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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 16:47:59 UTC

Update Date

2021-09-23 16:48:00 UTC

HMDB ID

HMDB0302311

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Germacranolide

Description

3,6,10-trimethyl-2H,3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-2-one 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 very few articles have been published on 3,6,10-trimethyl-2H,3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-2-one.

Structure

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

HMDB0302311
     RDKit          3D
Germacranolide
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.3681    4.0129    0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244    2.5503    0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2943    2.3407   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8421    1.0174   -0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393    0.0973    0.8123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0879   -1.2976    0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3230   -1.9986    0.9083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3238   -1.9593   -0.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0937   -1.5839   -1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9345   -0.8373   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1872    0.5833   -0.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9559    1.5057    0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5742    0.5647   -1.3891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359   -0.4404   -0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4645   -0.3655   -0.4125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2928   -1.5251   -0.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6334   -2.1305    0.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3878    4.5370   -0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3150    4.5059    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3777    4.0313    0.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9897    3.2221   -0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5115    0.4628   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9474    1.1782   -0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8815    0.4113    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1887    0.2233    1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1647   -1.3166    0.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166   -2.0609    1.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4932   -2.9503    0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875   -3.0142   -0.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4460   -2.5655   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668   -1.1835   -2.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6194   -0.8458    0.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761    0.8083   -1.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9669    0.9414    1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9731    2.0355    0.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3691   -2.2797   -1.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0484   -3.0461    1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3614   -1.3650    1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7189   -2.2633    0.9662 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
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 12  2  1  0
 16 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
M  END


  Mrv1533007301516522D          

 19 20  0  0  0  0            999 V2000
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  1  1  0  0  0  0
 10  5  1  0  0  0  0
 10  7  2  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 11  9  1  0  0  0  0
 12  3  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  1  0  0  0  0
 14  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 16 15  2  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18  6  1  0  0  0  0
 19  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302311

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C1=C(C)/CC2OC(=O)C(C)C2C\C([H])=C(C)\CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h6-7,12-14H,4-5,8-9H2,1-3H3/b10-7+,11-6+

> <INCHI_KEY>
QJRFOUJEGHRZIU-NXAIOARDSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.339

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.85986773156359

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6,10-trimethyl-2H,3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-2-one

> <ALOGPS_LOGP>
4.23

> <JCHEM_LOGP>
3.5186044823333336

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.08296359818532

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
70.297

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6,10-trimethyl-3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302311
     RDKit          3D
Germacranolide
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.3681    4.0129    0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244    2.5503    0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2943    2.3407   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8421    1.0174   -0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393    0.0973    0.8123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0879   -1.2976    0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3230   -1.9986    0.9083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3238   -1.9593   -0.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0937   -1.5839   -1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9345   -0.8373   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1872    0.5833   -0.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9559    1.5057    0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5742    0.5647   -1.3891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359   -0.4404   -0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4645   -0.3655   -0.4125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2928   -1.5251   -0.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6334   -2.1305    0.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3878    4.5370   -0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3150    4.5059    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3777    4.0313    0.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9897    3.2221   -0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5115    0.4628   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9474    1.1782   -0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8815    0.4113    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1887    0.2233    1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1647   -1.3166    0.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166   -2.0609    1.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4932   -2.9503    0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875   -3.0142   -0.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4460   -2.5655   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668   -1.1835   -2.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6194   -0.8458    0.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761    0.8083   -1.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9669    0.9414    1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9731    2.0355    0.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3691   -2.2797   -1.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0484   -3.0461    1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3614   -1.3650    1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7189   -2.2633    0.9662 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
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 12  2  1  0
 16 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
M  END

HEADER    PROTEIN                                 30-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-15         0                                  
HETATM    1  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.762   1.246   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.941   3.481   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.465   2.016   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.910   0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.465  -0.476   0.000  0.00  0.00           O+0
HETATM   18  H   UNK     0       4.001  -2.310   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       4.001   0.770   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4    5    6                                                       
CONECT    5    4   10                                                       
CONECT    6    4   11   18                                                  
CONECT    7    8   10   19                                                  
CONECT    8    7   13                                                       
CONECT    9   11   14                                                       
CONECT   10    1    5    7                                                  
CONECT   11    2    6    9                                                  
CONECT   12    3   13   15                                                  
CONECT   13    8   12   14                                                  
CONECT   14    9   13   17                                                  
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   14   15                                                       
CONECT   18    6                                                            
CONECT   19    7                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0302311
HETATM    1  C1  UNL     1      -0.368   4.013   0.258  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.024   2.550   0.078  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.294   2.341  -0.155  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.842   1.017  -0.352  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.939   0.097   0.812  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.088  -1.298   0.321  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.323  -1.999   0.908  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.324  -1.959  -0.509  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.094  -1.584  -1.226  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.934  -0.837  -0.449  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.187   0.583  -0.969  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.956   1.506   0.174  1.00  0.00           C  
HETATM   13  O1  UNL     1      -2.574   0.565  -1.389  1.00  0.00           O  
HETATM   14  C13 UNL     1      -3.236  -0.440  -0.714  1.00  0.00           C  
HETATM   15  O2  UNL     1      -4.464  -0.365  -0.412  1.00  0.00           O  
HETATM   16  C14 UNL     1      -2.293  -1.525  -0.442  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.633  -2.131   0.901  1.00  0.00           C  
HETATM   18  H1  UNL     1      -0.388   4.537  -0.697  1.00  0.00           H  
HETATM   19  H2  UNL     1       0.315   4.506   0.965  1.00  0.00           H  
HETATM   20  H3  UNL     1      -1.378   4.031   0.723  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.990   3.222  -0.204  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.512   0.463  -1.248  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.947   1.178  -0.657  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.881   0.411   1.392  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.189   0.223   1.610  1.00  0.00           H  
HETATM   26  H9  UNL     1       4.165  -1.317   0.662  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.217  -2.061   1.995  1.00  0.00           H  
HETATM   28  H11 UNL     1       3.493  -2.950   0.416  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.688  -3.014  -0.707  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.446  -2.566  -1.503  1.00  0.00           H  
HETATM   31  H14 UNL     1       0.267  -1.184  -2.265  1.00  0.00           H  
HETATM   32  H15 UNL     1      -0.619  -0.846   0.613  1.00  0.00           H  
HETATM   33  H16 UNL     1      -0.676   0.808  -1.905  1.00  0.00           H  
HETATM   34  H17 UNL     1      -0.967   0.941   1.161  1.00  0.00           H  
HETATM   35  H18 UNL     1      -1.973   2.035   0.297  1.00  0.00           H  
HETATM   36  H19 UNL     1      -2.369  -2.280  -1.251  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.048  -3.046   1.122  1.00  0.00           H  
HETATM   38  H21 UNL     1      -2.361  -1.365   1.679  1.00  0.00           H  
HETATM   39  H22 UNL     1      -3.719  -2.263   0.966  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   12
CONECT    3    4   21
CONECT    4    5   22   23
CONECT    5    6   24   25
CONECT    6    7    8    8
CONECT    7   26   27   28
CONECT    8    9   29
CONECT    9   10   30   31
CONECT   10   11   16   32
CONECT   11   12   13   33
CONECT   12   34   35
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17   36
CONECT   17   37   38   39
END

HMDB0302311
     RDKit          3D
Germacranolide
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.3681    4.0129    0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244    2.5503    0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2943    2.3407   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8421    1.0174   -0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393    0.0973    0.8123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0879   -1.2976    0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3230   -1.9986    0.9083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3238   -1.9593   -0.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0937   -1.5839   -1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9345   -0.8373   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1872    0.5833   -0.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9559    1.5057    0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5742    0.5647   -1.3891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2359   -0.4404   -0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4645   -0.3655   -0.4125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2928   -1.5251   -0.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6334   -2.1305    0.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3878    4.5370   -0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3150    4.5059    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3777    4.0313    0.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9897    3.2221   -0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5115    0.4628   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9474    1.1782   -0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8815    0.4113    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1887    0.2233    1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1647   -1.3166    0.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166   -2.0609    1.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4932   -2.9503    0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875   -3.0142   -0.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4460   -2.5655   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668   -1.1835   -2.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6194   -0.8458    0.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761    0.8083   -1.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9669    0.9414    1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9731    2.0355    0.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3691   -2.2797   -1.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0484   -3.0461    1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3614   -1.3650    1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7189   -2.2633    0.9662 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
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 12  2  1  0
 16 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₂

Average Molecular Weight

234.339

Monoisotopic Molecular Weight

234.161979948

IUPAC Name

3,6,10-trimethyl-2H,3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-2-one

Traditional Name

3,6,10-trimethyl-3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-2-one

CAS Registry Number

Not Available

SMILES

[H]\C1=C(C)/CC2OC(=O)C(C)C2C\C([H])=C(C)\CC1

InChI Identifier

InChI=1S/C15H22O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h6-7,12-14H,4-5,8-9H2,1-3H3/b10-7+,11-6+

InChI Key

QJRFOUJEGHRZIU-NXAIOARDSA-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
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Dandelion (FooDB: FOOD00181)

Vegetable

Root vegetable

Burdock (FooDB: FOOD00017)

Process

Not Available

Role

Not Available

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
logP	4.23	ALOGPS
logP	3.52	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.3 m³·mol⁻¹	ChemAxon
Polarizability	26.86 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	155.783	32859911
AllCCS	[M+H-H2O]+	151.913	32859911
AllCCS	[M+Na]+	160.417	32859911
AllCCS	[M+NH4]+	159.381	32859911
AllCCS	[M-H]-	161.971	32859911
AllCCS	[M+Na-2H]-	162.266	32859911
AllCCS	[M+HCOO]-	162.7	32859911
DeepCCS	[M+H]+	165.068	30932474
DeepCCS	[M-H]-	162.71	30932474
DeepCCS	[M-2H]-	196.428	30932474
DeepCCS	[M+Na]+	171.656	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacranolide 10V, Positive-QTOF	splash10-000i-0490000000-e51bd1dc812294ba6315	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacranolide 20V, Positive-QTOF	splash10-000i-1930000000-de02d0d19dc8d8be83ad	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacranolide 40V, Positive-QTOF	splash10-0i00-7910000000-c72868d944eb3c82c898	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacranolide 10V, Negative-QTOF	splash10-001i-0390000000-86e5ae418870032794ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacranolide 20V, Negative-QTOF	splash10-001r-1890000000-7e0f12c885255a02e59e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacranolide 40V, Negative-QTOF	splash10-0i09-9710000000-f6e4c8fb9cfc069501a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacranolide 10V, Positive-QTOF	splash10-000i-0690000000-e57daa5472d1a7f1c9ef	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacranolide 20V, Positive-QTOF	splash10-01p9-0930000000-6d4943b3371324844b39	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacranolide 40V, Positive-QTOF	splash10-08fs-0900000000-46001800771146ac6c8b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacranolide 10V, Negative-QTOF	splash10-001i-0090000000-9087f47ed0ae51229a17	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacranolide 20V, Negative-QTOF	splash10-01q9-0890000000-ed1a1621b7fb765f8722	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacranolide 40V, Negative-QTOF	splash10-0a4i-3900000000-9c0e105cd8e1cfb09ede	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB004104

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91694425

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for Germacranolide (HMDB0302311)

MOL for HMDB0302311 (Germacranolide)

3D MOL for HMDB0302311 (Germacranolide)

3D SDF for HMDB0302311 (Germacranolide)

3D-SDF for HMDB0302311 (Germacranolide)

PDB for HMDB0302311 (Germacranolide)

3D PDB for HMDB0302311 (Germacranolide)

SMILES for HMDB0302311 (Germacranolide)

INCHI for HMDB0302311 (Germacranolide)

Structure for HMDB0302311 (Germacranolide)

3D Structure for HMDB0302311 (Germacranolide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra