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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:37:50 UTC

Update Date

2022-03-07 02:54:34 UTC

HMDB ID

HMDB0035620

Secondary Accession Numbers

HMDB35620

Metabolite Identification

Common Name

Artabsinolide A

Description

Artabsinolide A belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Artabsinolide A has been detected, but not quantified in, alcoholic beverages and herbs and spices. This could make artabsinolide a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Artabsinolide A.

Structure

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

HMDB0035620
     RDKit          3D
Artabsinolide A
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.6831   -0.6309    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7831   -0.7503   -0.3919 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3106   -2.1399   -0.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0616   -3.1439   -0.6453 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9200   -2.1185   -0.7108 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4713   -0.7815   -0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8204   -0.5511   -0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3398    0.6473    0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6427    0.4642    0.6987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5749    1.3227    0.7383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6476   -0.9118    1.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6806   -1.6220    0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4344   -2.2223   -0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9898   -2.6037    1.0378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8086    2.0105   -0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658    2.7660    1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8444    2.6896   -0.8842 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3629    1.9988   -1.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6147    1.4296   -0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5194    0.0048   -0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2023   -1.1815    1.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7844    0.4444    1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6700   -1.0596    0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2510   -0.3267   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -0.5148   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1610   -0.9006    2.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6446   -1.3733    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0139   -3.0921   -0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1556   -1.4922   -1.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7422   -2.4949   -1.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6555   -3.0374    1.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4192    3.2685    1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3818    3.5169    1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6502    2.0374    1.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9779    2.2539   -1.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5862    3.0633   -1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0967    1.4987   -2.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4157    1.5207   -1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388    2.0330    0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2366   -0.0214    0.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  8 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
 20  6  1  0
 12  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  6 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
M  END


  Mrv0541 05061308432D          

 20 22  0  0  0  0            999 V2000
   -1.3057    0.6850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6504    0.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2168    2.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3388    0.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821   -0.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7444    1.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1552    0.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7814    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0090    0.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4946    1.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6696    1.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802    1.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254    0.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9491    2.1831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4699    0.6850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2252    2.4780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0090   -0.7590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2505    2.9511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2151    2.1831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  1  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 14  2  1  0  0  0  0
 14  5  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 11  1  0  0  0  0
 16  9  2  0  0  0  0
 17 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 20 12  1  0  0  0  0
 20 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035620

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2CCC(C)(O)C3=C(C2OC1=O)C(C)(O)CC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O5/c1-7-8-4-5-14(2,18)10-9(16)6-15(3,19)11(10)12(8)20-13(7)17/h7-8,12,18-19H,4-6H2,1-3H3

> <INCHI_KEY>
ZSOYDVICJGNUTP-UHFFFAOYSA-N

> <FORMULA>
C15H20O5

> <MOLECULAR_WEIGHT>
280.3163

> <EXACT_MASS>
280.13107375

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.855675788304154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,9-dihydroxy-3,6,9-trimethyl-2H,3H,3aH,4H,5H,6H,7H,8H,9H,9bH-azuleno[4,5-b]furan-2,7-dione

> <ALOGPS_LOGP>
0.43

> <JCHEM_LOGP>
0.2717256676666667

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.47563335865593

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.841322496667626

> <JCHEM_PKA_STRONGEST_BASIC>
-3.146173898540611

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
70.8688

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,9-dihydroxy-3,6,9-trimethyl-3H,3aH,4H,5H,8H,9bH-azuleno[4,5-b]furan-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035620
     RDKit          3D
Artabsinolide A
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.6831   -0.6309    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7831   -0.7503   -0.3919 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3106   -2.1399   -0.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0616   -3.1439   -0.6453 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9200   -2.1185   -0.7108 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4713   -0.7815   -0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8204   -0.5511   -0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3398    0.6473    0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6427    0.4642    0.6987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5749    1.3227    0.7383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6476   -0.9118    1.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6806   -1.6220    0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4344   -2.2223   -0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9898   -2.6037    1.0378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8086    2.0105   -0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658    2.7660    1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8444    2.6896   -0.8842 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3629    1.9988   -1.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6147    1.4296   -0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5194    0.0048   -0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2023   -1.1815    1.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7844    0.4444    1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6700   -1.0596    0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2510   -0.3267   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -0.5148   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1610   -0.9006    2.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6446   -1.3733    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0139   -3.0921   -0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1556   -1.4922   -1.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7422   -2.4949   -1.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6555   -3.0374    1.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4192    3.2685    1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3818    3.5169    1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6502    2.0374    1.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9779    2.2539   -1.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5862    3.0633   -1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0967    1.4987   -2.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4157    1.5207   -1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388    2.0330    0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2366   -0.0214    0.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  8 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
 20  6  1  0
 12  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  6 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  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      -2.437   1.279   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.947   0.085   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.271   4.784   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.632   0.085   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.020  -0.584   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.123   3.665   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.152   2.127   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.290   1.586   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.192   2.127   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.750   1.586   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.790   2.790   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.250   2.790   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.083   3.665   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.407   0.085   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.638   4.075   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.477   1.279   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.287   4.626   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.750  -1.417   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.201   5.509   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.402   4.075   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4    5    8                                                       
CONECT    5    4   14                                                       
CONECT    6    9   15                                                       
CONECT    7    1    8   13                                                  
CONECT    8    4    7   12                                                  
CONECT    9    6   10   16                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   15                                                  
CONECT   12    8   11   20                                                  
CONECT   13    7   17   20                                                  
CONECT   14    2    5   10   18                                             
CONECT   15    3    6   11   19                                             
CONECT   16    9                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0035620
HETATM    1  C1  UNL     1       3.683  -0.631   0.817  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.783  -0.750  -0.392  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.311  -2.140  -0.594  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.062  -3.144  -0.645  1.00  0.00           O  
HETATM    5  O2  UNL     1       0.920  -2.118  -0.711  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.471  -0.782  -0.877  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.820  -0.551  -0.176  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.340   0.647   0.067  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.643   0.464   0.699  1.00  0.00           C  
HETATM   10  O3  UNL     1      -3.575   1.323   0.738  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.648  -0.912   1.274  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.681  -1.622   0.333  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.434  -2.222  -0.815  1.00  0.00           C  
HETATM   14  O4  UNL     1      -0.990  -2.604   1.038  1.00  0.00           O  
HETATM   15  C11 UNL     1      -0.809   2.010  -0.198  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.566   2.766   1.069  1.00  0.00           C  
HETATM   17  O5  UNL     1      -1.844   2.690  -0.884  1.00  0.00           O  
HETATM   18  C13 UNL     1       0.363   1.999  -1.129  1.00  0.00           C  
HETATM   19  C14 UNL     1       1.615   1.430  -0.532  1.00  0.00           C  
HETATM   20  C15 UNL     1       1.519   0.005  -0.128  1.00  0.00           C  
HETATM   21  H1  UNL     1       3.202  -1.181   1.652  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.784   0.444   1.064  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.670  -1.060   0.578  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.251  -0.327  -1.299  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.404  -0.515  -1.946  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.161  -0.901   2.276  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.645  -1.373   1.274  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.014  -3.092  -0.452  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.156  -1.492  -1.214  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.742  -2.495  -1.622  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.655  -3.037   1.633  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.419   3.269   1.101  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.382   3.517   1.282  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.650   2.037   1.927  1.00  0.00           H  
HETATM   35  H15 UNL     1      -1.978   2.254  -1.775  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.586   3.063  -1.386  1.00  0.00           H  
HETATM   37  H17 UNL     1       0.097   1.499  -2.059  1.00  0.00           H  
HETATM   38  H18 UNL     1       2.416   1.521  -1.294  1.00  0.00           H  
HETATM   39  H19 UNL     1       1.939   2.033   0.343  1.00  0.00           H  
HETATM   40  H20 UNL     1       1.237  -0.021   0.964  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   20   24
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   20   25
CONECT    7    8    8   12
CONECT    8    9   15
CONECT    9   10   10   11
CONECT   11   12   26   27
CONECT   12   13   14
CONECT   13   28   29   30
CONECT   14   31
CONECT   15   16   17   18
CONECT   16   32   33   34
CONECT   17   35
CONECT   18   19   36   37
CONECT   19   20   38   39
CONECT   20   40
END

HMDB0035620
     RDKit          3D
Artabsinolide A
 40 42  0  0  0  0  0  0  0  0999 V2000
    3.6831   -0.6309    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7831   -0.7503   -0.3919 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3106   -2.1399   -0.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0616   -3.1439   -0.6453 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9200   -2.1185   -0.7108 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4713   -0.7815   -0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8204   -0.5511   -0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3398    0.6473    0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6427    0.4642    0.6987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5749    1.3227    0.7383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6476   -0.9118    1.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6806   -1.6220    0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4344   -2.2223   -0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9898   -2.6037    1.0378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8086    2.0105   -0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658    2.7660    1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8444    2.6896   -0.8842 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3629    1.9988   -1.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6147    1.4296   -0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5194    0.0048   -0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2023   -1.1815    1.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7844    0.4444    1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6700   -1.0596    0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2510   -0.3267   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4040   -0.5148   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1610   -0.9006    2.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6446   -1.3733    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0139   -3.0921   -0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1556   -1.4922   -1.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7422   -2.4949   -1.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6555   -3.0374    1.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4192    3.2685    1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3818    3.5169    1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6502    2.0374    1.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9779    2.2539   -1.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5862    3.0633   -1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0967    1.4987   -2.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4157    1.5207   -1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388    2.0330    0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2366   -0.0214    0.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  8 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
 20  6  1  0
 12  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  6 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4,10-Dihydroxy-2-oxo-1(5)-guaien-12,6-olide	HMDB

Chemical Formula

C₁₅H₂₀O₅

Average Molecular Weight

280.3163

Monoisotopic Molecular Weight

280.13107375

IUPAC Name

6,9-dihydroxy-3,6,9-trimethyl-2H,3H,3aH,4H,5H,6H,7H,8H,9H,9bH-azuleno[4,5-b]furan-2,7-dione

Traditional Name

6,9-dihydroxy-3,6,9-trimethyl-3H,3aH,4H,5H,8H,9bH-azuleno[4,5-b]furan-2,7-dione

CAS Registry Number

82078-63-5

SMILES

CC1C2CCC(C)(O)C3=C(C2OC1=O)C(C)(O)CC3=O

InChI Identifier

InChI=1S/C15H20O5/c1-7-8-4-5-14(2,18)10-9(16)6-15(3,19)11(10)12(8)20-13(7)17/h7-8,12,18-19H,4-6H2,1-3H3

InChI Key

ZSOYDVICJGNUTP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0035620)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035620)

Source

Endogenous

Endogenous (HMDB: HMDB0035620)

Plant

Plant (HMDB: HMDB0035620)

Exogenous

Food

Food (HMDB: HMDB0035620)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0035620)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035620)

Nutrient

Nutrient (HMDB: HMDB0035620)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035620)

Emulsifier (HMDB: HMDB0035620)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	160 - 162 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	28800 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.9 g/L	ALOGPS
logP	0.43	ALOGPS
logP	0.27	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	13.84	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.87 m³·mol⁻¹	ChemAxon
Polarizability	28.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	165.732	31661259
DarkChem	[M-H]-	163.075	31661259
DeepCCS	[M+H]+	172.062	30932474
DeepCCS	[M-H]-	169.704	30932474
DeepCCS	[M-2H]-	202.59	30932474
DeepCCS	[M+Na]+	178.155	30932474
AllCCS	[M+H]+	163.9	32859911
AllCCS	[M+H-H2O]+	160.5	32859911
AllCCS	[M+NH4]+	167.1	32859911
AllCCS	[M+Na]+	168.0	32859911
AllCCS	[M-H]-	168.8	32859911
AllCCS	[M+Na-2H]-	168.7	32859911
AllCCS	[M+HCOO]-	168.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Artabsinolide A	CC1C2CCC(C)(O)C3=C(C2OC1=O)C(C)(O)CC3=O	3556.2	Standard polar	33892256
Artabsinolide A	CC1C2CCC(C)(O)C3=C(C2OC1=O)C(C)(O)CC3=O	2188.7	Standard non polar	33892256
Artabsinolide A	CC1C2CCC(C)(O)C3=C(C2OC1=O)C(C)(O)CC3=O	2363.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Artabsinolide A,1TMS,isomer #1	CC1C(=O)OC2C3=C(C(=O)CC3(C)O)C(C)(O[Si](C)(C)C)CCC12	2285.4	Semi standard non polar	33892256
Artabsinolide A,1TMS,isomer #2	CC1C(=O)OC2C3=C(C(=O)CC3(C)O[Si](C)(C)C)C(C)(O)CCC12	2271.7	Semi standard non polar	33892256
Artabsinolide A,1TMS,isomer #3	CC1C(=O)OC2C3=C(C(O[Si](C)(C)C)=CC3(C)O)C(C)(O)CCC12	2201.1	Semi standard non polar	33892256
Artabsinolide A,2TMS,isomer #1	CC1C(=O)OC2C3=C(C(=O)CC3(C)O[Si](C)(C)C)C(C)(O[Si](C)(C)C)CCC12	2359.2	Semi standard non polar	33892256
Artabsinolide A,2TMS,isomer #2	CC1C(=O)OC2C3=C(C(O[Si](C)(C)C)=CC3(C)O)C(C)(O[Si](C)(C)C)CCC12	2270.7	Semi standard non polar	33892256
Artabsinolide A,2TMS,isomer #3	CC1C(=O)OC2C3=C(C(O[Si](C)(C)C)=CC3(C)O[Si](C)(C)C)C(C)(O)CCC12	2287.3	Semi standard non polar	33892256
Artabsinolide A,3TMS,isomer #1	CC1C(=O)OC2C3=C(C(O[Si](C)(C)C)=CC3(C)O[Si](C)(C)C)C(C)(O[Si](C)(C)C)CCC12	2339.8	Semi standard non polar	33892256
Artabsinolide A,3TMS,isomer #1	CC1C(=O)OC2C3=C(C(O[Si](C)(C)C)=CC3(C)O[Si](C)(C)C)C(C)(O[Si](C)(C)C)CCC12	2344.1	Standard non polar	33892256
Artabsinolide A,1TBDMS,isomer #1	CC1C(=O)OC2C3=C(C(=O)CC3(C)O)C(C)(O[Si](C)(C)C(C)(C)C)CCC12	2517.8	Semi standard non polar	33892256
Artabsinolide A,1TBDMS,isomer #2	CC1C(=O)OC2C3=C(C(=O)CC3(C)O[Si](C)(C)C(C)(C)C)C(C)(O)CCC12	2503.4	Semi standard non polar	33892256
Artabsinolide A,1TBDMS,isomer #3	CC1C(=O)OC2C3=C(C(O[Si](C)(C)C(C)(C)C)=CC3(C)O)C(C)(O)CCC12	2408.8	Semi standard non polar	33892256
Artabsinolide A,2TBDMS,isomer #1	CC1C(=O)OC2C3=C(C(=O)CC3(C)O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)CCC12	2812.8	Semi standard non polar	33892256
Artabsinolide A,2TBDMS,isomer #2	CC1C(=O)OC2C3=C(C(O[Si](C)(C)C(C)(C)C)=CC3(C)O)C(C)(O[Si](C)(C)C(C)(C)C)CCC12	2678.7	Semi standard non polar	33892256
Artabsinolide A,2TBDMS,isomer #3	CC1C(=O)OC2C3=C(C(O[Si](C)(C)C(C)(C)C)=CC3(C)O[Si](C)(C)C(C)(C)C)C(C)(O)CCC12	2694.6	Semi standard non polar	33892256
Artabsinolide A,3TBDMS,isomer #1	CC1C(=O)OC2C3=C(C(O[Si](C)(C)C(C)(C)C)=CC3(C)O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)CCC12	2972.2	Semi standard non polar	33892256
Artabsinolide A,3TBDMS,isomer #1	CC1C(=O)OC2C3=C(C(O[Si](C)(C)C(C)(C)C)=CC3(C)O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)CCC12	2935.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Artabsinolide A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0550-3290000000-f31e7f0c98841f605753	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artabsinolide A GC-MS (2 TMS) - 70eV, Positive	splash10-0adr-5129300000-650f432b2803a5c5732b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artabsinolide A 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 - Artabsinolide A 10V, Positive-QTOF	splash10-03ea-0090000000-7e4e5dbb46d2d636d1b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide A 20V, Positive-QTOF	splash10-03dj-0390000000-17d2a76d31c8b41de2f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide A 40V, Positive-QTOF	splash10-0005-2790000000-bdfd7dfd521297080199	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide A 10V, Negative-QTOF	splash10-004i-0090000000-6d37b2999e4dc9d24998	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide A 20V, Negative-QTOF	splash10-01tl-0290000000-7ad0f95598c6c4c16c91	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide A 40V, Negative-QTOF	splash10-0w2d-7920000000-2e8ffc2bc529856421e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide A 10V, Positive-QTOF	splash10-001i-0090000000-f9ebfc984e61ed34f2ec	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide A 20V, Positive-QTOF	splash10-03ea-0190000000-c83c14a3f4c451b1bec6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide A 40V, Positive-QTOF	splash10-03du-2920000000-57e6c82ae2fbcb6ed3f3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide A 10V, Negative-QTOF	splash10-004i-0090000000-48f5e9ec9dacb4aa8b83	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide A 20V, Negative-QTOF	splash10-004i-0090000000-04acb8be493a3e98e782	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide A 40V, Negative-QTOF	splash10-01tc-2970000000-f288a4a0838f4a23f0f9	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB014325

KNApSAcK ID

C00020872

Chemspider ID

35013956

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74039602

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1850711

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Artabsinolide A (HMDB0035620)

MOL for HMDB0035620 (Artabsinolide A)

3D MOL for HMDB0035620 (Artabsinolide A)

3D SDF for HMDB0035620 (Artabsinolide A)

3D-SDF for HMDB0035620 (Artabsinolide A)

PDB for HMDB0035620 (Artabsinolide A)

3D PDB for HMDB0035620 (Artabsinolide A)

SMILES for HMDB0035620 (Artabsinolide A)

INCHI for HMDB0035620 (Artabsinolide A)

Structure for HMDB0035620 (Artabsinolide A)

3D Structure for HMDB0035620 (Artabsinolide A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra