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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:28:57 UTC

Update Date

2022-03-07 02:55:40 UTC

HMDB ID

HMDB0038202

Secondary Accession Numbers

HMDB38202

Metabolite Identification

Common Name

Zedoarol

Description

Zedoarol 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. Based on a literature review a small amount of articles have been published on Zedoarol.

Structure

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

HMDB0038202
     RDKit          3D
Zedoarol
 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.3753    3.3578    0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0742    2.1221    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5008    1.9874    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    0.8428   -0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3898    0.9487   -0.6489 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7946   -0.1907   -1.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7723   -1.0971   -0.9668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7399   -2.5185   -1.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7424   -0.4508   -0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4636   -0.9850    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4096   -2.2404    0.0487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7271   -0.2322    0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8289   -0.0348    1.8348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0162   -0.8937    0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2184   -2.2517    0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9977    0.1363    0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3159    1.4487    0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8834    1.0907   -0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618    4.2122    0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4138    3.5518   -0.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048    2.9491    0.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5965    1.8591    1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7438   -0.3768   -1.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1302   -2.7053   -2.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7908   -2.8128   -1.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4769   -3.1852   -0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4277   -0.7642    2.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0585   -0.8568   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4841   -2.5129    1.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2705   -2.4062    0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0672   -2.9973   -0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9955    0.0508    0.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0236    0.0311    1.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8055    1.8648   -0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049    2.1244    1.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8589    0.9346   -1.3398 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
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
  9  4  2  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
M  END


  Mrv0541 05061310172D          

 18 20  0  0  0  0            999 V2000
    2.7580    1.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0539   -1.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0030   -1.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4556   -0.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7799    0.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9409    0.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6013   -0.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1159    0.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9800   -0.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769   -0.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6016    0.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4553    0.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2717   -0.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5284   -0.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851   -0.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5284   -1.6643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8222   -1.3055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2770    0.3970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  1  2  0  0  0  0
  8  6  1  0  0  0  0
  9  2  1  0  0  0  0
  9  7  2  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  2  0  0  0  0
 17 15  1  0  0  0  0
 18  7  1  0  0  0  0
 18 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038202

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2C(=C)CC3=C(C(C)=CO3)C(=O)C12O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-8-6-12-13(9(2)7-18-12)14(16)15(17)10(3)4-5-11(8)15/h7,10-11,17H,1,4-6H2,2-3H3

> <INCHI_KEY>
CKDRPCYJCDMPFO-UHFFFAOYSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.3016

> <EXACT_MASS>
246.125594442

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.75539675644575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4a-hydroxy-3,5-dimethyl-8-methylidene-4H,4aH,5H,6H,7H,7aH,8H,9H-azuleno[6,5-b]furan-4-one

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
2.4332693023333336

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.462766867530771

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6699460532065324

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
68.71039999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4a-hydroxy-3,5-dimethyl-8-methylidene-5H,6H,7H,7aH,9H-azuleno[6,5-b]furan-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038202
     RDKit          3D
Zedoarol
 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.3753    3.3578    0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0742    2.1221    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5008    1.9874    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    0.8428   -0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3898    0.9487   -0.6489 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7946   -0.1907   -1.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7723   -1.0971   -0.9668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7399   -2.5185   -1.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7424   -0.4508   -0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4636   -0.9850    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4096   -2.2404    0.0487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7271   -0.2322    0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8289   -0.0348    1.8348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0162   -0.8937    0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2184   -2.2517    0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9977    0.1363    0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3159    1.4487    0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8834    1.0907   -0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618    4.2122    0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4138    3.5518   -0.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048    2.9491    0.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5965    1.8591    1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7438   -0.3768   -1.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1302   -2.7053   -2.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7908   -2.8128   -1.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4769   -3.1852   -0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4277   -0.7642    2.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0585   -0.8568   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4841   -2.5129    1.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2705   -2.4062    0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0672   -2.9973   -0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9955    0.0508    0.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0236    0.0311    1.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8055    1.8648   -0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049    2.1244    1.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8589    0.9346   -1.3398 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
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
  9  4  2  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  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       5.148   3.194   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.434  -3.222   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.739  -3.222   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.717  -0.675   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.322   0.741   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.356   1.807   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.456  -0.675   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.816   1.807   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.296  -1.688   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.877  -1.688   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.856   0.603   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.317   0.603   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.974  -0.898   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.586  -1.567   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.199  -0.898   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.586  -3.107   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.268  -2.437   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.850   0.741   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    5   10                                                       
CONECT    5    4   11                                                       
CONECT    6    8   12                                                       
CONECT    7    9   18                                                       
CONECT    8    1    6   11                                                  
CONECT    9    2    7   13                                                  
CONECT   10    3    4   15                                                  
CONECT   11    5    8   15                                                  
CONECT   12    6   13   18                                                  
CONECT   13    9   12   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   10   11   14   17                                             
CONECT   16   14                                                            
CONECT   17   15                                                            
CONECT   18    7   12                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0038202
HETATM    1  C1  UNL     1      -0.375   3.358   0.169  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.074   2.122   0.134  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.501   1.987   0.470  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.181   0.843  -0.154  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.390   0.949  -0.649  1.00  0.00           O  
HETATM    6  C5  UNL     1       3.795  -0.191  -1.151  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.772  -1.097  -0.967  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.740  -2.518  -1.360  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.742  -0.451  -0.334  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.464  -0.985   0.068  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.410  -2.240   0.049  1.00  0.00           O  
HETATM   12  C10 UNL     1      -0.727  -0.232   0.480  1.00  0.00           C  
HETATM   13  O3  UNL     1      -0.829  -0.035   1.835  1.00  0.00           O  
HETATM   14  C11 UNL     1      -2.016  -0.894   0.008  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.218  -2.252   0.594  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.998   0.136   0.527  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.316   1.449   0.192  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.883   1.091  -0.223  1.00  0.00           C  
HETATM   19  H1  UNL     1       0.262   4.212   0.426  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.414   3.552  -0.065  1.00  0.00           H  
HETATM   21  H3  UNL     1       2.005   2.949   0.230  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.597   1.859   1.568  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.744  -0.377  -1.617  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.130  -2.705  -2.257  1.00  0.00           H  
HETATM   25  H7  UNL     1       3.791  -2.813  -1.644  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.477  -3.185  -0.512  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.428  -0.764   2.369  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.058  -0.857  -1.090  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.484  -2.513   1.392  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.270  -2.406   0.947  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.067  -2.997  -0.216  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.995   0.051   0.081  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.024   0.031   1.647  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.806   1.865  -0.686  1.00  0.00           H  
HETATM   35  H17 UNL     1      -2.305   2.124   1.079  1.00  0.00           H  
HETATM   36  H18 UNL     1      -0.859   0.935  -1.340  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3   18
CONECT    3    4   21   22
CONECT    4    5    9    9
CONECT    5    6
CONECT    6    7    7   23
CONECT    7    8    9
CONECT    8   24   25   26
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   14   18
CONECT   13   27
CONECT   14   15   16   28
CONECT   15   29   30   31
CONECT   16   17   32   33
CONECT   17   18   34   35
CONECT   18   36
END

HMDB0038202
     RDKit          3D
Zedoarol
 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.3753    3.3578    0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0742    2.1221    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5008    1.9874    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    0.8428   -0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3898    0.9487   -0.6489 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7946   -0.1907   -1.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7723   -1.0971   -0.9668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7399   -2.5185   -1.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7424   -0.4508   -0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4636   -0.9850    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4096   -2.2404    0.0487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7271   -0.2322    0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8289   -0.0348    1.8348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0162   -0.8937    0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2184   -2.2517    0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9977    0.1363    0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3159    1.4487    0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8834    1.0907   -0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618    4.2122    0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4138    3.5518   -0.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048    2.9491    0.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5965    1.8591    1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7438   -0.3768   -1.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1302   -2.7053   -2.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7908   -2.8128   -1.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4769   -3.1852   -0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4277   -0.7642    2.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0585   -0.8568   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4841   -2.5129    1.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2705   -2.4062    0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0672   -2.9973   -0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9955    0.0508    0.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0236    0.0311    1.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8055    1.8648   -0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049    2.1244    1.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8589    0.9346   -1.3398 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
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
  9  4  2  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₃

Average Molecular Weight

246.3016

Monoisotopic Molecular Weight

246.125594442

IUPAC Name

4a-hydroxy-3,5-dimethyl-8-methylidene-4H,4aH,5H,6H,7H,7aH,8H,9H-azuleno[6,5-b]furan-4-one

Traditional Name

4a-hydroxy-3,5-dimethyl-8-methylidene-5H,6H,7H,7aH,9H-azuleno[6,5-b]furan-4-one

CAS Registry Number

103994-22-5

SMILES

CC1CCC2C(=C)CC3=C(C(C)=CO3)C(=O)C12O

InChI Identifier

InChI=1S/C15H18O3/c1-8-6-12-13(9(2)7-18-12)14(16)15(17)10(3)4-5-11(8)15/h7,10-11,17H,1,4-6H2,2-3H3

InChI Key

CKDRPCYJCDMPFO-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
Cycloheptafuran
Aryl ketone
Aryl alkyl ketone
Cyclic alcohol
Furan
Tertiary alcohol
Heteroaromatic compound
Ketone
Organoheterocyclic compound
Oxacycle
Alcohol
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0038202)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038202)

Source

Endogenous

Endogenous (HMDB: HMDB0038202)

Animal

Animal (HMDB: HMDB0038202)

Exogenous

Food

Food (HMDB: HMDB0038202)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0038202)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0038202)

Cellular process

Cell signaling (HMDB: HMDB0038202)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0038202)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0038202)

Nutrient

Nutrient (HMDB: HMDB0038202)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038202)

Emulsifier (HMDB: HMDB0038202)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	146.8 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	2.06	ALOGPS
logP	2.43	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.46	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.71 m³·mol⁻¹	ChemAxon
Polarizability	26.76 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]+	156.22	31661259
DarkChem	[M-H]-	155.161	31661259
DeepCCS	[M-2H]-	191.646	30932474
DeepCCS	[M+Na]+	167.211	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	151.8	32859911
AllCCS	[M+NH4]+	159.1	32859911
AllCCS	[M+Na]+	160.2	32859911
AllCCS	[M-H]-	161.8	32859911
AllCCS	[M+Na-2H]-	161.6	32859911
AllCCS	[M+HCOO]-	161.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zedoarol	CC1CCC2C(=C)CC3=C(C(C)=CO3)C(=O)C12O	2796.7	Standard polar	33892256
Zedoarol	CC1CCC2C(=C)CC3=C(C(C)=CO3)C(=O)C12O	1920.1	Standard non polar	33892256
Zedoarol	CC1CCC2C(=C)CC3=C(C(C)=CO3)C(=O)C12O	1868.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Zedoarol,1TMS,isomer #1	C=C1CC2=C(C(=O)C3(O[Si](C)(C)C)C(C)CCC13)C(C)=CO2	2052.1	Semi standard non polar	33892256
Zedoarol,1TBDMS,isomer #1	C=C1CC2=C(C(=O)C3(O[Si](C)(C)C(C)(C)C)C(C)CCC13)C(C)=CO2	2261.7	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 - Zedoarol GC-MS (Non-derivatized) - 70eV, Positive	splash10-05u2-7920000000-59a04e3a2e4cb78c00ec	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zedoarol GC-MS (1 TMS) - 70eV, Positive	splash10-0fdn-9731000000-76a252b6f18f0a0eeabe	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zedoarol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zedoarol 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 - Zedoarol 10V, Positive-QTOF	splash10-0002-0090000000-d0ea8342b45d1cb88a33	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarol 20V, Positive-QTOF	splash10-0f6t-7590000000-b4cdaf09957c845afbde	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarol 40V, Positive-QTOF	splash10-0f6x-9120000000-3413747b5c83bd7adc47	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarol 10V, Negative-QTOF	splash10-0002-0090000000-e10f3f664863537b9bdb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarol 20V, Negative-QTOF	splash10-0002-0090000000-3ebcca8feb4b8610df2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarol 40V, Negative-QTOF	splash10-0037-9530000000-29e8ab0b9398bdc2b752	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarol 10V, Positive-QTOF	splash10-0002-0090000000-db338c5d740c9ec52210	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarol 20V, Positive-QTOF	splash10-00kb-3950000000-87bb791439f30710511c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarol 40V, Positive-QTOF	splash10-0a7l-9680000000-dfda63175e95a2cc7922	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarol 10V, Negative-QTOF	splash10-0002-0090000000-851e47b490f6973ef9e5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarol 20V, Negative-QTOF	splash10-0002-0090000000-3df4d946ab283032c6b9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zedoarol 40V, Negative-QTOF	splash10-00bm-2790000000-d1a9e60deee5c4361c57	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

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

75144776

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1866291

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 Zedoarol (HMDB0038202)

MOL for HMDB0038202 (Zedoarol)

3D MOL for HMDB0038202 (Zedoarol)

3D SDF for HMDB0038202 (Zedoarol)

3D-SDF for HMDB0038202 (Zedoarol)

PDB for HMDB0038202 (Zedoarol)

3D PDB for HMDB0038202 (Zedoarol)

SMILES for HMDB0038202 (Zedoarol)

INCHI for HMDB0038202 (Zedoarol)

Structure for HMDB0038202 (Zedoarol)

3D Structure for HMDB0038202 (Zedoarol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra