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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:48:15 UTC

Update Date

2022-03-07 02:55:00 UTC

HMDB ID

HMDB0036641

Secondary Accession Numbers

HMDB36641

Metabolite Identification

Common Name

Artabsin

Description

Artabsin 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. Artabsin has been detected, but not quantified in, alcoholic beverages and herbs and spices. This could make artabsin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Artabsin.

Structure

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

HMDB0036641
     RDKit          3D
Artabsin
 38 40  0  0  0  0  0  0  0  0999 V2000
   -0.6093    3.5434   -0.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2365    2.1832   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6363    1.0313   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6406   -0.0230   -0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8517    0.5172   -0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791    1.9556   -0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5551   -1.4814    0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0247   -1.7830    1.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451   -2.1572   -0.6971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1661   -2.0278    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5180   -1.2894   -1.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4541   -0.2266   -0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800   -0.7068    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9048   -0.5902   -0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328    0.2430    1.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3494    0.4683    2.3519 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671    0.7996    1.4617 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7974    0.9187    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3530    3.7206   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    4.3318   -0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3275    3.6105    0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109   -0.0024   -0.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2440    2.4999    0.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0131    2.3323   -1.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111   -1.6121    1.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7704   -2.8579    1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4354   -1.1687    2.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9647   -2.8768   -1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3338   -1.9166    1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2210   -3.0964   -0.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2285   -0.8128   -1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0859   -2.0003   -1.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0196    0.1260   -1.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3623   -1.7347    0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1707   -1.5712   -0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9842    0.2415   -0.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5941   -0.4327    0.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973    1.8453   -0.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  4  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
  6  2  1  0
 18 12  1  0
 18  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 18 38  1  0
M  END

  Mrv0541 05061309152D          

 18 20  0  0  0  0            999 V2000
    1.6592    2.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
    2.7444    1.9636    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
    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
    1.9491    2.1831    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
    2.0090    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
   -1.2252    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
    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  6  1  0  0  0  0
  8  1  1  0  0  0  0
  8  4  1  0  0  0  0
  9  2  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 12  8  2  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14  9  1  0  0  0  0
 15  3  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  1  0  0  0  0
 16 14  2  0  0  0  0
 17 15  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036641

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2CCC(C)(O)C3=CCC(C)=C3C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-4-5-11-12(8)13-10(6-7-15(11,3)17)9(2)14(16)18-13/h5,9-10,13,17H,4,6-7H2,1-3H3

> <INCHI_KEY>
BXBCLQRTBGRRDB-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.49621338801204

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
1.6147755826666663

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.918780298780423

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.358023398042334

> <JCHEM_PKA_STRONGEST_BASIC>
-3.070076365652228

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
69.5745

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.87e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036641
     RDKit          3D
Artabsin
 38 40  0  0  0  0  0  0  0  0999 V2000
   -0.6093    3.5434   -0.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2365    2.1832   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6363    1.0313   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6406   -0.0230   -0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8517    0.5172   -0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791    1.9556   -0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5551   -1.4814    0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0247   -1.7830    1.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451   -2.1572   -0.6971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1661   -2.0278    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5180   -1.2894   -1.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4541   -0.2266   -0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800   -0.7068    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9048   -0.5902   -0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328    0.2430    1.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3494    0.4683    2.3519 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671    0.7996    1.4617 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7974    0.9187    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3530    3.7206   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    4.3318   -0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3275    3.6105    0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109   -0.0024   -0.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2440    2.4999    0.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0131    2.3323   -1.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111   -1.6121    1.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7704   -2.8579    1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4354   -1.1687    2.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9647   -2.8768   -1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3338   -1.9166    1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2210   -3.0964   -0.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2285   -0.8128   -1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0859   -2.0003   -1.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0196    0.1260   -1.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3623   -1.7347    0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1707   -1.5712   -0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9842    0.2415   -0.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5941   -0.4327    0.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973    1.8453   -0.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  4  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
  6  2  1  0
 18 12  1  0
 18  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 18 38  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       3.097   5.517   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.437   1.279   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.947   0.085   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.123   3.665   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.192   2.127   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.632   0.085   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.020  -0.584   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.638   4.075   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.152   2.127   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.290   1.586   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.750   1.586   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.790   2.790   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.250   2.790   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.083   3.665   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.407   0.085   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.287   4.626   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.750  -1.417   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.402   4.075   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   15                                                            
CONECT    4    5    8                                                       
CONECT    5    4   11                                                       
CONECT    6    7   10                                                       
CONECT    7    6   15                                                       
CONECT    8    1    4   12                                                  
CONECT    9    2   10   14                                                  
CONECT   10    6    9   13                                                  
CONECT   11    5   12   15                                                  
CONECT   12    8   11   13                                                  
CONECT   13   10   12   18                                                  
CONECT   14    9   16   18                                                  
CONECT   15    3    7   11   17                                             
CONECT   16   14                                                            
CONECT   17   15                                                            
CONECT   18   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0036641
HETATM    1  C1  UNL     1      -0.609   3.543  -0.477  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.237   2.183  -0.348  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.636   1.031  -0.105  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.641  -0.023  -0.066  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.852   0.517  -0.290  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.679   1.956  -0.485  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.555  -1.481   0.163  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.025  -1.783   1.572  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.445  -2.157  -0.697  1.00  0.00           O  
HETATM   10  C9  UNL     1      -0.166  -2.028   0.020  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.518  -1.289  -1.088  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.454  -0.227  -0.619  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.480  -0.707   0.355  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.905  -0.590  -0.197  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.433   0.243   1.520  1.00  0.00           C  
HETATM   16  O2  UNL     1       3.349   0.468   2.352  1.00  0.00           O  
HETATM   17  O3  UNL     1       1.167   0.800   1.462  1.00  0.00           O  
HETATM   18  C15 UNL     1       0.797   0.919   0.082  1.00  0.00           C  
HETATM   19  H1  UNL     1      -0.353   3.721  -1.534  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.282   4.332  -0.090  1.00  0.00           H  
HETATM   21  H3  UNL     1       0.328   3.610   0.109  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.811  -0.002  -0.325  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.244   2.500   0.325  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.013   2.332  -1.461  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.111  -1.612   1.695  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.770  -2.858   1.757  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.435  -1.169   2.288  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.965  -2.877  -1.178  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.334  -1.917   1.002  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.221  -3.096  -0.238  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.228  -0.813  -1.761  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.086  -2.000  -1.713  1.00  0.00           H  
HETATM   33  H15 UNL     1       2.020   0.126  -1.533  1.00  0.00           H  
HETATM   34  H16 UNL     1       2.362  -1.735   0.692  1.00  0.00           H  
HETATM   35  H17 UNL     1       4.171  -1.571  -0.650  1.00  0.00           H  
HETATM   36  H18 UNL     1       3.984   0.242  -0.929  1.00  0.00           H  
HETATM   37  H19 UNL     1       4.594  -0.433   0.657  1.00  0.00           H  
HETATM   38  H20 UNL     1       1.297   1.845  -0.268  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    6
CONECT    3    4   18
CONECT    4    5    5    7
CONECT    5    6   22
CONECT    6   23   24
CONECT    7    8    9   10
CONECT    8   25   26   27
CONECT    9   28
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   18   33
CONECT   13   14   15   34
CONECT   14   35   36   37
CONECT   15   16   16   17
CONECT   17   18
CONECT   18   38
END

HMDB0036641
     RDKit          3D
Artabsin
 38 40  0  0  0  0  0  0  0  0999 V2000
   -0.6093    3.5434   -0.4775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2365    2.1832   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6363    1.0313   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6406   -0.0230   -0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8517    0.5172   -0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6791    1.9556   -0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5551   -1.4814    0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0247   -1.7830    1.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451   -2.1572   -0.6971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1661   -2.0278    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5180   -1.2894   -1.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4541   -0.2266   -0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800   -0.7068    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9048   -0.5902   -0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4328    0.2430    1.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3494    0.4683    2.3519 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671    0.7996    1.4617 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7974    0.9187    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3530    3.7206   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823    4.3318   -0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3275    3.6105    0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8109   -0.0024   -0.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2440    2.4999    0.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0131    2.3323   -1.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111   -1.6121    1.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7704   -2.8579    1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4354   -1.1687    2.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9647   -2.8768   -1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3338   -1.9166    1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2210   -3.0964   -0.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2285   -0.8128   -1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0859   -2.0003   -1.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0196    0.1260   -1.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3623   -1.7347    0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1707   -1.5712   -0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9842    0.2415   -0.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5941   -0.4327    0.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973    1.8453   -0.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  4  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
  6  2  1  0
 18 12  1  0
 18  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Prochamazulenogenin	HMDB

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

IUPAC Name

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

Traditional Name

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

CAS Registry Number

24399-20-0

SMILES

CC1C2CCC(C)(O)C3=CCC(C)=C3C2OC1=O

InChI Identifier

InChI=1S/C15H20O3/c1-8-4-5-11-12(8)13-10(6-7-15(11,3)17)9(2)14(16)18-13/h5,9-10,13,17H,4,6-7H2,1-3H3

InChI Key

BXBCLQRTBGRRDB-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
Cyclic alcohol
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

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036641)

Source

Endogenous

Endogenous (HMDB: HMDB0036641)

Plant

Plant (HMDB: HMDB0036641)

Exogenous

Food

Food (HMDB: HMDB0036641)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0036641)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036641)

Role

Biological role

Energy source (HMDB: HMDB0036641)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036641)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	133 - 135 °C	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
Water Solubility	0.69 g/L	ALOGPS
logP	3.03	ALOGPS
logP	1.61	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	14.36	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.57 m³·mol⁻¹	ChemAxon
Polarizability	27.5 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]+	158.655	31661259
DarkChem	[M-H]-	154.535	31661259
DeepCCS	[M+H]+	161.109	30932474
DeepCCS	[M-H]-	158.751	30932474
DeepCCS	[M-2H]-	191.831	30932474
DeepCCS	[M+Na]+	167.202	30932474
AllCCS	[M+H]+	158.0	32859911
AllCCS	[M+H-H2O]+	154.3	32859911
AllCCS	[M+NH4]+	161.5	32859911
AllCCS	[M+Na]+	162.4	32859911
AllCCS	[M-H]-	164.0	32859911
AllCCS	[M+Na-2H]-	164.0	32859911
AllCCS	[M+HCOO]-	164.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Artabsin	CC1C2CCC(C)(O)C3=CCC(C)=C3C2OC1=O	3207.9	Standard polar	33892256
Artabsin	CC1C2CCC(C)(O)C3=CCC(C)=C3C2OC1=O	2106.7	Standard non polar	33892256
Artabsin	CC1C2CCC(C)(O)C3=CCC(C)=C3C2OC1=O	2093.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Artabsin,1TMS,isomer #1	CC1=C2C(=CC1)C(C)(O[Si](C)(C)C)CCC1C(C)C(=O)OC21	2085.8	Semi standard non polar	33892256
Artabsin,1TBDMS,isomer #1	CC1=C2C(=CC1)C(C)(O[Si](C)(C)C(C)(C)C)CCC1C(C)C(=O)OC21	2299.2	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 - Artabsin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-4940000000-72297d0f95d070f04d21	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artabsin GC-MS (1 TMS) - 70eV, Positive	splash10-03fr-4191000000-4afc9d3ddc58fa2d4490	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artabsin 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 - Artabsin 10V, Positive-QTOF	splash10-001j-0290000000-1917e08848b05a99e4d6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsin 20V, Positive-QTOF	splash10-053s-1980000000-56d795286e6db101799f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsin 40V, Positive-QTOF	splash10-0zfr-9410000000-69cdf2311357d41a9fd4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsin 10V, Negative-QTOF	splash10-0002-0090000000-beb49b6e9e2d0213ddbf	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsin 20V, Negative-QTOF	splash10-0f92-0190000000-cc821321595501d485f1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsin 40V, Negative-QTOF	splash10-0kdi-3910000000-bbdae7e448f9a984281c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsin 10V, Positive-QTOF	splash10-000t-0090000000-ef7ba2258284971f651d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsin 20V, Positive-QTOF	splash10-003s-4790000000-4e1519d59d0b01e19f92	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsin 40V, Positive-QTOF	splash10-004i-5930000000-f8a50e7d49a5cf943d33	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsin 10V, Negative-QTOF	splash10-0002-0090000000-7b3a58b796a0e4263959	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsin 20V, Negative-QTOF	splash10-0002-0090000000-81ede0c30bc8d32bac56	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artabsin 40V, Negative-QTOF	splash10-004i-2980000000-ccefc146f50cd70eb369	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5089295

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

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

Showing metabocard for Artabsin (HMDB0036641)

MOL for HMDB0036641 (Artabsin)

3D MOL for HMDB0036641 (Artabsin)

3D SDF for HMDB0036641 (Artabsin)

3D-SDF for HMDB0036641 (Artabsin)

PDB for HMDB0036641 (Artabsin)

3D PDB for HMDB0036641 (Artabsin)

SMILES for HMDB0036641 (Artabsin)

INCHI for HMDB0036641 (Artabsin)

Structure for HMDB0036641 (Artabsin)

3D Structure for HMDB0036641 (Artabsin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra