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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:39:17 UTC

Update Date

2022-03-07 02:54:35 UTC

HMDB ID

HMDB0035644

Secondary Accession Numbers

HMDB35644

Metabolite Identification

Common Name

(6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide

Description

(6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a small amount of articles have been published on (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide.

Structure

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

HMDB0035644
     RDKit          3D
(6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide
 41 43  0  0  0  0  0  0  0  0999 V2000
    3.6561   -1.5190    0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9926   -0.2774    0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7284    0.0445    0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5757   -0.7291    0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9104   -2.0650    0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6535   -0.5576   -0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5653   -1.6576   -1.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9085   -0.8656    0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643   -0.6188    2.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1101   -0.1231    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9550    1.3574    0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270    1.7996   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7804    0.7282   -0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4781    1.2621   -1.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5751    1.3676   -0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2584    2.3364    0.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8176    1.7113   -0.9894 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7355    0.7647   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9957    0.7599   -0.7995 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1745   -1.8806    1.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130   -2.3168   -0.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7207   -1.3002    0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3720   -0.3113    1.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2166   -2.4244   -0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6624   -2.6563   -0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4156   -1.5149   -1.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565   -1.5358   -1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1789   -1.9612    0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7743   -0.7547    2.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1371   -1.4273    2.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4227    0.3774    2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9858   -0.4214    0.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2334   -0.4503   -1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2453    1.7728    1.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6691    1.8025   -0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0434    2.1357    0.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5968    2.6776   -0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4617    0.5234   -1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8493    0.5596   -2.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2752    2.2356   -1.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7893    3.1522    0.3883 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
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18  2  1  0
 15  3  1  0
 13  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
M  END


  Mrv0541 02241210562D          

 19 21  0  0  0  0            999 V2000
    1.1674    0.8758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6513    0.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4763    0.2090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3327   -1.4410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0463   -1.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0463   -0.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3327   -0.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822   -0.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1674   -0.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217   -1.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7613   -1.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7613   -0.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4763   -0.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4763    0.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7613    1.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0463    0.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3327    1.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822    0.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4688    1.4410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 18  1  0  0  0  0
  2  3  2  0  0  0  0
  2  9  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  6 16  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 18  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035644

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCCC2CC3(O)OC(=O)C(C)=C3C(O)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-8-5-4-6-10-7-15(18)11(9(2)13(17)19-15)12(16)14(8,10)3/h8,10,12,16,18H,4-7H2,1-3H3

> <INCHI_KEY>
HOZOKRDCQVUMIA-UHFFFAOYSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.3328

> <EXACT_MASS>
266.151809192

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.61711332573137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,9a-dihydroxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
2.188694253333334

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.005102176807554

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.185835594219103

> <JCHEM_PKA_STRONGEST_BASIC>
-3.27554105632678

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
70.088

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,9a-dihydroxy-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035644
     RDKit          3D
(6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide
 41 43  0  0  0  0  0  0  0  0999 V2000
    3.6561   -1.5190    0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9926   -0.2774    0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7284    0.0445    0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5757   -0.7291    0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9104   -2.0650    0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6535   -0.5576   -0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5653   -1.6576   -1.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9085   -0.8656    0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643   -0.6188    2.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1101   -0.1231    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9550    1.3574    0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270    1.7996   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7804    0.7282   -0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4781    1.2621   -1.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5751    1.3676   -0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2584    2.3364    0.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8176    1.7113   -0.9894 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7355    0.7647   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9957    0.7599   -0.7995 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1745   -1.8806    1.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130   -2.3168   -0.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7207   -1.3002    0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3720   -0.3113    1.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2166   -2.4244   -0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6624   -2.6563   -0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4156   -1.5149   -1.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565   -1.5358   -1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1789   -1.9612    0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7743   -0.7547    2.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1371   -1.4273    2.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4227    0.3774    2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9858   -0.4214    0.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2334   -0.4503   -1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2453    1.7728    1.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6691    1.8025   -0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0434    2.1357    0.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5968    2.6776   -0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4617    0.5234   -1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8493    0.5596   -2.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2752    2.2356   -1.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7893    3.1522    0.3883 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
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18  2  1  0
 15  3  1  0
 13  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       2.179   1.635   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.082   0.390   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.622   0.390   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.621  -2.690   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.953  -1.920   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.953  -0.380   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.621  -1.150   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.713  -0.380   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.179  -0.857   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.654  -2.320   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.288  -2.690   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.288  -1.150   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.622  -0.380   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.622   1.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.288   1.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.953   1.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.621   1.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.713   1.160   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.875   2.690   0.000  0.00  0.00           O+0
CONECT    1    2   18                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2                                                            
CONECT    4    7                                                            
CONECT    5    6                                                            
CONECT    6    5    7   12   16                                             
CONECT    7    4    6    8                                                  
CONECT    8    7    9   18                                                  
CONECT    9    2    8   10                                                  
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12    6   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16    6   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18    1    8   17   19                                             
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0035644
HETATM    1  C1  UNL     1       3.656  -1.519   0.609  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.993  -0.277   0.085  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.728   0.044   0.107  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.576  -0.729   0.653  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.910  -2.065   0.839  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.654  -0.558  -0.192  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.565  -1.658  -1.270  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.908  -0.866   0.585  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.764  -0.619   2.066  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.110  -0.123   0.053  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.955   1.357   0.100  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.527   1.800  -0.154  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.780   0.728  -0.924  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.478   1.262  -1.524  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.575   1.368  -0.488  1.00  0.00           C  
HETATM   16  O2  UNL     1       1.258   2.336   0.479  1.00  0.00           O  
HETATM   17  O3  UNL     1       2.818   1.711  -0.989  1.00  0.00           O  
HETATM   18  C15 UNL     1       3.735   0.765  -0.607  1.00  0.00           C  
HETATM   19  O4  UNL     1       4.996   0.760  -0.800  1.00  0.00           O  
HETATM   20  H1  UNL     1       3.175  -1.881   1.521  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.613  -2.317  -0.165  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.721  -1.300   0.873  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.372  -0.311   1.655  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.217  -2.424  -0.042  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.662  -2.656  -0.811  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.416  -1.515  -1.976  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.356  -1.536  -1.875  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.179  -1.961   0.498  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.774  -0.755   2.510  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.137  -1.427   2.544  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.423   0.377   2.337  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.986  -0.421   0.645  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.233  -0.450  -1.011  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.245   1.773   1.094  1.00  0.00           H  
HETATM   35  H16 UNL     1      -3.669   1.802  -0.633  1.00  0.00           H  
HETATM   36  H17 UNL     1      -1.043   2.136   0.755  1.00  0.00           H  
HETATM   37  H18 UNL     1      -1.597   2.678  -0.840  1.00  0.00           H  
HETATM   38  H19 UNL     1      -1.462   0.523  -1.811  1.00  0.00           H  
HETATM   39  H20 UNL     1       0.849   0.560  -2.304  1.00  0.00           H  
HETATM   40  H21 UNL     1       0.275   2.236  -1.978  1.00  0.00           H  
HETATM   41  H22 UNL     1       1.789   3.152   0.388  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   18
CONECT    3    4   15
CONECT    4    5    6   23
CONECT    5   24
CONECT    6    7    8   13
CONECT    7   25   26   27
CONECT    8    9   10   28
CONECT    9   29   30   31
CONECT   10   11   32   33
CONECT   11   12   34   35
CONECT   12   13   36   37
CONECT   13   14   38
CONECT   14   15   39   40
CONECT   15   16   17
CONECT   16   41
CONECT   17   18
CONECT   18   19   19
END

HMDB0035644
     RDKit          3D
(6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide
 41 43  0  0  0  0  0  0  0  0999 V2000
    3.6561   -1.5190    0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9926   -0.2774    0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7284    0.0445    0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5757   -0.7291    0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9104   -2.0650    0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6535   -0.5576   -0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5653   -1.6576   -1.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9085   -0.8656    0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643   -0.6188    2.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1101   -0.1231    0.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9550    1.3574    0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270    1.7996   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7804    0.7282   -0.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4781    1.2621   -1.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5751    1.3676   -0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2584    2.3364    0.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8176    1.7113   -0.9894 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7355    0.7647   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9957    0.7599   -0.7995 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1745   -1.8806    1.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130   -2.3168   -0.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7207   -1.3002    0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3720   -0.3113    1.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2166   -2.4244   -0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6624   -2.6563   -0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4156   -1.5149   -1.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565   -1.5358   -1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1789   -1.9612    0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7743   -0.7547    2.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1371   -1.4273    2.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4227    0.3774    2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9858   -0.4214    0.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2334   -0.4503   -1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2453    1.7728    1.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6691    1.8025   -0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0434    2.1357    0.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5968    2.6776   -0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4617    0.5234   -1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8493    0.5596   -2.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2752    2.2356   -1.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7893    3.1522    0.3883 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
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18  2  1  0
 15  3  1  0
 13  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(6b,8BetaOH)-6,8-dihydroxy-7(11)-eremophilen-12,8-olide	Generator
(6Β,8betaoh)-6,8-dihydroxy-7(11)-eremophilen-12,8-olide	Generator
6beta,8beta-Dihydroxyeremophil-7(11)-en-12,8alpha-olide	HMDB
6beta,8beta-Dihydroxyeremophilenolide	HMDB

Chemical Formula

C₁₅H₂₂O₄

Average Molecular Weight

266.3328

Monoisotopic Molecular Weight

266.151809192

IUPAC Name

4,9a-dihydroxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

Traditional Name

4,9a-dihydroxy-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-2-one

CAS Registry Number

58848-38-7

SMILES

CC1CCCC2CC3(O)OC(=O)C(C)=C3C(O)C12C

InChI Identifier

InChI=1S/C15H22O4/c1-8-5-4-6-10-7-15(18)11(9(2)13(17)19-15)12(16)14(8,10)3/h8,10,12,16,18H,4-7H2,1-3H3

InChI Key

HOZOKRDCQVUMIA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Eremophilanolide or secoeremophilanolide
Sesquiterpenoid
Naphthofuran
2-furanone
Cyclic alcohol
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Hemiacetal
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0035644)

Cellular substructure

Extracellular (HMDB: HMDB0035644)
Cytoplasm (HMDB: HMDB0035644)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035644)

Source

Endogenous

Endogenous (HMDB: HMDB0035644)

Plant

Plant (HMDB: HMDB0035644)

Animal

Animal (HMDB: HMDB0035644)

Exogenous

Food

Food (HMDB: HMDB0035644)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0035644)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0035644)

Cellular process

Cell signaling (HMDB: HMDB0035644)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0035644)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035644)

Nutrient

Nutrient (HMDB: HMDB0035644)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035644)

Emulsifier (HMDB: HMDB0035644)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	217 - 218 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.81 g/L	ALOGPS
logP	1.73	ALOGPS
logP	2.19	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	11.19	ChemAxon
pKa (Strongest Basic)	-3.3	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	70.09 m³·mol⁻¹	ChemAxon
Polarizability	28.62 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]+	162.681	31661259
DarkChem	[M-H]-	157.69	31661259
DeepCCS	[M-2H]-	198.031	30932474
DeepCCS	[M+Na]+	173.596	30932474
AllCCS	[M+H]+	162.8	32859911
AllCCS	[M+H-H2O]+	159.3	32859911
AllCCS	[M+NH4]+	166.1	32859911
AllCCS	[M+Na]+	167.0	32859911
AllCCS	[M-H]-	168.2	32859911
AllCCS	[M+Na-2H]-	168.3	32859911
AllCCS	[M+HCOO]-	168.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide	CC1CCCC2CC3(O)OC(=O)C(C)=C3C(O)C12C	3487.7	Standard polar	33892256
(6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide	CC1CCCC2CC3(O)OC(=O)C(C)=C3C(O)C12C	2138.7	Standard non polar	33892256
(6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide	CC1CCCC2CC3(O)OC(=O)C(C)=C3C(O)C12C	2247.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide,1TMS,isomer #1	CC1=C2C(O)C3(C)C(C)CCCC3CC2(O[Si](C)(C)C)OC1=O	2237.3	Semi standard non polar	33892256
(6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide,1TMS,isomer #2	CC1=C2C(O[Si](C)(C)C)C3(C)C(C)CCCC3CC2(O)OC1=O	2205.4	Semi standard non polar	33892256
(6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide,2TMS,isomer #1	CC1=C2C(O[Si](C)(C)C)C3(C)C(C)CCCC3CC2(O[Si](C)(C)C)OC1=O	2301.3	Semi standard non polar	33892256
(6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide,1TBDMS,isomer #1	CC1=C2C(O)C3(C)C(C)CCCC3CC2(O[Si](C)(C)C(C)(C)C)OC1=O	2465.9	Semi standard non polar	33892256
(6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide,1TBDMS,isomer #2	CC1=C2C(O[Si](C)(C)C(C)(C)C)C3(C)C(C)CCCC3CC2(O)OC1=O	2443.0	Semi standard non polar	33892256
(6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide,2TBDMS,isomer #1	CC1=C2C(O[Si](C)(C)C(C)(C)C)C3(C)C(C)CCCC3CC2(O[Si](C)(C)C(C)(C)C)OC1=O	2767.4	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 - (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-1950000000-18a59350a0b7622d7131	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide GC-MS (2 TMS) - 70eV, Positive	splash10-00fr-3529000000-3dbf333c81c186f04f6d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide 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 - (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide 10V, Positive-QTOF	splash10-00kb-0390000000-7ccf3f46798e73b08193	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide 20V, Positive-QTOF	splash10-00kb-4690000000-8a8abf558aeb811df0da	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide 40V, Positive-QTOF	splash10-01bc-9500000000-88cc6d00185aa4d2988f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide 10V, Negative-QTOF	splash10-014i-0190000000-08e3baed78ceaa6ada02	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide 20V, Negative-QTOF	splash10-01ba-1190000000-a539091775b5c94199af	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide 40V, Negative-QTOF	splash10-05fr-4940000000-8cc2a595cc86b2fd2a69	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide 10V, Positive-QTOF	splash10-014i-0090000000-5dc7bbd27f095b8ae418	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide 20V, Positive-QTOF	splash10-014j-0490000000-a812aa43eade66e85003	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide 40V, Positive-QTOF	splash10-0aou-9510000000-86f7076c518815fcd72d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide 10V, Negative-QTOF	splash10-014i-0090000000-c6cc318d73093d112373	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide 20V, Negative-QTOF	splash10-014i-1090000000-5072af805dbd91ff0d73	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide 40V, Negative-QTOF	splash10-0229-1960000000-5aae4093e242e9eab542	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB021141

KNApSAcK ID

C00017306

Chemspider ID

35013968

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78173026

PDB ID

Not Available

ChEBI ID

174497

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 (6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide (HMDB0035644)

MOL for HMDB0035644 ((6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide)

3D MOL for HMDB0035644 ((6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide)

3D SDF for HMDB0035644 ((6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide)

3D-SDF for HMDB0035644 ((6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide)

PDB for HMDB0035644 ((6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide)

3D PDB for HMDB0035644 ((6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide)

SMILES for HMDB0035644 ((6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide)

INCHI for HMDB0035644 ((6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide)

Structure for HMDB0035644 ((6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide)

3D Structure for HMDB0035644 ((6beta,8betaOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra