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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 02:09:06 UTC

Update Date

2021-09-26 22:59:09 UTC

HMDB ID

HMDB0248707

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Atractylenolide II

Description

3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one 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. 3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one 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 ). Atractylenolide ii is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Atractylenolide II 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

HMDB0248707
     RDKit          3D
Atractylenolide II
 37 39  0  0  0  0  0  0  0  0999 V2000
   -1.4109    2.5545   -0.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5782    1.2439   -0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9288    0.7556   -1.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1964   -0.6264   -0.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0031   -1.5064   -0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7775   -0.8387    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1936   -0.3307    1.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3247   -1.8597    0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5962   -1.3911   -0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7335   -2.1131   -0.1189 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6790   -1.2276    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8469   -1.5365    0.7557 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1090    0.1109    0.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7792    1.3848    0.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8951    0.0029   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8377    1.0605   -0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099    0.3239   -0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2470    3.2438   -0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4106    2.9256   -0.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6775    1.4378   -0.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564    0.8125   -2.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -1.0860   -1.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6470   -0.6144    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6867   -1.8461   -1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2524   -2.4202    0.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345    0.7393    1.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3017   -0.4516    2.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0324   -0.9650    1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471   -2.0302    1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0096   -2.8020   -0.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5007   -1.4626   -1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839    2.1244    1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4859    1.2142    1.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3566    1.8304   -0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955    1.6243    0.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1532    1.7181   -1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2124    0.0008   -1.8469 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  2  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
 14 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
M  END

  Mrv1533004171503092D          

 17 19  0  0  0  0            999 V2000
    1.5983   -0.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -1.9354    0.0000 O   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  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248707

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2CC3C(=C)CCCC3(C)CC2OC1=O

> <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/h12-13H,1,4-8H2,2-3H3

> <INCHI_KEY>
OQYBLUDOOFOBPO-UHFFFAOYSA-N

> <FORMULA>
C15H20O2

> <MOLECULAR_WEIGHT>
232.323

> <EXACT_MASS>
232.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.03805386369318

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.49

> <JCHEM_LOGP>
3.334337557

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.413403514015243

> <JCHEM_PKA_STRONGEST_BASIC>
-6.883907775610832

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
66.9263

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e-01 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0248707
     RDKit          3D
Atractylenolide II
 37 39  0  0  0  0  0  0  0  0999 V2000
   -1.4109    2.5545   -0.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5782    1.2439   -0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9288    0.7556   -1.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1964   -0.6264   -0.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0031   -1.5064   -0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7775   -0.8387    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1936   -0.3307    1.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3247   -1.8597    0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5962   -1.3911   -0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7335   -2.1131   -0.1189 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6790   -1.2276    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8469   -1.5365    0.7557 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1090    0.1109    0.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7792    1.3848    0.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8951    0.0029   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8377    1.0605   -0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099    0.3239   -0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2470    3.2438   -0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4106    2.9256   -0.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6775    1.4378   -0.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564    0.8125   -2.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -1.0860   -1.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6470   -0.6144    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6867   -1.8461   -1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2524   -2.4202    0.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345    0.7393    1.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3017   -0.4516    2.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0324   -0.9650    1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471   -2.0302    1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0096   -2.8020   -0.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5007   -1.4626   -1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839    2.1244    1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4859    1.2142    1.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3566    1.8304   -0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955    1.6243    0.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1532    1.7181   -1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2124    0.0008   -1.8469 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  2  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
 14 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       2.983  -0.902   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.925  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.591  -5.923   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.459  -4.859   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.014  -3.613   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    5   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    2   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0248707
HETATM    1  C1  UNL     1      -1.411   2.555  -0.672  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.578   1.244  -0.848  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.929   0.756  -1.103  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.196  -0.626  -0.578  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.003  -1.506  -0.557  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.778  -0.839   0.068  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.194  -0.331   1.429  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.325  -1.860   0.221  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.596  -1.391  -0.452  1.00  0.00           C  
HETATM   10  O1  UNL     1       2.733  -2.113  -0.119  1.00  0.00           O  
HETATM   11  C10 UNL     1       3.679  -1.228   0.363  1.00  0.00           C  
HETATM   12  O2  UNL     1       4.847  -1.537   0.756  1.00  0.00           O  
HETATM   13  C11 UNL     1       3.109   0.111   0.341  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.779   1.385   0.778  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.895   0.003  -0.132  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.838   1.060  -0.350  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.410   0.324  -0.787  1.00  0.00           C  
HETATM   18  H1  UNL     1      -2.247   3.244  -0.715  1.00  0.00           H  
HETATM   19  H2  UNL     1      -0.411   2.926  -0.485  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.678   1.438  -0.611  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.156   0.813  -2.188  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.958  -1.086  -1.239  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.647  -0.614   0.444  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.687  -1.846  -1.573  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.252  -2.420   0.030  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.434   0.739   1.422  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.302  -0.452   2.103  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.032  -0.965   1.804  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.547  -2.030   1.287  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.010  -2.802  -0.219  1.00  0.00           H  
HETATM   31  H14 UNL     1       1.501  -1.463  -1.572  1.00  0.00           H  
HETATM   32  H15 UNL     1       2.984   2.124   1.010  1.00  0.00           H  
HETATM   33  H16 UNL     1       4.486   1.214   1.593  1.00  0.00           H  
HETATM   34  H17 UNL     1       4.357   1.830  -0.081  1.00  0.00           H  
HETATM   35  H18 UNL     1       0.695   1.624   0.593  1.00  0.00           H  
HETATM   36  H19 UNL     1       1.153   1.718  -1.160  1.00  0.00           H  
HETATM   37  H20 UNL     1      -0.212   0.001  -1.847  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   15
CONECT   14   32   33   34
CONECT   15   16
CONECT   16   17   35   36
CONECT   17   37
END

HMDB0248707
     RDKit          3D
Atractylenolide II
 37 39  0  0  0  0  0  0  0  0999 V2000
   -1.4109    2.5545   -0.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5782    1.2439   -0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9288    0.7556   -1.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1964   -0.6264   -0.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0031   -1.5064   -0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7775   -0.8387    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1936   -0.3307    1.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3247   -1.8597    0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5962   -1.3911   -0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7335   -2.1131   -0.1189 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6790   -1.2276    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8469   -1.5365    0.7557 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1090    0.1109    0.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7792    1.3848    0.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8951    0.0029   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8377    1.0605   -0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099    0.3239   -0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2470    3.2438   -0.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4106    2.9256   -0.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6775    1.4378   -0.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564    0.8125   -2.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -1.0860   -1.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6470   -0.6144    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6867   -1.8461   -1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2524   -2.4202    0.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345    0.7393    1.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3017   -0.4516    2.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0324   -0.9650    1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471   -2.0302    1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0096   -2.8020   -0.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5007   -1.4626   -1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839    2.1244    1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4859    1.2142    1.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3566    1.8304   -0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955    1.6243    0.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1532    1.7181   -1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2124    0.0008   -1.8469 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  2  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
 14 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₂

Average Molecular Weight

232.323

Monoisotopic Molecular Weight

232.146329884

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC1=C2CC3C(=C)CCCC3(C)CC2OC1=O

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/h12-13H,1,4-8H2,2-3H3

InChI Key

OQYBLUDOOFOBPO-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
2-furanone
Dihydrofuran
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

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	3.49	ALOGPS
logP	3.33	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.41	ChemAxon
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	66.93 m³·mol⁻¹	ChemAxon
Polarizability	26.04 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]+	150.606	30932474
DeepCCS	[M-H]-	148.248	30932474
DeepCCS	[M-2H]-	183.356	30932474
DeepCCS	[M+Na]+	157.956	30932474
AllCCS	[M+H]+	155.3	32859911
AllCCS	[M+H-H2O]+	151.4	32859911
AllCCS	[M+NH4]+	158.9	32859911
AllCCS	[M+Na]+	159.9	32859911
AllCCS	[M-H]-	161.9	32859911
AllCCS	[M+Na-2H]-	161.9	32859911
AllCCS	[M+HCOO]-	162.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Atractylenolide II	CC1=C2CC3C(=C)CCCC3(C)CC2OC1=O	2760.7	Standard polar	33892256
Atractylenolide II	CC1=C2CC3C(=C)CCCC3(C)CC2OC1=O	1934.2	Standard non polar	33892256
Atractylenolide II	CC1=C2CC3C(=C)CCCC3(C)CC2OC1=O	2088.0	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 - Atractylenolide II GC-MS (Non-derivatized) - 70eV, Positive	splash10-0avi-2930000000-5e83f3f150f4f8ae3de9	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Atractylenolide II 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 - Atractylenolide II 10V, Negative-QTOF	splash10-001i-0090000000-403b175a8d75af9b9dc4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atractylenolide II 20V, Negative-QTOF	splash10-000i-0900000000-2b45de21d3a595a05188	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atractylenolide II 40V, Negative-QTOF	splash10-0079-0930000000-4683c5ff5166a05f5550	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atractylenolide II 10V, Positive-QTOF	splash10-001i-0190000000-5a92836a02c5a0beeea3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atractylenolide II 20V, Positive-QTOF	splash10-001r-0890000000-7a5b03eb04eae232d6d1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atractylenolide II 40V, Positive-QTOF	splash10-0a4i-3900000000-66d005a2ee23bacc5888	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

14448069

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 Atractylenolide II (HMDB0248707)

MOL for HMDB0248707 (Atractylenolide II)

3D MOL for HMDB0248707 (Atractylenolide II)

3D SDF for HMDB0248707 (Atractylenolide II)

3D-SDF for HMDB0248707 (Atractylenolide II)

PDB for HMDB0248707 (Atractylenolide II)

3D PDB for HMDB0248707 (Atractylenolide II)

SMILES for HMDB0248707 (Atractylenolide II)

INCHI for HMDB0248707 (Atractylenolide II)

Structure for HMDB0248707 (Atractylenolide II)

3D Structure for HMDB0248707 (Atractylenolide II)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra