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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:52:20 UTC

Update Date

2022-03-07 02:54:17 UTC

HMDB ID

HMDB0034941

Secondary Accession Numbers

HMDB34941

Metabolite Identification

Common Name

Artabsinolide D

Description

Artabsinolide D 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 D has been detected, but not quantified in, alcoholic beverages and herbs and spices. This could make artabsinolide D a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Artabsinolide D.

Structure

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

HMDB0034941
     RDKit          3D
Artabsinolide D
 42 44  0  0  0  0  0  0  0  0999 V2000
    3.9548   -1.1500    0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8854   -0.9674   -0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540   -2.2807   -0.9557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8445   -3.3443   -1.2903 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701   -2.1808   -0.8369 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5861   -0.7894   -0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7554   -0.4324   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1782    0.7631   -0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6879    0.6848    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1768    1.5689    0.9417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8642   -0.7558    0.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554   -1.4335   -0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4194   -2.7670    0.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3704   -1.5208   -1.7388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303    2.0229    0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8050    3.0154   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1696    2.5517    1.3814 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219    2.0015    0.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7598    1.2741   -0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6953   -0.2027   -0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -0.3710    0.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4565   -1.0766    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3633   -2.1770    0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2548   -0.4534   -1.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8066   -0.5102   -1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1299    0.8293   -1.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0814    1.2594    1.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8845   -1.1188    0.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -0.8125    1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3289   -3.2711    0.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257   -3.3955   -0.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6534   -2.7123    0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8281   -2.3552   -1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9786    4.0344   -0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7114    2.7388   -1.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0286    3.0453   -1.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5182    2.9826    1.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1336    1.5606    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834    3.0495    0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3826    1.4221   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8119    1.6153   -0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5686   -0.3412    0.9862 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  1  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
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
M  END

  Mrv0541 05061308512D          

 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  1  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>
HMDB0034941

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2CCC(C)(O)C3=C(C2OC1=O)C(C)(O)CC3O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O5/c1-7-8-4-5-14(2,18)10-9(16)6-15(3,19)11(10)12(8)20-13(7)17/h7-9,12,16,18-19H,4-6H2,1-3H3

> <INCHI_KEY>
YZKOCDPFUHYTHX-UHFFFAOYSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.3322

> <EXACT_MASS>
282.146723814

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.568067789219967

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.19

> <JCHEM_LOGP>
-0.520503504

> <ALOGPS_LOGS>
-1.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.394289986969572

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.844509553644695

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0636228550672957

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
71.80149999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034941
     RDKit          3D
Artabsinolide D
 42 44  0  0  0  0  0  0  0  0999 V2000
    3.9548   -1.1500    0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8854   -0.9674   -0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540   -2.2807   -0.9557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8445   -3.3443   -1.2903 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701   -2.1808   -0.8369 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5861   -0.7894   -0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7554   -0.4324   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1782    0.7631   -0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6879    0.6848    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1768    1.5689    0.9417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8642   -0.7558    0.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554   -1.4335   -0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4194   -2.7670    0.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3704   -1.5208   -1.7388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303    2.0229    0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8050    3.0154   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1696    2.5517    1.3814 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219    2.0015    0.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7598    1.2741   -0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6953   -0.2027   -0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -0.3710    0.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4565   -1.0766    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3633   -2.1770    0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2548   -0.4534   -1.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8066   -0.5102   -1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1299    0.8293   -1.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0814    1.2594    1.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8845   -1.1188    0.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -0.8125    1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3289   -3.2711    0.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257   -3.3955   -0.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6534   -2.7123    0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8281   -2.3552   -1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9786    4.0344   -0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7114    2.7388   -1.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0286    3.0453   -1.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5182    2.9826    1.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1336    1.5606    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834    3.0495    0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3826    1.4221   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8119    1.6153   -0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5686   -0.3412    0.9862 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  1  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
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  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    HMDB0034941
HETATM    1  C1  UNL     1       3.955  -1.150   0.422  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.885  -0.967  -0.632  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.254  -2.281  -0.956  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.844  -3.344  -1.290  1.00  0.00           O  
HETATM    5  O2  UNL     1       0.870  -2.181  -0.837  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.586  -0.789  -0.916  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.755  -0.432  -0.487  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.178   0.763  -0.092  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.688   0.685   0.004  1.00  0.00           C  
HETATM   10  O3  UNL     1      -3.177   1.569   0.942  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.864  -0.756   0.448  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.855  -1.433  -0.448  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.419  -2.767   0.083  1.00  0.00           C  
HETATM   14  O4  UNL     1      -2.370  -1.521  -1.739  1.00  0.00           O  
HETATM   15  C11 UNL     1      -0.530   2.023   0.239  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.805   3.015  -0.888  1.00  0.00           C  
HETATM   17  O5  UNL     1      -1.170   2.552   1.381  1.00  0.00           O  
HETATM   18  C13 UNL     1       0.922   2.001   0.504  1.00  0.00           C  
HETATM   19  C14 UNL     1       1.760   1.274  -0.480  1.00  0.00           C  
HETATM   20  C15 UNL     1       1.695  -0.203  -0.093  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.718  -0.371   0.294  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.456  -1.077   1.404  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.363  -2.177   0.329  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.255  -0.453  -1.523  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.807  -0.510  -1.987  1.00  0.00           H  
HETATM   26  H6  UNL     1      -3.130   0.829  -1.003  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.081   1.259   1.218  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.885  -1.119   0.301  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.527  -0.812   1.502  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.329  -3.271   0.522  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.126  -3.395  -0.773  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.653  -2.712   0.854  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.828  -2.355  -1.933  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.979   4.034  -0.491  1.00  0.00           H  
HETATM   35  H15 UNL     1      -1.711   2.739  -1.458  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.029   3.045  -1.594  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.518   2.983   1.985  1.00  0.00           H  
HETATM   38  H18 UNL     1       1.134   1.561   1.521  1.00  0.00           H  
HETATM   39  H19 UNL     1       1.283   3.049   0.565  1.00  0.00           H  
HETATM   40  H20 UNL     1       1.383   1.422  -1.514  1.00  0.00           H  
HETATM   41  H21 UNL     1       2.812   1.615  -0.370  1.00  0.00           H  
HETATM   42  H22 UNL     1       1.569  -0.341   0.986  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   11   26
CONECT   10   27
CONECT   11   12   28   29
CONECT   12   13   14
CONECT   13   30   31   32
CONECT   14   33
CONECT   15   16   17   18
CONECT   16   34   35   36
CONECT   17   37
CONECT   18   19   38   39
CONECT   19   20   40   41
CONECT   20   42
END

HMDB0034941
     RDKit          3D
Artabsinolide D
 42 44  0  0  0  0  0  0  0  0999 V2000
    3.9548   -1.1500    0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8854   -0.9674   -0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540   -2.2807   -0.9557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8445   -3.3443   -1.2903 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701   -2.1808   -0.8369 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5861   -0.7894   -0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7554   -0.4324   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1782    0.7631   -0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6879    0.6848    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1768    1.5689    0.9417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8642   -0.7558    0.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554   -1.4335   -0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4194   -2.7670    0.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3704   -1.5208   -1.7388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303    2.0229    0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8050    3.0154   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1696    2.5517    1.3814 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219    2.0015    0.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7598    1.2741   -0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6953   -0.2027   -0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -0.3710    0.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4565   -1.0766    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3633   -2.1770    0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2548   -0.4534   -1.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8066   -0.5102   -1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1299    0.8293   -1.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0814    1.2594    1.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8845   -1.1188    0.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -0.8125    1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3289   -3.2711    0.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257   -3.3955   -0.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6534   -2.7123    0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8281   -2.3552   -1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9786    4.0344   -0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7114    2.7388   -1.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0286    3.0453   -1.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5182    2.9826    1.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1336    1.5606    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834    3.0495    0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3826    1.4221   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8119    1.6153   -0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5686   -0.3412    0.9862 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  1  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
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₅

Average Molecular Weight

282.3322

Monoisotopic Molecular Weight

282.146723814

IUPAC Name

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

Traditional Name

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

CAS Registry Number

81907-04-2

SMILES

CC1C2CCC(C)(O)C3=C(C2OC1=O)C(C)(O)CC3O

InChI Identifier

InChI=1S/C15H22O5/c1-7-8-4-5-14(2,18)10-9(16)6-15(3,19)11(10)12(8)20-13(7)17/h7-9,12,16,18-19H,4-6H2,1-3H3

InChI Key

YZKOCDPFUHYTHX-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
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Oxacycle
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
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: HMDB0034941)

Source

Exogenous

Food

Food (HMDB: HMDB0034941)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0034941)

Endogenous

Plant

Plant (HMDB: HMDB0034941)

Endogenous (HMDB: HMDB0034941)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0034941)

Role

Biological role

Energy source (HMDB: HMDB0034941)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034941)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	143 - 145 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	18090 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	11.5 g/L	ALOGPS
logP	0.19	ALOGPS
logP	-0.52	ChemAxon
logS	-1.4	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	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.8 m³·mol⁻¹	ChemAxon
Polarizability	29.57 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	165.447	31661259
DarkChem	[M-H]-	161.773	31661259
DeepCCS	[M+H]+	172.238	30932474
DeepCCS	[M-H]-	169.88	30932474
DeepCCS	[M-2H]-	202.766	30932474
DeepCCS	[M+Na]+	178.332	30932474
AllCCS	[M+H]+	165.8	32859911
AllCCS	[M+H-H2O]+	162.5	32859911
AllCCS	[M+NH4]+	168.9	32859911
AllCCS	[M+Na]+	169.8	32859911
AllCCS	[M-H]-	169.6	32859911
AllCCS	[M+Na-2H]-	169.6	32859911
AllCCS	[M+HCOO]-	169.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Artabsinolide D	CC1C2CCC(C)(O)C3=C(C2OC1=O)C(C)(O)CC3O	3569.0	Standard polar	33892256
Artabsinolide D	CC1C2CCC(C)(O)C3=C(C2OC1=O)C(C)(O)CC3O	2286.7	Standard non polar	33892256
Artabsinolide D	CC1C2CCC(C)(O)C3=C(C2OC1=O)C(C)(O)CC3O	2319.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Artabsinolide D,1TMS,isomer #1	CC1C(=O)OC2C3=C(C(O)CC3(C)O)C(C)(O[Si](C)(C)C)CCC12	2301.9	Semi standard non polar	33892256
Artabsinolide D,1TMS,isomer #2	CC1C(=O)OC2C3=C(C(O)CC3(C)O[Si](C)(C)C)C(C)(O)CCC12	2337.4	Semi standard non polar	33892256
Artabsinolide D,1TMS,isomer #3	CC1C(=O)OC2C3=C(C(O[Si](C)(C)C)CC3(C)O)C(C)(O)CCC12	2326.6	Semi standard non polar	33892256
Artabsinolide D,2TMS,isomer #1	CC1C(=O)OC2C3=C(C(O[Si](C)(C)C)CC3(C)O)C(C)(O[Si](C)(C)C)CCC12	2351.1	Semi standard non polar	33892256
Artabsinolide D,2TMS,isomer #2	CC1C(=O)OC2C3=C(C(O)CC3(C)O[Si](C)(C)C)C(C)(O[Si](C)(C)C)CCC12	2372.8	Semi standard non polar	33892256
Artabsinolide D,2TMS,isomer #3	CC1C(=O)OC2C3=C(C(O[Si](C)(C)C)CC3(C)O[Si](C)(C)C)C(C)(O)CCC12	2362.5	Semi standard non polar	33892256
Artabsinolide D,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	2417.8	Semi standard non polar	33892256
Artabsinolide D,1TBDMS,isomer #1	CC1C(=O)OC2C3=C(C(O)CC3(C)O)C(C)(O[Si](C)(C)C(C)(C)C)CCC12	2558.1	Semi standard non polar	33892256
Artabsinolide D,1TBDMS,isomer #2	CC1C(=O)OC2C3=C(C(O)CC3(C)O[Si](C)(C)C(C)(C)C)C(C)(O)CCC12	2576.0	Semi standard non polar	33892256
Artabsinolide D,1TBDMS,isomer #3	CC1C(=O)OC2C3=C(C(O[Si](C)(C)C(C)(C)C)CC3(C)O)C(C)(O)CCC12	2572.8	Semi standard non polar	33892256
Artabsinolide D,2TBDMS,isomer #1	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	2792.1	Semi standard non polar	33892256
Artabsinolide D,2TBDMS,isomer #2	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	2817.8	Semi standard non polar	33892256
Artabsinolide D,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	2797.3	Semi standard non polar	33892256
Artabsinolide D,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	3075.0	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 - Artabsinolide D GC-MS (Non-derivatized) - 70eV, Positive	splash10-0300-2390000000-513c4050baec4130c054	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artabsinolide D GC-MS (3 TMS) - 70eV, Positive	splash10-06ur-2001900000-3b8c2d72d4c73aa324fb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artabsinolide D 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 D 10V, Positive-QTOF	splash10-014j-0090000000-5341ada221d2bcd680bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide D 20V, Positive-QTOF	splash10-00kb-0490000000-dd52683136ad4324f3b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide D 40V, Positive-QTOF	splash10-0005-1690000000-00998b38749377e26102	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide D 10V, Negative-QTOF	splash10-001i-0090000000-59695e8e7944ac744b01	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide D 20V, Negative-QTOF	splash10-03e9-0090000000-94c8a9a0a573a381dae0	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide D 40V, Negative-QTOF	splash10-0udl-9520000000-a6e03a6dc019688bbdc0	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide D 10V, Negative-QTOF	splash10-001i-0090000000-4206ab54dd729eeefe27	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide D 20V, Negative-QTOF	splash10-001i-0090000000-ae18ad965d4fbc7a2fc2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide D 40V, Negative-QTOF	splash10-004i-2890000000-67a599088e989225b01d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide D 10V, Positive-QTOF	splash10-001i-0090000000-1c245b7d9de3be531223	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide D 20V, Positive-QTOF	splash10-00li-1290000000-6e4c59e5f3e9a3b8f4d7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsinolide D 40V, Positive-QTOF	splash10-08g0-1920000000-973cacbb39b81e86edca	2021-09-23	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

FDB013534

KNApSAcK ID

C00020869

Chemspider ID

35013799

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751640

PDB ID

Not Available

ChEBI ID

174699

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1846511

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 D (HMDB0034941)

MOL for HMDB0034941 (Artabsinolide D)

3D MOL for HMDB0034941 (Artabsinolide D)

3D SDF for HMDB0034941 (Artabsinolide D)

3D-SDF for HMDB0034941 (Artabsinolide D)

PDB for HMDB0034941 (Artabsinolide D)

3D PDB for HMDB0034941 (Artabsinolide D)

SMILES for HMDB0034941 (Artabsinolide D)

INCHI for HMDB0034941 (Artabsinolide D)

Structure for HMDB0034941 (Artabsinolide D)

3D Structure for HMDB0034941 (Artabsinolide D)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra