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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 20:58:54 UTC

Update Date

2022-09-22 18:34:26 UTC

HMDB ID

HMDB0035934

Secondary Accession Numbers

HMDB35934

Metabolite Identification

Common Name

Isoalantolactone

Description

Isoalantolactone belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Based on a literature review a small amount of articles have been published on Isoalantolactone.

Structure

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

HMDB0035934
     RDKit          3D
Isoalantolactone
 37 39  0  0  0  0  0  0  0  0999 V2000
    3.7894    1.3330   -0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609    0.4017    0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5640   -0.7993    0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7789   -1.0922    1.0213 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4334   -1.5404    1.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4080   -1.1772    0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0254   -1.3897    0.8658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9071   -0.9610   -0.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7592   -1.9676   -1.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2986   -1.1006    0.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8370    0.0492    0.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7358    1.3066    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2560    1.4957   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6947    2.5794    0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5817    0.3939   -0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537    0.7096   -0.9245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6070    0.3501    0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8729    1.2799   -0.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3407    2.1953   -0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6535   -1.5511   -0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2107   -0.7029    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2278   -2.4361    1.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9373   -2.9975   -0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1700   -1.8804   -1.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337   -1.8118   -2.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0166   -1.3327   -0.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592   -2.0079    0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522    0.2370    1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9232   -0.1067    1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2503    1.1003   -0.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723    2.1364    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3323    3.2968    0.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3462    2.8592    0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205    0.4325   -1.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0428    1.7568   -1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3220    0.1137   -1.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372    0.8280    1.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 17  6  1  0
 15  8  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
M  END

  Mrv0541 05061308482D          

 17 19  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830    0.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    0.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2380    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    2.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  9  1  2  0  0  0  0
  9  5  1  0  0  0  0
 10  2  2  0  0  0  0
 11  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 15  3  1  0  0  0  0
 15  6  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 16 14  2  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035934

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCCC(=C)C1CC1C(C2)OC(=O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3

> <INCHI_KEY>
CVUANYCQTOGILD-UHFFFAOYSA-N

> <FORMULA>
C15H20O2

> <MOLECULAR_WEIGHT>
232.3181

> <EXACT_MASS>
232.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.456967674758026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8a-methyl-3,5-dimethylidene-dodecahydronaphtho[2,3-b]furan-2-one

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
3.357975322

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.864710029813113

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
66.1974

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0035934
     RDKit          3D
Isoalantolactone
 37 39  0  0  0  0  0  0  0  0999 V2000
    3.7894    1.3330   -0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609    0.4017    0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5640   -0.7993    0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7789   -1.0922    1.0213 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4334   -1.5404    1.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4080   -1.1772    0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0254   -1.3897    0.8658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9071   -0.9610   -0.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7592   -1.9676   -1.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2986   -1.1006    0.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8370    0.0492    0.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7358    1.3066    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2560    1.4957   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6947    2.5794    0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5817    0.3939   -0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537    0.7096   -0.9245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6070    0.3501    0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8729    1.2799   -0.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3407    2.1953   -0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6535   -1.5511   -0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2107   -0.7029    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2278   -2.4361    1.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9373   -2.9975   -0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1700   -1.8804   -1.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337   -1.8118   -2.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0166   -1.3327   -0.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592   -2.0079    0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522    0.2370    1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9232   -0.1067    1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2503    1.1003   -0.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723    2.1364    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3323    3.2968    0.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3462    2.8592    0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205    0.4325   -1.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0428    1.7568   -1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3220    0.1137   -1.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372    0.8280    1.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 17  6  1  0
 15  8  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.942   0.369   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.466   1.834   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.371   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.911   3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.466   4.326   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   15                                                            
CONECT    4    5    6                                                       
CONECT    5    4    9                                                       
CONECT    6    4   15                                                       
CONECT    7   11   12                                                       
CONECT    8   13   15                                                       
CONECT    9    1    5   12                                                  
CONECT   10    2   11   14                                                  
CONECT   11    7   10   13                                                  
CONECT   12    7    9   15                                                  
CONECT   13    8   11   17                                                  
CONECT   14   10   16   17                                                  
CONECT   15    3    6    8   12                                             
CONECT   16   14                                                            
CONECT   17   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0035934
HETATM    1  C1  UNL     1       3.789   1.333  -0.356  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.061   0.402   0.215  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.564  -0.799   0.869  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.779  -1.092   1.021  1.00  0.00           O  
HETATM    5  O2  UNL     1       2.433  -1.540   1.280  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.408  -1.177   0.426  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.025  -1.390   0.866  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.907  -0.961  -0.272  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.759  -1.968  -1.396  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.299  -1.101   0.240  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.837   0.049   0.995  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.736   1.307   0.121  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.256   1.496  -0.074  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.695   2.579   0.403  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.582   0.394  -0.806  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.854   0.710  -0.924  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.607   0.350   0.329  1.00  0.00           C  
HETATM   18  H1  UNL     1       4.873   1.280  -0.389  1.00  0.00           H  
HETATM   19  H2  UNL     1       3.341   2.195  -0.820  1.00  0.00           H  
HETATM   20  H3  UNL     1       1.653  -1.551  -0.587  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.211  -0.703   1.707  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.228  -2.436   1.110  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.937  -2.997  -0.971  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.170  -1.880  -1.949  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.634  -1.812  -2.092  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.017  -1.333  -0.594  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.359  -2.008   0.906  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.352   0.237   1.968  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.923  -0.107   1.152  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.250   1.100  -0.823  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.172   2.136   0.695  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.332   3.297   0.921  1.00  0.00           H  
HETATM   33  H16 UNL     1       0.346   2.859   0.347  1.00  0.00           H  
HETATM   34  H17 UNL     1      -1.020   0.433  -1.850  1.00  0.00           H  
HETATM   35  H18 UNL     1       1.043   1.757  -1.170  1.00  0.00           H  
HETATM   36  H19 UNL     1       1.322   0.114  -1.738  1.00  0.00           H  
HETATM   37  H20 UNL     1       1.237   0.828   1.241  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3   17
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   17   20
CONECT    7    8   21   22
CONECT    8    9   10   15
CONECT    9   23   24   25
CONECT   10   11   26   27
CONECT   11   12   28   29
CONECT   12   13   30   31
CONECT   13   14   14   15
CONECT   14   32   33
CONECT   15   16   34
CONECT   16   17   35   36
CONECT   17   37
END

HMDB0035934
     RDKit          3D
Isoalantolactone
 37 39  0  0  0  0  0  0  0  0999 V2000
    3.7894    1.3330   -0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609    0.4017    0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5640   -0.7993    0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7789   -1.0922    1.0213 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4334   -1.5404    1.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4080   -1.1772    0.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0254   -1.3897    0.8658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9071   -0.9610   -0.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7592   -1.9676   -1.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2986   -1.1006    0.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8370    0.0492    0.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7358    1.3066    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2560    1.4957   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6947    2.5794    0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5817    0.3939   -0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537    0.7096   -0.9245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6070    0.3501    0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8729    1.2799   -0.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3407    2.1953   -0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6535   -1.5511   -0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2107   -0.7029    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2278   -2.4361    1.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9373   -2.9975   -0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1700   -1.8804   -1.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337   -1.8118   -2.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0166   -1.3327   -0.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592   -2.0079    0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522    0.2370    1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9232   -0.1067    1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2503    1.1003   -0.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723    2.1364    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3323    3.2968    0.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3462    2.8592    0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205    0.4325   -1.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0428    1.7568   -1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3220    0.1137   -1.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372    0.8280    1.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 17  6  1  0
 15  8  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isohelenin	HMDB

Chemical Formula

C₁₅H₂₀O₂

Average Molecular Weight

232.3181

Monoisotopic Molecular Weight

232.146329884

IUPAC Name

8a-methyl-3,5-dimethylidene-dodecahydronaphtho[2,3-b]furan-2-one

Traditional Name

8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one

CAS Registry Number

470-17-7

SMILES

CC12CCCC(=C)C1CC1C(C2)OC(=O)C1=C

InChI Identifier

InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3

InChI Key

CVUANYCQTOGILD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035934)

Source

Endogenous

Endogenous (HMDB: HMDB0035934)

Plant

Plant (HMDB: HMDB0035934)

Animal

Animal (HMDB: HMDB0035934)

Exogenous

Food

Food (HMDB: HMDB0035934)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0035934)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035934)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035934)

Lipid metabolism pathway (HMDB: HMDB0035934)

Cellular process

Cell signaling (HMDB: HMDB0035934)

Biochemical process

Lipid transport (HMDB: HMDB0035934)

Role

Biological role

Energy source (HMDB: HMDB0035934)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035934)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	115 °C	Not Available
Boiling Point	364.00 to 365.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	35.49 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.42	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.063 g/L	ALOGPS
logP	3.15	ALOGPS
logP	3.36	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.2 m³·mol⁻¹	ChemAxon
Polarizability	26.46 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
DarkChem	[M+H]+	152.95	31661259
DarkChem	[M-H]-	150.138	31661259
DeepCCS	[M-2H]-	188.29	30932474
DeepCCS	[M+Na]+	163.774	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	151.8	32859911
AllCCS	[M+NH4]+	159.2	32859911
AllCCS	[M+Na]+	160.2	32859911
AllCCS	[M-H]-	161.3	32859911
AllCCS	[M+Na-2H]-	161.3	32859911
AllCCS	[M+HCOO]-	161.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoalantolactone	CC12CCCC(=C)C1CC1C(C2)OC(=O)C1=C	2567.2	Standard polar	33892256
Isoalantolactone	CC12CCCC(=C)C1CC1C(C2)OC(=O)C1=C	1892.0	Standard non polar	33892256
Isoalantolactone	CC12CCCC(=C)C1CC1C(C2)OC(=O)C1=C	2007.8	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 - Isoalantolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1920000000-9b5d82ce2d414b53a21d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoalantolactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoalantolactone 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 - Isoalantolactone 10V, Positive-QTOF	splash10-001i-0490000000-dfc1007aa212c5c01c72	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 20V, Positive-QTOF	splash10-053i-1930000000-599c13fb890140ea2cc4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 40V, Positive-QTOF	splash10-0gbc-9710000000-3bea9f3ad650c75df3de	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 10V, Positive-QTOF	splash10-001i-0490000000-dfc1007aa212c5c01c72	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 20V, Positive-QTOF	splash10-053i-1930000000-599c13fb890140ea2cc4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 40V, Positive-QTOF	splash10-0gbc-9710000000-3bea9f3ad650c75df3de	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 10V, Negative-QTOF	splash10-001i-0290000000-241b9389e5e00f1c05c6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 20V, Negative-QTOF	splash10-001r-0790000000-2c20c4eb68d8cb0a9699	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 40V, Negative-QTOF	splash10-0079-2900000000-edc4a447c8f51da83d4b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 10V, Negative-QTOF	splash10-001i-0290000000-241b9389e5e00f1c05c6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 20V, Negative-QTOF	splash10-001r-0790000000-2c20c4eb68d8cb0a9699	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 40V, Negative-QTOF	splash10-0079-2900000000-edc4a447c8f51da83d4b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 10V, Negative-QTOF	splash10-001i-0090000000-403b175a8d75af9b9dc4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 20V, Negative-QTOF	splash10-001i-0390000000-64e109a295e3ed5cb769	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 40V, Negative-QTOF	splash10-05di-1920000000-c4ee629fe827100b9751	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 10V, Positive-QTOF	splash10-001i-0090000000-9ff721d02a369a8ce528	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 20V, Positive-QTOF	splash10-053r-0950000000-b6a83084d417e599f13d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoalantolactone 40V, Positive-QTOF	splash10-0aou-9700000000-44f32b7a10604426618a	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Helenin

METLIN ID

Not Available

PubChem Compound

605266

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1065851

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Isoalantolactone (HMDB0035934)

MOL for HMDB0035934 (Isoalantolactone)

3D MOL for HMDB0035934 (Isoalantolactone)

3D SDF for HMDB0035934 (Isoalantolactone)

3D-SDF for HMDB0035934 (Isoalantolactone)

PDB for HMDB0035934 (Isoalantolactone)

3D PDB for HMDB0035934 (Isoalantolactone)

SMILES for HMDB0035934 (Isoalantolactone)

INCHI for HMDB0035934 (Isoalantolactone)

Structure for HMDB0035934 (Isoalantolactone)

3D Structure for HMDB0035934 (Isoalantolactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra