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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:13:18 UTC

Update Date

2022-03-07 02:55:08 UTC

HMDB ID

HMDB0036979

Secondary Accession Numbers

HMDB36979

Metabolite Identification

Common Name

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

Description

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

Structure

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

HMDB0036979
     RDKit          3D
6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.7869   -2.0156    1.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2169   -0.8038    1.3037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9302   -0.6247   -0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454   -1.5617   -0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -0.8263   -0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4972   -1.8677   -1.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8136   -1.5886   -0.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1955   -0.1488   -0.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1371    0.8004   -0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6199    1.5949    1.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8046    0.1431    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7932   -0.4939    1.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2084    1.2759    0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2403    2.3896   -0.4175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5292    0.7849   -0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4727    1.4234   -0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5169    2.8848   -1.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5352    0.4986   -1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6224    0.7233   -1.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1428   -0.7321   -0.7249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735   -2.9000    1.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8079   -2.0934    1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8869   -2.0521    2.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719   -1.9879   -1.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6203   -2.3877    0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2605   -0.2272   -1.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6101   -1.9865   -2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1713   -2.8846   -0.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847   -2.0169    0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5918   -2.1539   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5576    0.0687   -1.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1137   -0.0270    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9738    1.5386   -0.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2686    0.9843    1.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2529    2.4181    0.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7582    2.0331    1.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1503    0.0961    2.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -0.4230    2.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4098   -1.5176    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3410    1.5878    1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0578    2.2855   -1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5604    3.2416   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1522    3.0584   -2.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9124    3.4900   -0.4981 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 15  3  1  0
 20  3  1  0
 11  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
M  END


  Mrv0541 02241208412D          

 20 22  0  0  0  0            999 V2000
    1.1672    0.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6513   -0.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4762   -0.0337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3327   -1.6836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0463   -1.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0463   -0.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3327   -0.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3821   -0.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1672   -0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4216   -1.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7613   -1.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7613   -0.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4762   -0.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4762    0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7613    0.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0463    0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3327    0.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3821    0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4688    1.1983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    1.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 18  1  0  0  0  0
  2  3  2  0  0  0  0
  2  9  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  6 16  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 18  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036979

> <DATABASE_NAME>
hmdb

> <SMILES>
COC12CC3CCCC(C)C3(C)C(O)C1=C(C)C(=O)O2

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

> <INCHI_KEY>
UTOHVMLCPJSXEB-UHFFFAOYSA-N

> <FORMULA>
C16H24O4

> <MOLECULAR_WEIGHT>
280.3594

> <EXACT_MASS>
280.167459256

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.364088249495428

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
2.8318207570000014

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.90979610753537

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2756551825640283

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
74.8392

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036979
     RDKit          3D
6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.7869   -2.0156    1.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2169   -0.8038    1.3037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9302   -0.6247   -0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454   -1.5617   -0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -0.8263   -0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4972   -1.8677   -1.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8136   -1.5886   -0.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1955   -0.1488   -0.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1371    0.8004   -0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6199    1.5949    1.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8046    0.1431    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7932   -0.4939    1.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2084    1.2759    0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2403    2.3896   -0.4175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5292    0.7849   -0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4727    1.4234   -0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5169    2.8848   -1.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5352    0.4986   -1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6224    0.7233   -1.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1428   -0.7321   -0.7249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735   -2.9000    1.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8079   -2.0934    1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8869   -2.0521    2.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719   -1.9879   -1.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6203   -2.3877    0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2605   -0.2272   -1.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6101   -1.9865   -2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1713   -2.8846   -0.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847   -2.0169    0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5918   -2.1539   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5576    0.0687   -1.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1137   -0.0270    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9738    1.5386   -0.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2686    0.9843    1.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2529    2.4181    0.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7582    2.0331    1.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1503    0.0961    2.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -0.4230    2.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4098   -1.5176    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3410    1.5878    1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0578    2.2855   -1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5604    3.2416   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1522    3.0584   -2.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9124    3.4900   -0.4981 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 15  3  1  0
 20  3  1  0
 11  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 17 42  1  0
 17 43  1  0
 17 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  O   UNK     0       2.179   1.182   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.082  -0.063   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.622  -0.063   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.621  -3.143   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.953  -2.373   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.953  -0.833   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.621  -1.603   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.713  -0.833   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.179  -1.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.654  -2.773   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.288  -3.143   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.288  -1.603   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.622  -0.833   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.622   0.707   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.288   1.477   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.953   0.707   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.621   1.477   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.713   0.707   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.875   2.237   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.369   3.143   0.000  0.00  0.00           C+0
CONECT    1    2   18                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2                                                            
CONECT    4    7                                                            
CONECT    5    6                                                            
CONECT    6    5    7   12   16                                             
CONECT    7    4    6    8                                                  
CONECT    8    7    9   18                                                  
CONECT    9    2    8   10                                                  
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12    6   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16    6   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18    1    8   17   19                                             
CONECT   19   18   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0036979
HETATM    1  C1  UNL     1      -2.787  -2.016   1.598  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.217  -0.804   1.304  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.930  -0.625  -0.065  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.845  -1.562  -0.523  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.454  -0.826  -0.807  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.497  -1.868  -1.051  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.814  -1.589  -0.397  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.195  -0.149  -0.445  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.137   0.800  -0.020  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.620   1.595   1.187  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.805   0.143   0.272  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.793  -0.494   1.645  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.208   1.276   0.289  1.00  0.00           C  
HETATM   14  O2  UNL     1       0.240   2.390  -0.417  1.00  0.00           O  
HETATM   15  C13 UNL     1      -1.529   0.785  -0.213  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.473   1.423  -0.827  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.517   2.885  -1.199  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.535   0.499  -1.177  1.00  0.00           C  
HETATM   19  O3  UNL     1      -4.622   0.723  -1.776  1.00  0.00           O  
HETATM   20  O4  UNL     1      -3.143  -0.732  -0.725  1.00  0.00           O  
HETATM   21  H1  UNL     1      -2.174  -2.900   1.336  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.808  -2.093   1.168  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.887  -2.052   2.714  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.172  -1.988  -1.500  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.620  -2.388   0.145  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.261  -0.227  -1.744  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.610  -1.986  -2.166  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.171  -2.885  -0.703  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.885  -2.017   0.631  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.592  -2.154  -0.989  1.00  0.00           H  
HETATM   31  H11 UNL     1       3.558   0.069  -1.492  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.114  -0.027   0.190  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.974   1.539  -0.833  1.00  0.00           H  
HETATM   34  H14 UNL     1       3.269   0.984   1.845  1.00  0.00           H  
HETATM   35  H15 UNL     1       3.253   2.418   0.803  1.00  0.00           H  
HETATM   36  H16 UNL     1       1.758   2.033   1.704  1.00  0.00           H  
HETATM   37  H17 UNL     1       0.150   0.096   2.362  1.00  0.00           H  
HETATM   38  H18 UNL     1       1.817  -0.423   2.124  1.00  0.00           H  
HETATM   39  H19 UNL     1       0.410  -1.518   1.663  1.00  0.00           H  
HETATM   40  H20 UNL     1      -0.341   1.588   1.340  1.00  0.00           H  
HETATM   41  H21 UNL     1       0.058   2.286  -1.405  1.00  0.00           H  
HETATM   42  H22 UNL     1      -3.560   3.242  -1.131  1.00  0.00           H  
HETATM   43  H23 UNL     1      -2.152   3.058  -2.213  1.00  0.00           H  
HETATM   44  H24 UNL     1      -1.912   3.490  -0.498  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4   15   20
CONECT    4    5   24   25
CONECT    5    6   11   26
CONECT    6    7   27   28
CONECT    7    8   29   30
CONECT    8    9   31   32
CONECT    9   10   11   33
CONECT   10   34   35   36
CONECT   11   12   13
CONECT   12   37   38   39
CONECT   13   14   15   40
CONECT   14   41
CONECT   15   16   16
CONECT   16   17   18
CONECT   17   42   43   44
CONECT   18   19   19   20
END

HMDB0036979
     RDKit          3D
6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.7869   -2.0156    1.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2169   -0.8038    1.3037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9302   -0.6247   -0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454   -1.5617   -0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -0.8263   -0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4972   -1.8677   -1.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8136   -1.5886   -0.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1955   -0.1488   -0.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1371    0.8004   -0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6199    1.5949    1.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8046    0.1431    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7932   -0.4939    1.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2084    1.2759    0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2403    2.3896   -0.4175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5292    0.7849   -0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4727    1.4234   -0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5169    2.8848   -1.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5352    0.4986   -1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6224    0.7233   -1.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1428   -0.7321   -0.7249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735   -2.9000    1.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8079   -2.0934    1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8869   -2.0521    2.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719   -1.9879   -1.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6203   -2.3877    0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2605   -0.2272   -1.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6101   -1.9865   -2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1713   -2.8846   -0.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847   -2.0169    0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5918   -2.1539   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5576    0.0687   -1.4917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1137   -0.0270    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9738    1.5386   -0.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2686    0.9843    1.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2529    2.4181    0.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7582    2.0331    1.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1503    0.0961    2.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -0.4230    2.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4098   -1.5176    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3410    1.5878    1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0578    2.2855   -1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5604    3.2416   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1522    3.0584   -2.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9124    3.4900   -0.4981 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 15  3  1  0
 20  3  1  0
 11  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Hydroxy-8-methoxy-7(11)-eremophilen-12,8-olide	HMDB

Chemical Formula

C₁₆H₂₄O₄

Average Molecular Weight

280.3594

Monoisotopic Molecular Weight

280.167459256

IUPAC Name

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

Traditional Name

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

CAS Registry Number

58848-45-6

SMILES

COC12CC3CCCC(C)C3(C)C(O)C1=C(C)C(=O)O2

InChI Identifier

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

InChI Key

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Green vegetables (FooDB: FOOD00872)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	128 - 129.5 °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	0.22 g/L	ALOGPS
logP	2.22	ALOGPS
logP	2.83	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	13.91	ChemAxon
pKa (Strongest Basic)	-3.3	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	74.84 m³·mol⁻¹	ChemAxon
Polarizability	30.36 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]+	164.69	31661259
DarkChem	[M-H]-	162.286	31661259
DeepCCS	[M-2H]-	204.686	30932474
DeepCCS	[M+Na]+	180.25	30932474
AllCCS	[M+H]+	166.3	32859911
AllCCS	[M+H-H2O]+	162.9	32859911
AllCCS	[M+NH4]+	169.5	32859911
AllCCS	[M+Na]+	170.4	32859911
AllCCS	[M-H]-	172.9	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
6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide	COC12CC3CCCC(C)C3(C)C(O)C1=C(C)C(=O)O2	3242.6	Standard polar	33892256
6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide	COC12CC3CCCC(C)C3(C)C(O)C1=C(C)C(=O)O2	2102.1	Standard non polar	33892256
6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide	COC12CC3CCCC(C)C3(C)C(O)C1=C(C)C(=O)O2	2207.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide,1TMS,isomer #1	COC12CC3CCCC(C)C3(C)C(O[Si](C)(C)C)C1=C(C)C(=O)O2	2228.8	Semi standard non polar	33892256
6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide,1TBDMS,isomer #1	COC12CC3CCCC(C)C3(C)C(O[Si](C)(C)C(C)(C)C)C1=C(C)C(=O)O2	2457.9	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 - 6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-1790000000-75f487574110094e4d88	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide GC-MS (1 TMS) - 70eV, Positive	splash10-05g3-5579000000-b5ef0071a50ea5fc0720	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide 10V, Positive-QTOF	splash10-03e9-0190000000-6f1aff3cd4025af61c6d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide 20V, Positive-QTOF	splash10-08gi-3290000000-d900c887ce84355cff88	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide 40V, Positive-QTOF	splash10-01bc-9520000000-afd40be3615e4f6a0e29	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide 10V, Negative-QTOF	splash10-004i-0090000000-3cd4a64798894a2b55ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide 20V, Negative-QTOF	splash10-01t9-0090000000-c4f30c87b8312563e4b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide 40V, Negative-QTOF	splash10-0c03-4950000000-e2bbd45ac2b196c91fed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide 10V, Negative-QTOF	splash10-004i-0090000000-8597d5b937876f2bed9f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide 20V, Negative-QTOF	splash10-004i-0090000000-28e537071034a3fd6333	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide 40V, Negative-QTOF	splash10-0kft-3950000000-5e3947f240d51ec21173	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide 10V, Positive-QTOF	splash10-001i-0090000000-90e2273a8d9d61c8d0f4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide 20V, Positive-QTOF	splash10-01q9-0290000000-4e2afe90f4c00f3e4ff6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide 40V, Positive-QTOF	splash10-06r7-9400000000-b80e159c29a5b3ed9864	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

FDB021142

KNApSAcK ID

Not Available

Chemspider ID

35014338

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752123

PDB ID

Not Available

ChEBI ID

174673

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 6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide (HMDB0036979)

MOL for HMDB0036979 (6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide)

3D MOL for HMDB0036979 (6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide)

3D SDF for HMDB0036979 (6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide)

3D-SDF for HMDB0036979 (6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide)

PDB for HMDB0036979 (6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide)

3D PDB for HMDB0036979 (6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide)

SMILES for HMDB0036979 (6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide)

INCHI for HMDB0036979 (6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide)

Structure for HMDB0036979 (6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide)

3D Structure for HMDB0036979 (6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra