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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:05:35 UTC

Update Date

2021-09-26 23:08:52 UTC

HMDB ID

HMDB0254704

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Micheliolide

Description

9-hydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-2-one belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Based on a literature review very few articles have been published on 9-hydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-2-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). Micheliolide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Micheliolide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0254704
     RDKit          3D
Micheliolide
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.7547   -1.6370   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4862   -1.5501    0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776   -2.5601    0.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2194   -3.6302    1.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4408   -2.1348    1.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4845   -0.7075    0.9550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4797   -0.4912   -0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1642    0.8223   -0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4475    1.9042    0.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0982    2.0496   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1792    3.3120   -0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729    1.1602    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116    1.2998   -0.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4620   -0.1019   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7203   -1.0417   -0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7743   -1.7746    0.6324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9880   -1.9739   -0.9116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8790   -0.1751    0.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2502   -0.8671   -0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3532   -2.4881    0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8720   -0.3605    1.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9858   -0.7360   -1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2339    0.7652    0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2203    1.1725   -1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3083    1.6137    1.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945    2.8497    0.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715    3.8808   -0.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5878    3.1582   -1.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8573    3.9158   -0.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2619    2.0477   -1.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9553    1.5353    0.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1271   -0.1673   -2.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5656   -0.2540   -1.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3692   -2.4379   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4306   -1.0544    1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2697   -2.3998    1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4297   -2.8655   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010   -0.0781    1.6770 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
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  7  2  1  0
 18 12  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
M  END

  Mrv1533004261512232D          

 18 20  0  0  0  0            999 V2000
    3.6754    3.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    3.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    2.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    2.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4555    0.3761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4218    0.7640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    1.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    0.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    2.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    2.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    2.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    3.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    3.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254704

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2CCC(C)(O)C2C2OC(=O)C(=C)C2CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-4-5-11-9(2)14(16)18-13(11)12-10(8)6-7-15(12,3)17/h11-13,17H,2,4-7H2,1,3H3

> <INCHI_KEY>
RDJAFOWISVMOJY-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.464716011687216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-2-one

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.9697053053333335

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.624484933552093

> <JCHEM_PKA_STRONGEST_BASIC>
-2.963050290064313

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
68.66010000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-6,9-dimethyl-3-methylidene-3aH,4H,5H,7H,8H,9aH,9bH-azuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254704
     RDKit          3D
Micheliolide
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.7547   -1.6370   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4862   -1.5501    0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776   -2.5601    0.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2194   -3.6302    1.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4408   -2.1348    1.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4845   -0.7075    0.9550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4797   -0.4912   -0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1642    0.8223   -0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4475    1.9042    0.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0982    2.0496   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1792    3.3120   -0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729    1.1602    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116    1.2998   -0.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4620   -0.1019   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7203   -1.0417   -0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7743   -1.7746    0.6324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9880   -1.9739   -0.9116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8790   -0.1751    0.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2502   -0.8671   -0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3532   -2.4881    0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8720   -0.3605    1.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9858   -0.7360   -1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2339    0.7652    0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2203    1.1725   -1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3083    1.6137    1.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945    2.8497    0.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715    3.8808   -0.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5878    3.1582   -1.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8573    3.9158   -0.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2619    2.0477   -1.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9553    1.5353    0.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1271   -0.1673   -2.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5656   -0.2540   -1.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3692   -2.4379   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4306   -1.0544    1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2697   -2.3998    1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4297   -2.8655   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010   -0.0781    1.6770 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
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  7  2  1  0
 18 12  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
M  END

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       6.861   7.086   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.657   6.126   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.999   4.625   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.441   4.084   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.372   2.545   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.888   2.136   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.450   0.702   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.521   1.426   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.039   3.421   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.499   3.421   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.651   2.136   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.166   2.545   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.038   1.585   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.097   4.084   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.188   4.932   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.539   4.625   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.882   6.126   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.269   6.794   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6    3   10                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    2                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0254704
HETATM    1  C1  UNL     1       3.755  -1.637  -0.205  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.486  -1.550   0.141  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.778  -2.560   0.916  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.219  -3.630   1.393  1.00  0.00           O  
HETATM    5  O2  UNL     1       0.441  -2.135   1.061  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.484  -0.707   0.955  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.480  -0.491  -0.128  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.164   0.822  -0.130  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.447   1.904   0.625  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.098   2.050  -0.009  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.179   3.312  -0.746  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.873   1.160   0.025  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.212   1.300  -0.602  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.462  -0.102  -1.126  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.720  -1.042  -0.203  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.774  -1.775   0.632  1.00  0.00           C  
HETATM   17  O3  UNL     1      -0.988  -1.974  -0.912  1.00  0.00           O  
HETATM   18  C15 UNL     1      -0.879  -0.175   0.680  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.250  -0.867  -0.781  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.353  -2.488   0.077  1.00  0.00           H  
HETATM   21  H3  UNL     1       0.872  -0.360   1.946  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.986  -0.736  -1.100  1.00  0.00           H  
HETATM   23  H5  UNL     1       3.234   0.765   0.192  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.220   1.172  -1.203  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.308   1.614   1.675  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.994   2.850   0.511  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.772   3.881  -0.785  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.588   3.158  -1.745  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.857   3.916  -0.083  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.262   2.048  -1.392  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.955   1.535   0.214  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.127  -0.167  -2.175  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.566  -0.254  -1.078  1.00  0.00           H  
HETATM   34  H16 UNL     1      -3.369  -2.438  -0.031  1.00  0.00           H  
HETATM   35  H17 UNL     1      -3.431  -1.054   1.156  1.00  0.00           H  
HETATM   36  H18 UNL     1      -2.270  -2.400   1.420  1.00  0.00           H  
HETATM   37  H19 UNL     1      -1.430  -2.865  -0.862  1.00  0.00           H  
HETATM   38  H20 UNL     1      -1.401  -0.078   1.677  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   18   21
CONECT    7    8   22
CONECT    8    9   23   24
CONECT    9   10   25   26
CONECT   10   11   12   12
CONECT   11   27   28   29
CONECT   12   13   18
CONECT   13   14   30   31
CONECT   14   15   32   33
CONECT   15   16   17   18
CONECT   16   34   35   36
CONECT   17   37
CONECT   18   38
END

HMDB0254704
     RDKit          3D
Micheliolide
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.7547   -1.6370   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4862   -1.5501    0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776   -2.5601    0.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2194   -3.6302    1.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4408   -2.1348    1.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4845   -0.7075    0.9550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4797   -0.4912   -0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1642    0.8223   -0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4475    1.9042    0.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0982    2.0496   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1792    3.3120   -0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729    1.1602    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116    1.2998   -0.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4620   -0.1019   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7203   -1.0417   -0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7743   -1.7746    0.6324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9880   -1.9739   -0.9116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8790   -0.1751    0.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2502   -0.8671   -0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3532   -2.4881    0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8720   -0.3605    1.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9858   -0.7360   -1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2339    0.7652    0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2203    1.1725   -1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3083    1.6137    1.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945    2.8497    0.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7715    3.8808   -0.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5878    3.1582   -1.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8573    3.9158   -0.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2619    2.0477   -1.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9553    1.5353    0.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1271   -0.1673   -2.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5656   -0.2540   -1.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3692   -2.4379   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4306   -1.0544    1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2697   -2.3998    1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4297   -2.8655   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010   -0.0781    1.6770 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
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  7  2  1  0
 18 12  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.322

Monoisotopic Molecular Weight

248.141244504

IUPAC Name

9-hydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-2-one

Traditional Name

9-hydroxy-6,9-dimethyl-3-methylidene-3aH,4H,5H,7H,8H,9aH,9bH-azuleno[4,5-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CC1=C2CCC(C)(O)C2C2OC(=O)C(=C)C2CC1

InChI Identifier

InChI=1S/C15H20O3/c1-8-4-5-11-9(2)14(16)18-13(11)12-10(8)6-7-15(12,3)17/h11-13,17H,2,4-7H2,1,3H3

InChI Key

RDJAFOWISVMOJY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	1.74	ALOGPS
logP	1.97	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	14.62	ChemAxon
pKa (Strongest Basic)	-3	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	68.66 m³·mol⁻¹	ChemAxon
Polarizability	27.46 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	160.356	30932474
DeepCCS	[M-H]-	157.998	30932474
DeepCCS	[M-2H]-	191.095	30932474
DeepCCS	[M+Na]+	166.449	30932474
AllCCS	[M+H]+	158.5	32859911
AllCCS	[M+H-H2O]+	154.9	32859911
AllCCS	[M+NH4]+	162.0	32859911
AllCCS	[M+Na]+	162.9	32859911
AllCCS	[M-H]-	163.5	32859911
AllCCS	[M+Na-2H]-	163.4	32859911
AllCCS	[M+HCOO]-	163.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Micheliolide	CC1=C2CCC(C)(O)C2C2OC(=O)C(=C)C2CC1	2970.4	Standard polar	33892256
Micheliolide	CC1=C2CCC(C)(O)C2C2OC(=O)C(=C)C2CC1	2020.9	Standard non polar	33892256
Micheliolide	CC1=C2CCC(C)(O)C2C2OC(=O)C(=C)C2CC1	2158.7	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 - Micheliolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ec-4980000000-ed3ce0a3edf99607e09d	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Micheliolide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Micheliolide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Micheliolide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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 - Micheliolide 10V, Positive-QTOF	splash10-0002-0190000000-9d5e7e13cc231dc2dbc8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Micheliolide 20V, Positive-QTOF	splash10-00np-1970000000-7246de638d49e7b44793	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Micheliolide 40V, Positive-QTOF	splash10-01di-1900000000-dcdc5285c982a53d31bd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Micheliolide 10V, Negative-QTOF	splash10-0002-0090000000-7b3a58b796a0e4263959	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Micheliolide 20V, Negative-QTOF	splash10-0002-0090000000-5ff6235e23122df9ca52	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Micheliolide 40V, Negative-QTOF	splash10-004i-2950000000-5bf2be9d1d7c6aad1671	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

285560

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

322515

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Micheliolide (HMDB0254704)

MOL for HMDB0254704 (Micheliolide)

3D MOL for HMDB0254704 (Micheliolide)

3D SDF for HMDB0254704 (Micheliolide)

3D-SDF for HMDB0254704 (Micheliolide)

PDB for HMDB0254704 (Micheliolide)

3D PDB for HMDB0254704 (Micheliolide)

SMILES for HMDB0254704 (Micheliolide)

INCHI for HMDB0254704 (Micheliolide)

Structure for HMDB0254704 (Micheliolide)

3D Structure for HMDB0254704 (Micheliolide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra