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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 19:59:12 UTC

Update Date

2021-09-23 19:59:12 UTC

HMDB ID

HMDB0302710

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Verlotorin

Description

7-hydroperoxy-10-methyl-3,6-dimethylidene-2H,3H,3aH,4H,5H,6H,7H,8H,9H,11aH-cyclodeca[b]furan-2-one belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review very few articles have been published on 7-hydroperoxy-10-methyl-3,6-dimethylidene-2H,3H,3aH,4H,5H,6H,7H,8H,9H,11aH-cyclodeca[b]furan-2-one.

Structure

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

HMDB0302710
     RDKit          3D
Verlotorin
 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.6189   -0.8439   -1.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2549   -1.2311   -0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0637   -2.0848   -0.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2237   -1.3716   -0.8753 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5816   -0.4297    0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9524   -0.6851    0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7155   -1.7357    0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2260    0.5888    1.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835    0.8448    2.2626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2393    1.5287    1.0713 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901    0.9892   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7196    1.7355   -0.7872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5077    2.0024   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4339    2.8408   -1.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831    1.5690    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3799    0.7046    0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0965   -0.7668    0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423   -1.1193    1.7960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4265   -1.9046    2.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4913   -0.2094   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0484   -1.1528   -2.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816   -2.9337   -1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0587   -2.5177    0.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0353   -2.0865   -1.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0483   -0.8440   -1.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9338   -0.5538    1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6716   -1.7023    1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4743   -2.6616    0.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7461    0.9927   -0.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9933    2.1774   -1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1558    3.4146   -0.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8358    3.5651   -1.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9825    2.1257   -1.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385    2.5039    1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5543    1.1580    1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2043    0.8680    1.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8488    1.0429   -0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0959   -1.2831    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9484   -2.5344    1.9296 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  2  3
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17  2  1  0
 11  5  1  0
  1 20  1  0
  1 21  1  0
  3 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
 11 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
M  END


  Mrv0541 02241221232D          

 19 20  0  0  0  0            999 V2000
    1.3561   -0.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279   -0.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614   -0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037   -0.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124   -0.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1352   -1.5216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8439   -2.2935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983   -1.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0002   -0.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070   -1.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929   -1.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -1.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460   -1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304   -1.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
  6 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302710

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C1=C/C2OC(=O)C(=C)C2CCC(=C)C(CC1)OO

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-9-4-7-13(19-17)10(2)5-6-12-11(3)15(16)18-14(12)8-9/h8,12-14,17H,2-7H2,1H3/b9-8+

> <INCHI_KEY>
IXRHWRRLTANMPL-CMDGGOBGSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.78249926719655

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroperoxy-10-methyl-3,6-dimethylidene-2H,3H,3aH,4H,5H,6H,7H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
3.0926246273333335

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.711276580410768

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2372876237283466

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
71.7396

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroperoxy-10-methyl-3,6-dimethylidene-3aH,4H,5H,7H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302710
     RDKit          3D
Verlotorin
 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.6189   -0.8439   -1.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2549   -1.2311   -0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0637   -2.0848   -0.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2237   -1.3716   -0.8753 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5816   -0.4297    0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9524   -0.6851    0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7155   -1.7357    0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2260    0.5888    1.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835    0.8448    2.2626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2393    1.5287    1.0713 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901    0.9892   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7196    1.7355   -0.7872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5077    2.0024   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4339    2.8408   -1.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831    1.5690    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3799    0.7046    0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0965   -0.7668    0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423   -1.1193    1.7960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4265   -1.9046    2.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4913   -0.2094   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0484   -1.1528   -2.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816   -2.9337   -1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0587   -2.5177    0.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0353   -2.0865   -1.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0483   -0.8440   -1.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9338   -0.5538    1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6716   -1.7023    1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4743   -2.6616    0.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7461    0.9927   -0.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9933    2.1774   -1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1558    3.4146   -0.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8358    3.5651   -1.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9825    2.1257   -1.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385    2.5039    1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5543    1.1580    1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2043    0.8680    1.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8488    1.0429   -0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0959   -1.2831    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9484   -2.5344    1.9296 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  2  3
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17  2  1  0
 11  5  1  0
  1 20  1  0
  1 21  1  0
  3 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
 11 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 19 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  O   UNK     0       2.531  -0.296   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.972  -0.840   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.259   0.006   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.461  -0.957   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.981  -0.707   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.525   0.734   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.044   0.983   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.020  -0.208   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.476  -1.649   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.452  -2.840   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      10.909  -4.281   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.957  -1.898   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.467  -1.508   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.413  -3.339   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.893  -3.589   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.918  -2.397   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.379  -2.325   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.417  -3.528   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.549   1.925   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    4   17                                                  
CONECT   17   16    2   18                                                  
CONECT   18   17                                                            
CONECT   19    6                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0302710
HETATM    1  C1  UNL     1      -1.619  -0.844  -1.794  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.255  -1.231  -0.579  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.064  -2.085  -0.436  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.224  -1.372  -0.875  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.582  -0.430   0.212  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.952  -0.685   0.805  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.716  -1.736   0.766  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.226   0.589   1.463  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.184   0.845   2.263  1.00  0.00           O  
HETATM   10  O2  UNL     1       2.239   1.529   1.071  1.00  0.00           O  
HETATM   11  C9  UNL     1       1.790   0.989  -0.180  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.720   1.735  -0.787  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.508   2.002  -0.415  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.434   2.841  -1.288  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.183   1.569   0.842  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.380   0.705   0.526  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.097  -0.767   0.554  1.00  0.00           C  
HETATM   18  O3  UNL     1      -1.642  -1.119   1.796  1.00  0.00           O  
HETATM   19  O4  UNL     1      -2.427  -1.905   2.464  1.00  0.00           O  
HETATM   20  H1  UNL     1      -2.491  -0.209  -1.989  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.048  -1.153  -2.649  1.00  0.00           H  
HETATM   22  H3  UNL     1      -0.182  -2.934  -1.159  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.059  -2.518   0.560  1.00  0.00           H  
HETATM   24  H5  UNL     1       2.035  -2.086  -1.047  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.048  -0.844  -1.833  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.934  -0.554   1.128  1.00  0.00           H  
HETATM   27  H8  UNL     1       4.672  -1.702   1.265  1.00  0.00           H  
HETATM   28  H9  UNL     1       3.474  -2.662   0.268  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.746   0.993  -0.799  1.00  0.00           H  
HETATM   30  H11 UNL     1       0.993   2.177  -1.781  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.156   3.415  -0.710  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.836   3.565  -1.880  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.983   2.126  -1.922  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.639   2.504   1.320  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.554   1.158   1.610  1.00  0.00           H  
HETATM   36  H17 UNL     1      -3.204   0.868   1.284  1.00  0.00           H  
HETATM   37  H18 UNL     1      -2.849   1.043  -0.431  1.00  0.00           H  
HETATM   38  H19 UNL     1      -3.096  -1.283   0.428  1.00  0.00           H  
HETATM   39  H20 UNL     1      -2.948  -2.534   1.930  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   17
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6   11   26
CONECT    6    7    7    8
CONECT    7   27   28
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   29
CONECT   12   13   13   30
CONECT   13   14   15
CONECT   14   31   32   33
CONECT   15   16   34   35
CONECT   16   17   36   37
CONECT   17   18   38
CONECT   18   19
CONECT   19   39
END

HMDB0302710
     RDKit          3D
Verlotorin
 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.6189   -0.8439   -1.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2549   -1.2311   -0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0637   -2.0848   -0.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2237   -1.3716   -0.8753 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5816   -0.4297    0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9524   -0.6851    0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7155   -1.7357    0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2260    0.5888    1.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835    0.8448    2.2626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2393    1.5287    1.0713 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901    0.9892   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7196    1.7355   -0.7872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5077    2.0024   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4339    2.8408   -1.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831    1.5690    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3799    0.7046    0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0965   -0.7668    0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423   -1.1193    1.7960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4265   -1.9046    2.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4913   -0.2094   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0484   -1.1528   -2.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816   -2.9337   -1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0587   -2.5177    0.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0353   -2.0865   -1.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0483   -0.8440   -1.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9338   -0.5538    1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6716   -1.7023    1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4743   -2.6616    0.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7461    0.9927   -0.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9933    2.1774   -1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1558    3.4146   -0.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8358    3.5651   -1.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9825    2.1257   -1.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385    2.5039    1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5543    1.1580    1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2043    0.8680    1.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8488    1.0429   -0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0959   -1.2831    0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9484   -2.5344    1.9296 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  2  3
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17  2  1  0
 11  5  1  0
  1 20  1  0
  1 21  1  0
  3 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
 11 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

7-hydroperoxy-10-methyl-3,6-dimethylidene-2H,3H,3aH,4H,5H,6H,7H,8H,9H,11aH-cyclodeca[b]furan-2-one

Traditional Name

7-hydroperoxy-10-methyl-3,6-dimethylidene-3aH,4H,5H,7H,8H,9H,11aH-cyclodeca[b]furan-2-one

CAS Registry Number

Not Available

SMILES

C\C1=C/C2OC(=O)C(=C)C2CCC(=C)C(CC1)OO

InChI Identifier

InChI=1S/C15H20O4/c1-9-4-7-13(19-17)10(2)5-6-12-11(3)15(16)18-14(12)8-9/h8,12-14,17H,2-7H2,1H3/b9-8+

InChI Key

IXRHWRRLTANMPL-CMDGGOBGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Germacrane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Hydroperoxide
Lactone
Carboxylic acid ester
Alkyl hydroperoxide
Peroxol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Sweet bay (FooDB: FOOD00097)

Process

Not Available

Role

Biological role

allergen (HMDB: HMDB0302710)

Indirect biological role

oxidising agent (HMDB: HMDB0302710)

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	2.76	ALOGPS
logP	3.09	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.74 m³·mol⁻¹	ChemAxon
Polarizability	27.78 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
AllCCS	[M+H]+	164.291	32859911
AllCCS	[M+H-H2O]+	160.621	32859911
AllCCS	[M+Na]+	168.678	32859911
AllCCS	[M+NH4]+	167.698	32859911
AllCCS	[M-H]-	165.527	32859911
AllCCS	[M+Na-2H]-	165.654	32859911
AllCCS	[M+HCOO]-	165.911	32859911
DeepCCS	[M+H]+	163.387	30932474
DeepCCS	[M-H]-	161.029	30932474
DeepCCS	[M-2H]-	194.054	30932474
DeepCCS	[M+Na]+	169.48	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verlotorin 10V, Positive-QTOF	splash10-014i-0190000000-0d44b36004151e263708	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verlotorin 20V, Positive-QTOF	splash10-014l-0980000000-96aa6fd09aba6a1cd6d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verlotorin 40V, Positive-QTOF	splash10-0ldl-9300000000-0862109bc2862976157a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verlotorin 10V, Negative-QTOF	splash10-03di-0090000000-0c17c94cd5fd54ddf841	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verlotorin 20V, Negative-QTOF	splash10-03xs-0090000000-7c428bd95073333c5c04	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verlotorin 40V, Negative-QTOF	splash10-014i-9320000000-8df95ee62f86f62d69d3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verlotorin 10V, Positive-QTOF	splash10-00lr-0090000000-01c043a10303e868a705	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verlotorin 20V, Positive-QTOF	splash10-001i-0190000000-6033269781ec1addbe1a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verlotorin 40V, Positive-QTOF	splash10-0bu9-0920000000-9bd3f08365bb9a18fa65	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verlotorin 10V, Negative-QTOF	splash10-004i-0090000000-b9f45f6533549dcfebc9	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verlotorin 20V, Negative-QTOF	splash10-004i-0390000000-c77bf2c336ffa44ab36e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Verlotorin 40V, Negative-QTOF	splash10-05bf-3970000000-a19bd1178f80a4b89e36	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005902

KNApSAcK ID

Not Available

Chemspider ID

4514034

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5358982

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Verlotorin (HMDB0302710)

MOL for HMDB0302710 (Verlotorin)

3D MOL for HMDB0302710 (Verlotorin)

3D SDF for HMDB0302710 (Verlotorin)

3D-SDF for HMDB0302710 (Verlotorin)

PDB for HMDB0302710 (Verlotorin)

3D PDB for HMDB0302710 (Verlotorin)

SMILES for HMDB0302710 (Verlotorin)

INCHI for HMDB0302710 (Verlotorin)

Structure for HMDB0302710 (Verlotorin)

3D Structure for HMDB0302710 (Verlotorin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra