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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:49:38 UTC

Update Date

2022-03-07 02:55:00 UTC

HMDB ID

HMDB0036662

Secondary Accession Numbers

HMDB36662

Metabolite Identification

Common Name

2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide

Description

2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Based on a literature review a significant number of articles have been published on 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide.

Structure

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

HMDB0036662
     RDKit          3D
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.5571   -1.1269    0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9016   -0.4573   -0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5164    0.1653   -1.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7451    0.1309   -1.6165 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5450    0.8244   -1.9567 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2732    0.6917   -1.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8248    2.0089   -0.9039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247    2.2362   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8658    3.5885   -0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4571    1.1734   -0.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7818    0.7124    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7942    1.6162    1.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447   -0.6179    0.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796   -1.7489    0.9307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5080   -3.0260    1.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2587   -1.8194    0.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3728   -2.2689    1.8708 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6427   -1.4726   -0.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6199   -2.5149   -0.3762 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4272   -0.2125   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6281   -1.2713    0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0286   -1.5554    1.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6350    0.2340   -2.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5304    2.8264   -0.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1283    3.9139    0.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8305    4.2952   -1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8460    3.5945    0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2516    0.3567   -1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3411    1.7139   -1.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9476    0.9435    1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    1.4695    0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4641   -0.7366    0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9525   -3.7805    1.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4192   -2.7867    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8222   -3.4024    0.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724   -1.5336   -1.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673   -2.4379   -1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882    0.2743    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20  2  1  0
 20  6  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END

  Mrv0541 05061309162D          

 20 21  0  0  0  0            999 V2000
    5.0298    3.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6722   -0.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8558   -0.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983    1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929    2.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037    0.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070    2.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124    1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701    2.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614    1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755    1.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279    1.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1352    2.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0735    1.4129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    0.9838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460    2.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  7  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  2  1  0  0  0  0
  8  6  2  0  0  0  0
  9  3  2  0  0  0  0
 10  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 12  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19 15  2  0  0  0  0
 20 11  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036662

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C1=C\C2OC(=O)C(=C)C2C(O)C(=O)\C(C)=C/C(O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O5/c1-7-4-10(16)6-8(2)13(17)14(18)12-9(3)15(19)20-11(12)5-7/h5-6,10-12,14,16,18H,3-4H2,1-2H3/b7-5-,8-6-

> <INCHI_KEY>
BPDUDXQLWXZOHB-SFECMWDFSA-N

> <FORMULA>
C15H18O5

> <MOLECULAR_WEIGHT>
278.3004

> <EXACT_MASS>
278.115423686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.21837170856788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,8-dihydroxy-6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2,5-dione

> <ALOGPS_LOGP>
-0.06

> <JCHEM_LOGP>
1.0885630246666667

> <ALOGPS_LOGS>
-1.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.354226580498565

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.719949997998356

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8966896247174283

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
73.54849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,8-dihydroxy-6,10-dimethyl-3-methylidene-3aH,4H,8H,9H,11aH-cyclodeca[b]furan-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036662
     RDKit          3D
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.5571   -1.1269    0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9016   -0.4573   -0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5164    0.1653   -1.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7451    0.1309   -1.6165 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5450    0.8244   -1.9567 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2732    0.6917   -1.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8248    2.0089   -0.9039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247    2.2362   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8658    3.5885   -0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4571    1.1734   -0.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7818    0.7124    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7942    1.6162    1.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447   -0.6179    0.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796   -1.7489    0.9307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5080   -3.0260    1.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2587   -1.8194    0.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3728   -2.2689    1.8708 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6427   -1.4726   -0.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6199   -2.5149   -0.3762 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4272   -0.2125   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6281   -1.2713    0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0286   -1.5554    1.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6350    0.2340   -2.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5304    2.8264   -0.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1283    3.9139    0.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8305    4.2952   -1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8460    3.5945    0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2516    0.3567   -1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3411    1.7139   -1.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9476    0.9435    1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    1.4695    0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4641   -0.7366    0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9525   -3.7805    1.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4192   -2.7867    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8222   -3.4024    0.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724   -1.5336   -1.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673   -2.4379   -1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882    0.2743    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20  2  1  0
 20  6  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  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       9.389   6.071   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.588  -0.884   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.331  -0.004   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.957   3.438   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.893   5.129   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.020   1.748   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.413   4.879   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.044   0.557   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.259   1.534   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.476   3.189   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.918   3.937   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.461   2.497   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.525   0.806   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.981   2.247   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.972   2.380   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.452   4.380   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.549  -0.385   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.471   2.637   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.531   1.836   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.379   3.865   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4    7   10                                                       
CONECT    5    7   11                                                       
CONECT    6    8   10                                                       
CONECT    7    1    4    5                                                  
CONECT    8    2    6   13                                                  
CONECT    9    3   12   15                                                  
CONECT   10    4    6   16                                                  
CONECT   11    5   12   20                                                  
CONECT   12    9   11   14                                                  
CONECT   13    8   14   17                                                  
CONECT   14   12   13   18                                                  
CONECT   15    9   19   20                                                  
CONECT   16   10                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0036662
HETATM    1  C1  UNL     1       3.557  -1.127   0.810  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.902  -0.457  -0.110  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.516   0.165  -1.266  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.745   0.131  -1.616  1.00  0.00           O  
HETATM    5  O2  UNL     1       2.545   0.824  -1.957  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.273   0.692  -1.347  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.825   2.009  -0.904  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.425   2.236  -0.620  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.866   3.588  -0.169  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.457   1.173  -0.719  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.782   0.712   0.647  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.794   1.616   1.113  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.345  -0.618   0.839  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.680  -1.749   0.931  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.508  -3.026   1.141  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.259  -1.819   0.826  1.00  0.00           C  
HETATM   17  O4  UNL     1       0.373  -2.269   1.871  1.00  0.00           O  
HETATM   18  C14 UNL     1       0.643  -1.473  -0.284  1.00  0.00           C  
HETATM   19  O5  UNL     1       1.620  -2.515  -0.376  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.427  -0.213  -0.144  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.628  -1.271   0.781  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.029  -1.555   1.632  1.00  0.00           H  
HETATM   23  H3  UNL     1       0.635   0.234  -2.131  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.530   2.826  -0.802  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.128   3.914   0.613  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.831   4.295  -1.033  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.846   3.595   0.306  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.252   0.357  -1.388  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.341   1.714  -1.198  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.948   0.944   1.371  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.558   1.470   0.470  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.464  -0.737   0.913  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.953  -3.780   1.678  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.419  -2.787   1.705  1.00  0.00           H  
HETATM   35  H15 UNL     1      -2.822  -3.402   0.152  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.172  -1.534  -1.303  1.00  0.00           H  
HETATM   37  H17 UNL     1       2.067  -2.438  -1.240  1.00  0.00           H  
HETATM   38  H18 UNL     1       1.188   0.274   0.807  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3   20
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   20   23
CONECT    7    8    8   24
CONECT    8    9   10
CONECT    9   25   26   27
CONECT   10   11   28   29
CONECT   11   12   13   30
CONECT   12   31
CONECT   13   14   14   32
CONECT   14   15   16
CONECT   15   33   34   35
CONECT   16   17   17   18
CONECT   18   19   20   36
CONECT   19   37
CONECT   20   38
END

HMDB0036662
     RDKit          3D
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.5571   -1.1269    0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9016   -0.4573   -0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5164    0.1653   -1.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7451    0.1309   -1.6165 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5450    0.8244   -1.9567 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2732    0.6917   -1.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8248    2.0089   -0.9039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247    2.2362   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8658    3.5885   -0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4571    1.1734   -0.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7818    0.7124    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7942    1.6162    1.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3447   -0.6179    0.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796   -1.7489    0.9307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5080   -3.0260    1.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2587   -1.8194    0.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3728   -2.2689    1.8708 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6427   -1.4726   -0.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6199   -2.5149   -0.3762 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4272   -0.2125   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6281   -1.2713    0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0286   -1.5554    1.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6350    0.2340   -2.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5304    2.8264   -0.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1283    3.9139    0.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8305    4.2952   -1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8460    3.5945    0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2516    0.3567   -1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3411    1.7139   -1.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9476    0.9435    1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    1.4695    0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4641   -0.7366    0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9525   -3.7805    1.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4192   -2.7867    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8222   -3.4024    0.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724   -1.5336   -1.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673   -2.4379   -1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882    0.2743    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20  2  1  0
 20  6  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2b,9XI-dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6a-olide	Generator
2Β,9xi-dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6α-olide	Generator
2b,9X-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6a-olide	HMDB

Chemical Formula

C₁₅H₁₈O₅

Average Molecular Weight

278.3004

Monoisotopic Molecular Weight

278.115423686

IUPAC Name

4,8-dihydroxy-6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2,5-dione

Traditional Name

4,8-dihydroxy-6,10-dimethyl-3-methylidene-3aH,4H,8H,9H,11aH-cyclodeca[b]furan-2,5-dione

CAS Registry Number

Not Available

SMILES

C\C1=C\C2OC(=O)C(=C)C2C(O)C(=O)\C(C)=C/C(O)C1

InChI Identifier

InChI=1S/C15H18O5/c1-7-4-10(16)6-8(2)13(17)14(18)12-9(3)15(19)20-11(12)5-7/h5-6,10-12,14,16,18H,3-4H2,1-2H3/b7-5-,8-6-

InChI Key

BPDUDXQLWXZOHB-SFECMWDFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
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: HMDB0036662)

Source

Endogenous

Endogenous (HMDB: HMDB0036662)

Plant

Plant (HMDB: HMDB0036662)

Animal

Animal (HMDB: HMDB0036662)

Exogenous

Food

Food (HMDB: HMDB0036662)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0036662)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036662)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036662)

Lipid metabolism pathway (HMDB: HMDB0036662)

Cellular process

Cell signaling (HMDB: HMDB0036662)

Biochemical process

Lipid transport (HMDB: HMDB0036662)

Role

Biological role

Energy source (HMDB: HMDB0036662)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036662)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.96 g/L	ALOGPS
logP	-0.06	ALOGPS
logP	1.09	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	4.72	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.55 m³·mol⁻¹	ChemAxon
Polarizability	28.22 Å³	ChemAxon
Number of Rings	2	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
DeepCCS	[M+H]+	168.205	30932474
DeepCCS	[M-H]-	165.847	30932474
DeepCCS	[M-2H]-	199.625	30932474
DeepCCS	[M+Na]+	174.852	30932474
AllCCS	[M+H]+	165.8	32859911
AllCCS	[M+H-H2O]+	162.2	32859911
AllCCS	[M+NH4]+	169.1	32859911
AllCCS	[M+Na]+	170.1	32859911
AllCCS	[M-H]-	166.5	32859911
AllCCS	[M+Na-2H]-	166.6	32859911
AllCCS	[M+HCOO]-	166.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide	C\C1=C\C2OC(=O)C(=C)C2C(O)C(=O)\C(C)=C/C(O)C1	3428.6	Standard polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide	C\C1=C\C2OC(=O)C(=C)C2C(O)C(=O)\C(C)=C/C(O)C1	2240.6	Standard non polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide	C\C1=C\C2OC(=O)C(=C)C2C(O)C(=O)\C(C)=C/C(O)C1	2370.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide,1TMS,isomer #1	C=C1C(=O)OC2/C=C(/C)CC(O)/C=C(/C)C(=O)C(O[Si](C)(C)C)C12	2454.7	Semi standard non polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide,1TMS,isomer #2	C=C1C(=O)OC2/C=C(/C)CC(O[Si](C)(C)C)/C=C(/C)C(=O)C(O)C12	2481.5	Semi standard non polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide,1TMS,isomer #3	C=C1C(=O)OC2/C=C(/C)CC(O)/C=C(/C)C(O[Si](C)(C)C)=C(O)C12	2414.3	Semi standard non polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide,2TMS,isomer #1	C=C1C(=O)OC2/C=C(/C)CC(O[Si](C)(C)C)/C=C(/C)C(=O)C(O[Si](C)(C)C)C12	2499.9	Semi standard non polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide,2TMS,isomer #2	C=C1C(=O)OC2/C=C(/C)CC(O)/C=C(/C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C12	2477.9	Semi standard non polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide,2TMS,isomer #3	C=C1C(=O)OC2/C=C(/C)CC(O[Si](C)(C)C)/C=C(/C)C(O[Si](C)(C)C)=C(O)C12	2452.8	Semi standard non polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide,3TMS,isomer #1	C=C1C(=O)OC2/C=C(/C)CC(O[Si](C)(C)C)/C=C(/C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C12	2505.2	Semi standard non polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide,3TMS,isomer #1	C=C1C(=O)OC2/C=C(/C)CC(O[Si](C)(C)C)/C=C(/C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C12	2391.4	Standard non polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide,1TBDMS,isomer #1	C=C1C(=O)OC2/C=C(/C)CC(O)/C=C(/C)C(=O)C(O[Si](C)(C)C(C)(C)C)C12	2670.2	Semi standard non polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide,1TBDMS,isomer #2	C=C1C(=O)OC2/C=C(/C)CC(O[Si](C)(C)C(C)(C)C)/C=C(/C)C(=O)C(O)C12	2691.8	Semi standard non polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide,1TBDMS,isomer #3	C=C1C(=O)OC2/C=C(/C)CC(O)/C=C(/C)C(O[Si](C)(C)C(C)(C)C)=C(O)C12	2626.5	Semi standard non polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide,2TBDMS,isomer #1	C=C1C(=O)OC2/C=C(/C)CC(O[Si](C)(C)C(C)(C)C)/C=C(/C)C(=O)C(O[Si](C)(C)C(C)(C)C)C12	2902.6	Semi standard non polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide,2TBDMS,isomer #2	C=C1C(=O)OC2/C=C(/C)CC(O)/C=C(/C)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C12	2891.2	Semi standard non polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide,2TBDMS,isomer #3	C=C1C(=O)OC2/C=C(/C)CC(O[Si](C)(C)C(C)(C)C)/C=C(/C)C(O[Si](C)(C)C(C)(C)C)=C(O)C12	2880.8	Semi standard non polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide,3TBDMS,isomer #1	C=C1C(=O)OC2/C=C(/C)CC(O[Si](C)(C)C(C)(C)C)/C=C(/C)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C12	3133.3	Semi standard non polar	33892256
2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide,3TBDMS,isomer #1	C=C1C(=O)OC2/C=C(/C)CC(O[Si](C)(C)C(C)(C)C)/C=C(/C)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C12	2913.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9040000000-551ff2942b0c6d77b858	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide GC-MS (2 TMS) - 70eV, Positive	splash10-05di-9005200000-9bc5489592e8ff707dbc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-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 - 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide 10V, Positive-QTOF	splash10-03fr-0090000000-46d8f3c8d2e6e737cb72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide 20V, Positive-QTOF	splash10-03g0-0390000000-1fbe19e415bc17485bc4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide 40V, Positive-QTOF	splash10-0006-7920000000-36a44315ee08413ab3d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide 10V, Negative-QTOF	splash10-004i-0090000000-db183b131f68c0a52990	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide 20V, Negative-QTOF	splash10-057i-0090000000-4523c1089c150572e08f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide 40V, Negative-QTOF	splash10-0v4i-8920000000-237175453b7de08b8afd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide 10V, Positive-QTOF	splash10-01t9-0090000000-2df43ed0283ba3a7903e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide 20V, Positive-QTOF	splash10-004i-0090000000-85ef2fce1a09a0fb13b7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide 40V, Positive-QTOF	splash10-03di-0090000000-6c37185475d7dda81135	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide 10V, Negative-QTOF	splash10-004i-0090000000-abea1c522af17e3f81ae	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide 20V, Negative-QTOF	splash10-004i-1090000000-5747682e7971d0c05ffb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide 40V, Negative-QTOF	splash10-0a4r-0290000000-ac0638a4d5cfa6c8c1a7	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

FDB015589

KNApSAcK ID

Not Available

Chemspider ID

35014184

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752027

PDB ID

Not Available

ChEBI ID

168308

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 2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide (HMDB0036662)

MOL for HMDB0036662 (2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide)

3D MOL for HMDB0036662 (2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide)

3D SDF for HMDB0036662 (2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide)

3D-SDF for HMDB0036662 (2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide)

PDB for HMDB0036662 (2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide)

3D PDB for HMDB0036662 (2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide)

SMILES for HMDB0036662 (2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide)

INCHI for HMDB0036662 (2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide)

Structure for HMDB0036662 (2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide)

3D Structure for HMDB0036662 (2beta,9xi-Dihydroxy-8-oxo-1(10),4,11(13)-germacratrien-12,6alpha-olide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra