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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:11:29 UTC

Update Date

2022-03-07 02:54:47 UTC

HMDB ID

HMDB0036125

Secondary Accession Numbers

HMDB36125

Metabolite Identification

Common Name

(1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide

Description

(1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Based on a literature review a small amount of articles have been published on (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide.

Structure

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

HMDB0036125
     RDKit          3D
(1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide
 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.4980    3.0443    0.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1993    1.7292    0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940    1.6939    0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455    0.3996   -0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1761   -0.5633   -0.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7390   -0.0373   -2.0857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9488   -0.7615    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5599   -1.2275    1.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352   -1.8607   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2839   -1.5919   -0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5174   -1.5013   -2.2043 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2191   -2.5406   -0.3517 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2157   -1.9430    0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1936   -2.4839    0.9223 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8821   -0.5279    0.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6368    0.5784    1.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7782   -0.3061   -0.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8857    0.8558   -0.5873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3454    0.5496    0.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2270    3.8198    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0724    3.3682   -0.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1948    2.8637    1.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563    2.6164    0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9339    0.6059   -0.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6575   -0.0525    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6589   -1.5354   -1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6272   -0.7119   -2.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0820   -0.4078    1.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7341   -1.6619    2.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136   -2.0847    1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1613   -2.7480    0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5906   -2.2812   -1.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7802   -0.9460   -2.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    0.1339    2.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9411    1.3907    1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3717    1.0053    0.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693    1.7542   -0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6390    0.8669   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1165    0.4986    1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  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  2  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 19  7  1  0
 17 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END


  Mrv0541 02241211302D          

 19 21  0  0  0  0            999 V2000
   -2.4737    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4737   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0465   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0465    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3322   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3805   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3805    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3322    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1649   -0.6668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6480    0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1649    0.6653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595    1.6507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0465    1.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3805    1.2392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4209   -1.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4737    0.0006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595   -1.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3 19  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 15  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  2  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
  9 16  1  0  0  0  0
 11 12  1  0  0  0  0
 11 17  1  0  0  0  0
 12 13  1  0  0  0  0
 12 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036125

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2CC3C(C)=CCC(O)C3(C)CC2(O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8-4-5-12(16)14(3)7-15(18)11(6-10(8)14)9(2)13(17)19-15/h4,10,12,16,18H,5-7H2,1-3H3

> <INCHI_KEY>
OHYLFUASNKOIGF-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.08795925324799

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
1.6272073120000008

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.626564094112744

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.244711046612784

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9650377678577486

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
71.092

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036125
     RDKit          3D
(1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide
 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.4980    3.0443    0.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1993    1.7292    0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940    1.6939    0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455    0.3996   -0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1761   -0.5633   -0.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7390   -0.0373   -2.0857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9488   -0.7615    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5599   -1.2275    1.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352   -1.8607   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2839   -1.5919   -0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5174   -1.5013   -2.2043 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2191   -2.5406   -0.3517 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2157   -1.9430    0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1936   -2.4839    0.9223 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8821   -0.5279    0.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6368    0.5784    1.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7782   -0.3061   -0.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8857    0.8558   -0.5873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3454    0.5496    0.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2270    3.8198    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0724    3.3682   -0.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1948    2.8637    1.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563    2.6164    0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9339    0.6059   -0.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6575   -0.0525    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6589   -1.5354   -1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6272   -0.7119   -2.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0820   -0.4078    1.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7341   -1.6619    2.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136   -2.0847    1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1613   -2.7480    0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5906   -2.2812   -1.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7802   -0.9460   -2.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    0.1339    2.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9411    1.3907    1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3717    1.0053    0.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693    1.7542   -0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6390    0.8669   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1165    0.4986    1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  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  2  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 19  7  1  0
 17 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  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  C   UNK     0      -4.618   0.772   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.618  -0.769   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.284  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.954  -0.769   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.954   0.772   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.284   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.620  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.710  -0.769   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.710   0.772   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.620   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.175  -1.245   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.076   0.001   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.175   1.242   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -3.284   3.081   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.954   2.313   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.710   2.313   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.652  -2.709   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.618   0.001   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.284  -3.081   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   15                                             
CONECT    6    1    5   14                                                  
CONECT    7    4    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10   13   16                                             
CONECT   10    5    9                                                       
CONECT   11    8   12   17                                                  
CONECT   12   11   13   18                                                  
CONECT   13    9   12                                                       
CONECT   14    6                                                            
CONECT   15    5                                                            
CONECT   16    9                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19    3                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0036125
HETATM    1  C1  UNL     1      -0.498   3.044   0.591  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.199   1.729   0.296  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.494   1.694   0.069  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.145   0.400  -0.215  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.176  -0.563  -0.872  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.739  -0.037  -2.086  1.00  0.00           O  
HETATM    7  C6  UNL     1      -0.949  -0.762   0.034  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.560  -1.227   1.377  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.135  -1.861  -0.504  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.284  -1.592  -0.805  1.00  0.00           C  
HETATM   11  O2  UNL     1       1.517  -1.501  -2.204  1.00  0.00           O  
HETATM   12  O3  UNL     1       2.219  -2.541  -0.352  1.00  0.00           O  
HETATM   13  C10 UNL     1       3.216  -1.943   0.389  1.00  0.00           C  
HETATM   14  O4  UNL     1       4.194  -2.484   0.922  1.00  0.00           O  
HETATM   15  C11 UNL     1       2.882  -0.528   0.420  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.637   0.578   1.098  1.00  0.00           C  
HETATM   17  C13 UNL     1       1.778  -0.306  -0.254  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.886   0.856  -0.587  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.345   0.550   0.290  1.00  0.00           C  
HETATM   20  H1  UNL     1      -1.227   3.820   0.863  1.00  0.00           H  
HETATM   21  H2  UNL     1       0.072   3.368  -0.312  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.195   2.864   1.437  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.056   2.616   0.095  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.934   0.606  -0.991  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.658  -0.052   0.633  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.659  -1.535  -1.029  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.627  -0.712  -2.789  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.082  -0.408   1.880  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.734  -1.662   2.013  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.214  -2.085   1.119  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.161  -2.748   0.187  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.591  -2.281  -1.453  1.00  0.00           H  
HETATM   33  H14 UNL     1       0.780  -0.946  -2.550  1.00  0.00           H  
HETATM   34  H15 UNL     1       4.086   0.134   2.007  1.00  0.00           H  
HETATM   35  H16 UNL     1       2.941   1.391   1.391  1.00  0.00           H  
HETATM   36  H17 UNL     1       4.372   1.005   0.398  1.00  0.00           H  
HETATM   37  H18 UNL     1       1.369   1.754  -0.197  1.00  0.00           H  
HETATM   38  H19 UNL     1       0.639   0.867  -1.645  1.00  0.00           H  
HETATM   39  H20 UNL     1       0.117   0.499   1.335  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   19
CONECT    3    4   23
CONECT    4    5   24   25
CONECT    5    6    7   26
CONECT    6   27
CONECT    7    8    9   19
CONECT    8   28   29   30
CONECT    9   10   31   32
CONECT   10   11   12   17
CONECT   11   33
CONECT   12   13
CONECT   13   14   14   15
CONECT   15   16   17   17
CONECT   16   34   35   36
CONECT   17   18
CONECT   18   19   37   38
CONECT   19   39
END

HMDB0036125
     RDKit          3D
(1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide
 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.4980    3.0443    0.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1993    1.7292    0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940    1.6939    0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455    0.3996   -0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1761   -0.5633   -0.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7390   -0.0373   -2.0857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9488   -0.7615    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5599   -1.2275    1.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352   -1.8607   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2839   -1.5919   -0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5174   -1.5013   -2.2043 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2191   -2.5406   -0.3517 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2157   -1.9430    0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1936   -2.4839    0.9223 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8821   -0.5279    0.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6368    0.5784    1.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7782   -0.3061   -0.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8857    0.8558   -0.5873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3454    0.5496    0.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2270    3.8198    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0724    3.3682   -0.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1948    2.8637    1.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563    2.6164    0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9339    0.6059   -0.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6575   -0.0525    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6589   -1.5354   -1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6272   -0.7119   -2.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0820   -0.4078    1.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7341   -1.6619    2.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136   -2.0847    1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1613   -2.7480    0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5906   -2.2812   -1.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7802   -0.9460   -2.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    0.1339    2.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9411    1.3907    1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3717    1.0053    0.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693    1.7542   -0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6390    0.8669   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1165    0.4986    1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  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  2  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 19  7  1  0
 17 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 11 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1b,8b)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide	Generator
(1Β,8β)-1,8-dihydroxy-3,7(11)-eudesmadien-12,8-olide	Generator

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

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

Traditional Name

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

CAS Registry Number

366494-92-0

SMILES

CC1=C2CC3C(C)=CCC(O)C3(C)CC2(O)OC1=O

InChI Identifier

InChI=1S/C15H20O4/c1-8-4-5-12(16)14(3)7-15(18)11(6-10(8)14)9(2)13(17)19-15/h4,10,12,16,18H,5-7H2,1-3H3

InChI Key

OHYLFUASNKOIGF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036125)

Source

Endogenous

Endogenous (HMDB: HMDB0036125)

Plant

Plant (HMDB: HMDB0036125)

Animal

Animal (HMDB: HMDB0036125)

Exogenous

Food

Food (HMDB: HMDB0036125)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0036125)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036125)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036125)

Lipid metabolism pathway (HMDB: HMDB0036125)

Cellular process

Cell signaling (HMDB: HMDB0036125)

Biochemical process

Lipid transport (HMDB: HMDB0036125)

Role

Biological role

Energy source (HMDB: HMDB0036125)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036125)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	193 - 195 °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	1.67 g/L	ALOGPS
logP	1.45	ALOGPS
logP	1.63	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	11.24	ChemAxon
pKa (Strongest Basic)	-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	71.09 m³·mol⁻¹	ChemAxon
Polarizability	28.09 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]+	162.482	31661259
DarkChem	[M-H]-	157.581	31661259
DeepCCS	[M+H]+	162.812	30932474
DeepCCS	[M-H]-	160.454	30932474
DeepCCS	[M-2H]-	193.341	30932474
DeepCCS	[M+Na]+	168.905	30932474
AllCCS	[M+H]+	162.1	32859911
AllCCS	[M+H-H2O]+	158.5	32859911
AllCCS	[M+NH4]+	165.4	32859911
AllCCS	[M+Na]+	166.4	32859911
AllCCS	[M-H]-	167.1	32859911
AllCCS	[M+Na-2H]-	167.0	32859911
AllCCS	[M+HCOO]-	167.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide	CC1=C2CC3C(C)=CCC(O)C3(C)CC2(O)OC1=O	3752.8	Standard polar	33892256
(1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide	CC1=C2CC3C(C)=CCC(O)C3(C)CC2(O)OC1=O	2170.0	Standard non polar	33892256
(1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide	CC1=C2CC3C(C)=CCC(O)C3(C)CC2(O)OC1=O	2320.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide,1TMS,isomer #1	CC1=CCC(O[Si](C)(C)C)C2(C)CC3(O)OC(=O)C(C)=C3CC12	2277.5	Semi standard non polar	33892256
(1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide,1TMS,isomer #2	CC1=CCC(O)C2(C)CC3(O[Si](C)(C)C)OC(=O)C(C)=C3CC12	2336.2	Semi standard non polar	33892256
(1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide,2TMS,isomer #1	CC1=CCC(O[Si](C)(C)C)C2(C)CC3(O[Si](C)(C)C)OC(=O)C(C)=C3CC12	2373.1	Semi standard non polar	33892256
(1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide,1TBDMS,isomer #1	CC1=CCC(O[Si](C)(C)C(C)(C)C)C2(C)CC3(O)OC(=O)C(C)=C3CC12	2527.2	Semi standard non polar	33892256
(1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide,1TBDMS,isomer #2	CC1=CCC(O)C2(C)CC3(O[Si](C)(C)C(C)(C)C)OC(=O)C(C)=C3CC12	2565.6	Semi standard non polar	33892256
(1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide,2TBDMS,isomer #1	CC1=CCC(O[Si](C)(C)C(C)(C)C)C2(C)CC3(O[Si](C)(C)C(C)(C)C)OC(=O)C(C)=C3CC12	2828.3	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 - (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-4950000000-ed7594d8e7080661b465	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide GC-MS (2 TMS) - 70eV, Positive	splash10-0002-2559000000-18f2253fec83d12ebcb4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-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 - (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide 10V, Positive-QTOF	splash10-00kb-0290000000-c24570a8b8958b52334b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide 20V, Positive-QTOF	splash10-002b-0890000000-2d953d0682e599e3b0e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide 40V, Positive-QTOF	splash10-0v0c-9720000000-b5c5d39c5e590072be9a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide 10V, Negative-QTOF	splash10-03di-0090000000-c27ad0d9fda9a4bd54f2	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide 20V, Negative-QTOF	splash10-0901-0090000000-18d9a4b863d8524633aa	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide 40V, Negative-QTOF	splash10-05o3-7790000000-f55fce92b5cb804476c8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide 10V, Positive-QTOF	splash10-014i-0090000000-ba6b11f12393faf93ad9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide 20V, Positive-QTOF	splash10-0ftb-0390000000-179e88eb9f97564c32fe	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide 40V, Positive-QTOF	splash10-01c9-2930000000-1a4df48efdf819f8925f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide 10V, Negative-QTOF	splash10-03di-0090000000-c4692ff9616acc5e7db2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide 20V, Negative-QTOF	splash10-03di-0090000000-8bcd6632c6c96c403027	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide 40V, Negative-QTOF	splash10-00bj-1960000000-d4c98e284195087f7cdd	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

FDB014973

KNApSAcK ID

Not Available

Chemspider ID

35014100

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751916

PDB ID

Not Available

ChEBI ID

174478

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 (1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide (HMDB0036125)

MOL for HMDB0036125 ((1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide)

3D MOL for HMDB0036125 ((1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide)

3D SDF for HMDB0036125 ((1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide)

3D-SDF for HMDB0036125 ((1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide)

PDB for HMDB0036125 ((1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide)

3D PDB for HMDB0036125 ((1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide)

SMILES for HMDB0036125 ((1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide)

INCHI for HMDB0036125 ((1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide)

Structure for HMDB0036125 ((1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide)

3D Structure for HMDB0036125 ((1beta,8beta)-1,8-Dihydroxy-3,7(11)-eudesmadien-12,8-olide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra