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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:46:55 UTC

Update Date

2022-03-07 02:53:11 UTC

HMDB ID

HMDB0031972

Secondary Accession Numbers

HMDB31972

Metabolite Identification

Common Name

Heliespirone A

Description

Heliespirone A belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Heliespirone A has been detected, but not quantified in, fats and oils. This could make heliespirone a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Heliespirone A.

Structure

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

HMDB0031972
     RDKit          3D
Heliespirone A
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.6619    3.5119   -0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1495    2.7511    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5485    1.3493    0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4625    0.8647   -0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1797   -0.6234   -0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4501   -1.3101   -0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9467   -0.8928    1.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3040   -2.8174   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4262   -0.9967   -1.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1215   -0.8386    0.2371 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    0.3574    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3861    0.5841   -0.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4973   -0.4025   -0.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7349   -1.1853   -1.8795 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3525   -0.4536    0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7652   -0.9272    0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8620   -0.0659    1.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4972    0.3905    1.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0671    0.8396    2.5734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3971    3.2052   -1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3515    4.5676   -0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5809    3.1725    0.9669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0521    1.1414    1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1510    1.2294   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5102    1.1307   -0.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9018   -1.0100   -1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8271   -1.5462    1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1534   -1.0709    1.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2364    0.1652    1.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3164   -3.2578   -0.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6042   -3.1899   -0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419   -3.1878    0.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9797   -0.2603   -0.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7584    0.4942   -1.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8182    1.5872   -0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9385   -1.4790   -0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9583   -1.6577    0.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875   -0.0739    0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816   -0.0952    2.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 11  3  1  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
M  END

  Mrv0541 02241215112D          

 19 20  0  0  0  0            999 V2000
   -1.8170   -0.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8170   -1.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1025   -1.6862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -1.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -0.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1025   -0.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881    0.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3966   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8815   -0.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3966    0.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0555    0.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0555    1.6862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065   -0.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1190    0.6783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1190   -0.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5315   -0.0362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3264   -1.6862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5315   -1.6862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5315   -0.0362    0.0000 O   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  1  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  7  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
  4 17  2  0  0  0  0
  2 18  1  0  0  0  0
  1 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031972

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(=O)C2(CC1=O)OC(CC2C=C)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-5-10-7-13(14(3,4)18)19-15(10)8-11(16)9(2)6-12(15)17/h5-6,10,13,18H,1,7-8H2,2-4H3

> <INCHI_KEY>
MATQAMIEUDKYBO-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.171474239373243

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-ethenyl-2-(2-hydroxypropan-2-yl)-8-methyl-1-oxaspiro[4.5]dec-7-ene-6,9-dione

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
2.0441893616666675

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.239447199636405

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.26643065566726

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0948634970024917

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
72.04719999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.87e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-ethenyl-2-(2-hydroxypropan-2-yl)-8-methyl-1-oxaspiro[4.5]dec-7-ene-6,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031972
     RDKit          3D
Heliespirone A
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.6619    3.5119   -0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1495    2.7511    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5485    1.3493    0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4625    0.8647   -0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1797   -0.6234   -0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4501   -1.3101   -0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9467   -0.8928    1.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3040   -2.8174   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4262   -0.9967   -1.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1215   -0.8386    0.2371 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    0.3574    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3861    0.5841   -0.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4973   -0.4025   -0.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7349   -1.1853   -1.8795 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3525   -0.4536    0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7652   -0.9272    0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8620   -0.0659    1.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4972    0.3905    1.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0671    0.8396    2.5734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3971    3.2052   -1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3515    4.5676   -0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5809    3.1725    0.9669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0521    1.1414    1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1510    1.2294   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5102    1.1307   -0.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9018   -1.0100   -1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8271   -1.5462    1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1534   -1.0709    1.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2364    0.1652    1.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3164   -3.2578   -0.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6042   -3.1899   -0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419   -3.1878    0.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9797   -0.2603   -0.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7584    0.4942   -1.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8182    1.5872   -0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9385   -1.4790   -0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9583   -1.6577    0.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875   -0.0739    0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816   -0.0952    2.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 11  3  1  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.392  -0.838   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.392  -2.378   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.058  -3.148   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.724  -2.378   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.724  -0.838   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.058  -0.068   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.724   0.702   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.740  -1.314   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.645  -0.068   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.740   1.178   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.970   1.608   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.970   3.148   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.185  -0.068   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.955   1.266   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.955  -1.401   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.725  -0.068   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.609  -3.148   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.725  -3.148   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.725  -0.068   0.000  0.00  0.00           O+0
CONECT    1    2    6   19                                                  
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6    7    8                                             
CONECT    6    5    1                                                       
CONECT    7    5   10   11                                                  
CONECT    8    5    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9    7                                                       
CONECT   11    7   12                                                       
CONECT   12   11                                                            
CONECT   13    9   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17    4                                                            
CONECT   18    2                                                            
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0031972
HETATM    1  C1  UNL     1      -0.662   3.512  -0.653  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.149   2.751   0.295  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.549   1.349   0.456  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.463   0.865  -0.660  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.180  -0.623  -0.604  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.450  -1.310  -0.199  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.947  -0.893   1.155  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.304  -2.817  -0.188  1.00  0.00           C  
HETATM    9  O1  UNL     1      -3.426  -0.997  -1.147  1.00  0.00           O  
HETATM   10  O2  UNL     1      -0.121  -0.839   0.237  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.588   0.357   0.329  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.386   0.584  -0.929  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.497  -0.402  -0.931  1.00  0.00           C  
HETATM   14  O3  UNL     1       2.735  -1.185  -1.880  1.00  0.00           O  
HETATM   15  C12 UNL     1       3.353  -0.454   0.241  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.765  -0.927   0.171  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.862  -0.066   1.416  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.497   0.391   1.478  1.00  0.00           C  
HETATM   19  O4  UNL     1       1.067   0.840   2.573  1.00  0.00           O  
HETATM   20  H1  UNL     1      -1.397   3.205  -1.383  1.00  0.00           H  
HETATM   21  H2  UNL     1      -0.352   4.568  -0.763  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.581   3.172   0.967  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.052   1.141   1.411  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.151   1.229  -1.663  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.510   1.131  -0.514  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.902  -1.010  -1.608  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.827  -1.546   1.388  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.153  -1.071   1.910  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.236   0.165   1.223  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.316  -3.258  -0.384  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.604  -3.190  -0.950  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.042  -3.188   0.846  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.980  -0.260  -0.782  1.00  0.00           H  
HETATM   34  H15 UNL     1       0.758   0.494  -1.845  1.00  0.00           H  
HETATM   35  H16 UNL     1       1.818   1.587  -0.879  1.00  0.00           H  
HETATM   36  H17 UNL     1       4.938  -1.479  -0.784  1.00  0.00           H  
HETATM   37  H18 UNL     1       4.958  -1.658   0.984  1.00  0.00           H  
HETATM   38  H19 UNL     1       5.488  -0.074   0.220  1.00  0.00           H  
HETATM   39  H20 UNL     1       3.482  -0.095   2.305  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   22
CONECT    3    4   11   23
CONECT    4    5   24   25
CONECT    5    6   10   26
CONECT    6    7    8    9
CONECT    7   27   28   29
CONECT    8   30   31   32
CONECT    9   33
CONECT   10   11
CONECT   11   12   18
CONECT   12   13   34   35
CONECT   13   14   14   15
CONECT   15   16   17   17
CONECT   16   36   37   38
CONECT   17   18   39
CONECT   18   19   19
END

HMDB0031972
     RDKit          3D
Heliespirone A
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.6619    3.5119   -0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1495    2.7511    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5485    1.3493    0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4625    0.8647   -0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1797   -0.6234   -0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4501   -1.3101   -0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9467   -0.8928    1.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3040   -2.8174   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4262   -0.9967   -1.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1215   -0.8386    0.2371 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    0.3574    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3861    0.5841   -0.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4973   -0.4025   -0.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7349   -1.1853   -1.8795 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3525   -0.4536    0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7652   -0.9272    0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8620   -0.0659    1.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4972    0.3905    1.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0671    0.8396    2.5734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3971    3.2052   -1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3515    4.5676   -0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5809    3.1725    0.9669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0521    1.1414    1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1510    1.2294   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5102    1.1307   -0.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9018   -1.0100   -1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8271   -1.5462    1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1534   -1.0709    1.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2364    0.1652    1.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3164   -3.2578   -0.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6042   -3.1899   -0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0419   -3.1878    0.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9797   -0.2603   -0.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7584    0.4942   -1.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8182    1.5872   -0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9385   -1.4790   -0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9583   -1.6577    0.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875   -0.0739    0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816   -0.0952    2.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 11  3  1  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Heliespirone a	MeSH

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

4-ethenyl-2-(2-hydroxypropan-2-yl)-8-methyl-1-oxaspiro[4.5]dec-7-ene-6,9-dione

Traditional Name

4-ethenyl-2-(2-hydroxypropan-2-yl)-8-methyl-1-oxaspiro[4.5]dec-7-ene-6,9-dione

CAS Registry Number

202533-71-9

SMILES

CC1=CC(=O)C2(CC1=O)OC(CC2C=C)C(C)(C)O

InChI Identifier

InChI=1S/C15H20O4/c1-5-10-7-13(14(3,4)18)19-15(10)8-11(16)9(2)6-12(15)17/h5-6,10,13,18H,1,7-8H2,2-4H3

InChI Key

MATQAMIEUDKYBO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Tetrahydrofuran
Tertiary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031972)

Source

Endogenous

Endogenous (HMDB: HMDB0031972)

Exogenous

Food

Food (HMDB: HMDB0031972)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0031972)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0031972)

Role

Biological role

Energy source (HMDB: HMDB0031972)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031972)

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	1027 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.87 g/L	ALOGPS
logP	0.93	ALOGPS
logP	2.04	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	14.27	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	72.05 m³·mol⁻¹	ChemAxon
Polarizability	28.17 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]+	161.687	31661259
DarkChem	[M-H]-	158.169	31661259
DeepCCS	[M+H]+	161.087	30932474
DeepCCS	[M-H]-	158.719	30932474
DeepCCS	[M-2H]-	191.604	30932474
DeepCCS	[M+Na]+	167.17	30932474
AllCCS	[M+H]+	161.4	32859911
AllCCS	[M+H-H2O]+	157.8	32859911
AllCCS	[M+NH4]+	164.8	32859911
AllCCS	[M+Na]+	165.8	32859911
AllCCS	[M-H]-	167.0	32859911
AllCCS	[M+Na-2H]-	167.2	32859911
AllCCS	[M+HCOO]-	167.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Heliespirone A	CC1=CC(=O)C2(CC1=O)OC(CC2C=C)C(C)(C)O	2815.0	Standard polar	33892256
Heliespirone A	CC1=CC(=O)C2(CC1=O)OC(CC2C=C)C(C)(C)O	1835.2	Standard non polar	33892256
Heliespirone A	CC1=CC(=O)C2(CC1=O)OC(CC2C=C)C(C)(C)O	1929.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Heliespirone A,1TMS,isomer #1	C=CC1CC(C(C)(C)O[Si](C)(C)C)OC12CC(=O)C(C)=CC2=O	2141.2	Semi standard non polar	33892256
Heliespirone A,1TMS,isomer #2	C=CC1CC(C(C)(C)O)OC12C=C(O[Si](C)(C)C)C(C)=CC2=O	2153.4	Semi standard non polar	33892256
Heliespirone A,2TMS,isomer #1	C=CC1CC(C(C)(C)O[Si](C)(C)C)OC12C=C(O[Si](C)(C)C)C(C)=CC2=O	2203.1	Semi standard non polar	33892256
Heliespirone A,2TMS,isomer #1	C=CC1CC(C(C)(C)O[Si](C)(C)C)OC12C=C(O[Si](C)(C)C)C(C)=CC2=O	2085.1	Standard non polar	33892256
Heliespirone A,1TBDMS,isomer #1	C=CC1CC(C(C)(C)O[Si](C)(C)C(C)(C)C)OC12CC(=O)C(C)=CC2=O	2380.4	Semi standard non polar	33892256
Heliespirone A,1TBDMS,isomer #2	C=CC1CC(C(C)(C)O)OC12C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC2=O	2391.9	Semi standard non polar	33892256
Heliespirone A,2TBDMS,isomer #1	C=CC1CC(C(C)(C)O[Si](C)(C)C(C)(C)C)OC12C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC2=O	2679.6	Semi standard non polar	33892256
Heliespirone A,2TBDMS,isomer #1	C=CC1CC(C(C)(C)O[Si](C)(C)C(C)(C)C)OC12C=C(O[Si](C)(C)C(C)(C)C)C(C)=CC2=O	2500.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Heliespirone A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-9210000000-a7296add6d334152fcca	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliespirone A GC-MS (1 TMS) - 70eV, Positive	splash10-00a9-9301000000-1e78a55116cefc35ef69	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliespirone A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliespirone A 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 - Heliespirone A 10V, Positive-QTOF	splash10-00kb-0390000000-95c5c9375f8f2594515a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliespirone A 20V, Positive-QTOF	splash10-0fba-4970000000-afc98afeafc763ea2699	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliespirone A 40V, Positive-QTOF	splash10-0udi-9400000000-9505770f82fc018ca91c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliespirone A 10V, Negative-QTOF	splash10-03di-0090000000-0bc2fbf51891a205728c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliespirone A 20V, Negative-QTOF	splash10-03dj-1190000000-325cfb89c2e01bcf424b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliespirone A 40V, Negative-QTOF	splash10-00kr-8900000000-0d88b0e4aee7cfd8b8a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliespirone A 10V, Positive-QTOF	splash10-014i-0290000000-7fe5c89a673a3eefc499	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliespirone A 20V, Positive-QTOF	splash10-01b9-3940000000-3ba6cb67e1ab95bd58a8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliespirone A 40V, Positive-QTOF	splash10-0kvo-9400000000-36fccf9059a76232def7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliespirone A 10V, Negative-QTOF	splash10-03di-0190000000-1b27a7d0e1fd68062562	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliespirone A 20V, Negative-QTOF	splash10-0bt9-5980000000-f73eb1f1d70374758441	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliespirone A 40V, Negative-QTOF	splash10-01bc-9510000000-992107921094dbe51ef3	2021-09-23	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

FDB008664

KNApSAcK ID

Not Available

Chemspider ID

24785660

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

75231864

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1829131

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Heliespirone A (HMDB0031972)

MOL for HMDB0031972 (Heliespirone A)

3D MOL for HMDB0031972 (Heliespirone A)

3D SDF for HMDB0031972 (Heliespirone A)

3D-SDF for HMDB0031972 (Heliespirone A)

PDB for HMDB0031972 (Heliespirone A)

3D PDB for HMDB0031972 (Heliespirone A)

SMILES for HMDB0031972 (Heliespirone A)

INCHI for HMDB0031972 (Heliespirone A)

Structure for HMDB0031972 (Heliespirone A)

3D Structure for HMDB0031972 (Heliespirone A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra