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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-28 17:57:12 UTC

Update Date

2021-09-26 22:47:35 UTC

HMDB ID

HMDB0242219

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(-)-Parthenolide

Description

(-)-Parthenolide 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 (-)-Parthenolide. This compound has been identified in human blood as reported by (PMID: 31557052 ). (-)-parthenolide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (-)-Parthenolide 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

HMDB0242434
     RDKit          3D
(1S,2R,4R,7E)-4,8-Dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.02,4]tetra...
 38 40  0  0  0  0  0  0  0  0999 V2000
   -2.5095   -2.7776    1.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0627   -2.1421    0.5064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3964   -2.4077   -0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1441   -3.3332   -1.3196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7469   -1.4596   -1.6860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5660   -0.3304   -0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1064   -0.9940    0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2749   -1.5941    0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060   -0.8976    1.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189   -0.1862    0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4493   -1.0283   -0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3095    1.0927    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2868    2.0656    0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6471    2.6696   -0.7598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761    2.0012   -0.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7649    2.4899   -0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1166    1.6557   -2.2117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5740    0.6479   -1.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2038   -3.5932    1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377   -2.5487    2.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382    0.1537   -0.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959   -0.3283    1.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5244   -1.5527   -0.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2828   -2.6838    0.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8669   -1.6454    1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7903   -0.2417    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0023   -0.4600   -0.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398   -1.2623    0.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0266   -1.9169   -0.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1262    1.5049   -0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5129    1.6348    1.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8140    2.8495    1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3135    2.6292   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792    3.7531   -0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7350    3.5994   -0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7600    2.1658   -0.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5088    2.2179    1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3717    0.2529   -1.7745 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
 17 18  1  0
  7  2  1  0
 18 15  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
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
M  END


  Mrv1652308282120072D          

 18 20  0  0  0  0            999 V2000
    0.6546    4.9851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0050    4.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8271    4.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1774    3.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7058    2.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0562    1.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5846    1.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4066    1.2506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7626    1.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122    2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5334    3.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4065    2.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9705    2.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5620    1.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3089    0.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1605    0.8266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8031    2.3479    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  4  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  8  1  0  0  0  0
  7  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
  2 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  9 17  1  0  0  0  0
  6 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242219

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CCCC2(C)OC2C2OC(=O)C(=C)C2CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3

> <INCHI_KEY>
KTEXNACQROZXEV-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.650380030312366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0^{2,4}]tetradec-7-en-13-one

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
3.071292598333333

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2427719335752

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
68.5529

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0^{2,4}]tetradec-7-en-13-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0242434
     RDKit          3D
(1S,2R,4R,7E)-4,8-Dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.02,4]tetra...
 38 40  0  0  0  0  0  0  0  0999 V2000
   -2.5095   -2.7776    1.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0627   -2.1421    0.5064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3964   -2.4077   -0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1441   -3.3332   -1.3196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7469   -1.4596   -1.6860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5660   -0.3304   -0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1064   -0.9940    0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2749   -1.5941    0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060   -0.8976    1.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189   -0.1862    0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4493   -1.0283   -0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3095    1.0927    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2868    2.0656    0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6471    2.6696   -0.7598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761    2.0012   -0.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7649    2.4899   -0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1166    1.6557   -2.2117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5740    0.6479   -1.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2038   -3.5932    1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377   -2.5487    2.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382    0.1537   -0.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959   -0.3283    1.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5244   -1.5527   -0.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2828   -2.6838    0.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8669   -1.6454    1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7903   -0.2417    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0023   -0.4600   -0.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398   -1.2623    0.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0266   -1.9169   -0.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1262    1.5049   -0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5129    1.6348    1.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8140    2.8495    1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3135    2.6292   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792    3.7531   -0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7350    3.5994   -0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7600    2.1658   -0.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5088    2.2179    1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3717    0.2529   -1.7745 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
 17 18  1  0
  7  2  1  0
 18 15  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
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
M  END

HEADER    PROTEIN                                 28-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-AUG-21         0                                  
HETATM    1  C   UNK     0       1.222   9.306   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.876   7.911   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.410   7.781   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.065   6.386   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.184   5.123   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.838   3.729   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.958   2.465   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.492   2.335   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.423   2.596   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.769   3.990   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.650   5.254   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.996   6.648   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.759   3.799   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.812   4.923   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.049   2.286   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.443   1.632   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.300   1.543   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.232   4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   18                                             
CONECT    7    6    8    9                                                  
CONECT    8    7    6                                                       
CONECT    9    7   10   17                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    2                                                       
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    9                                                       
CONECT   18    6                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0242434
HETATM    1  C1  UNL     1      -2.509  -2.778   1.572  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.063  -2.142   0.506  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.396  -2.408  -0.888  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.144  -3.333  -1.320  1.00  0.00           O  
HETATM    5  O2  UNL     1      -1.747  -1.460  -1.686  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.566  -0.330  -0.851  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.106  -0.994   0.449  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.275  -1.594   0.292  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.306  -0.898   1.146  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.319  -0.186   0.333  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.449  -1.028  -0.208  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.310   1.093   0.054  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.287   2.066   0.497  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.647   2.670  -0.760  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.676   2.001  -0.948  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.765   2.490  -0.018  1.00  0.00           C  
HETATM   17  O3  UNL     1      -1.117   1.656  -2.212  1.00  0.00           O  
HETATM   18  C15 UNL     1      -0.574   0.648  -1.377  1.00  0.00           C  
HETATM   19  H1  UNL     1      -3.204  -3.593   1.425  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.238  -2.549   2.575  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.538   0.154  -0.630  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.196  -0.328   1.312  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.524  -1.553  -0.797  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.283  -2.684   0.558  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.867  -1.645   1.780  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.790  -0.242   1.878  1.00  0.00           H  
HETATM   27  H9  UNL     1       4.002  -0.460  -0.999  1.00  0.00           H  
HETATM   28  H10 UNL     1       4.140  -1.262   0.612  1.00  0.00           H  
HETATM   29  H11 UNL     1       3.027  -1.917  -0.715  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.126   1.505  -0.565  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.513   1.635   1.128  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.814   2.850   1.081  1.00  0.00           H  
HETATM   33  H15 UNL     1       1.314   2.629  -1.624  1.00  0.00           H  
HETATM   34  H16 UNL     1       0.479   3.753  -0.497  1.00  0.00           H  
HETATM   35  H17 UNL     1      -1.735   3.599  -0.050  1.00  0.00           H  
HETATM   36  H18 UNL     1      -2.760   2.166  -0.318  1.00  0.00           H  
HETATM   37  H19 UNL     1      -1.509   2.218   1.038  1.00  0.00           H  
HETATM   38  H20 UNL     1       0.372   0.253  -1.775  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   30
CONECT   13   14   31   32
CONECT   14   15   33   34
CONECT   15   16   17   18
CONECT   16   35   36   37
CONECT   17   18
CONECT   18   38
END

HMDB0242434
     RDKit          3D
(1S,2R,4R,7E)-4,8-Dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.02,4]tetra...
 38 40  0  0  0  0  0  0  0  0999 V2000
   -2.5095   -2.7776    1.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0627   -2.1421    0.5064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3964   -2.4077   -0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1441   -3.3332   -1.3196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7469   -1.4596   -1.6860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5660   -0.3304   -0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1064   -0.9940    0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2749   -1.5941    0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3060   -0.8976    1.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189   -0.1862    0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4493   -1.0283   -0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3095    1.0927    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2868    2.0656    0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6471    2.6696   -0.7598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761    2.0012   -0.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7649    2.4899   -0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1166    1.6557   -2.2117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5740    0.6479   -1.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2038   -3.5932    1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377   -2.5487    2.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382    0.1537   -0.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959   -0.3283    1.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5244   -1.5527   -0.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2828   -2.6838    0.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8669   -1.6454    1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7903   -0.2417    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0023   -0.4600   -0.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398   -1.2623    0.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0266   -1.9169   -0.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1262    1.5049   -0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5129    1.6348    1.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8140    2.8495    1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3135    2.6292   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792    3.7531   -0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7350    3.5994   -0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7600    2.1658   -0.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5088    2.2179    1.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3717    0.2529   -1.7745 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
 17 18  1  0
  7  2  1  0
 18 15  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
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Parthenolide, (1ar-(1ar,4E,7as,10as,10br))-isomer	HMDB

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.322

Monoisotopic Molecular Weight

248.141244504

IUPAC Name

4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0^{2,4}]tetradec-7-en-13-one

Traditional Name

4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0^{2,4}]tetradec-7-en-13-one

CAS Registry Number

Not Available

SMILES

CC1=CCCC2(C)OC2C2OC(=O)C(=C)C2CC1

InChI Identifier

InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3

InChI Key

KTEXNACQROZXEV-UHFFFAOYSA-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
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
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)

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	3.03	ALOGPS
logP	3.07	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.55 m³·mol⁻¹	ChemAxon
Polarizability	26.65 Å³	ChemAxon
Number of Rings	3	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
DeepCCS	[M+H]+	158.386	30932474
DeepCCS	[M-H]-	156.028	30932474
DeepCCS	[M-2H]-	189.109	30932474
DeepCCS	[M+Na]+	164.479	30932474
AllCCS	[M+H]+	159.3	32859911
AllCCS	[M+H-H2O]+	155.5	32859911
AllCCS	[M+NH4]+	162.8	32859911
AllCCS	[M+Na]+	163.8	32859911
AllCCS	[M-H]-	164.4	32859911
AllCCS	[M+Na-2H]-	164.3	32859911
AllCCS	[M+HCOO]-	164.3	32859911

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Parthenolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-5960000000-5ac50ae58e8909a69586	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Parthenolide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Parthenolide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Parthenolide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Parthenolide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Parthenolide 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 - (-)-Parthenolide 10V, Positive-QTOF	splash10-0002-0090000000-308c6024b53a399d0d74	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Parthenolide 20V, Positive-QTOF	splash10-0002-0190000000-0d8aac5015201d73c601	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Parthenolide 40V, Positive-QTOF	splash10-0032-1980000000-e5680ba3528f930ffa42	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Parthenolide 10V, Negative-QTOF	splash10-0002-0090000000-7b3a58b796a0e4263959	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Parthenolide 20V, Negative-QTOF	splash10-0002-0090000000-717909ee4df9ba3b89f8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Parthenolide 40V, Negative-QTOF	splash10-002g-1090000000-e822bc693a6fb3c5c561	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

4530

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4692

PDB ID

Not Available

ChEBI ID

95124

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 (-)-Parthenolide (HMDB0242219)

MOL for HMDB0242219 ((-)-Parthenolide)

3D MOL for HMDB0242219 ((-)-Parthenolide)

3D SDF for HMDB0242219 ((-)-Parthenolide)

3D-SDF for HMDB0242219 ((-)-Parthenolide)

PDB for HMDB0242219 ((-)-Parthenolide)

3D PDB for HMDB0242219 ((-)-Parthenolide)

SMILES for HMDB0242219 ((-)-Parthenolide)

INCHI for HMDB0242219 ((-)-Parthenolide)

Structure for HMDB0242219 ((-)-Parthenolide)

3D Structure for HMDB0242219 ((-)-Parthenolide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra