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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:51:42 UTC

Update Date

2022-03-07 02:54:17 UTC

HMDB ID

HMDB0034930

Secondary Accession Numbers

HMDB34930

Metabolite Identification

Common Name

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

Description

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

Structure

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

HMDB0034930
     RDKit          3D
(3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate
 45 47  0  0  0  0  0  0  0  0999 V2000
    3.4130   -2.3172    0.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4298   -1.4484   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295   -1.4779   -1.5697 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6859   -0.5522    0.4109 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7361    0.3186   -0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0288    1.7394    0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1633    2.4292    0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5534    1.9460    0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7965    3.7572    0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5220    3.8378    0.2254 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0085    2.6549    0.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3966    2.3020   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5706    0.8368   -0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0231    0.4804   -0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1444   -0.9435   -0.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3726   -1.8277   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3857   -3.1241   -0.6129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9262   -1.4507    0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2848   -2.3858    1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6890   -0.0028    0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9010    0.4088    1.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8781   -3.2161    0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1810   -2.6499   -0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8647   -1.8177    1.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6894    0.1552   -1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167    1.6181    1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2832    2.7582    0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8094    1.1563   -0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4241    4.6144    0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6822    2.8271   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349    2.6473    0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2479    0.5946   -1.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4316    0.5105    0.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5833    1.2065   -1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6325   -0.9493   -1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1766   -1.2834   -1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8931   -1.8786    0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2829   -3.4694   -0.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4503   -1.6538   -0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633   -3.2272    0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703   -2.8909    1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3889   -1.9044    1.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293   -0.4090    2.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7590    1.0976    1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0027    0.9833    2.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 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
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20  5  1  0
 11  6  2  0
 20 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  8 26  1  0
  8 27  1  0
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 15 35  1  0
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 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
M  END


  Mrv0541 05061308082D          

 21 23  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
    3.5724   -3.7125    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
    3.5724   -2.8875    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
    4.2868   -2.4750    0.0000 O   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
    4.3570   -0.1576    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
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  8  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 12  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14  7  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17  4  1  0  0  0  0
 17 10  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
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 19 13  1  0  0  0  0
 20  8  1  0  0  0  0
 20 14  1  0  0  0  0
 21 11  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034930

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O4/c1-9-8-20-14-7-12-5-6-13(19)10(2)17(12,4)16(15(9)14)21-11(3)18/h8,10,12-13,16,19H,5-7H2,1-4H3

> <INCHI_KEY>
CXZIQFLLAXJLDS-UHFFFAOYSA-N

> <FORMULA>
C17H24O4

> <MOLECULAR_WEIGHT>
292.3701

> <EXACT_MASS>
292.167459256

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.06966005775904

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
2.487233438

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.93666711678976

> <JCHEM_PKA_STRONGEST_BASIC>
-2.077936546348572

> <JCHEM_POLAR_SURFACE_AREA>
59.67

> <JCHEM_REFRACTIVITY>
78.7525

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.61e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034930
     RDKit          3D
(3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate
 45 47  0  0  0  0  0  0  0  0999 V2000
    3.4130   -2.3172    0.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4298   -1.4484   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295   -1.4779   -1.5697 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6859   -0.5522    0.4109 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7361    0.3186   -0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0288    1.7394    0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1633    2.4292    0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5534    1.9460    0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7965    3.7572    0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5220    3.8378    0.2254 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0085    2.6549    0.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3966    2.3020   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5706    0.8368   -0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0231    0.4804   -0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1444   -0.9435   -0.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3726   -1.8277   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3857   -3.1241   -0.6129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9262   -1.4507    0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2848   -2.3858    1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6890   -0.0028    0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9010    0.4088    1.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8781   -3.2161    0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1810   -2.6499   -0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8647   -1.8177    1.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6894    0.1552   -1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167    1.6181    1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2832    2.7582    0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8094    1.1563   -0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4241    4.6144    0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6822    2.8271   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349    2.6473    0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2479    0.5946   -1.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4316    0.5105    0.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5833    1.2065   -1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6325   -0.9493   -1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1766   -1.2834   -1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8931   -1.8786    0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2829   -3.4694   -0.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4503   -1.6538   -0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633   -3.2272    0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703   -2.8909    1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3889   -1.9044    1.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293   -0.4090    2.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7590    1.0976    1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0027    0.9833    2.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 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
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20  5  1  0
 11  6  2  0
 20 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  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       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   17                                                            
CONECT    5    6   12                                                       
CONECT    6    5   13                                                       
CONECT    7   12   14                                                       
CONECT    8    9   20                                                       
CONECT    9    1    8   15                                                  
CONECT   10    2   13   17                                                  
CONECT   11    3   18   21                                                  
CONECT   12    5    7   17                                                  
CONECT   13    6   10   19                                                  
CONECT   14    7   15   20                                                  
CONECT   15    9   14   16                                                  
CONECT   16   15   17   21                                                  
CONECT   17    4   10   12   16                                             
CONECT   18   11                                                            
CONECT   19   13                                                            
CONECT   20    8   14                                                       
CONECT   21   11   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0034930
HETATM    1  C1  UNL     1       3.413  -2.317   0.354  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.430  -1.448  -0.335  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.229  -1.478  -1.570  1.00  0.00           O  
HETATM    4  O2  UNL     1       1.686  -0.552   0.411  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.736   0.319  -0.088  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.029   1.739   0.112  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.163   2.429   0.400  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.553   1.946   0.620  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.796   3.757   0.463  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.522   3.838   0.225  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.009   2.655   0.007  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.397   2.302  -0.300  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.571   0.837  -0.508  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.023   0.480  -0.419  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.144  -0.944  -0.977  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.373  -1.828  -0.052  1.00  0.00           C  
HETATM   17  O4  UNL     1      -2.386  -3.124  -0.613  1.00  0.00           O  
HETATM   18  C14 UNL     1      -0.926  -1.451   0.102  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.285  -2.386   1.068  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.689  -0.003   0.387  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.901   0.409   1.795  1.00  0.00           C  
HETATM   22  H1  UNL     1       2.878  -3.216   0.762  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.181  -2.650  -0.376  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.865  -1.818   1.239  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.689   0.155  -1.206  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.617   1.618   1.675  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.283   2.758   0.486  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.809   1.156  -0.108  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.424   4.614   0.671  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.682   2.827  -1.232  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.035   2.647   0.546  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.248   0.595  -1.563  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.432   0.511   0.593  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.583   1.206  -1.032  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.632  -0.949  -1.958  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.177  -1.283  -1.011  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.893  -1.879   0.933  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.283  -3.469  -0.741  1.00  0.00           H  
HETATM   39  H18 UNL     1      -0.450  -1.654  -0.905  1.00  0.00           H  
HETATM   40  H19 UNL     1       0.263  -3.227   0.551  1.00  0.00           H  
HETATM   41  H20 UNL     1      -1.070  -2.891   1.668  1.00  0.00           H  
HETATM   42  H21 UNL     1       0.389  -1.904   1.802  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.029  -0.409   2.514  1.00  0.00           H  
HETATM   44  H23 UNL     1      -1.759   1.098   1.928  1.00  0.00           H  
HETATM   45  H24 UNL     1       0.003   0.983   2.130  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   20   25
CONECT    6    7   11   11
CONECT    7    8    9    9
CONECT    8   26   27   28
CONECT    9   10   29
CONECT   10   11
CONECT   11   12
CONECT   12   13   30   31
CONECT   13   14   20   32
CONECT   14   15   33   34
CONECT   15   16   35   36
CONECT   16   17   18   37
CONECT   17   38
CONECT   18   19   20   39
CONECT   19   40   41   42
CONECT   20   21
CONECT   21   43   44   45
END

HMDB0034930
     RDKit          3D
(3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate
 45 47  0  0  0  0  0  0  0  0999 V2000
    3.4130   -2.3172    0.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4298   -1.4484   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295   -1.4779   -1.5697 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6859   -0.5522    0.4109 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7361    0.3186   -0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0288    1.7394    0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1633    2.4292    0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5534    1.9460    0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7965    3.7572    0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5220    3.8378    0.2254 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0085    2.6549    0.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3966    2.3020   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5706    0.8368   -0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0231    0.4804   -0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1444   -0.9435   -0.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3726   -1.8277   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3857   -3.1241   -0.6129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9262   -1.4507    0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2848   -2.3858    1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6890   -0.0028    0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9010    0.4088    1.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8781   -3.2161    0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1810   -2.6499   -0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8647   -1.8177    1.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6894    0.1552   -1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167    1.6181    1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2832    2.7582    0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8094    1.1563   -0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4241    4.6144    0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6822    2.8271   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0349    2.6473    0.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2479    0.5946   -1.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4316    0.5105    0.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5833    1.2065   -1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6325   -0.9493   -1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1766   -1.2834   -1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8931   -1.8786    0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2829   -3.4694   -0.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4503   -1.6538   -0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633   -3.2272    0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703   -2.8909    1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3889   -1.9044    1.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293   -0.4090    2.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7590    1.0976    1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0027    0.9833    2.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 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
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20  5  1  0
 11  6  2  0
 20 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3b,6b)-Furanoeremophilane-3,6-diol 6-acetate	Generator
(3b,6b)-Furanoeremophilane-3,6-diol 6-acetic acid	Generator
(3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetic acid	Generator
(3Β,6β)-furanoeremophilane-3,6-diol 6-acetate	Generator
(3Β,6β)-furanoeremophilane-3,6-diol 6-acetic acid	Generator
6-Acetylfuranofukinol	HMDB
6-Hydroxy-3,4a,5-trimethyl-4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-4-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₄O₄

Average Molecular Weight

292.3701

Monoisotopic Molecular Weight

292.167459256

IUPAC Name

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

Traditional Name

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

CAS Registry Number

34335-95-0

SMILES

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

InChI Identifier

InChI=1S/C17H24O4/c1-9-8-20-14-7-12-5-6-13(19)10(2)17(12,4)16(15(9)14)21-11(3)18/h8,10,12-13,16,19H,5-7H2,1-4H3

InChI Key

CXZIQFLLAXJLDS-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
Cyclic alcohol
Heteroaromatic compound
Furan
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034930)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034930)

Source

Endogenous

Endogenous (HMDB: HMDB0034930)

Plant

Plant (HMDB: HMDB0034930)

Animal

Animal (HMDB: HMDB0034930)

Exogenous

Food

Food (HMDB: HMDB0034930)

Vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0034930)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0034930)

Cellular process

Cell signaling (HMDB: HMDB0034930)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0034930)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0034930)

Nutrient

Nutrient (HMDB: HMDB0034930)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.056 g/L	ALOGPS
logP	2.73	ALOGPS
logP	2.49	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	14.94	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.75 m³·mol⁻¹	ChemAxon
Polarizability	32.07 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]+	167.594	31661259
DarkChem	[M-H]-	164.036	31661259
DeepCCS	[M-2H]-	200.443	30932474
DeepCCS	[M+Na]+	176.008	30932474
AllCCS	[M+H]+	168.9	32859911
AllCCS	[M+H-H2O]+	165.6	32859911
AllCCS	[M+NH4]+	172.0	32859911
AllCCS	[M+Na]+	172.9	32859911
AllCCS	[M-H]-	175.6	32859911
AllCCS	[M+Na-2H]-	175.7	32859911
AllCCS	[M+HCOO]-	175.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate	CC1C(O)CCC2CC3=C(C(OC(C)=O)C12C)C(C)=CO3	3095.4	Standard polar	33892256
(3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate	CC1C(O)CCC2CC3=C(C(OC(C)=O)C12C)C(C)=CO3	2048.0	Standard non polar	33892256
(3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate	CC1C(O)CCC2CC3=C(C(OC(C)=O)C12C)C(C)=CO3	2194.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate,1TMS,isomer #1	CC(=O)OC1C2=C(CC3CCC(O[Si](C)(C)C)C(C)C31C)OC=C2C	2237.1	Semi standard non polar	33892256
(3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate,1TBDMS,isomer #1	CC(=O)OC1C2=C(CC3CCC(O[Si](C)(C)C(C)(C)C)C(C)C31C)OC=C2C	2476.0	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 6-acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00c3-5590000000-12437cfd3de3af50856c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate GC-MS (1 TMS) - 70eV, Positive	splash10-007d-9456000000-15e86743450662cb7820	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate 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 6-acetate 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 6-acetate 10V, Positive-QTOF	splash10-004l-0090000000-0ca1b9f04c754e1dd2e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate 20V, Positive-QTOF	splash10-003r-1490000000-a335864744bac28f06d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate 40V, Positive-QTOF	splash10-100s-8940000000-179d88daf1e6e12785b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate 10V, Negative-QTOF	splash10-0006-0090000000-7b2f9d74f667a74f49d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate 20V, Negative-QTOF	splash10-0537-2090000000-0d8324a9daefc5b5b93d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate 40V, Negative-QTOF	splash10-0apl-4390000000-11106f5285d98464705b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate 10V, Positive-QTOF	splash10-0006-0090000000-bc513b44cc71645c05e0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate 20V, Positive-QTOF	splash10-00ng-0290000000-4e8923e6d25c7f1e3f97	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate 40V, Positive-QTOF	splash10-05nb-5950000000-28171af4c4989b787e84	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate 10V, Negative-QTOF	splash10-000x-2090000000-bde5696fae9b61d576af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate 20V, Negative-QTOF	splash10-0a4i-9060000000-0515f875aae548e7f721	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate 40V, Negative-QTOF	splash10-052f-9130000000-185c9bb908293d7aabcc	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB013520

KNApSAcK ID

C00017350

Chemspider ID

35013798

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78384665

PDB ID

Not Available

ChEBI ID

168723

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 (3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate (HMDB0034930)

MOL for HMDB0034930 ((3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate)

3D MOL for HMDB0034930 ((3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate)

3D SDF for HMDB0034930 ((3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate)

3D-SDF for HMDB0034930 ((3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate)

PDB for HMDB0034930 ((3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate)

3D PDB for HMDB0034930 ((3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate)

SMILES for HMDB0034930 ((3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate)

INCHI for HMDB0034930 ((3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate)

Structure for HMDB0034930 ((3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate)

3D Structure for HMDB0034930 ((3beta,6beta)-Furanoeremophilane-3,6-diol 6-acetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra