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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:56:33 UTC

Update Date

2022-03-07 02:53:38 UTC

HMDB ID

HMDB0033229

Secondary Accession Numbers

HMDB33229

Metabolite Identification

Common Name

Absindiol

Description

Absindiol belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Based on a literature review a small amount of articles have been published on Absindiol.

Structure

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

HMDB0033229
     RDKit          3D
Absindiol
 41 43  0  0  0  0  0  0  0  0999 V2000
    1.5794    2.3640   -1.8909 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7402    1.4368   -0.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8753    1.3799   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2212    2.6169    0.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2851    0.4726    1.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5805   -0.5390    0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429   -1.5086    0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676   -2.6593    1.4098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3309   -2.1231    0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6442   -1.3930    0.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6404   -2.2341   -0.2635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5783   -0.1882   -0.6573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8574    0.6157   -0.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5610    0.6149    0.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3177    1.9983   -0.9183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0606    2.9475   -1.2535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9412    1.9893   -0.7210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5150    0.7715   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8016    0.3066   -0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7332    2.3802   -2.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3201    3.1526   -1.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6960    0.8342   -0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0596    2.9326    0.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6120    1.0856    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0794    0.0467    1.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3508   -1.0814   -0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3436   -1.0983    1.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1278   -3.4465    1.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442   -3.0272    0.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4934   -2.2482    2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0116   -2.1122   -0.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5090   -3.1716    0.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8838   -1.1250    1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5407   -2.2499   -1.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3380   -0.5069   -1.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5485    0.2968   -1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8592    0.6581    1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1698    1.5645    0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2783   -0.2056    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5353    0.7576    0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6438   -0.3049   -1.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 19  6  1  0
 18 12  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 18 40  1  0
 19 41  1  0
M  END


  Mrv0541 05061307002D          

 19 21  0  0  0  0            999 V2000
    3.6754   -0.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    3.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    0.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871   -0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    2.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    1.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    1.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5944    2.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -0.1941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    2.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    2.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  4  1  0  0  0  0
  7  2  2  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  8  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 15  2  0  0  0  0
 19 14  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033229

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2C(OC1=O)C1C(CC(O)C1=C)C(C)CC2O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h6,8-14,16-17H,2,4-5H2,1,3H3

> <INCHI_KEY>
IBIJTDJAWRYXRF-UHFFFAOYSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.3328

> <EXACT_MASS>
266.151809192

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.9972078291772

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,8-dihydroxy-3,6-dimethyl-9-methylidene-dodecahydroazuleno[4,5-b]furan-2-one

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
0.7052734569999992

> <ALOGPS_LOGS>
-1.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.034494874439225

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.405351759647715

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8736275694041575

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
69.4767

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,8-dihydroxy-3,6-dimethyl-9-methylidene-decahydroazuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033229
     RDKit          3D
Absindiol
 41 43  0  0  0  0  0  0  0  0999 V2000
    1.5794    2.3640   -1.8909 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7402    1.4368   -0.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8753    1.3799   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2212    2.6169    0.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2851    0.4726    1.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5805   -0.5390    0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429   -1.5086    0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676   -2.6593    1.4098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3309   -2.1231    0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6442   -1.3930    0.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6404   -2.2341   -0.2635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5783   -0.1882   -0.6573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8574    0.6157   -0.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5610    0.6149    0.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3177    1.9983   -0.9183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0606    2.9475   -1.2535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9412    1.9893   -0.7210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5150    0.7715   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8016    0.3066   -0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7332    2.3802   -2.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3201    3.1526   -1.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6960    0.8342   -0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0596    2.9326    0.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6120    1.0856    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0794    0.0467    1.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3508   -1.0814   -0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3436   -1.0983    1.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1278   -3.4465    1.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442   -3.0272    0.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4934   -2.2482    2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0116   -2.1122   -0.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5090   -3.1716    0.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8838   -1.1250    1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5407   -2.2499   -1.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3380   -0.5069   -1.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5485    0.2968   -1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8592    0.6581    1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1698    1.5645    0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2783   -0.2056    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5353    0.7576    0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6438   -0.3049   -1.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 19  6  1  0
 18 12  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 18 40  1  0
 19 41  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       6.861  -0.362   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.347   6.030   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.188   1.792   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.269  -0.070   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.441   2.640   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.657   0.598   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.888   4.588   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.097   2.640   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.999   2.099   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.372   4.179   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.882   0.598   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.039   3.303   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.539   2.099   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.499   3.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.166   4.179   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.576   5.139   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.678  -0.362   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.038   5.139   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.651   4.588   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    6   11                                                       
CONECT    5    9   10                                                       
CONECT    6    1    4    9                                                  
CONECT    7    2   10   12                                                  
CONECT    8    3   13   15                                                  
CONECT    9    5    6   12                                                  
CONECT   10    5    7   16                                                  
CONECT   11    4   13   17                                                  
CONECT   12    7    9   14                                                  
CONECT   13    8   11   14                                                  
CONECT   14   12   13   19                                                  
CONECT   15    8   18   19                                                  
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   15                                                            
CONECT   19   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0033229
HETATM    1  C1  UNL     1       1.579   2.364  -1.891  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.740   1.437  -0.968  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.875   1.380  -0.017  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.221   2.617   0.497  1.00  0.00           O  
HETATM    5  C4  UNL     1       2.285   0.473   1.071  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.581  -0.539   0.231  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.743  -1.509   0.990  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.668  -2.659   1.410  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.331  -2.123   0.129  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.644  -1.393   0.237  1.00  0.00           C  
HETATM   11  O2  UNL     1      -2.640  -2.234  -0.264  1.00  0.00           O  
HETATM   12  C10 UNL     1      -1.578  -0.188  -0.657  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.857   0.616  -0.660  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.561   0.615   0.656  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.318   1.998  -0.918  1.00  0.00           C  
HETATM   16  O3  UNL     1      -3.061   2.947  -1.253  1.00  0.00           O  
HETATM   17  O4  UNL     1      -0.941   1.989  -0.721  1.00  0.00           O  
HETATM   18  C14 UNL     1      -0.515   0.771  -0.163  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.802   0.307  -0.744  1.00  0.00           C  
HETATM   20  H1  UNL     1       0.733   2.380  -2.577  1.00  0.00           H  
HETATM   21  H2  UNL     1       2.320   3.153  -1.979  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.696   0.834  -0.483  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.060   2.933   0.070  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.612   1.086   1.694  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.079   0.047   1.707  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.351  -1.081  -0.361  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.344  -1.098   1.944  1.00  0.00           H  
HETATM   28  H9  UNL     1       1.128  -3.446   1.939  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.144  -3.027   0.456  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.493  -2.248   2.010  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.012  -2.112  -0.929  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.509  -3.172   0.447  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.884  -1.125   1.279  1.00  0.00           H  
HETATM   34  H15 UNL     1      -2.541  -2.250  -1.250  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.338  -0.507  -1.676  1.00  0.00           H  
HETATM   36  H17 UNL     1      -3.548   0.297  -1.467  1.00  0.00           H  
HETATM   37  H18 UNL     1      -2.859   0.658   1.505  1.00  0.00           H  
HETATM   38  H19 UNL     1      -4.170   1.565   0.711  1.00  0.00           H  
HETATM   39  H20 UNL     1      -4.278  -0.206   0.713  1.00  0.00           H  
HETATM   40  H21 UNL     1      -0.535   0.758   0.938  1.00  0.00           H  
HETATM   41  H22 UNL     1       0.644  -0.305  -1.656  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   19
CONECT    3    4    5   22
CONECT    4   23
CONECT    5    6   24   25
CONECT    6    7   19   26
CONECT    7    8    9   27
CONECT    8   28   29   30
CONECT    9   10   31   32
CONECT   10   11   12   33
CONECT   11   34
CONECT   12   13   18   35
CONECT   13   14   15   36
CONECT   14   37   38   39
CONECT   15   16   16   17
CONECT   17   18
CONECT   18   19   40
CONECT   19   41
END

HMDB0033229
     RDKit          3D
Absindiol
 41 43  0  0  0  0  0  0  0  0999 V2000
    1.5794    2.3640   -1.8909 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7402    1.4368   -0.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8753    1.3799   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2212    2.6169    0.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2851    0.4726    1.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5805   -0.5390    0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429   -1.5086    0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676   -2.6593    1.4098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3309   -2.1231    0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6442   -1.3930    0.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6404   -2.2341   -0.2635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5783   -0.1882   -0.6573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8574    0.6157   -0.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5610    0.6149    0.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3177    1.9983   -0.9183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0606    2.9475   -1.2535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9412    1.9893   -0.7210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5150    0.7715   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8016    0.3066   -0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7332    2.3802   -2.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3201    3.1526   -1.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6960    0.8342   -0.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0596    2.9326    0.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6120    1.0856    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0794    0.0467    1.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3508   -1.0814   -0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3436   -1.0983    1.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1278   -3.4465    1.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442   -3.0272    0.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4934   -2.2482    2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0116   -2.1122   -0.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5090   -3.1716    0.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8838   -1.1250    1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5407   -2.2499   -1.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3380   -0.5069   -1.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5485    0.2968   -1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8592    0.6581    1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1698    1.5645    0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2783   -0.2056    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5353    0.7576    0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6438   -0.3049   -1.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 19  6  1  0
 18 12  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 18 40  1  0
 19 41  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₄

Average Molecular Weight

266.3328

Monoisotopic Molecular Weight

266.151809192

IUPAC Name

4,8-dihydroxy-3,6-dimethyl-9-methylidene-dodecahydroazuleno[4,5-b]furan-2-one

Traditional Name

4,8-dihydroxy-3,6-dimethyl-9-methylidene-decahydroazuleno[4,5-b]furan-2-one

CAS Registry Number

213198-34-6

SMILES

CC1C2C(OC1=O)C1C(CC(O)C1=C)C(C)CC2O

InChI Identifier

InChI=1S/C15H22O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h6,8-14,16-17H,2,4-5H2,1,3H3

InChI Key

IBIJTDJAWRYXRF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033229)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033229)

Source

Endogenous

Endogenous (HMDB: HMDB0033229)

Plant

Plant (HMDB: HMDB0033229)

Animal

Animal (HMDB: HMDB0033229)

Exogenous

Food

Food (HMDB: HMDB0033229)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0033229)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0033229)

Cellular process

Cell signaling (HMDB: HMDB0033229)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0033229)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0033229)

Nutrient

Nutrient (HMDB: HMDB0033229)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033229)

Emulsifier (HMDB: HMDB0033229)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	161 - 163 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5299 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	11.8 g/L	ALOGPS
logP	0.53	ALOGPS
logP	0.71	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	14.41	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.48 m³·mol⁻¹	ChemAxon
Polarizability	29 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	162.071	31661259
DarkChem	[M-H]-	157.179	31661259
DeepCCS	[M+H]+	163.301	30932474
DeepCCS	[M-H]-	160.943	30932474
DeepCCS	[M-2H]-	193.829	30932474
DeepCCS	[M+Na]+	169.394	30932474
AllCCS	[M+H]+	163.2	32859911
AllCCS	[M+H-H2O]+	159.8	32859911
AllCCS	[M+NH4]+	166.5	32859911
AllCCS	[M+Na]+	167.4	32859911
AllCCS	[M-H]-	166.4	32859911
AllCCS	[M+Na-2H]-	166.3	32859911
AllCCS	[M+HCOO]-	166.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Absindiol	CC1C2C(OC1=O)C1C(CC(O)C1=C)C(C)CC2O	3324.6	Standard polar	33892256
Absindiol	CC1C2C(OC1=O)C1C(CC(O)C1=C)C(C)CC2O	2298.8	Standard non polar	33892256
Absindiol	CC1C2C(OC1=O)C1C(CC(O)C1=C)C(C)CC2O	2385.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Absindiol,1TMS,isomer #1	C=C1C(O[Si](C)(C)C)CC2C(C)CC(O)C3C(C)C(=O)OC3C12	2200.9	Semi standard non polar	33892256
Absindiol,1TMS,isomer #2	C=C1C(O)CC2C(C)CC(O[Si](C)(C)C)C3C(C)C(=O)OC3C12	2193.0	Semi standard non polar	33892256
Absindiol,2TMS,isomer #1	C=C1C(O[Si](C)(C)C)CC2C(C)CC(O[Si](C)(C)C)C3C(C)C(=O)OC3C12	2259.9	Semi standard non polar	33892256
Absindiol,1TBDMS,isomer #1	C=C1C(O[Si](C)(C)C(C)(C)C)CC2C(C)CC(O)C3C(C)C(=O)OC3C12	2425.6	Semi standard non polar	33892256
Absindiol,1TBDMS,isomer #2	C=C1C(O)CC2C(C)CC(O[Si](C)(C)C(C)(C)C)C3C(C)C(=O)OC3C12	2416.5	Semi standard non polar	33892256
Absindiol,2TBDMS,isomer #1	C=C1C(O[Si](C)(C)C(C)(C)C)CC2C(C)CC(O[Si](C)(C)C(C)(C)C)C3C(C)C(=O)OC3C12	2696.3	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 - Absindiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-7980000000-ddb4f51f303ec07c869d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Absindiol GC-MS (2 TMS) - 70eV, Positive	splash10-01vk-3449000000-d63d75d5bdf90ef3771f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Absindiol 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 - Absindiol 10V, Positive-QTOF	splash10-00kb-0190000000-9b66a28bd8004e09c1a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Absindiol 20V, Positive-QTOF	splash10-0032-0790000000-5842adfe51edcd324fae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Absindiol 40V, Positive-QTOF	splash10-0kmi-5920000000-63010be7132a7d88ebf8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Absindiol 10V, Negative-QTOF	splash10-014i-0090000000-1f997419c9a5f2102bd1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Absindiol 20V, Negative-QTOF	splash10-00r2-0090000000-66a53043e5e2c4a8eba1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Absindiol 40V, Negative-QTOF	splash10-0f7x-8920000000-78e782bead6390b3bb0e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Absindiol 10V, Negative-QTOF	splash10-014i-0090000000-d1b8f6279b11a5fde054	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Absindiol 20V, Negative-QTOF	splash10-014j-0090000000-d9294d580238c1a4aaf2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Absindiol 40V, Negative-QTOF	splash10-0007-5940000000-99c9f8332554bc78c97f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Absindiol 10V, Positive-QTOF	splash10-000t-0090000000-c10bba7d39d99ec828c0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Absindiol 20V, Positive-QTOF	splash10-001i-0190000000-59ab51998ae0e348768e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Absindiol 40V, Positive-QTOF	splash10-0kdi-2940000000-50ced9345fef712c16fa	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB011244

KNApSAcK ID

C00055191

Chemspider ID

35013561

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751394

PDB ID

Not Available

ChEBI ID

174494

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1834011

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 Absindiol (HMDB0033229)

MOL for HMDB0033229 (Absindiol)

3D MOL for HMDB0033229 (Absindiol)

3D SDF for HMDB0033229 (Absindiol)

3D-SDF for HMDB0033229 (Absindiol)

PDB for HMDB0033229 (Absindiol)

3D PDB for HMDB0033229 (Absindiol)

SMILES for HMDB0033229 (Absindiol)

INCHI for HMDB0033229 (Absindiol)

Structure for HMDB0033229 (Absindiol)

3D Structure for HMDB0033229 (Absindiol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra