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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 02:09:21 UTC

Update Date

2021-09-26 22:59:09 UTC

HMDB ID

HMDB0248711

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Atractylon

Description

3,8a-dimethyl-5-methylidene-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. 3,8a-dimethyl-5-methylidene-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Atractylon is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Atractylon is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0248711
     RDKit          3D
Atractylon
 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.7938    2.6605   -0.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2949    1.6882   -0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7184    1.6573    0.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9216    0.4534    1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4355   -0.7901    0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0140   -0.7453    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9633   -1.1110   -1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2488   -1.7800    0.8799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2218   -1.6047    0.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2204   -2.4273    0.9909 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3633   -1.8776    0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1511   -0.6040    0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691    0.3830   -0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7803   -0.4466    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877    0.7379   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4135    0.5928    0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2261    2.7525   -1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4649    3.4722   -1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0172    2.5775    0.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3271    1.4643   -0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0139    0.3329    1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4702    0.6120    2.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362   -1.6422    1.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342   -0.9767   -0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4323   -2.1145   -1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5750   -0.4225   -1.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0635   -1.1956   -1.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5692   -2.8106    0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047   -1.6476    1.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3527   -2.2993    0.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9459    0.5118    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6896    1.3550   -0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6811    0.0461   -1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9916    0.8745   -1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4200    1.6528    0.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3153    0.6707    1.4972 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
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16  2  1  0
 16  6  1  0
 14  9  2  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
M  END


  Mrv1533004241521142D          

 16 18  0  0  0  0            999 V2000
    3.8974   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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    0.0000    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
    0.7145    1.2375    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248711

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=COC2=C1CC1C(=C)CCCC1(C)C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O/c1-10-5-4-6-15(3)8-14-12(7-13(10)15)11(2)9-16-14/h9,13H,1,4-8H2,2-3H3

> <INCHI_KEY>
TYPSVDGIQAOBAD-UHFFFAOYSA-N

> <FORMULA>
C15H20O

> <MOLECULAR_WEIGHT>
216.324

> <EXACT_MASS>
216.151415264

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.65739865742029

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,8a-dimethyl-5-methylidene-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
4.082130620666666

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.642141440291068

> <JCHEM_POLAR_SURFACE_AREA>
13.14

> <JCHEM_REFRACTIVITY>
66.4245

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,8a-dimethyl-5-methylidene-4H,4aH,6H,7H,8H,9H-naphtho[2,3-b]furan

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0248711
     RDKit          3D
Atractylon
 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.7938    2.6605   -0.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2949    1.6882   -0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7184    1.6573    0.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9216    0.4534    1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4355   -0.7901    0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0140   -0.7453    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9633   -1.1110   -1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2488   -1.7800    0.8799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2218   -1.6047    0.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2204   -2.4273    0.9909 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3633   -1.8776    0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1511   -0.6040    0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691    0.3830   -0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7803   -0.4466    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877    0.7379   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4135    0.5928    0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2261    2.7525   -1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4649    3.4722   -1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0172    2.5775    0.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3271    1.4643   -0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0139    0.3329    1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4702    0.6120    2.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362   -1.6422    1.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342   -0.9767   -0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4323   -2.1145   -1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5750   -0.4225   -1.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0635   -1.1956   -1.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5692   -2.8106    0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047   -1.6476    1.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3527   -2.2993    0.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9459    0.5118    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6896    1.3550   -0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6811    0.0461   -1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9916    0.8745   -1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4200    1.6528    0.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3153    0.6707    1.4972 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
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16  2  1  0
 16  6  1  0
 14  9  2  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       7.275  -1.941   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.799  -0.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.705   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.799   2.016   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8   15   16                                             
CONECT   15   14    5                                                       
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0248711
HETATM    1  C1  UNL     1      -0.794   2.661  -0.799  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.295   1.688  -0.069  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.718   1.657   0.321  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.922   0.453   1.236  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.436  -0.790   0.545  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.014  -0.745   0.099  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.963  -1.111  -1.367  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.249  -1.780   0.880  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.222  -1.605   0.729  1.00  0.00           C  
HETATM   10  O1  UNL     1       2.220  -2.427   0.991  1.00  0.00           O  
HETATM   11  C10 UNL     1       3.363  -1.878   0.714  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.151  -0.604   0.233  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.169   0.383  -0.206  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.780  -0.447   0.250  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.988   0.738  -0.165  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.414   0.593   0.378  1.00  0.00           C  
HETATM   17  H1  UNL     1       0.226   2.753  -1.122  1.00  0.00           H  
HETATM   18  H2  UNL     1      -1.465   3.472  -1.125  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.017   2.578   0.860  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.327   1.464  -0.582  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.014   0.333   1.392  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.470   0.612   2.227  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.636  -1.642   1.258  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.134  -0.977  -0.307  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.432  -2.114  -1.458  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.575  -0.422  -1.975  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.064  -1.196  -1.758  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.569  -2.811   0.601  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.505  -1.648   1.952  1.00  0.00           H  
HETATM   30  H14 UNL     1       4.353  -2.299   0.821  1.00  0.00           H  
HETATM   31  H15 UNL     1       4.946   0.512   0.597  1.00  0.00           H  
HETATM   32  H16 UNL     1       3.690   1.355  -0.411  1.00  0.00           H  
HETATM   33  H17 UNL     1       4.681   0.046  -1.123  1.00  0.00           H  
HETATM   34  H18 UNL     1       0.992   0.875  -1.257  1.00  0.00           H  
HETATM   35  H19 UNL     1       1.420   1.653   0.289  1.00  0.00           H  
HETATM   36  H20 UNL     1      -0.315   0.671   1.497  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3   16
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7    8   16
CONECT    7   25   26   27
CONECT    8    9   28   29
CONECT    9   10   14   14
CONECT   10   11
CONECT   11   12   12   30
CONECT   12   13   14
CONECT   13   31   32   33
CONECT   14   15
CONECT   15   16   34   35
CONECT   16   36
END

HMDB0248711
     RDKit          3D
Atractylon
 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.7938    2.6605   -0.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2949    1.6882   -0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7184    1.6573    0.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9216    0.4534    1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4355   -0.7901    0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0140   -0.7453    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9633   -1.1110   -1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2488   -1.7800    0.8799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2218   -1.6047    0.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2204   -2.4273    0.9909 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3633   -1.8776    0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1511   -0.6040    0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691    0.3830   -0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7803   -0.4466    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877    0.7379   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4135    0.5928    0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2261    2.7525   -1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4649    3.4722   -1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0172    2.5775    0.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3271    1.4643   -0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0139    0.3329    1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4702    0.6120    2.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362   -1.6422    1.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342   -0.9767   -0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4323   -2.1145   -1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5750   -0.4225   -1.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0635   -1.1956   -1.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5692   -2.8106    0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047   -1.6476    1.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3527   -2.2993    0.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9459    0.5118    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6896    1.3550   -0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6811    0.0461   -1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9916    0.8745   -1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4200    1.6528    0.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3153    0.6707    1.4972 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
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16  2  1  0
 16  6  1  0
 14  9  2  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O

Average Molecular Weight

216.324

Monoisotopic Molecular Weight

216.151415264

IUPAC Name

3,8a-dimethyl-5-methylidene-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan

Traditional Name

3,8a-dimethyl-5-methylidene-4H,4aH,6H,7H,8H,9H-naphtho[2,3-b]furan

CAS Registry Number

Not Available

SMILES

CC1=COC2=C1CC1C(=C)CCCC1(C)C2

InChI Identifier

InChI=1S/C15H20O/c1-10-5-4-6-15(3)8-14-12(7-13(10)15)11(2)9-16-14/h9,13H,1,4-8H2,2-3H3

InChI Key

TYPSVDGIQAOBAD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.21	ALOGPS
logP	4.08	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	13.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.42 m³·mol⁻¹	ChemAxon
Polarizability	25.66 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
DeepCCS	[M+H]+	156.759	30932474
DeepCCS	[M-H]-	154.401	30932474
DeepCCS	[M-2H]-	188.525	30932474
DeepCCS	[M+Na]+	163.445	30932474
AllCCS	[M+H]+	151.6	32859911
AllCCS	[M+H-H2O]+	147.7	32859911
AllCCS	[M+NH4]+	155.2	32859911
AllCCS	[M+Na]+	156.3	32859911
AllCCS	[M-H]-	157.2	32859911
AllCCS	[M+Na-2H]-	157.2	32859911
AllCCS	[M+HCOO]-	157.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Atractylon	CC1=COC2=C1CC1C(=C)CCCC1(C)C2	2128.8	Standard polar	33892256
Atractylon	CC1=COC2=C1CC1C(=C)CCCC1(C)C2	1615.2	Standard non polar	33892256
Atractylon	CC1=COC2=C1CC1C(=C)CCCC1(C)C2	1651.0	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 - Atractylon GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uki-1920000000-212ede3aad20b860775f	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Atractylon 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 - Atractylon 10V, Positive-QTOF	splash10-014i-0090000000-244efbc802751a164afa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atractylon 20V, Positive-QTOF	splash10-014i-2890000000-c309a5fe6ff701fb9dbc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atractylon 40V, Positive-QTOF	splash10-06fr-5900000000-b437223bd6104e132328	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atractylon 10V, Negative-QTOF	splash10-014i-0090000000-93c59166c81b3b7c46b8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atractylon 20V, Negative-QTOF	splash10-014i-0090000000-93c59166c81b3b7c46b8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atractylon 40V, Negative-QTOF	splash10-014i-2930000000-817cbca11e7b4b8b903b	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321065

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Atractylon (HMDB0248711)

MOL for HMDB0248711 (Atractylon)

3D MOL for HMDB0248711 (Atractylon)

3D SDF for HMDB0248711 (Atractylon)

3D-SDF for HMDB0248711 (Atractylon)

PDB for HMDB0248711 (Atractylon)

3D PDB for HMDB0248711 (Atractylon)

SMILES for HMDB0248711 (Atractylon)

INCHI for HMDB0248711 (Atractylon)

Structure for HMDB0248711 (Atractylon)

3D Structure for HMDB0248711 (Atractylon)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra