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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:03:41 UTC

Update Date

2022-03-07 02:54:22 UTC

HMDB ID

HMDB0035117

Secondary Accession Numbers

HMDB35117

Metabolite Identification

Common Name

(3beta,6beta)-Furanoeremophilane-3,6-diol

Description

(3beta,6beta)-Furanoeremophilane-3,6-diol belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review a small amount of articles have been published on (3beta,6beta)-Furanoeremophilane-3,6-diol.

Structure

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

HMDB0035117
     RDKit          3D
(3beta,6beta)-Furanoeremophilane-3,6-diol
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.6255   -1.8485    0.8373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2458   -0.5961    0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0069    0.2219   -0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2830    1.2336   -1.1053 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0682    1.1612   -0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9846    0.0335    0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7608   -0.3710    0.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9071   -0.0808    2.2209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5161    0.2298    0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0532    1.2220    1.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2726    0.9401   -0.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877    1.5340   -1.5842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966    0.4423   -1.7897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667   -0.3817   -0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4817   -1.5260   -0.9937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5084   -0.8874    0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8776   -1.6134    1.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8391    1.9891   -0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8345   -1.6838    1.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4204   -2.3758    0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7271   -2.5325    0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0651    0.0551   -0.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7002   -1.4998    0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245    0.5971    2.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4182    2.1477    0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8557    0.7825    1.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1982    1.5278    1.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1375    0.1929   -1.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1725    1.8640   -2.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8856    2.4249   -1.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1121   -0.1993   -2.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4317    0.9087   -2.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3820    0.1932    0.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8588   -2.2644   -1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0252   -1.6060   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9347   -1.4431    1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7501   -2.7134    1.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2630   -1.2815    2.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6840    2.5886    0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8341    2.6144   -1.6772 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 11 18  1  0
  6  2  1  0
 16  9  1  0
 18  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END


  Mrv0541 05061308142D          

 18 20  0  0  0  0            999 V2000
    4.6119   -2.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  7  2  0  0  0  0
  9  2  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15  3  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 17 14  1  0  0  0  0
 18  7  1  0  0  0  0
 18 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035117

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C(O)CCC2CC3=C(C(O)C12C)C(C)=CO3

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-8-7-18-12-6-10-4-5-11(16)9(2)15(10,3)14(17)13(8)12/h7,9-11,14,16-17H,4-6H2,1-3H3

> <INCHI_KEY>
JWKRZHJQYDUUNQ-UHFFFAOYSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.3334

> <EXACT_MASS>
250.15689457

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.128110703703815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
2.046108027666667

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.9625010837308

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.582926907953066

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0772396746398933

> <JCHEM_POLAR_SURFACE_AREA>
53.6

> <JCHEM_REFRACTIVITY>
69.601

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.51e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035117
     RDKit          3D
(3beta,6beta)-Furanoeremophilane-3,6-diol
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.6255   -1.8485    0.8373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2458   -0.5961    0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0069    0.2219   -0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2830    1.2336   -1.1053 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0682    1.1612   -0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9846    0.0335    0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7608   -0.3710    0.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9071   -0.0808    2.2209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5161    0.2298    0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0532    1.2220    1.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2726    0.9401   -0.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877    1.5340   -1.5842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966    0.4423   -1.7897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667   -0.3817   -0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4817   -1.5260   -0.9937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5084   -0.8874    0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8776   -1.6134    1.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8391    1.9891   -0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8345   -1.6838    1.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4204   -2.3758    0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7271   -2.5325    0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0651    0.0551   -0.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7002   -1.4998    0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245    0.5971    2.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4182    2.1477    0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8557    0.7825    1.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1982    1.5278    1.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1375    0.1929   -1.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1725    1.8640   -2.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8856    2.4249   -1.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1121   -0.1993   -2.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4317    0.9087   -2.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3820    0.1932    0.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8588   -2.2644   -1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0252   -1.6060   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9347   -1.4431    1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7501   -2.7134    1.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2630   -1.2815    2.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6840    2.5886    0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8341    2.6144   -1.6772 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 11 18  1  0
  6  2  1  0
 16  9  1  0
 18  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.609  -4.251   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   15                                                            
CONECT    4    5   10                                                       
CONECT    5    4   11                                                       
CONECT    6   10   12                                                       
CONECT    7    8   18                                                       
CONECT    8    1    7   13                                                  
CONECT    9    2   11   15                                                  
CONECT   10    4    6   15                                                  
CONECT   11    5    9   16                                                  
CONECT   12    6   13   18                                                  
CONECT   13    8   12   14                                                  
CONECT   14   13   15   17                                                  
CONECT   15    3    9   10   14                                             
CONECT   16   11                                                            
CONECT   17   14                                                            
CONECT   18    7   12                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0035117
HETATM    1  C1  UNL     1       3.626  -1.848   0.837  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.246  -0.596   0.131  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.007   0.222  -0.677  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.283   1.234  -1.105  1.00  0.00           O  
HETATM    5  C4  UNL     1       2.068   1.161  -0.640  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.985   0.034   0.143  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.761  -0.371   0.840  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.907  -0.081   2.221  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.516   0.230   0.334  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.053   1.222   1.348  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.273   0.940  -0.946  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.488   1.534  -1.584  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.497   0.442  -1.790  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.767  -0.382  -0.574  1.00  0.00           C  
HETATM   15  O3  UNL     1      -3.482  -1.526  -0.994  1.00  0.00           O  
HETATM   16  C13 UNL     1      -1.508  -0.887   0.081  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.878  -1.613   1.341  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.839   1.989  -0.773  1.00  0.00           C  
HETATM   19  H1  UNL     1       3.834  -1.684   1.915  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.420  -2.376   0.302  1.00  0.00           H  
HETATM   21  H3  UNL     1       2.727  -2.533   0.812  1.00  0.00           H  
HETATM   22  H4  UNL     1       5.065   0.055  -0.929  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.700  -1.500   0.829  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.624   0.597   2.324  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.418   2.148   0.862  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.856   0.783   1.979  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.198   1.528   1.985  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.138   0.193  -1.681  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.172   1.864  -2.619  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.886   2.425  -1.101  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.112  -0.199  -2.624  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.432   0.909  -2.134  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.382   0.193   0.126  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.859  -2.264  -1.213  1.00  0.00           H  
HETATM   35  H17 UNL     1      -1.025  -1.606  -0.608  1.00  0.00           H  
HETATM   36  H18 UNL     1      -2.935  -1.443   1.650  1.00  0.00           H  
HETATM   37  H19 UNL     1      -1.750  -2.713   1.271  1.00  0.00           H  
HETATM   38  H20 UNL     1      -1.263  -1.282   2.214  1.00  0.00           H  
HETATM   39  H21 UNL     1       0.684   2.589   0.126  1.00  0.00           H  
HETATM   40  H22 UNL     1       0.834   2.614  -1.677  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    6
CONECT    3    4   22
CONECT    4    5
CONECT    5    6    6   18
CONECT    6    7
CONECT    7    8    9   23
CONECT    8   24
CONECT    9   10   11   16
CONECT   10   25   26   27
CONECT   11   12   18   28
CONECT   12   13   29   30
CONECT   13   14   31   32
CONECT   14   15   16   33
CONECT   15   34
CONECT   16   17   35
CONECT   17   36   37   38
CONECT   18   39   40
END

HMDB0035117
     RDKit          3D
(3beta,6beta)-Furanoeremophilane-3,6-diol
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.6255   -1.8485    0.8373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2458   -0.5961    0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0069    0.2219   -0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2830    1.2336   -1.1053 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0682    1.1612   -0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9846    0.0335    0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7608   -0.3710    0.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9071   -0.0808    2.2209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5161    0.2298    0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0532    1.2220    1.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2726    0.9401   -0.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877    1.5340   -1.5842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966    0.4423   -1.7897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667   -0.3817   -0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4817   -1.5260   -0.9937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5084   -0.8874    0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8776   -1.6134    1.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8391    1.9891   -0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8345   -1.6838    1.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4204   -2.3758    0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7271   -2.5325    0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0651    0.0551   -0.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7002   -1.4998    0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245    0.5971    2.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4182    2.1477    0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8557    0.7825    1.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1982    1.5278    1.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1375    0.1929   -1.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1725    1.8640   -2.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8856    2.4249   -1.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1121   -0.1993   -2.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4317    0.9087   -2.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3820    0.1932    0.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8588   -2.2644   -1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0252   -1.6060   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9347   -1.4431    1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7501   -2.7134    1.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2630   -1.2815    2.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6840    2.5886    0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8341    2.6144   -1.6772 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 11 18  1  0
  6  2  1  0
 16  9  1  0
 18  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3b,6b)-Furanoeremophilane-3,6-diol	Generator
(3Β,6β)-furanoeremophilane-3,6-diol	Generator
Furanofukinol	HMDB

Chemical Formula

C₁₅H₂₂O₃

Average Molecular Weight

250.3334

Monoisotopic Molecular Weight

250.15689457

IUPAC Name

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

Traditional Name

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

CAS Registry Number

34335-94-9

SMILES

CC1C(O)CCC2CC3=C(C(O)C12C)C(C)=CO3

InChI Identifier

InChI=1S/C15H22O3/c1-8-7-18-12-6-10-4-5-11(16)9(2)15(10,3)14(17)13(8)12/h7,9-11,14,16-17H,4-6H2,1-3H3

InChI Key

JWKRZHJQYDUUNQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Heteroaromatic compound
Furan
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0035117)

Cellular substructure

Extracellular (HMDB: HMDB0035117)
Cytoplasm (HMDB: HMDB0035117)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035117)

Source

Endogenous

Endogenous (HMDB: HMDB0035117)

Plant

Plant (HMDB: HMDB0035117)

Animal

Animal (HMDB: HMDB0035117)

Exogenous

Food

Food (HMDB: HMDB0035117)

Vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0035117)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0035117)

Cellular process

Cell signaling (HMDB: HMDB0035117)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0035117)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035117)

Nutrient

Nutrient (HMDB: HMDB0035117)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	178 - 180 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	53.45 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	1.83	ALOGPS
logP	2.05	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.58	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.6 m³·mol⁻¹	ChemAxon
Polarizability	28.13 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]+	158.642	31661259
DarkChem	[M-H]-	154.669	31661259
DeepCCS	[M-2H]-	191.314	30932474
DeepCCS	[M+Na]+	166.879	30932474
AllCCS	[M+H]+	159.6	32859911
AllCCS	[M+H-H2O]+	155.9	32859911
AllCCS	[M+NH4]+	163.0	32859911
AllCCS	[M+Na]+	164.0	32859911
AllCCS	[M-H]-	165.4	32859911
AllCCS	[M+Na-2H]-	165.5	32859911
AllCCS	[M+HCOO]-	165.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(3beta,6beta)-Furanoeremophilane-3,6-diol	CC1C(O)CCC2CC3=C(C(O)C12C)C(C)=CO3	3189.6	Standard polar	33892256
(3beta,6beta)-Furanoeremophilane-3,6-diol	CC1C(O)CCC2CC3=C(C(O)C12C)C(C)=CO3	1986.4	Standard non polar	33892256
(3beta,6beta)-Furanoeremophilane-3,6-diol	CC1C(O)CCC2CC3=C(C(O)C12C)C(C)=CO3	2088.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(3beta,6beta)-Furanoeremophilane-3,6-diol,1TMS,isomer #1	CC1=COC2=C1C(O)C1(C)C(CCC(O[Si](C)(C)C)C1C)C2	2205.6	Semi standard non polar	33892256
(3beta,6beta)-Furanoeremophilane-3,6-diol,1TMS,isomer #2	CC1=COC2=C1C(O[Si](C)(C)C)C1(C)C(CCC(O)C1C)C2	2178.7	Semi standard non polar	33892256
(3beta,6beta)-Furanoeremophilane-3,6-diol,2TMS,isomer #1	CC1=COC2=C1C(O[Si](C)(C)C)C1(C)C(CCC(O[Si](C)(C)C)C1C)C2	2163.5	Semi standard non polar	33892256
(3beta,6beta)-Furanoeremophilane-3,6-diol,1TBDMS,isomer #1	CC1=COC2=C1C(O)C1(C)C(CCC(O[Si](C)(C)C(C)(C)C)C1C)C2	2473.9	Semi standard non polar	33892256
(3beta,6beta)-Furanoeremophilane-3,6-diol,1TBDMS,isomer #2	CC1=COC2=C1C(O[Si](C)(C)C(C)(C)C)C1(C)C(CCC(O)C1C)C2	2441.6	Semi standard non polar	33892256
(3beta,6beta)-Furanoeremophilane-3,6-diol,2TBDMS,isomer #1	CC1=COC2=C1C(O[Si](C)(C)C(C)(C)C)C1(C)C(CCC(O[Si](C)(C)C(C)(C)C)C1C)C2	2614.3	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 - (3beta,6beta)-Furanoeremophilane-3,6-diol GC-MS (Non-derivatized) - 70eV, Positive	splash10-05cu-3980000000-5ed3e42450b6f0461bc8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol GC-MS (2 TMS) - 70eV, Positive	splash10-004i-3039000000-37b106376b1cdc6284fc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 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 - (3beta,6beta)-Furanoeremophilane-3,6-diol 10V, Positive-QTOF	splash10-0f89-0090000000-4ab5034443d3e5859f39	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 20V, Positive-QTOF	splash10-00lr-0590000000-a0f662c2646c0fec8b75	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 40V, Positive-QTOF	splash10-0udi-8950000000-212fd6fc0c78d42c7bfb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 10V, Negative-QTOF	splash10-0002-0090000000-0a20a5a061f56f8113c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 20V, Negative-QTOF	splash10-000t-0090000000-30d1651f12dc6b1e22db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 40V, Negative-QTOF	splash10-0gbl-1960000000-89378a09623031387232	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 10V, Positive-QTOF	splash10-0udi-0190000000-68bcd1b74a5866f5172d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 20V, Positive-QTOF	splash10-0v59-1790000000-1ee39581d5f8b9ba4159	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 40V, Positive-QTOF	splash10-0a4i-3900000000-cab2e296a6bf98921542	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 10V, Negative-QTOF	splash10-0002-0090000000-0dd1e5565d33dd37f20a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 20V, Negative-QTOF	splash10-0002-0090000000-234963f3243291330544	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 40V, Negative-QTOF	splash10-009t-0790000000-ccc1ee03eec7b9b1ddec	2021-09-25	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

FDB013749

KNApSAcK ID

C00017349

Chemspider ID

35013847

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12309961

PDB ID

Not Available

ChEBI ID

174298

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1847761

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 (3beta,6beta)-Furanoeremophilane-3,6-diol (HMDB0035117)

MOL for HMDB0035117 ((3beta,6beta)-Furanoeremophilane-3,6-diol)

3D MOL for HMDB0035117 ((3beta,6beta)-Furanoeremophilane-3,6-diol)

3D SDF for HMDB0035117 ((3beta,6beta)-Furanoeremophilane-3,6-diol)

3D-SDF for HMDB0035117 ((3beta,6beta)-Furanoeremophilane-3,6-diol)

PDB for HMDB0035117 ((3beta,6beta)-Furanoeremophilane-3,6-diol)

3D PDB for HMDB0035117 ((3beta,6beta)-Furanoeremophilane-3,6-diol)

SMILES for HMDB0035117 ((3beta,6beta)-Furanoeremophilane-3,6-diol)

INCHI for HMDB0035117 ((3beta,6beta)-Furanoeremophilane-3,6-diol)

Structure for HMDB0035117 ((3beta,6beta)-Furanoeremophilane-3,6-diol)

3D Structure for HMDB0035117 ((3beta,6beta)-Furanoeremophilane-3,6-diol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra