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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:58:58 UTC

Update Date

2022-03-07 02:54:42 UTC

HMDB ID

HMDB0035935

Secondary Accession Numbers

HMDB35935

Metabolite Identification

Common Name

Dihydroisoalantolactone

Description

Dihydroisoalantolactone 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 Dihydroisoalantolactone.

Structure

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

HMDB0035935
     RDKit          3D
Dihydroisoalantolactone
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.0120    2.9327   -0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3990    1.7401   -0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7739    1.5880    0.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8847    0.2382    0.9639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086   -0.7809   -0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0001   -0.7360   -0.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8304   -1.3536   -1.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4078   -1.7097    0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0608   -1.6168    0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958   -2.3546   -0.1339 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9382   -1.6404   -0.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0283   -2.1737   -0.7575 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579   -0.2093   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7833    0.6287    0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6207   -0.2435    0.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5896    0.8491    0.7983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4204    0.6188   -0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6905    3.7701   -0.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152    3.0910   -1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4520    1.5802   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1094    2.4210    0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8866    0.0390    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557    0.2154    1.7916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8075   -1.7777    0.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0702   -0.4944   -1.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0693   -2.4134   -1.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1572   -1.0666   -2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5727   -0.8056   -2.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6403   -2.7351    0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9433   -1.6211    1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3046   -2.1043    1.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0723    0.1169   -1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3701    0.7323   -0.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4161    1.6045    0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3094    0.1176    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436   -0.0467    1.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1284    1.0113    1.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235    1.7907    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1499    0.7977   -1.2625 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 17  6  1  0
 15  9  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  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  1  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>
HMDB0035935

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2CC3C(=C)CCCC3(C)CC2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h10-13H,1,4-8H2,2-3H3

> <INCHI_KEY>
YYJRTJYCOMIDIC-UHFFFAOYSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.160130452874032

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.45

> <JCHEM_LOGP>
3.2163206176666668

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.082164813493459

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
66.394

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,8a-dimethyl-5-methylidene-octahydro-3H-naphtho[2,3-b]furan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0035935
     RDKit          3D
Dihydroisoalantolactone
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.0120    2.9327   -0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3990    1.7401   -0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7739    1.5880    0.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8847    0.2382    0.9639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086   -0.7809   -0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0001   -0.7360   -0.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8304   -1.3536   -1.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4078   -1.7097    0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0608   -1.6168    0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958   -2.3546   -0.1339 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9382   -1.6404   -0.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0283   -2.1737   -0.7575 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579   -0.2093   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7833    0.6287    0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6207   -0.2435    0.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5896    0.8491    0.7983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4204    0.6188   -0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6905    3.7701   -0.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152    3.0910   -1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4520    1.5802   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1094    2.4210    0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8866    0.0390    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557    0.2154    1.7916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8075   -1.7777    0.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0702   -0.4944   -1.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0693   -2.4134   -1.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1572   -1.0666   -2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5727   -0.8056   -2.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6403   -2.7351    0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9433   -1.6211    1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3046   -2.1043    1.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0723    0.1169   -1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3701    0.7323   -0.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4161    1.6045    0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3094    0.1176    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436   -0.0467    1.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1284    1.0113    1.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235    1.7907    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1499    0.7977   -1.2625 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 17  6  1  0
 15  9  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  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    HMDB0035935
HETATM    1  C1  UNL     1      -1.012   2.933  -0.625  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.399   1.740  -0.218  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.774   1.588   0.296  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.885   0.238   0.964  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.509  -0.781  -0.099  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.000  -0.736  -0.333  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.830  -1.354  -1.730  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.408  -1.710   0.644  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.061  -1.617   0.825  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.796  -2.355  -0.134  1.00  0.00           O  
HETATM   11  C10 UNL     1       2.938  -1.640  -0.445  1.00  0.00           C  
HETATM   12  O2  UNL     1       4.028  -2.174  -0.758  1.00  0.00           O  
HETATM   13  C11 UNL     1       2.558  -0.209  -0.320  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.783   0.629   0.012  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.621  -0.243   0.868  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.590   0.849   0.798  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.420   0.619  -0.302  1.00  0.00           C  
HETATM   18  H1  UNL     1      -1.691   3.770  -0.580  1.00  0.00           H  
HETATM   19  H2  UNL     1      -0.015   3.091  -1.009  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.452   1.580  -0.601  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.109   2.421   0.923  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.887   0.039   1.368  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.156   0.215   1.792  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.807  -1.778   0.286  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.070  -0.494  -1.011  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.069  -2.413  -1.746  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.157  -1.067  -2.080  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.573  -0.806  -2.369  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.640  -2.735   0.271  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.943  -1.621   1.621  1.00  0.00           H  
HETATM   31  H14 UNL     1       1.305  -2.104   1.817  1.00  0.00           H  
HETATM   32  H15 UNL     1       2.072   0.117  -1.249  1.00  0.00           H  
HETATM   33  H16 UNL     1       4.370   0.732  -0.918  1.00  0.00           H  
HETATM   34  H17 UNL     1       3.416   1.604   0.376  1.00  0.00           H  
HETATM   35  H18 UNL     1       4.309   0.118   0.827  1.00  0.00           H  
HETATM   36  H19 UNL     1       2.244  -0.047   1.768  1.00  0.00           H  
HETATM   37  H20 UNL     1       0.128   1.011   1.786  1.00  0.00           H  
HETATM   38  H21 UNL     1       1.124   1.791   0.546  1.00  0.00           H  
HETATM   39  H22 UNL     1       0.150   0.798  -1.262  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3   17
CONECT    3    4   20   21
CONECT    4    5   22   23
CONECT    5    6   24   25
CONECT    6    7    8   17
CONECT    7   26   27   28
CONECT    8    9   29   30
CONECT    9   10   15   31
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   15   32
CONECT   14   33   34   35
CONECT   15   16   36
CONECT   16   17   37   38
CONECT   17   39
END

HMDB0035935
     RDKit          3D
Dihydroisoalantolactone
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.0120    2.9327   -0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3990    1.7401   -0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7739    1.5880    0.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8847    0.2382    0.9639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086   -0.7809   -0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0001   -0.7360   -0.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8304   -1.3536   -1.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4078   -1.7097    0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0608   -1.6168    0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958   -2.3546   -0.1339 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9382   -1.6404   -0.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0283   -2.1737   -0.7575 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579   -0.2093   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7833    0.6287    0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6207   -0.2435    0.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5896    0.8491    0.7983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4204    0.6188   -0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6905    3.7701   -0.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152    3.0910   -1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4520    1.5802   -0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1094    2.4210    0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8866    0.0390    1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557    0.2154    1.7916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8075   -1.7777    0.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0702   -0.4944   -1.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0693   -2.4134   -1.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1572   -1.0666   -2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5727   -0.8056   -2.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6403   -2.7351    0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9433   -1.6211    1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3046   -2.1043    1.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0723    0.1169   -1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3701    0.7323   -0.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4161    1.6045    0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3094    0.1176    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436   -0.0467    1.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1284    1.0113    1.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235    1.7907    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1499    0.7977   -1.2625 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 17  6  1  0
 15  9  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 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
4(15)-Eudesmen-12,8b-olide	HMDB

Chemical Formula

C₁₅H₂₂O₂

Average Molecular Weight

234.334

Monoisotopic Molecular Weight

234.161979948

IUPAC Name

3,8a-dimethyl-5-methylidene-dodecahydronaphtho[2,3-b]furan-2-one

Traditional Name

3,8a-dimethyl-5-methylidene-octahydro-3H-naphtho[2,3-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CC1C2CC3C(=C)CCCC3(C)CC2OC1=O

InChI Identifier

InChI=1S/C15H22O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h10-13H,1,4-8H2,2-3H3

InChI Key

YYJRTJYCOMIDIC-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
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0035935)
Cell membrane (HMDB: HMDB0035935)

Cellular substructure

Extracellular (HMDB: HMDB0035935)
Membrane (HMDB: HMDB0035935)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035935)

Source

Endogenous

Endogenous (HMDB: HMDB0035935)

Plant

Plant (HMDB: HMDB0035935)

Animal

Animal (HMDB: HMDB0035935)

Exogenous

Food

Food (HMDB: HMDB0035935)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0035935)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0035935)

Cellular process

Cell signaling (HMDB: HMDB0035935)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0035935)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035935)

Nutrient

Nutrient (HMDB: HMDB0035935)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035935)

Emulsifier (HMDB: HMDB0035935)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	172 - 173 °C	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
Water Solubility	0.043 g/L	ALOGPS
logP	3.45	ALOGPS
logP	3.22	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-7.1	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	66.39 m³·mol⁻¹	ChemAxon
Polarizability	27.16 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]+	156.056	31661259
DarkChem	[M-H]-	152.54	31661259
DeepCCS	[M+H]+	151.364	30932474
DeepCCS	[M-H]-	148.297	30932474
DeepCCS	[M-2H]-	184.734	30932474
DeepCCS	[M+Na]+	160.272	30932474
AllCCS	[M+H]+	156.4	32859911
AllCCS	[M+H-H2O]+	152.6	32859911
AllCCS	[M+NH4]+	159.9	32859911
AllCCS	[M+Na]+	160.9	32859911
AllCCS	[M-H]-	163.0	32859911
AllCCS	[M+Na-2H]-	163.1	32859911
AllCCS	[M+HCOO]-	163.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydroisoalantolactone	CC1C2CC3C(=C)CCCC3(C)CC2OC1=O	2575.9	Standard polar	33892256
Dihydroisoalantolactone	CC1C2CC3C(=C)CCCC3(C)CC2OC1=O	1945.9	Standard non polar	33892256
Dihydroisoalantolactone	CC1C2CC3C(=C)CCCC3(C)CC2OC1=O	1997.8	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 - Dihydroisoalantolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i0-1920000000-4a428ecac726eec138ca	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroisoalantolactone 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 - Dihydroisoalantolactone 10V, Positive-QTOF	splash10-000i-0490000000-918af1857b0ee7a0b288	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisoalantolactone 20V, Positive-QTOF	splash10-000l-2930000000-ee105d5d6bc2e86c6825	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisoalantolactone 40V, Positive-QTOF	splash10-0gbc-9510000000-24fbfe06bf8d8db0c862	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisoalantolactone 10V, Negative-QTOF	splash10-001i-0390000000-88142d5b3c1724a365ea	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisoalantolactone 20V, Negative-QTOF	splash10-001r-1790000000-306a84470ba7dddb2bf7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisoalantolactone 40V, Negative-QTOF	splash10-0079-2900000000-3927d5f43bb3f7b85f86	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisoalantolactone 10V, Negative-QTOF	splash10-001i-0090000000-9087f47ed0ae51229a17	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisoalantolactone 20V, Negative-QTOF	splash10-000i-0900000000-8e3065cda4a27c948e14	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisoalantolactone 40V, Negative-QTOF	splash10-0a4r-3930000000-9c2619c69ff9c8beb25a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisoalantolactone 10V, Positive-QTOF	splash10-000i-0190000000-fa50a39e29274a23a704	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisoalantolactone 20V, Positive-QTOF	splash10-000i-0950000000-79c1c02723d98b246a24	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroisoalantolactone 40V, Positive-QTOF	splash10-0a4i-3900000000-df6ed91897ee591df2ca	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB014738

KNApSAcK ID

C00022678

Chemspider ID

4280210

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5104810

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

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 Dihydroisoalantolactone (HMDB0035935)

MOL for HMDB0035935 (Dihydroisoalantolactone)

3D MOL for HMDB0035935 (Dihydroisoalantolactone)

3D SDF for HMDB0035935 (Dihydroisoalantolactone)

3D-SDF for HMDB0035935 (Dihydroisoalantolactone)

PDB for HMDB0035935 (Dihydroisoalantolactone)

3D PDB for HMDB0035935 (Dihydroisoalantolactone)

SMILES for HMDB0035935 (Dihydroisoalantolactone)

INCHI for HMDB0035935 (Dihydroisoalantolactone)

Structure for HMDB0035935 (Dihydroisoalantolactone)

3D Structure for HMDB0035935 (Dihydroisoalantolactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra