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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:56:41 UTC

Update Date

2022-03-07 02:55:03 UTC

HMDB ID

HMDB0036770

Secondary Accession Numbers

HMDB36770

Metabolite Identification

Common Name

Desacetyllaurenobiolide

Description

Desacetyllaurenobiolide 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 small amount of articles have been published on Desacetyllaurenobiolide.

Structure

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

HMDB0036770
     RDKit          3D
Desacetyllaurenobiolide
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.0164   -2.7860   -0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5489   -1.7027   -0.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2452   -0.9290    0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2569   -1.2965    1.3946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    0.2813    0.7784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2628    0.1223    0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8849    1.4182   -0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438    2.1212    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2370    2.7972    1.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3965    2.1512    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8224    1.5125   -1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369   -0.0040   -1.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8166   -0.5206    0.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8376    0.0236    1.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9431   -1.4337    0.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0742   -1.9994   -0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4473   -2.5785   -1.4589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2332   -1.0725   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4665   -3.3413   -1.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9947   -3.1930   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563   -0.0092    1.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5593    1.2501   -1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7771    2.1073   -0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2377    3.9036    1.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2343    2.4587    2.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4910    2.5819    2.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1577    2.6817    0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8531    1.8994   -1.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2076    1.8459   -2.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1009   -0.3907   -1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8376   -0.3260   -1.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441   -0.8861    1.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3985    0.6704    1.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6617    0.5193    0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -1.7391    1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363   -2.8891    0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1551   -2.4527   -2.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2441   -0.7955   -1.6479 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  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18  2  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
M  END


  Mrv0541 05061309192D          

 18 19  0  0  0  0            999 V2000
    5.8628    3.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5933   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841    2.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628    1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3779    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5933    2.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8086    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3779    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5933    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8086    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237    1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237    3.2398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.8250    0.0000 O   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
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  2  1  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 11  3  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 15  2  0  0  0  0
 18 13  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036770

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C1=C\CC\C(C)=C/C(O)C2C(C1)OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-9-5-4-6-10(2)8-13-14(12(16)7-9)11(3)15(17)18-13/h6-7,12-14,16H,3-5,8H2,1-2H3/b9-7-,10-6-

> <INCHI_KEY>
FRDLPOYYWWRSPZ-ZVEIMFCASA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.78192610689755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
2.4710048466666663

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.18268648207417

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.624850725106088

> <JCHEM_PKA_STRONGEST_BASIC>
-3.058393678865861

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
71.5171

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.20e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036770
     RDKit          3D
Desacetyllaurenobiolide
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.0164   -2.7860   -0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5489   -1.7027   -0.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2452   -0.9290    0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2569   -1.2965    1.3946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    0.2813    0.7784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2628    0.1223    0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8849    1.4182   -0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438    2.1212    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2370    2.7972    1.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3965    2.1512    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8224    1.5125   -1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369   -0.0040   -1.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8166   -0.5206    0.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8376    0.0236    1.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9431   -1.4337    0.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0742   -1.9994   -0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4473   -2.5785   -1.4589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2332   -1.0725   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4665   -3.3413   -1.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9947   -3.1930   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563   -0.0092    1.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5593    1.2501   -1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7771    2.1073   -0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2377    3.9036    1.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2343    2.4587    2.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4910    2.5819    2.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1577    2.6817    0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8531    1.8994   -1.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2076    1.8459   -2.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1009   -0.3907   -1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8376   -0.3260   -1.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441   -0.8861    1.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3985    0.6704    1.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6617    0.5193    0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -1.7391    1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363   -2.8891    0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1551   -2.4527   -2.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2441   -0.7955   -1.6479 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  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18  2  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 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      10.944   6.048   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.574  -1.246   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.264   5.496   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.944   2.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.944   3.556   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.039   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.574   5.278   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.109   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.039   4.802   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.574   0.294   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.740   4.032   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.109   4.802   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.204   2.016   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.204   3.556   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.835   2.786   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.204   6.048   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.295   2.786   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.740   1.540   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4    5    6                                                       
CONECT    5    4    9                                                       
CONECT    6    4   10                                                       
CONECT    7    9   12                                                       
CONECT    8   10   13                                                       
CONECT    9    1    5    7                                                  
CONECT   10    2    6    8                                                  
CONECT   11    3   14   15                                                  
CONECT   12    7   14   16                                                  
CONECT   13    8   14   18                                                  
CONECT   14   11   12   13                                                  
CONECT   15   11   17   18                                                  
CONECT   16   12                                                            
CONECT   17   15                                                            
CONECT   18   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0036770
HETATM    1  C1  UNL     1      -3.016  -2.786  -0.887  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.549  -1.703  -0.304  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.245  -0.929   0.707  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.257  -1.297   1.395  1.00  0.00           O  
HETATM    5  O2  UNL     1      -2.600   0.281   0.778  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.263   0.122   0.345  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.885   1.418  -0.369  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.144   2.121   0.432  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.237   2.797   1.724  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.397   2.151   0.007  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.822   1.512  -1.239  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.837  -0.004  -1.189  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.817  -0.521   0.184  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.838   0.024   1.139  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.943  -1.434   0.599  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.074  -1.999  -0.287  1.00  0.00           C  
HETATM   17  O3  UNL     1       0.447  -2.578  -1.459  1.00  0.00           O  
HETATM   18  C15 UNL     1      -1.233  -1.072  -0.567  1.00  0.00           C  
HETATM   19  H1  UNL     1      -2.466  -3.341  -1.642  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.995  -3.193  -0.644  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.656  -0.009   1.256  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.559   1.250  -1.389  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.777   2.107  -0.456  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.238   3.904   1.578  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.234   2.459   2.045  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.491   2.582   2.523  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.158   2.682   0.619  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.853   1.899  -1.499  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.208   1.846  -2.127  1.00  0.00           H  
HETATM   30  H12 UNL     1       1.101  -0.391  -1.877  1.00  0.00           H  
HETATM   31  H13 UNL     1       2.838  -0.326  -1.611  1.00  0.00           H  
HETATM   32  H14 UNL     1       3.244  -0.886   1.671  1.00  0.00           H  
HETATM   33  H15 UNL     1       2.399   0.670   1.906  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.662   0.519   0.636  1.00  0.00           H  
HETATM   35  H17 UNL     1       1.025  -1.739   1.637  1.00  0.00           H  
HETATM   36  H18 UNL     1      -0.536  -2.889   0.244  1.00  0.00           H  
HETATM   37  H19 UNL     1      -0.155  -2.453  -2.234  1.00  0.00           H  
HETATM   38  H20 UNL     1      -1.244  -0.795  -1.648  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3   18
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   18   21
CONECT    7    8   22   23
CONECT    8    9   10   10
CONECT    9   24   25   26
CONECT   10   11   27
CONECT   11   12   28   29
CONECT   12   13   30   31
CONECT   13   14   15   15
CONECT   14   32   33   34
CONECT   15   16   35
CONECT   16   17   18   36
CONECT   17   37
CONECT   18   38
END

HMDB0036770
     RDKit          3D
Desacetyllaurenobiolide
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.0164   -2.7860   -0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5489   -1.7027   -0.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2452   -0.9290    0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2569   -1.2965    1.3946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    0.2813    0.7784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2628    0.1223    0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8849    1.4182   -0.3690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438    2.1212    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2370    2.7972    1.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3965    2.1512    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8224    1.5125   -1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369   -0.0040   -1.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8166   -0.5206    0.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8376    0.0236    1.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9431   -1.4337    0.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0742   -1.9994   -0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4473   -2.5785   -1.4589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2332   -1.0725   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4665   -3.3413   -1.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9947   -3.1930   -0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563   -0.0092    1.2562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5593    1.2501   -1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7771    2.1073   -0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2377    3.9036    1.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2343    2.4587    2.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4910    2.5819    2.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1577    2.6817    0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8531    1.8994   -1.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2076    1.8459   -2.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1009   -0.3907   -1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8376   -0.3260   -1.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441   -0.8861    1.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3985    0.6704    1.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6617    0.5193    0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250   -1.7391    1.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363   -2.8891    0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1551   -2.4527   -2.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2441   -0.7955   -1.6479 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  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18  2  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Chamissellin	HMDB
Deacetyllaurenobiolide	HMDB

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

IUPAC Name

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

Traditional Name

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

CAS Registry Number

35001-24-2

SMILES

C\C1=C\CC\C(C)=C/C(O)C2C(C1)OC(=O)C2=C

InChI Identifier

InChI=1S/C15H20O3/c1-9-5-4-6-10(2)8-13-14(12(16)7-9)11(3)15(17)18-13/h6-7,12-14,16H,3-5,8H2,1-2H3/b9-7-,10-6-

InChI Key

FRDLPOYYWWRSPZ-ZVEIMFCASA-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
Secondary alcohol
Lactone
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

Cell membrane (HMDB: HMDB0036770)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036770)

Source

Endogenous

Endogenous (HMDB: HMDB0036770)

Plant

Plant (HMDB: HMDB0036770)

Animal

Animal (HMDB: HMDB0036770)

Exogenous

Food

Food (HMDB: HMDB0036770)

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036770)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036770)

Cellular process

Cell signaling (HMDB: HMDB0036770)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036770)

Role

Biological role

allergen (HMDB: HMDB0036770)
Membrane stabilizer (HMDB: HMDB0036770)

Nutrient

Nutrient (HMDB: HMDB0036770)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036770)

Emulsifier (HMDB: HMDB0036770)

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	0.72 g/L	ALOGPS
logP	2.45	ALOGPS
logP	2.47	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	6.62	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.52 m³·mol⁻¹	ChemAxon
Polarizability	26.78 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
DarkChem	[M+H]+	159.714	31661259
DarkChem	[M-H]-	155.821	31661259
DeepCCS	[M+H]+	164.441	30932474
DeepCCS	[M-H]-	162.084	30932474
DeepCCS	[M-2H]-	194.969	30932474
DeepCCS	[M+Na]+	170.535	30932474
AllCCS	[M+H]+	159.2	32859911
AllCCS	[M+H-H2O]+	155.4	32859911
AllCCS	[M+NH4]+	162.8	32859911
AllCCS	[M+Na]+	163.8	32859911
AllCCS	[M-H]-	162.6	32859911
AllCCS	[M+Na-2H]-	162.7	32859911
AllCCS	[M+HCOO]-	163.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Desacetyllaurenobiolide	C\C1=C\CC\C(C)=C/C(O)C2C(C1)OC(=O)C2=C	2887.3	Standard polar	33892256
Desacetyllaurenobiolide	C\C1=C\CC\C(C)=C/C(O)C2C(C1)OC(=O)C2=C	2051.9	Standard non polar	33892256
Desacetyllaurenobiolide	C\C1=C\CC\C(C)=C/C(O)C2C(C1)OC(=O)C2=C	2182.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Desacetyllaurenobiolide,1TMS,isomer #1	C=C1C(=O)OC2C/C(C)=C\CC/C(C)=C\C(O[Si](C)(C)C)C12	2155.0	Semi standard non polar	33892256
Desacetyllaurenobiolide,1TBDMS,isomer #1	C=C1C(=O)OC2C/C(C)=C\CC/C(C)=C\C(O[Si](C)(C)C(C)(C)C)C12	2364.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Desacetyllaurenobiolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9660000000-8c0c3ca8ca0a5980b822	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desacetyllaurenobiolide GC-MS (1 TMS) - 70eV, Positive	splash10-00bi-9042000000-ebf37e82b027d2dc9094	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desacetyllaurenobiolide 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 - Desacetyllaurenobiolide 10V, Positive-QTOF	splash10-001j-0190000000-b79f474eaa2b9ff09b73	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desacetyllaurenobiolide 20V, Positive-QTOF	splash10-053s-0790000000-5c61fe4f2045f5bade24	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desacetyllaurenobiolide 40V, Positive-QTOF	splash10-0gi3-9810000000-8555d8eaa3f10dbff010	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desacetyllaurenobiolide 10V, Negative-QTOF	splash10-0002-0090000000-379da8138a34c28b0659	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desacetyllaurenobiolide 20V, Negative-QTOF	splash10-0f92-0190000000-8a15f17be4738bc36dd5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desacetyllaurenobiolide 40V, Negative-QTOF	splash10-00r6-9410000000-533d56c2d7e164eebcc3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desacetyllaurenobiolide 10V, Negative-QTOF	splash10-0002-0090000000-7b3a58b796a0e4263959	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desacetyllaurenobiolide 20V, Negative-QTOF	splash10-002b-0190000000-9f898299397f1c67c215	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desacetyllaurenobiolide 40V, Negative-QTOF	splash10-0200-5890000000-48077b22a9ae77218d24	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desacetyllaurenobiolide 10V, Positive-QTOF	splash10-0002-0090000000-b1efe9307de63f05c06f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desacetyllaurenobiolide 20V, Positive-QTOF	splash10-000t-0390000000-4ede3bf6f793e6b7a0a4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desacetyllaurenobiolide 40V, Positive-QTOF	splash10-0a59-0920000000-8e3849ce524657df3ca1	2021-09-24	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

FDB015712

KNApSAcK ID

C00012386

Chemspider ID

35014242

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752050

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

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 Desacetyllaurenobiolide (HMDB0036770)

MOL for HMDB0036770 (Desacetyllaurenobiolide)

3D MOL for HMDB0036770 (Desacetyllaurenobiolide)

3D SDF for HMDB0036770 (Desacetyllaurenobiolide)

3D-SDF for HMDB0036770 (Desacetyllaurenobiolide)

PDB for HMDB0036770 (Desacetyllaurenobiolide)

3D PDB for HMDB0036770 (Desacetyllaurenobiolide)

SMILES for HMDB0036770 (Desacetyllaurenobiolide)

INCHI for HMDB0036770 (Desacetyllaurenobiolide)

Structure for HMDB0036770 (Desacetyllaurenobiolide)

3D Structure for HMDB0036770 (Desacetyllaurenobiolide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra