -2.2071   -0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    3.3381   -1.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5133    3.0161   -0.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177    4.0955   -0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1213    0.2273   -2.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1102    1.2665   -1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9099   -1.6229   -1.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7644   -0.6373    0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6533   -3.1500   -0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6427   -2.8691    1.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4121   -2.9573    1.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4804   -0.8924    2.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3759   -1.1208   -1.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6013    0.1142    1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4753    0.1897   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6507    1.7690    0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3366    2.2759   -0.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5236    2.2969    1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8249    3.4659    0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7888   -0.1798    2.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5618   -1.7383    1.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9235   -0.1282    0.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4661   -2.1825   -1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1929   -2.3030   -0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989   -3.0863    0.0041 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
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 13  2  1  0
  9  3  1  0
 14 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END


  Mrv0541 05061308022D          

 16 18  0  0  0  0            999 V2000
    3.8892    1.9504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6821   -0.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5684   -1.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9571   -1.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5246    1.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8225    1.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3654    0.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4142   -0.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3011    1.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671    0.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7234    0.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225   -0.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019   -0.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5033   -0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6460   -0.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0254   -1.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  7  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15  4  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034718

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2CCC(C)(O)C2C2C(CC1)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-9-5-6-11-13(14(11,2)3)12-10(9)7-8-15(12,4)16/h11-13,16H,5-8H2,1-4H3

> <INCHI_KEY>
FPRYGNYXOFHMLF-UHFFFAOYSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.3505

> <EXACT_MASS>
220.18271539

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.74934137184984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,1,2,5-tetramethyl-1H,1aH,1bH,2H,3H,4H,6H,7H,7aH-cyclopropa[e]azulen-2-ol

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
2.7292651129999994

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.743479134282556

> <JCHEM_PKA_STRONGEST_BASIC>
-0.72400222666481

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
67.1834

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,1,2,5-tetramethyl-1aH,1bH,3H,4H,6H,7H,7aH-cyclopropa[e]azulen-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0034718
     RDKit          3D
Isospathulenol
 40 42  0  0  0  0  0  0  0  0999 V2000
   -1.4517    3.1620   -0.6738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6000    2.0006   -0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845    0.7972   -0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3689    0.4787   -1.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271   -0.7990   -0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6835   -1.1776    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5958   -2.6621    0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8844   -0.4815    1.6185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5166   -0.5849   -0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285   -0.3862    0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6775    0.3098   -0.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8880    1.6812   -0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6614    2.3619    0.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0389   -0.9219    0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1277   -0.7582    1.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1626   -2.2071   -0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    3.3381   -1.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5133    3.0161   -0.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177    4.0955   -0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1213    0.2273   -2.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1102    1.2665   -1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9099   -1.6229   -1.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7644   -0.6373    0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6533   -3.1500   -0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6427   -2.8691    1.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4121   -2.9573    1.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4804   -0.8924    2.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3759   -1.1208   -1.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6013    0.1142    1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4753    0.1897   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6507    1.7690    0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3366    2.2759   -0.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5236    2.2969    1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8249    3.4659    0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7888   -0.1798    2.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5618   -1.7383    1.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9235   -0.1282    0.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4661   -2.1825   -1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1929   -2.3030   -0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989   -3.0863    0.0041 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
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 13  2  1  0
  9  3  1  0
 14 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  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       7.260   3.641   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.273  -0.593   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.928  -2.275   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.520  -2.232   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.713   3.081   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.402   2.273   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.149   0.715   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.240  -0.823   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.162   2.561   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.659   1.103   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.217   0.744   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.829  -0.194   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.297  -0.354   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.806  -0.740   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.806  -1.384   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.514  -2.752   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    6    9                                                       
CONECT    6    5   11                                                       
CONECT    7    8   10                                                       
CONECT    8    7   15                                                       
CONECT    9    1    5   10                                                  
CONECT   10    7    9   12                                                  
CONECT   11    6   13   14                                                  
CONECT   12   10   13   15                                                  
CONECT   13   11   12   14                                                  
CONECT   14    2    3   11   13                                             
CONECT   15    4    8   12   16                                             
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0034718
HETATM    1  C1  UNL     1      -1.452   3.162  -0.674  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.600   2.001  -0.256  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.085   0.797  -0.541  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.369   0.479  -1.222  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.827  -0.799  -0.502  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.683  -1.178   0.435  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.596  -2.662   0.635  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.884  -0.482   1.618  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.517  -0.585  -0.277  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.729  -0.386   0.478  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.678   0.310  -0.544  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.888   1.681  -0.058  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.661   2.362   0.429  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.039  -0.922   0.178  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.128  -0.758   1.213  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.163  -2.207  -0.616  1.00  0.00           C  
HETATM   17  H1  UNL     1      -1.415   3.338  -1.761  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.513   3.016  -0.315  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.118   4.095  -0.176  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.121   0.227  -2.289  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.110   1.266  -1.176  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.910  -1.623  -1.241  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.764  -0.637   0.033  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.653  -3.150  -0.352  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.643  -2.869   1.160  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.412  -2.957   1.324  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.480  -0.892   2.403  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.376  -1.121  -1.236  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.601   0.114   1.459  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.475   0.190  -1.614  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.651   1.769   0.756  1.00  0.00           H  
HETATM   32  H16 UNL     1       2.337   2.276  -0.904  1.00  0.00           H  
HETATM   33  H17 UNL     1       0.524   2.297   1.536  1.00  0.00           H  
HETATM   34  H18 UNL     1       0.825   3.466   0.253  1.00  0.00           H  
HETATM   35  H19 UNL     1       2.789  -0.180   2.088  1.00  0.00           H  
HETATM   36  H20 UNL     1       3.562  -1.738   1.515  1.00  0.00           H  
HETATM   37  H21 UNL     1       3.923  -0.128   0.720  1.00  0.00           H  
HETATM   38  H22 UNL     1       1.466  -2.183  -1.496  1.00  0.00           H  
HETATM   39  H23 UNL     1       3.193  -2.303  -0.988  1.00  0.00           H  
HETATM   40  H24 UNL     1       1.899  -3.086   0.004  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3   13
CONECT    3    4    9
CONECT    4    5   20   21
CONECT    5    6   22   23
CONECT    6    7    8    9
CONECT    7   24   25   26
CONECT    8   27
CONECT    9   10   28
CONECT   10   11   14   29
CONECT   11   12   14   30
CONECT   12   13   31   32
CONECT   13   33   34
CONECT   14   15   16
CONECT   15   35   36   37
CONECT   16   38   39   40
END

HMDB0034718
     RDKit          3D
Isospathulenol
 40 42  0  0  0  0  0  0  0  0999 V2000
   -1.4517    3.1620   -0.6738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6000    2.0006   -0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845    0.7972   -0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3689    0.4787   -1.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271   -0.7990   -0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6835   -1.1776    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5958   -2.6621    0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8844   -0.4815    1.6185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5166   -0.5849   -0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285   -0.3862    0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6775    0.3098   -0.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8880    1.6812   -0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6614    2.3619    0.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0389   -0.9219    0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1277   -0.7582    1.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1626   -2.2071   -0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154    3.3381   -1.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5133    3.0161   -0.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177    4.0955   -0.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1213    0.2273   -2.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1102    1.2665   -1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9099   -1.6229   -1.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7644   -0.6373    0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6533   -3.1500   -0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6427   -2.8691    1.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4121   -2.9573    1.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4804   -0.8924    2.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3759   -1.1208   -1.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6013    0.1142    1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4753    0.1897   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6507    1.7690    0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3366    2.2759   -0.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5236    2.2969    1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8249    3.4659    0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7888   -0.1798    2.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5618   -1.7383    1.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9235   -0.1282    0.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4661   -2.1825   -1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1929   -2.3030   -0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989   -3.0863    0.0041 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
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 13  2  1  0
  9  3  1  0
 14 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isosparthulenol	HMDB

Chemical Formula

C₁₅H₂₄O

Average Molecular Weight

220.3505

Monoisotopic Molecular Weight

220.18271539

IUPAC Name

1,1,2,5-tetramethyl-1H,1aH,1bH,2H,3H,4H,6H,7H,7aH-cyclopropa[e]azulen-2-ol

Traditional Name

1,1,2,5-tetramethyl-1aH,1bH,3H,4H,6H,7H,7aH-cyclopropa[e]azulen-2-ol

CAS Registry Number

88395-46-4

SMILES

CC1=C2CCC(C)(O)C2C2C(CC1)C2(C)C

InChI Identifier

InChI=1S/C15H24O/c1-9-5-6-11-13(14(11,2)3)12-10(9)7-8-15(12,4)16/h11-13,16H,5-8H2,1-4H3

InChI Key

FPRYGNYXOFHMLF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

5,10-cycloaromadendrane sesquiterpenoids

Alternative Parents

Substituents

5,10-cycloaromadendrane 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

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034718)

Source

Endogenous

Endogenous (HMDB: HMDB0034718)

Plant

Plant (HMDB: HMDB0034718)

Animal

Animal (HMDB: HMDB0034718)

Exogenous

Food

Food (HMDB: HMDB0034718)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0034718)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034718)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034718)

Lipid metabolism pathway (HMDB: HMDB0034718)

Cellular process

Cell signaling (HMDB: HMDB0034718)

Biochemical process

Lipid transport (HMDB: HMDB0034718)

Role

Biological role

Energy source (HMDB: HMDB0034718)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034718)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	69 - 70.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	12.44 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	2.62	ALOGPS
logP	2.73	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	19.74	ChemAxon
pKa (Strongest Basic)	-0.72	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	0	ChemAxon
Refractivity	67.18 m³·mol⁻¹	ChemAxon
Polarizability	26.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.843	31661259
DarkChem	[M-H]-	147.694	31661259
DeepCCS	[M+H]+	156.94	30932474
DeepCCS	[M-H]-	154.582	30932474
DeepCCS	[M-2H]-	187.778	30932474
DeepCCS	[M+Na]+	163.033	30932474
AllCCS	[M+H]+	151.2	32859911
AllCCS	[M+H-H2O]+	147.4	32859911
AllCCS	[M+NH4]+	154.7	32859911
AllCCS	[M+Na]+	155.7	32859911
AllCCS	[M-H]-	161.1	32859911
AllCCS	[M+Na-2H]-	161.3	32859911
AllCCS	[M+HCOO]-	161.8	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.	5.07 minutes	32390414
Predicted by Siyang on May 30, 2022	17.1551 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.82 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2426.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	546.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	208.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	257.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	267.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	717.8 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	824.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	111.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1267.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	437.5 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	1453.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	482.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	397.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	434.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	624.0 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	11.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isospathulenol	CC1=C2CCC(C)(O)C2C2C(CC1)C2(C)C	2168.9	Standard polar	33892256
Isospathulenol	CC1=C2CCC(C)(O)C2C2C(CC1)C2(C)C	1605.8	Standard non polar	33892256
Isospathulenol	CC1=C2CCC(C)(O)C2C2C(CC1)C2(C)C	1601.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isospathulenol,1TMS,isomer #1	CC1=C2CCC(C)(O[Si](C)(C)C)C2C2C(CC1)C2(C)C	1764.8	Semi standard non polar	33892256
Isospathulenol,1TBDMS,isomer #1	CC1=C2CCC(C)(O[Si](C)(C)C(C)(C)C)C2C2C(CC1)C2(C)C	2011.0	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 - Isospathulenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-069u-9720000000-b1f45ea827373a765c89	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isospathulenol GC-MS (1 TMS) - 70eV, Positive	splash10-01ta-7390000000-0d1d94ea69b0c98aa5de	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isospathulenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isospathulenol 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 - Isospathulenol 10V, Positive-QTOF	splash10-0uk9-0190000000-64608f40884dcabeb671	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isospathulenol 20V, Positive-QTOF	splash10-0uk9-0690000000-acf9593654e86ca67d21	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isospathulenol 40V, Positive-QTOF	splash10-01p2-6900000000-5b2cc54e3dca096fc85b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isospathulenol 10V, Negative-QTOF	splash10-014i-0090000000-84d25a63bc4b24bc8775	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isospathulenol 20V, Negative-QTOF	splash10-014i-0190000000-a918377ce2107928f12f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isospathulenol 40V, Negative-QTOF	splash10-0uki-2930000000-dda937c913f3fdf86d99	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isospathulenol 10V, Negative-QTOF	splash10-014i-0090000000-4af4c4ee1c4acef7e18b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isospathulenol 20V, Negative-QTOF	splash10-014i-0090000000-4af4c4ee1c4acef7e18b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isospathulenol 40V, Negative-QTOF	splash10-014j-0790000000-18b349645ca8a56e23ba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isospathulenol 10V, Positive-QTOF	splash10-0uk9-0190000000-c6ae28103e1d148fb75c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isospathulenol 20V, Positive-QTOF	splash10-00fr-9540000000-1fdb440d851eb1080d43	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isospathulenol 40V, Positive-QTOF	splash10-017l-9410000000-5bedb2c299fdfad45d12	2021-09-22	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

FDB013254

KNApSAcK ID

C00021236

Chemspider ID

35013777

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14038848

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1565681

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 Isospathulenol (HMDB0034718)

MOL for HMDB0034718 (Isospathulenol)

3D MOL for HMDB0034718 (Isospathulenol)

3D SDF for HMDB0034718 (Isospathulenol)

3D-SDF for HMDB0034718 (Isospathulenol)

PDB for HMDB0034718 (Isospathulenol)

3D PDB for HMDB0034718 (Isospathulenol)

SMILES for HMDB0034718 (Isospathulenol)

INCHI for HMDB0034718 (Isospathulenol)

Structure for HMDB0034718 (Isospathulenol)

3D Structure for HMDB0034718 (Isospathulenol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra