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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:20:13 UTC

Update Date

2022-03-07 02:56:43 UTC

HMDB ID

HMDB0040755

Secondary Accession Numbers

HMDB40755

Metabolite Identification

Common Name

3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide

Description

3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a small amount of articles have been published on 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide.

Structure

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

HMDB0040755
     RDKit          3D
3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide
 44 46  0  0  0  0  0  0  0  0999 V2000
   -1.6985    2.6995   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0862    1.4811   -0.8580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9052    0.7175    0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551   -0.4074    0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8685   -0.6801   -0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4517    0.1610   -1.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3896   -1.9764   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3814   -2.5816   -0.6476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6284   -2.4773    0.8958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6482   -1.5271    1.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3032   -2.0598    0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8015   -1.0392    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0676   -1.6864    0.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6842   -1.1419   -0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6812   -0.3764   -1.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480    0.1356   -2.6703 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060    0.8033   -0.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5977    1.4915   -0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5133    0.3278    0.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0074    1.2906    1.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1416    3.3481    0.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6949    2.4971   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9411    3.1945   -1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3354    1.3521    1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1170    0.9415   -1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6448    0.5527   -2.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0712   -0.4985   -2.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6515   -1.0997    2.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1112   -2.9569    1.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782   -2.4159   -0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8772   -1.0671    2.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8800   -1.6663    1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9446   -2.8002    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6031   -0.5436   -0.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0680   -1.9580   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8497   -1.0278   -1.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3228   -0.0696   -2.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7668    1.5122   -1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3094    1.3709   -1.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4646    2.6115   -0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0832    1.0820    0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1523    1.3169    2.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8518    0.8661    2.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1222    2.3039    1.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  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
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  3  1  0
 10  4  1  0
 19 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
M  END

  Mrv0541 02241208182D          

 20 22  0  0  0  0            999 V2000
    1.7786   -0.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5241   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7391    0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0241   -0.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0241   -1.0326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6896   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6896    0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4046   -0.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4046   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182    0.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1182    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4046    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6896    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0241    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7391    1.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5241    1.2856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0082    0.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8332    0.6174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7391   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  3 16  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5 20  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040755

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1C2=C(C)C(=O)OC2CC2CCC(O)C(C)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O4/c1-8-13-12(20-15(8)18)7-10-5-6-11(17)9(2)16(10,3)14(13)19-4/h9-12,14,17H,5-7H2,1-4H3

> <INCHI_KEY>
OBOOZVIHEDVWHF-UHFFFAOYSA-N

> <FORMULA>
C16H24O4

> <MOLECULAR_WEIGHT>
280.3594

> <EXACT_MASS>
280.167459256

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.563226752274353

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
1.941441467666667

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.029234016492367

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.218221617930176

> <JCHEM_PKA_STRONGEST_BASIC>
-2.826469155385249

> <JCHEM_POLAR_SURFACE_AREA>
55.76

> <JCHEM_REFRACTIVITY>
74.85399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.09e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040755
     RDKit          3D
3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide
 44 46  0  0  0  0  0  0  0  0999 V2000
   -1.6985    2.6995   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0862    1.4811   -0.8580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9052    0.7175    0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551   -0.4074    0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8685   -0.6801   -0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4517    0.1610   -1.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3896   -1.9764   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3814   -2.5816   -0.6476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6284   -2.4773    0.8958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6482   -1.5271    1.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3032   -2.0598    0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8015   -1.0392    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0676   -1.6864    0.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6842   -1.1419   -0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6812   -0.3764   -1.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480    0.1356   -2.6703 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060    0.8033   -0.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5977    1.4915   -0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5133    0.3278    0.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0074    1.2906    1.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1416    3.3481    0.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6949    2.4971   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9411    3.1945   -1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3354    1.3521    1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1170    0.9415   -1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6448    0.5527   -2.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0712   -0.4985   -2.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6515   -1.0997    2.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1112   -2.9569    1.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782   -2.4159   -0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8772   -1.0671    2.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8800   -1.6663    1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9446   -2.8002    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6031   -0.5436   -0.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0680   -1.9580   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8497   -1.0278   -1.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3228   -0.0696   -2.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7668    1.5122   -1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3094    1.3709   -1.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4646    2.6115   -0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0832    1.0820    0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1523    1.3169    2.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8518    0.8661    2.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1222    2.3039    1.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  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
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  3  1  0
 10  4  1  0
 19 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  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       3.320  -1.558   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.845  -0.092   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.380   0.382   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.045  -0.388   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.045  -1.928   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.287  -1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.287   0.382   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.622  -0.388   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.622  -1.925   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.289  -0.385   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.954   0.382   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.954   1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.622   2.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.287   1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.045   2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.380   1.922   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.845   2.400   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.749   1.152   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.289   1.152   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.380  -2.695   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4   20                                                       
CONECT    6    7                                                            
CONECT    7    4    6    8   14                                             
CONECT    8    7    9   11                                                  
CONECT    9    8                                                            
CONECT   10   11                                                            
CONECT   11    8   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    7   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16    3   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18    2   17   19                                                  
CONECT   19   18                                                            
CONECT   20    5                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0040755
HETATM    1  C1  UNL     1      -1.699   2.699  -0.615  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.086   1.481  -0.858  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.905   0.717   0.293  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.855  -0.407   0.186  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.868  -0.680  -0.560  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.452   0.161  -1.670  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.390  -1.976  -0.150  1.00  0.00           C  
HETATM    8  O2  UNL     1      -4.381  -2.582  -0.648  1.00  0.00           O  
HETATM    9  O3  UNL     1      -2.628  -2.477   0.896  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.648  -1.527   1.138  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.303  -2.060   0.722  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.801  -1.039   0.954  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.068  -1.686   0.480  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.684  -1.142  -0.748  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.681  -0.376  -1.558  1.00  0.00           C  
HETATM   16  O4  UNL     1       2.348   0.136  -2.670  1.00  0.00           O  
HETATM   17  C13 UNL     1       1.306   0.803  -0.684  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.598   1.492  -0.297  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.513   0.328   0.534  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.007   1.291   1.642  1.00  0.00           C  
HETATM   21  H1  UNL     1      -1.142   3.348   0.072  1.00  0.00           H  
HETATM   22  H2  UNL     1      -2.695   2.497  -0.129  1.00  0.00           H  
HETATM   23  H3  UNL     1      -1.941   3.194  -1.572  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.335   1.352   1.129  1.00  0.00           H  
HETATM   25  H5  UNL     1      -4.117   0.941  -1.282  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.645   0.553  -2.332  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.071  -0.499  -2.325  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.652  -1.100   2.150  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.111  -2.957   1.361  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.378  -2.416  -0.301  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.877  -1.067   2.089  1.00  0.00           H  
HETATM   32  H12 UNL     1       2.880  -1.666   1.272  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.945  -2.800   0.308  1.00  0.00           H  
HETATM   34  H14 UNL     1       3.603  -0.544  -0.531  1.00  0.00           H  
HETATM   35  H15 UNL     1       3.068  -1.958  -1.430  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.850  -1.028  -1.813  1.00  0.00           H  
HETATM   37  H17 UNL     1       3.323  -0.070  -2.661  1.00  0.00           H  
HETATM   38  H18 UNL     1       0.767   1.512  -1.315  1.00  0.00           H  
HETATM   39  H19 UNL     1       3.309   1.371  -1.165  1.00  0.00           H  
HETATM   40  H20 UNL     1       2.465   2.611  -0.227  1.00  0.00           H  
HETATM   41  H21 UNL     1       3.083   1.082   0.582  1.00  0.00           H  
HETATM   42  H22 UNL     1       0.152   1.317   2.381  1.00  0.00           H  
HETATM   43  H23 UNL     1       1.852   0.866   2.190  1.00  0.00           H  
HETATM   44  H24 UNL     1       1.122   2.304   1.276  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4   19   24
CONECT    4    5    5   10
CONECT    5    6    7
CONECT    6   25   26   27
CONECT    7    8    8    9
CONECT    9   10
CONECT   10   11   28
CONECT   11   12   29   30
CONECT   12   13   19   31
CONECT   13   14   32   33
CONECT   14   15   34   35
CONECT   15   16   17   36
CONECT   16   37
CONECT   17   18   19   38
CONECT   18   39   40   41
CONECT   19   20
CONECT   20   42   43   44
END

HMDB0040755
     RDKit          3D
3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide
 44 46  0  0  0  0  0  0  0  0999 V2000
   -1.6985    2.6995   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0862    1.4811   -0.8580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9052    0.7175    0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551   -0.4074    0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8685   -0.6801   -0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4517    0.1610   -1.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3896   -1.9764   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3814   -2.5816   -0.6476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6284   -2.4773    0.8958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6482   -1.5271    1.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3032   -2.0598    0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8015   -1.0392    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0676   -1.6864    0.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6842   -1.1419   -0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6812   -0.3764   -1.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480    0.1356   -2.6703 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060    0.8033   -0.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5977    1.4915   -0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5133    0.3278    0.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0074    1.2906    1.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1416    3.3481    0.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6949    2.4971   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9411    3.1945   -1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3354    1.3521    1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1170    0.9415   -1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6448    0.5527   -2.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0712   -0.4985   -2.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6515   -1.0997    2.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1112   -2.9569    1.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782   -2.4159   -0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8772   -1.0671    2.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8800   -1.6663    1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9446   -2.8002    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6031   -0.5436   -0.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0680   -1.9580   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8497   -1.0278   -1.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3228   -0.0696   -2.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7668    1.5122   -1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3094    1.3709   -1.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4646    2.6115   -0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0832    1.0820    0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1523    1.3169    2.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8518    0.8661    2.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1222    2.3039    1.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  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
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  3  1  0
 10  4  1  0
 19 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₂₄O₄

Average Molecular Weight

280.3594

Monoisotopic Molecular Weight

280.167459256

IUPAC Name

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

Traditional Name

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

CAS Registry Number

162613-64-1

SMILES

COC1C2=C(C)C(=O)OC2CC2CCC(O)C(C)C12C

InChI Identifier

InChI=1S/C16H24O4/c1-8-13-12(20-15(8)18)7-10-5-6-11(17)9(2)16(10,3)14(13)19-4/h9-12,14,17H,5-7H2,1-4H3

InChI Key

OBOOZVIHEDVWHF-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0040755)

Food

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	180 - 181 °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	0.51 g/L	ALOGPS
logP	1.91	ALOGPS
logP	1.94	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	14.22	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.85 m³·mol⁻¹	ChemAxon
Polarizability	30.56 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]+	165.504	31661259
DarkChem	[M-H]-	163.727	31661259
DeepCCS	[M-2H]-	198.459	30932474
DeepCCS	[M+Na]+	173.875	30932474
AllCCS	[M+H]+	167.1	32859911
AllCCS	[M+H-H2O]+	163.8	32859911
AllCCS	[M+NH4]+	170.3	32859911
AllCCS	[M+Na]+	171.2	32859911
AllCCS	[M-H]-	172.8	32859911
AllCCS	[M+Na-2H]-	173.0	32859911
AllCCS	[M+HCOO]-	173.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide	COC1C2=C(C)C(=O)OC2CC2CCC(O)C(C)C12C	3371.3	Standard polar	33892256
3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide	COC1C2=C(C)C(=O)OC2CC2CCC(O)C(C)C12C	2217.3	Standard non polar	33892256
3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide	COC1C2=C(C)C(=O)OC2CC2CCC(O)C(C)C12C	2367.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide,1TMS,isomer #1	COC1C2=C(C)C(=O)OC2CC2CCC(O[Si](C)(C)C)C(C)C21C	2325.6	Semi standard non polar	33892256
3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide,1TBDMS,isomer #1	COC1C2=C(C)C(=O)OC2CC2CCC(O[Si](C)(C)C(C)(C)C)C(C)C21C	2559.9	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 - 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ri-0390000000-cd27babf0140f6ba4573	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-4498000000-783e1540f85cbcbe44bf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-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 - 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide 10V, Positive-QTOF	splash10-01q9-0090000000-898b3f9e0dc8e36b17bd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide 20V, Positive-QTOF	splash10-0btc-0790000000-94e877a35602a4794bf5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide 40V, Positive-QTOF	splash10-0udr-7900000000-62639a1202b21d1b3c99	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide 10V, Negative-QTOF	splash10-004i-0090000000-10f32aa735e2be2328cc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide 20V, Negative-QTOF	splash10-01ti-0090000000-5e18b389d2804a939d2b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide 40V, Negative-QTOF	splash10-0ar3-2890000000-1d0d663b9ffc08364c9a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide 10V, Negative-QTOF	splash10-004i-0090000000-8597d5b937876f2bed9f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide 20V, Negative-QTOF	splash10-004i-0090000000-12268bf1f8e490e33491	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide 40V, Negative-QTOF	splash10-002k-4970000000-896ef07ae7c55ca5f707	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide 10V, Positive-QTOF	splash10-01q9-0090000000-2ae39974c79c2324bc9f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide 20V, Positive-QTOF	splash10-001i-0290000000-fcc4a3c6b615f26dc821	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide 40V, Positive-QTOF	splash10-0400-5910000000-4a93ec2895e5ca771963	2021-09-24	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

FDB021190

KNApSAcK ID

Not Available

Chemspider ID

35015013

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752927

PDB ID

Not Available

ChEBI ID

174674

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 ]
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Showing metabocard for 3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide (HMDB0040755)

MOL for HMDB0040755 (3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide)

3D MOL for HMDB0040755 (3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide)

3D SDF for HMDB0040755 (3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide)

3D-SDF for HMDB0040755 (3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide)

PDB for HMDB0040755 (3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide)

3D PDB for HMDB0040755 (3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide)

SMILES for HMDB0040755 (3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide)

INCHI for HMDB0040755 (3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide)

Structure for HMDB0040755 (3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide)

3D Structure for HMDB0040755 (3b-Hydroxy-6b-methoxy-7(11)-eremophilen-12,8a-olide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra