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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:53:33 UTC

Update Date

2022-03-07 02:56:56 UTC

HMDB ID

HMDB0041227

Secondary Accession Numbers

HMDB41227

Metabolite Identification

Common Name

(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide

Description

(8betaOH,10beta)-8-Hydroxy-3-oxo-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 (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide.

Structure

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

HMDB0041227
     RDKit          3D
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.3060    1.4940   -1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8394    0.1813   -0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868   -0.0556   -0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7201    0.8426    0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6222    0.1942    0.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2589    0.5416    1.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7446   -1.2414    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8706   -1.6255   -0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1630   -0.9493   -0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955    0.5034   -0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7279    1.3206   -0.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961    0.9332   -0.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3228    2.4221   -0.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468   -2.0000   -0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7529   -1.4936    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423   -1.7506    1.5945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7996   -2.0598   -0.4753 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5291   -1.0646   -1.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5826   -1.2597   -1.7216 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0233    1.3922   -2.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4038    2.0402   -1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7673    2.1232   -0.5115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0496    1.1480    1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7379    1.7682   -0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9818   -0.2524    2.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3577    0.6427    1.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8660    1.4826    2.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0434   -1.7725    1.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5504   -1.4483   -1.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0068   -2.7196   -0.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8390   -1.0859   -1.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6736   -1.3746    0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1314    0.5995   -1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8982    2.7080    0.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6767    2.8120   -1.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2995    2.9634   -0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3512   -3.0704   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4644   -1.9609   -1.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9229   -0.9281    2.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18  2  1  0
 15  3  1  0
 12  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
M  END

  Mrv0541 05061312292D          

 19 21  0  0  0  0            999 V2000
   -0.3984    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549    0.2900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  5  1  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 14  3  1  0  0  0  0
 14  7  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15  6  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  2  0  0  0  0
 17 13  2  0  0  0  0
 18 15  1  0  0  0  0
 19 13  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041227

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C(=O)CCC2CC3(O)OC(=O)C(C)=C3CC12C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8-11-7-14(3)9(2)12(16)5-4-10(14)6-15(11,18)19-13(8)17/h9-10,18H,4-7H2,1-3H3

> <INCHI_KEY>
AQAVKEZEFHFROC-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.894535807910422

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
2.340347317000001

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.735115946021843

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.258244579579628

> <JCHEM_PKA_STRONGEST_BASIC>
-4.435443820191282

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
69.3938

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.18e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041227
     RDKit          3D
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.3060    1.4940   -1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8394    0.1813   -0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868   -0.0556   -0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7201    0.8426    0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6222    0.1942    0.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2589    0.5416    1.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7446   -1.2414    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8706   -1.6255   -0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1630   -0.9493   -0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955    0.5034   -0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7279    1.3206   -0.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961    0.9332   -0.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3228    2.4221   -0.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468   -2.0000   -0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7529   -1.4936    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423   -1.7506    1.5945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7996   -2.0598   -0.4753 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5291   -1.0646   -1.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5826   -1.2597   -1.7216 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0233    1.3922   -2.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4038    2.0402   -1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7673    2.1232   -0.5115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0496    1.1480    1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7379    1.7682   -0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9818   -0.2524    2.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3577    0.6427    1.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8660    1.4826    2.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0434   -1.7725    1.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5504   -1.4483   -1.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0068   -2.7196   -0.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8390   -1.0859   -1.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6736   -1.3746    0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1314    0.5995   -1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8982    2.7080    0.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6767    2.8120   -1.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2995    2.9634   -0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3512   -3.0704   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4644   -1.9609   -1.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9229   -0.9281    2.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18  2  1  0
 15  3  1  0
 12  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  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      -0.744   5.553   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.198   5.923   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.864   5.153   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.865   4.383   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.713   2.843   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.036   0.541   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   14                                                            
CONECT    4    5   10                                                       
CONECT    5    4   12                                                       
CONECT    6   10   15                                                       
CONECT    7   11   14                                                       
CONECT    8    1   11   13                                                  
CONECT    9    2   12   14                                                  
CONECT   10    4    6   14                                                  
CONECT   11    7    8   15                                                  
CONECT   12    5    9   16                                                  
CONECT   13    8   17   19                                                  
CONECT   14    3    7    9   10                                             
CONECT   15    6   11   18   19                                             
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18   15                                                            
CONECT   19   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0041227
HETATM    1  C1  UNL     1       3.306   1.494  -1.299  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.839   0.181  -0.780  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.787  -0.056  -0.070  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.720   0.843   0.452  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.622   0.194   0.466  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.259   0.542   1.824  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.745  -1.241   0.239  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.871  -1.625  -0.736  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.163  -0.949  -0.385  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.896   0.503  -0.290  1.00  0.00           C  
HETATM   11  O1  UNL     1      -3.728   1.321  -0.022  1.00  0.00           O  
HETATM   12  C11 UNL     1      -1.496   0.933  -0.552  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.323   2.422  -0.378  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.447  -2.000  -0.276  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.753  -1.494   0.238  1.00  0.00           C  
HETATM   16  O2  UNL     1       1.942  -1.751   1.594  1.00  0.00           O  
HETATM   17  O3  UNL     1       2.800  -2.060  -0.475  1.00  0.00           O  
HETATM   18  C15 UNL     1       3.529  -1.065  -1.069  1.00  0.00           C  
HETATM   19  O4  UNL     1       4.583  -1.260  -1.722  1.00  0.00           O  
HETATM   20  H1  UNL     1       4.023   1.392  -2.115  1.00  0.00           H  
HETATM   21  H2  UNL     1       2.404   2.040  -1.642  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.767   2.123  -0.511  1.00  0.00           H  
HETATM   23  H4  UNL     1       1.050   1.148   1.468  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.738   1.768  -0.158  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.982  -0.252   2.569  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.358   0.643   1.741  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.866   1.483   2.231  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.043  -1.773   1.194  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.550  -1.448  -1.759  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.007  -2.720  -0.612  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.839  -1.086  -1.269  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.674  -1.375   0.470  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.131   0.599  -1.549  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.898   2.708   0.603  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.677   2.812  -1.184  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.300   2.963  -0.444  1.00  0.00           H  
HETATM   37  H18 UNL     1       0.351  -3.070  -0.002  1.00  0.00           H  
HETATM   38  H19 UNL     1       0.464  -1.961  -1.384  1.00  0.00           H  
HETATM   39  H20 UNL     1       1.923  -0.928   2.142  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   18
CONECT    3    4   15
CONECT    4    5   23   24
CONECT    5    6    7   12
CONECT    6   25   26   27
CONECT    7    8   14   28
CONECT    8    9   29   30
CONECT    9   10   31   32
CONECT   10   11   11   12
CONECT   12   13   33
CONECT   13   34   35   36
CONECT   14   15   37   38
CONECT   15   16   17
CONECT   16   39
CONECT   17   18
CONECT   18   19   19
END

HMDB0041227
     RDKit          3D
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.3060    1.4940   -1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8394    0.1813   -0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868   -0.0556   -0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7201    0.8426    0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6222    0.1942    0.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2589    0.5416    1.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7446   -1.2414    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8706   -1.6255   -0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1630   -0.9493   -0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955    0.5034   -0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7279    1.3206   -0.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961    0.9332   -0.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3228    2.4221   -0.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468   -2.0000   -0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7529   -1.4936    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423   -1.7506    1.5945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7996   -2.0598   -0.4753 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5291   -1.0646   -1.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5826   -1.2597   -1.7216 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0233    1.3922   -2.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4038    2.0402   -1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7673    2.1232   -0.5115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0496    1.1480    1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7379    1.7682   -0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9818   -0.2524    2.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3577    0.6427    1.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8660    1.4826    2.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0434   -1.7725    1.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5504   -1.4483   -1.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0068   -2.7196   -0.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8390   -1.0859   -1.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6736   -1.3746    0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1314    0.5995   -1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8982    2.7080    0.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6767    2.8120   -1.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2995    2.9634   -0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3512   -3.0704   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4644   -1.9609   -1.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9229   -0.9281    2.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18  2  1  0
 15  3  1  0
 12  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(8BetaOH,10b)-8-hydroxy-3-oxo-7(11)-eremophilen-12,8-olide	Generator
(8BetaOH,10β)-8-hydroxy-3-oxo-7(11)-eremophilen-12,8-olide	Generator

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

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

Traditional Name

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

CAS Registry Number

171422-92-7

SMILES

CC1C(=O)CCC2CC3(O)OC(=O)C(C)=C3CC12C

InChI Identifier

InChI=1S/C15H20O4/c1-8-11-7-14(3)9(2)12(16)5-4-10(14)6-15(11,18)19-13(8)17/h9-10,18H,4-7H2,1-3H3

InChI Key

AQAVKEZEFHFROC-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
Lactone
Ketone
Hemiacetal
Carboxylic acid ester
Cyclic ketone
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041227)

Source

Endogenous

Endogenous (HMDB: HMDB0041227)

Plant

Plant (HMDB: HMDB0041227)

Animal

Animal (HMDB: HMDB0041227)

Exogenous

Food

Food (HMDB: HMDB0041227)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0041227)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0041227)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0041227)

Lipid metabolism pathway (HMDB: HMDB0041227)

Cellular process

Cell signaling (HMDB: HMDB0041227)

Biochemical process

Lipid transport (HMDB: HMDB0041227)

Role

Biological role

Energy source (HMDB: HMDB0041227)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0041227)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	204 - 206 °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	0.82 g/L	ALOGPS
logP	1.73	ALOGPS
logP	2.34	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	11.26	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.39 m³·mol⁻¹	ChemAxon
Polarizability	27.89 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]+	163.13	31661259
DarkChem	[M-H]-	156.133	31661259
DeepCCS	[M-2H]-	191.617	30932474
DeepCCS	[M+Na]+	166.742	30932474
AllCCS	[M+H]+	161.7	32859911
AllCCS	[M+H-H2O]+	158.1	32859911
AllCCS	[M+NH4]+	165.0	32859911
AllCCS	[M+Na]+	165.9	32859911
AllCCS	[M-H]-	167.8	32859911
AllCCS	[M+Na-2H]-	167.7	32859911
AllCCS	[M+HCOO]-	167.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide	CC1C(=O)CCC2CC3(O)OC(=O)C(C)=C3CC12C	3380.7	Standard polar	33892256
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide	CC1C(=O)CCC2CC3(O)OC(=O)C(C)=C3CC12C	2122.8	Standard non polar	33892256
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide	CC1C(=O)CCC2CC3(O)OC(=O)C(C)=C3CC12C	2300.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide,1TMS,isomer #1	CC1=C2CC3(C)C(CCC(=O)C3C)CC2(O[Si](C)(C)C)OC1=O	2315.6	Semi standard non polar	33892256
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide,1TMS,isomer #2	CC1=C2CC3(C)C(C)=C(O[Si](C)(C)C)CCC3CC2(O)OC1=O	2274.5	Semi standard non polar	33892256
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide,1TMS,isomer #3	CC1=C2CC3(C)C(CC=C(O[Si](C)(C)C)C3C)CC2(O)OC1=O	2290.9	Semi standard non polar	33892256
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide,2TMS,isomer #1	CC1=C2CC3(C)C(C)=C(O[Si](C)(C)C)CCC3CC2(O[Si](C)(C)C)OC1=O	2372.1	Semi standard non polar	33892256
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide,2TMS,isomer #1	CC1=C2CC3(C)C(C)=C(O[Si](C)(C)C)CCC3CC2(O[Si](C)(C)C)OC1=O	2229.1	Standard non polar	33892256
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide,2TMS,isomer #2	CC1=C2CC3(C)C(CC=C(O[Si](C)(C)C)C3C)CC2(O[Si](C)(C)C)OC1=O	2390.1	Semi standard non polar	33892256
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide,2TMS,isomer #2	CC1=C2CC3(C)C(CC=C(O[Si](C)(C)C)C3C)CC2(O[Si](C)(C)C)OC1=O	2171.0	Standard non polar	33892256
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide,1TBDMS,isomer #1	CC1=C2CC3(C)C(CCC(=O)C3C)CC2(O[Si](C)(C)C(C)(C)C)OC1=O	2551.0	Semi standard non polar	33892256
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide,1TBDMS,isomer #2	CC1=C2CC3(C)C(C)=C(O[Si](C)(C)C(C)(C)C)CCC3CC2(O)OC1=O	2493.3	Semi standard non polar	33892256
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide,1TBDMS,isomer #3	CC1=C2CC3(C)C(CC=C(O[Si](C)(C)C(C)(C)C)C3C)CC2(O)OC1=O	2500.8	Semi standard non polar	33892256
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide,2TBDMS,isomer #1	CC1=C2CC3(C)C(C)=C(O[Si](C)(C)C(C)(C)C)CCC3CC2(O[Si](C)(C)C(C)(C)C)OC1=O	2822.6	Semi standard non polar	33892256
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide,2TBDMS,isomer #1	CC1=C2CC3(C)C(C)=C(O[Si](C)(C)C(C)(C)C)CCC3CC2(O[Si](C)(C)C(C)(C)C)OC1=O	2741.3	Standard non polar	33892256
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide,2TBDMS,isomer #2	CC1=C2CC3(C)C(CC=C(O[Si](C)(C)C(C)(C)C)C3C)CC2(O[Si](C)(C)C(C)(C)C)OC1=O	2835.1	Semi standard non polar	33892256
(8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide,2TBDMS,isomer #2	CC1=C2CC3(C)C(CC=C(O[Si](C)(C)C(C)(C)C)C3C)CC2(O[Si](C)(C)C(C)(C)C)OC1=O	2576.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-01w3-0950000000-18289cd94d16aedeaffb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide GC-MS (1 TMS) - 70eV, Positive	splash10-00g0-7793000000-c24cc26b4d113119b8d6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (8betaOH,10beta)-8-Hydroxy-3-oxo-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 - (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide 10V, Positive-QTOF	splash10-014i-0390000000-d0bc0769a430e579c111	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide 20V, Positive-QTOF	splash10-00kv-0960000000-0f5f8eb2aa4569392410	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide 40V, Positive-QTOF	splash10-0gc0-9400000000-319a711b1ef0e9a07928	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide 10V, Negative-QTOF	splash10-03di-0090000000-d2c7110fd048769b8f9e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide 20V, Negative-QTOF	splash10-07vi-0090000000-a9af63e8ac1435b7b0c1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide 40V, Negative-QTOF	splash10-05mo-6690000000-f2e4407556fb71764510	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide 10V, Negative-QTOF	splash10-03di-0090000000-16d43704d08f3756e03a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide 20V, Negative-QTOF	splash10-03di-0090000000-a20608b0aca0e1e4b9a0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide 40V, Negative-QTOF	splash10-07p1-1390000000-7d71ac7c8c3459c7f4a2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide 10V, Positive-QTOF	splash10-014i-0090000000-27f9036d868b151212c3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide 20V, Positive-QTOF	splash10-01b9-0790000000-0d22e1c5a38532010230	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide 40V, Positive-QTOF	splash10-00or-5910000000-c5fee28880a0630db3c9	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021129

KNApSAcK ID

Not Available

Chemspider ID

35015132

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85231437

PDB ID

Not Available

ChEBI ID

174485

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 (8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide (HMDB0041227)

MOL for HMDB0041227 ((8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide)

3D MOL for HMDB0041227 ((8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide)

3D SDF for HMDB0041227 ((8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide)

3D-SDF for HMDB0041227 ((8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide)

PDB for HMDB0041227 ((8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide)

3D PDB for HMDB0041227 ((8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide)

SMILES for HMDB0041227 ((8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide)

INCHI for HMDB0041227 ((8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide)

Structure for HMDB0041227 ((8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide)

3D Structure for HMDB0041227 ((8betaOH,10beta)-8-Hydroxy-3-oxo-7(11)-eremophilen-12,8-olide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra