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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:57:14 UTC

Update Date

2022-03-07 02:54:41 UTC

HMDB ID

HMDB0035906

Secondary Accession Numbers

HMDB35906

Metabolite Identification

Common Name

Alantolactone

Description

Alantolactone, also known as helenin, 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 very few articles have been published on Alantolactone.

Structure

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

HMDB0035906
     RDKit          3D
Alantolactone
 37 39  0  0  0  0  0  0  0  0999 V2000
    3.0138    2.0727   -0.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9135    0.7556   -0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7921   -0.1689    0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8107    0.1051    0.9350 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2900   -1.4452   -0.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9274   -1.3321   -0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1014   -1.2029    0.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -0.8660    0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9824   -2.1247   -0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976   -0.5864    1.8382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6585    0.7671    1.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977    1.0598    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7325    1.0266   -0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6331    0.5511   -1.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4803    0.2649   -0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5532    0.6040   -1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8686   -0.0304   -1.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3256    2.6969   -1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7835    2.5583    0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7378   -2.2097   -1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5120   -0.3704    1.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1097   -2.1066    1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3971   -3.0331    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0076   -2.2832    0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110   -2.0773   -1.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2219   -0.5829    2.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6939   -1.4083    2.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2936    0.7958    2.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8690    1.5404    1.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9843    2.0477    0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3325    0.3190    0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4801    2.0989   -0.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2690    1.3834   -2.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0896    0.1628   -2.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3486   -0.2195   -1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4286    1.4525   -1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1698   -0.2150   -2.2657 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  1  0
 13 15  1  0
 15 16  2  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
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
M  END


  Mrv0541 05061308472D          

 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  1  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  2  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>
HMDB0035906

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCCC2(C)CC3OC(=O)C(=C)C3C=C12

> <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/h7,9,11,13H,2,4-6,8H2,1,3H3

> <INCHI_KEY>
PXOYOCNNSUAQNS-UHFFFAOYSA-N

> <FORMULA>
C15H20O2

> <MOLECULAR_WEIGHT>
232.3181

> <EXACT_MASS>
232.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.251606837825648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,8a-dimethyl-3-methylidene-2H,3H,3aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
3.3000416516666675

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.875766859959126

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
67.26989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
alantolactone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0035906
     RDKit          3D
Alantolactone
 37 39  0  0  0  0  0  0  0  0999 V2000
    3.0138    2.0727   -0.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9135    0.7556   -0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7921   -0.1689    0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8107    0.1051    0.9350 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2900   -1.4452   -0.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9274   -1.3321   -0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1014   -1.2029    0.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -0.8660    0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9824   -2.1247   -0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976   -0.5864    1.8382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6585    0.7671    1.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977    1.0598    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7325    1.0266   -0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6331    0.5511   -1.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4803    0.2649   -0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5532    0.6040   -1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8686   -0.0304   -1.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3256    2.6969   -1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7835    2.5583    0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7378   -2.2097   -1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5120   -0.3704    1.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1097   -2.1066    1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3971   -3.0331    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0076   -2.2832    0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110   -2.0773   -1.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2219   -0.5829    2.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6939   -1.4083    2.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2936    0.7958    2.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8690    1.5404    1.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9843    2.0477    0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3325    0.3190    0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4801    2.0989   -0.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2690    1.3834   -2.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0896    0.1628   -2.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3486   -0.2195   -1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4286    1.4525   -1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1698   -0.2150   -2.2657 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  1  0
 13 15  1  0
 15 16  2  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
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 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    HMDB0035906
HETATM    1  C1  UNL     1       3.014   2.073  -0.465  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.914   0.756  -0.474  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.792  -0.169   0.231  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.811   0.105   0.935  1.00  0.00           O  
HETATM    5  O2  UNL     1       3.290  -1.445  -0.018  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.927  -1.332  -0.465  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.101  -1.203   0.762  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.357  -0.866   0.496  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.982  -2.125  -0.105  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.998  -0.586   1.838  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.658   0.767   1.898  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.498   1.060   0.686  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.732   1.027  -0.592  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.633   0.551  -1.696  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.480   0.265  -0.455  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.553   0.604  -1.208  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.869  -0.030  -1.219  1.00  0.00           C  
HETATM   18  H1  UNL     1       2.326   2.697  -1.012  1.00  0.00           H  
HETATM   19  H2  UNL     1       3.783   2.558   0.088  1.00  0.00           H  
HETATM   20  H3  UNL     1       1.738  -2.210  -1.081  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.512  -0.370   1.374  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.110  -2.107   1.402  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.397  -3.033   0.147  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.008  -2.283   0.264  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.011  -2.077  -1.213  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.222  -0.583   2.630  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.694  -1.408   2.113  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.294   0.796   2.792  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.869   1.540   1.952  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.984   2.048   0.809  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.333   0.319   0.603  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.480   2.099  -0.857  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.269   1.383  -2.079  1.00  0.00           H  
HETATM   34  H17 UNL     1      -2.090   0.163  -2.574  1.00  0.00           H  
HETATM   35  H18 UNL     1      -3.349  -0.219  -1.335  1.00  0.00           H  
HETATM   36  H19 UNL     1       0.429   1.453  -1.907  1.00  0.00           H  
HETATM   37  H20 UNL     1       2.170  -0.215  -2.266  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   15   32
CONECT   14   33   34   35
CONECT   15   16   16
CONECT   16   17   36
CONECT   17   37
END

HMDB0035906
     RDKit          3D
Alantolactone
 37 39  0  0  0  0  0  0  0  0999 V2000
    3.0138    2.0727   -0.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9135    0.7556   -0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7921   -0.1689    0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8107    0.1051    0.9350 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2900   -1.4452   -0.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9274   -1.3321   -0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1014   -1.2029    0.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -0.8660    0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9824   -2.1247   -0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976   -0.5864    1.8382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6585    0.7671    1.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977    1.0598    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7325    1.0266   -0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6331    0.5511   -1.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4803    0.2649   -0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5532    0.6040   -1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8686   -0.0304   -1.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3256    2.6969   -1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7835    2.5583    0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7378   -2.2097   -1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5120   -0.3704    1.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1097   -2.1066    1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3971   -3.0331    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0076   -2.2832    0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110   -2.0773   -1.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2219   -0.5829    2.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6939   -1.4083    2.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2936    0.7958    2.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8690    1.5404    1.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9843    2.0477    0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3325    0.3190    0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4801    2.0989   -0.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2690    1.3834   -2.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0896    0.1628   -2.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3486   -0.2195   -1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4286    1.4525   -1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1698   -0.2150   -2.2657 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  1  0
 13 15  1  0
 15 16  2  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
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Helenin	MeSH
(+)-Alantolactone	HMDB
Alant camphor	HMDB
Alantic anhydride	HMDB
Elecampane camphor	HMDB
Eupatal	HMDB
Helenine	HMDB
Helenine?	HMDB
Inula camphor	HMDB
Alantolactone	MeSH

Chemical Formula

C₁₅H₂₀O₂

Average Molecular Weight

232.3181

Monoisotopic Molecular Weight

232.146329884

IUPAC Name

5,8a-dimethyl-3-methylidene-2H,3H,3aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

Traditional Name

alantolactone

CAS Registry Number

546-43-0

SMILES

CC1CCCC2(C)CC3OC(=O)C(=C)C3C=C12

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/h7,9,11,13H,2,4-6,8H2,1,3H3

InChI Key

PXOYOCNNSUAQNS-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: HMDB0035906)

Source

Endogenous

Endogenous (HMDB: HMDB0035906)

Plant

Plant (HMDB: HMDB0035906)

Exogenous

Food

Food (HMDB: HMDB0035906)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0035906)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0035906)

Role

Biological role

Energy source (HMDB: HMDB0035906)

Industrial application

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0035906)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035906)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	78 - 80 °C	Not Available
Boiling Point	275.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	38.39 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.38	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.051 g/L	ALOGPS
logP	4.13	ALOGPS
logP	3.3	ChemAxon
logS	-3.7	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	67.27 m³·mol⁻¹	ChemAxon
Polarizability	26.25 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]+	155.053	31661259
DarkChem	[M-H]-	151.399	31661259
DeepCCS	[M-2H]-	193.253	30932474
DeepCCS	[M+Na]+	168.759	30932474
AllCCS	[M+H]+	154.8	32859911
AllCCS	[M+H-H2O]+	151.0	32859911
AllCCS	[M+NH4]+	158.4	32859911
AllCCS	[M+Na]+	159.4	32859911
AllCCS	[M-H]-	161.8	32859911
AllCCS	[M+Na-2H]-	161.8	32859911
AllCCS	[M+HCOO]-	161.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.9 minutes	32390414
Predicted by Siyang on May 30, 2022	18.5111 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.38 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2633.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	602.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	227.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	341.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	422.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	732.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	833.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	107.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1577.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	497.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1610.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	556.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	473.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	540.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	596.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	17.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alantolactone	CC1CCCC2(C)CC3OC(=O)C(=C)C3C=C12	2610.9	Standard polar	33892256
Alantolactone	CC1CCCC2(C)CC3OC(=O)C(=C)C3C=C12	1884.4	Standard non polar	33892256
Alantolactone	CC1CCCC2(C)CC3OC(=O)C(=C)C3C=C12	1939.3	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 - Alantolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xr-0930000000-9c2fa7000869a20985d7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alantolactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alantolactone 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alantolactone LC-ESI-qTof , Positive-QTOF	splash10-000i-0439400000-eb9ea339fb74ab288f9b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alantolactone , positive-QTOF	splash10-02ar-2930000000-44fd51118e0718475b0b	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alantolactone 10V, Positive-QTOF	splash10-001i-0490000000-de88d5abcd6d4795f13d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alantolactone 20V, Positive-QTOF	splash10-0540-2940000000-cc17f650474d33cf26a6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alantolactone 40V, Positive-QTOF	splash10-0gbc-9710000000-7737cb9f7698b0917b29	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alantolactone 10V, Negative-QTOF	splash10-001i-0290000000-5bca3a3797668e55d19d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alantolactone 20V, Negative-QTOF	splash10-001r-0790000000-64e9dc3bf0d08f1b2bd5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alantolactone 40V, Negative-QTOF	splash10-000i-2900000000-e2d74e69a6dee1e7f9fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alantolactone 10V, Negative-QTOF	splash10-001i-0090000000-403b175a8d75af9b9dc4	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alantolactone 20V, Negative-QTOF	splash10-001i-0190000000-78a67aabbf310b40de68	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alantolactone 40V, Negative-QTOF	splash10-004i-3920000000-f0e8c7dcd679cd8da0e1	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alantolactone 10V, Positive-QTOF	splash10-001i-0290000000-61ef1ae8641b81bfd99a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alantolactone 20V, Positive-QTOF	splash10-00e9-0930000000-e322ff66f50c85690a16	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alantolactone 40V, Positive-QTOF	splash10-0a4i-0900000000-842e9eb5b0f85c0cdc6f	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Helenin

METLIN ID

Not Available

PubChem Compound

327378

PDB ID

Not Available

ChEBI ID

2540

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1389041

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Shi Y, Bao YL, Wu Y, Yu CL, Huang YX, Sun Y, Zheng LH, Li YX: Alantolactone inhibits cell proliferation by interrupting the interaction between Cripto-1 and activin receptor type II A in activin signaling pathway. J Biomol Screen. 2011 Jun;16(5):525-35. doi: 10.1177/1087057111398486. Epub 2011 Mar 4. [PubMed:21378277 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Alantolactone (HMDB0035906)

MOL for HMDB0035906 (Alantolactone)

3D MOL for HMDB0035906 (Alantolactone)

3D SDF for HMDB0035906 (Alantolactone)

3D-SDF for HMDB0035906 (Alantolactone)

PDB for HMDB0035906 (Alantolactone)

3D PDB for HMDB0035906 (Alantolactone)

SMILES for HMDB0035906 (Alantolactone)

INCHI for HMDB0035906 (Alantolactone)

Structure for HMDB0035906 (Alantolactone)

3D Structure for HMDB0035906 (Alantolactone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra