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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 03:06:42 UTC

Update Date

2021-09-23 03:06:42 UTC

HMDB ID

HMDB0301858

Secondary Accession Numbers

None

Metabolite Identification

Common Name

8-Deoxylactucin

Description

8-deoxylactucin is a member of the class of 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. 8-deoxylactucin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 8-deoxylactucin can be found in chicory, which makes 8-deoxylactucin a potential biomarker for the consumption of this food product.

Structure

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

HMDB0301858
     RDKit          3D
8-Deoxylactucin
 35 37  0  0  0  0  0  0  0  0999 V2000
    3.2717    0.3260    1.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3940    0.6942    0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8426    2.0372    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0596    3.0843    0.6689 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9660    1.9881   -1.0848 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4737    0.6305   -1.1115 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7399   -0.1088   -0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796   -1.5506   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792   -2.0209    0.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4081   -1.9011    0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2254   -3.1062    0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0732   -0.7958    0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5215   -0.6717    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085   -1.6409    0.2470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7910    0.7188   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6700    1.4197   -0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6450    2.8833   -0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9306    3.3976   -0.6783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5139    0.5631    0.0239 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6528    1.0331    1.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6558   -0.6872    1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0025    0.4276   -2.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665    0.0599   -1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1650   -2.0274   -1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314   -1.9518   -0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -3.1032    0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -1.4984    1.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9462   -3.0531    1.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8077   -3.3541   -0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5323   -3.9393    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7973    1.1081   -0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1957    3.4626    0.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    3.1077   -1.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4082    3.5409    0.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0294    0.9278    0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
  7  2  1  0
 19 12  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  6
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 15 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  1
M  END

  Mrv0541 02241212512D          

 21 23  0  0  0  0            999 V2000
   -1.5321    2.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2754    1.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4590    1.1438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6053    1.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7888    1.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5321    3.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9446    0.4988    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1995   -0.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5321   -0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8647   -0.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1197    0.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0801   -0.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5321   -1.5957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9837    2.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6049    1.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2807    1.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0576    3.1929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6932    0.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5182    0.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1990    0.9602    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6725    0.3469    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  5  1  1  0  0  0  0
  3  7  1  0  0  0  0
 11  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
  7 11  1  0  0  0  0
 10 12  2  0  0  0  0
  9 13  2  0  0  0  0
 14  2  1  0  0  0  0
  3  2  1  0  0  0  0
  3 16  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 14 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  4 20  1  6  0  0  0
  3 21  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0301858

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C1CC(C)=C2C(=O)C=C(CO)[C@]2([H])[C@H]2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O4/c1-7-3-4-10-8(2)15(18)19-14(10)13-9(6-16)5-11(17)12(7)13/h5,10,13-14,16H,2-4,6H2,1H3/t10?,13-,14-/m0/s1

> <INCHI_KEY>
NIYXMGSLECQTQT-RYQGGHCKSA-N

> <FORMULA>
C15H16O4

> <MOLECULAR_WEIGHT>
260.2851

> <EXACT_MASS>
260.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.162347611037063

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9aS,9bS)-9-(hydroxymethyl)-6-methyl-3-methylidene-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
1.3274206803333333

> <ALOGPS_LOGS>
-2.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.675709580234685

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.389920866011945

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7605630390411546

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
70.29440000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9aS,9bS)-9-(hydroxymethyl)-6-methyl-3-methylidene-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301858
     RDKit          3D
8-Deoxylactucin
 35 37  0  0  0  0  0  0  0  0999 V2000
    3.2717    0.3260    1.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3940    0.6942    0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8426    2.0372    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0596    3.0843    0.6689 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9660    1.9881   -1.0848 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4737    0.6305   -1.1115 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7399   -0.1088   -0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796   -1.5506   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792   -2.0209    0.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4081   -1.9011    0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2254   -3.1062    0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0732   -0.7958    0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5215   -0.6717    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085   -1.6409    0.2470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7910    0.7188   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6700    1.4197   -0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6450    2.8833   -0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9306    3.3976   -0.6783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5139    0.5631    0.0239 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6528    1.0331    1.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6558   -0.6872    1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0025    0.4276   -2.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665    0.0599   -1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1650   -2.0274   -1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314   -1.9518   -0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -3.1032    0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -1.4984    1.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9462   -3.0531    1.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8077   -3.3541   -0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5323   -3.9393    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7973    1.1081   -0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1957    3.4626    0.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    3.1077   -1.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4082    3.5409    0.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0294    0.9278    0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
  7  2  1  0
 19 12  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  6
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 15 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  1
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.860   4.305   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.247   3.636   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.590   2.135   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.130   2.135   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.472   3.636   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.860   5.845   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.630   0.931   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.106  -0.533   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.860  -1.439   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.614  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.090   0.931   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.150  -1.009   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.860  -2.979   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.570   4.426   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.729   3.413   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.124   1.997   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.708   5.960   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.894   0.663   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -8.434   0.663   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0       0.371   1.792   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      -4.989   0.648   0.000  0.00  0.00           H+0
CONECT    1    2    5    6                                                  
CONECT    2    1   14    3                                                  
CONECT    3    7    2   16   21                                             
CONECT    4   11    5   20                                                  
CONECT    5    1    4                                                       
CONECT    6    1                                                            
CONECT    7    3    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11    4   10    7                                                  
CONECT   12   10                                                            
CONECT   13    9                                                            
CONECT   14    2   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16    3   15   18                                                  
CONECT   17   14                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20    4                                                            
CONECT   21    3                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0301858
HETATM    1  C1  UNL     1       3.272   0.326   1.069  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.394   0.694   0.171  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.843   2.037   0.006  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.060   3.084   0.669  1.00  0.00           O  
HETATM    5  O2  UNL     1       0.966   1.988  -1.085  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.474   0.630  -1.111  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.740  -0.109  -0.886  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.680  -1.551  -0.655  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.079  -2.021   0.618  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.408  -1.901   0.494  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.225  -3.106   0.665  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.073  -0.796   0.240  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.522  -0.672   0.118  1.00  0.00           C  
HETATM   14  O3  UNL     1      -3.308  -1.641   0.247  1.00  0.00           O  
HETATM   15  C12 UNL     1      -2.791   0.719  -0.163  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.670   1.420  -0.219  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.645   2.883  -0.493  1.00  0.00           C  
HETATM   18  O4  UNL     1      -2.931   3.398  -0.678  1.00  0.00           O  
HETATM   19  C15 UNL     1      -0.514   0.563   0.024  1.00  0.00           C  
HETATM   20  H1  UNL     1       3.653   1.033   1.770  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.656  -0.687   1.155  1.00  0.00           H  
HETATM   22  H3  UNL     1      -0.002   0.428  -2.095  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.366   0.060  -1.811  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.165  -2.027  -1.516  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.731  -1.952  -0.698  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.295  -3.103   0.738  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.427  -1.498   1.506  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.946  -3.053   1.507  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.808  -3.354  -0.255  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.532  -3.939   0.929  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.797   1.108  -0.306  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.196   3.463   0.340  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.052   3.108  -1.409  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.408   3.541   0.180  1.00  0.00           H  
HETATM   35  H16 UNL     1       0.029   0.928   0.933  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   19   22
CONECT    7    8   23
CONECT    8    9   24   25
CONECT    9   10   26   27
CONECT   10   11   12   12
CONECT   11   28   29   30
CONECT   12   13   19
CONECT   13   14   14   15
CONECT   15   16   16   31
CONECT   16   17   19
CONECT   17   18   32   33
CONECT   18   34
CONECT   19   35
END

HMDB0301858
     RDKit          3D
8-Deoxylactucin
 35 37  0  0  0  0  0  0  0  0999 V2000
    3.2717    0.3260    1.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3940    0.6942    0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8426    2.0372    0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0596    3.0843    0.6689 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9660    1.9881   -1.0848 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4737    0.6305   -1.1115 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7399   -0.1088   -0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796   -1.5506   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792   -2.0209    0.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4081   -1.9011    0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2254   -3.1062    0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0732   -0.7958    0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5215   -0.6717    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085   -1.6409    0.2470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7910    0.7188   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6700    1.4197   -0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6450    2.8833   -0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9306    3.3976   -0.6783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5139    0.5631    0.0239 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6528    1.0331    1.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6558   -0.6872    1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0025    0.4276   -2.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665    0.0599   -1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1650   -2.0274   -1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314   -1.9518   -0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -3.1032    0.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -1.4984    1.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9462   -3.0531    1.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8077   -3.3541   -0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5323   -3.9393    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7973    1.1081   -0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1957    3.4626    0.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    3.1077   -1.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4082    3.5409    0.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0294    0.9278    0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
  7  2  1  0
 19 12  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  6
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 15 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₄

Average Molecular Weight

260.2851

Monoisotopic Molecular Weight

260.104859

IUPAC Name

(9aS,9bS)-9-(hydroxymethyl)-6-methyl-3-methylidene-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

Traditional Name

(9aS,9bS)-9-(hydroxymethyl)-6-methyl-3-methylidene-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

CAS Registry Number

Not Available

SMILES

[H]C1CC(C)=C2C(=O)C=C(CO)[C@]2([H])[C@H]2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C15H16O4/c1-7-3-4-10-8(2)15(18)19-14(10)13-9(6-16)5-11(17)12(7)13/h5,10,13-14,16H,2-4,6H2,1H3/t10?,13-,14-/m0/s1

InChI Key

NIYXMGSLECQTQT-RYQGGHCKSA-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
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organic oxide
Primary alcohol
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0301858)

Food

Vegetable

Root vegetable

Chicory (FooDB: FOOD00049)

Process

Not Available

Role

Biological role

Industrial application

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0301858)

Agriculture

Pesticide (HMDB: HMDB0301858)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.99	ALOGPS
logP	1.33	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	13.39	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.29 m³·mol⁻¹	ChemAxon
Polarizability	27.16 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
AllCCS	[M+H]+	159.205	32859911
AllCCS	[M+H-H2O]+	155.599	32859911
AllCCS	[M+Na]+	163.515	32859911
AllCCS	[M+NH4]+	162.552	32859911
AllCCS	[M-H]-	162.929	32859911
AllCCS	[M+Na-2H]-	162.647	32859911
AllCCS	[M+HCOO]-	162.452	32859911
DeepCCS	[M-2H]-	203.056	30932474
DeepCCS	[M+Na]+	178.212	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxylactucin 10V, Positive-QTOF	splash10-01ox-0190000000-28b6dee791dcf66c198b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxylactucin 20V, Positive-QTOF	splash10-009f-0960000000-5d093bcadd6767adc106	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxylactucin 40V, Positive-QTOF	splash10-0fmi-6910000000-6c610cde068f8c77a0b5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxylactucin 10V, Negative-QTOF	splash10-0a4i-0090000000-2d08d04b4f225fbe513c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxylactucin 20V, Negative-QTOF	splash10-0ar3-0190000000-fe6106cac6bb7ed48c99	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxylactucin 40V, Negative-QTOF	splash10-05fr-2910000000-3b5325295b5e9d82387e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxylactucin 10V, Positive-QTOF	splash10-03di-0090000000-6d0f70d96b0607a013f7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxylactucin 20V, Positive-QTOF	splash10-01qc-0090000000-865060ac3a04c3130e5a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxylactucin 40V, Positive-QTOF	splash10-001r-0950000000-d0774833940f5e81298c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxylactucin 10V, Negative-QTOF	splash10-0a4i-0090000000-07597ad49430bb51c246	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxylactucin 20V, Negative-QTOF	splash10-056r-0090000000-311b87db00ccb919d30d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxylactucin 40V, Negative-QTOF	splash10-06vr-1590000000-2571710ad361409f9793	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB001527

KNApSAcK ID

Not Available

Chemspider ID

59696194

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Showing metabocard for 8-Deoxylactucin (HMDB0301858)

MOL for HMDB0301858 (8-Deoxylactucin)

3D MOL for HMDB0301858 (8-Deoxylactucin)

3D SDF for HMDB0301858 (8-Deoxylactucin)

3D-SDF for HMDB0301858 (8-Deoxylactucin)

PDB for HMDB0301858 (8-Deoxylactucin)

3D PDB for HMDB0301858 (8-Deoxylactucin)

SMILES for HMDB0301858 (8-Deoxylactucin)

INCHI for HMDB0301858 (8-Deoxylactucin)

Structure for HMDB0301858 (8-Deoxylactucin)

3D Structure for HMDB0301858 (8-Deoxylactucin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra