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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 23:37:15 UTC

Update Date

2021-09-23 23:37:15 UTC

HMDB ID

HMDB0303142

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(11S,13)-Dihydro-8-deoxylactucin

Description

(9aS,9bS)-9-(hydroxymethyl)-3,6-dimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione 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. Based on a literature review very few articles have been published on (9aS,9bS)-9-(hydroxymethyl)-3,6-dimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione.

Structure

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

HMDB0303142
     RDKit          3D
(11S,13)-Dihydro-8-deoxylactucin
 37 39  0  0  0  0  0  0  0  0999 V2000
   -0.4119    3.6203    0.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0179    2.2541   -0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0077    1.3350   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3402    1.6286    0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7400    2.7543    0.7739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0912    0.3911    0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3462   -0.5735   -0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8745   -1.9809   -0.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7525   -2.2613   -1.8215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0046   -0.0848   -0.5120 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0227   -0.8843    0.2676 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2505   -2.0643   -0.4937 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5666   -2.4659   -0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0253   -3.5424   -0.7804 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3123   -1.4165    0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5953   -1.7897    1.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3644   -0.2475    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344    0.6325   -0.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3666    2.0821   -0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6461    3.5469    1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2165    4.0679   -0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5228    4.2362    0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1545    0.2956    0.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3134   -2.6562    0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9400   -2.0486   -0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0065   -2.8998   -2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -0.2507   -1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3210   -1.1904    1.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2652   -1.1405   -0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4606   -2.8661    2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9623   -1.2437    2.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6634   -1.5631    2.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4755    0.3462    1.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1455    0.2877   -1.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7483    0.5533   -1.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0677    2.5434    0.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5187    2.5947   -1.6921 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 10  3  1  0
 17 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  6
 11 28  1  1
 15 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
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
    0.1990    0.9603    0.0000 H   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
   -2.6725    0.3469    0.0000 H   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
  1  2  2  0  0  0  0
  5  1  1  0  0  0  0
  3  8  1  0  0  0  0
 12  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  6  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
  8 12  1  0  0  0  0
 11 13  1  6  0  0  0
 10 14  2  0  0  0  0
 15  2  1  0  0  0  0
  3  2  1  0  0  0  0
 17  3  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 15 18  2  0  0  0  0
  3 19  1  6  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303142

> <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/C15H18O4/c1-7-3-4-10-8(2)15(18)19-14(10)13-9(6-16)5-11(17)12(7)13/h5,8,10,13-14,16H,3-4,6H2,1-2H3/t8?,10?,13-,14-/m0/s1

> <INCHI_KEY>
SNIFBMIPCYBVSS-IGPXNYDSSA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.301

> <EXACT_MASS>
262.120509064

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.703768599588727

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
1.1857659759999997

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.683581212020261

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.661562206567076

> <JCHEM_PKA_STRONGEST_BASIC>
-2.760557716260429

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
70.49100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.19e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303142
     RDKit          3D
(11S,13)-Dihydro-8-deoxylactucin
 37 39  0  0  0  0  0  0  0  0999 V2000
   -0.4119    3.6203    0.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0179    2.2541   -0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0077    1.3350   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3402    1.6286    0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7400    2.7543    0.7739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0912    0.3911    0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3462   -0.5735   -0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8745   -1.9809   -0.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7525   -2.2613   -1.8215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0046   -0.0848   -0.5120 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0227   -0.8843    0.2676 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2505   -2.0643   -0.4937 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5666   -2.4659   -0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0253   -3.5424   -0.7804 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3123   -1.4165    0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5953   -1.7897    1.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3644   -0.2475    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344    0.6325   -0.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3666    2.0821   -0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6461    3.5469    1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2165    4.0679   -0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5228    4.2362    0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1545    0.2956    0.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3134   -2.6562    0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9400   -2.0486   -0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0065   -2.8998   -2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -0.2507   -1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3210   -1.1904    1.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2652   -1.1405   -0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4606   -2.8661    2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9623   -1.2437    2.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6634   -1.5631    2.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4755    0.3462    1.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1455    0.2877   -1.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7483    0.5533   -1.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0677    2.5434    0.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5187    2.5947   -1.6921 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 10  3  1  0
 17 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  6
 11 28  1  1
 15 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
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  H   UNK     0       0.371   1.793   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0      -3.630   0.931   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.106  -0.533   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.860  -1.439   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.614  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.090   0.931   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.150  -1.009   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.860  -2.979   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.570   4.426   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.729   3.413   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.124   1.997   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.708   5.960   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0      -4.989   0.648   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0      -6.894   0.663   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -8.434   0.663   0.000  0.00  0.00           O+0
CONECT    1    2    5    6                                                  
CONECT    2    1   15    3                                                  
CONECT    3    8    2   17   19                                             
CONECT    4   12    5    7                                                  
CONECT    5    1    4                                                       
CONECT    6    1                                                            
CONECT    7    4                                                            
CONECT    8    3    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12    4   11    8                                                  
CONECT   13   11                                                            
CONECT   14   10                                                            
CONECT   15    2   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17    3   16   20                                                  
CONECT   18   15                                                            
CONECT   19    3                                                            
CONECT   20   17   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0303142
HETATM    1  C1  UNL     1      -0.412   3.620   0.248  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.018   2.254  -0.224  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.008   1.335  -0.148  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.340   1.629   0.344  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.740   2.754   0.774  1.00  0.00           O  
HETATM    6  C5  UNL     1      -3.091   0.391   0.239  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.346  -0.573  -0.252  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.874  -1.981  -0.474  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.752  -2.261  -1.821  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.005  -0.085  -0.512  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.023  -0.884   0.268  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.251  -2.064  -0.494  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.567  -2.466  -0.353  1.00  0.00           C  
HETATM   14  O4  UNL     1       2.025  -3.542  -0.780  1.00  0.00           O  
HETATM   15  C11 UNL     1       2.312  -1.416   0.376  1.00  0.00           C  
HETATM   16  C12 UNL     1       2.595  -1.790   1.803  1.00  0.00           C  
HETATM   17  C13 UNL     1       1.364  -0.248   0.251  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.634   0.633  -0.918  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.367   2.082  -0.709  1.00  0.00           C  
HETATM   20  H1  UNL     1      -0.646   3.547   1.329  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.217   4.068  -0.357  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.523   4.236   0.210  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.154   0.296   0.540  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.313  -2.656   0.185  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.940  -2.049  -0.208  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.007  -2.900  -2.004  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.783  -0.251  -1.594  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.321  -1.190   1.255  1.00  0.00           H  
HETATM   29  H10 UNL     1       3.265  -1.141  -0.144  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.461  -2.866   2.010  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.962  -1.244   2.535  1.00  0.00           H  
HETATM   32  H13 UNL     1       3.663  -1.563   2.044  1.00  0.00           H  
HETATM   33  H14 UNL     1       1.475   0.346   1.193  1.00  0.00           H  
HETATM   34  H15 UNL     1       1.146   0.288  -1.839  1.00  0.00           H  
HETATM   35  H16 UNL     1       2.748   0.553  -1.121  1.00  0.00           H  
HETATM   36  H17 UNL     1       2.068   2.543   0.040  1.00  0.00           H  
HETATM   37  H18 UNL     1       1.519   2.595  -1.692  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   19
CONECT    3    4   10
CONECT    4    5    5    6
CONECT    6    7    7   23
CONECT    7    8   10
CONECT    8    9   24   25
CONECT    9   26
CONECT   10   11   27
CONECT   11   12   17   28
CONECT   12   13
CONECT   13   14   14   15
CONECT   15   16   17   29
CONECT   16   30   31   32
CONECT   17   18   33
CONECT   18   19   34   35
CONECT   19   36   37
END

HMDB0303142
     RDKit          3D
(11S,13)-Dihydro-8-deoxylactucin
 37 39  0  0  0  0  0  0  0  0999 V2000
   -0.4119    3.6203    0.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0179    2.2541   -0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0077    1.3350   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3402    1.6286    0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7400    2.7543    0.7739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0912    0.3911    0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3462   -0.5735   -0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8745   -1.9809   -0.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7525   -2.2613   -1.8215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0046   -0.0848   -0.5120 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0227   -0.8843    0.2676 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2505   -2.0643   -0.4937 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5666   -2.4659   -0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0253   -3.5424   -0.7804 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3123   -1.4165    0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5953   -1.7897    1.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3644   -0.2475    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344    0.6325   -0.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3666    2.0821   -0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6461    3.5469    1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2165    4.0679   -0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5228    4.2362    0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1545    0.2956    0.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3134   -2.6562    0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9400   -2.0486   -0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0065   -2.8998   -2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -0.2507   -1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3210   -1.1904    1.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2652   -1.1405   -0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4606   -2.8661    2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9623   -1.2437    2.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6634   -1.5631    2.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4755    0.3462    1.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1455    0.2877   -1.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7483    0.5533   -1.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0677    2.5434    0.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5187    2.5947   -1.6921 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
 10  3  1  0
 17 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  6
 11 28  1  1
 15 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₄

Average Molecular Weight

262.301

Monoisotopic Molecular Weight

262.120509064

IUPAC Name

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

Traditional Name

(9aS,9bS)-9-(hydroxymethyl)-3,6-dimethyl-3H,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/C15H18O4/c1-7-3-4-10-8(2)15(18)19-14(10)13-9(6-16)5-11(17)12(7)13/h5,8,10,13-14,16H,3-4,6H2,1-2H3/t8?,10?,13-,14-/m0/s1

InChI Key

SNIFBMIPCYBVSS-IGPXNYDSSA-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
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Chicory (FooDB: FOOD00049)

Process

Not Available

Role

Biological role

bitter (HMDB: HMDB0303142)

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	1.17	ALOGPS
logP	1.19	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	13.66	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	70.49 m³·mol⁻¹	ChemAxon
Polarizability	27.7 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]+	159.976	32859911
AllCCS	[M+H-H2O]+	156.42	32859911
AllCCS	[M+Na]+	164.226	32859911
AllCCS	[M+NH4]+	163.277	32859911
AllCCS	[M-H]-	164.68	32859911
AllCCS	[M+Na-2H]-	164.507	32859911
AllCCS	[M+HCOO]-	164.431	32859911
DeepCCS	[M-2H]-	204.022	30932474
DeepCCS	[M+Na]+	179.057	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 - (11S,13)-Dihydro-8-deoxylactucin 10V, Positive-QTOF	splash10-01ot-0190000000-ac66bdbb74893249fd0d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,13)-Dihydro-8-deoxylactucin 20V, Positive-QTOF	splash10-00ba-0960000000-ef9be809a79767b25af3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,13)-Dihydro-8-deoxylactucin 40V, Positive-QTOF	splash10-0umi-7910000000-6c59802ec51c65674d39	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,13)-Dihydro-8-deoxylactucin 10V, Negative-QTOF	splash10-03di-0090000000-91777ed03c63829497bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,13)-Dihydro-8-deoxylactucin 20V, Negative-QTOF	splash10-03yl-0190000000-1e18d5f2444266325897	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,13)-Dihydro-8-deoxylactucin 40V, Negative-QTOF	splash10-0h90-2910000000-2e81217885a9fdbbf0ae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,13)-Dihydro-8-deoxylactucin 10V, Positive-QTOF	splash10-03di-0090000000-5517b900675acd821851	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,13)-Dihydro-8-deoxylactucin 20V, Positive-QTOF	splash10-03ds-0190000000-f32c0f3398eb92c05f7a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,13)-Dihydro-8-deoxylactucin 40V, Positive-QTOF	splash10-015i-1940000000-dddf708fe6daa52e3ff4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,13)-Dihydro-8-deoxylactucin 10V, Negative-QTOF	splash10-03di-0090000000-92a5419893bc0c0dd3ae	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,13)-Dihydro-8-deoxylactucin 20V, Negative-QTOF	splash10-03di-0090000000-b6246076af38f2a4b74e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (11S,13)-Dihydro-8-deoxylactucin 40V, Negative-QTOF	splash10-056r-0590000000-8a2c0b978457261cf8c6	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

FDB007935

KNApSAcK ID

Not Available

Chemspider ID

59696454

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 (11S,13)-Dihydro-8-deoxylactucin (HMDB0303142)

MOL for HMDB0303142 ((11S,13)-Dihydro-8-deoxylactucin)

3D MOL for HMDB0303142 ((11S,13)-Dihydro-8-deoxylactucin)

3D SDF for HMDB0303142 ((11S,13)-Dihydro-8-deoxylactucin)

3D-SDF for HMDB0303142 ((11S,13)-Dihydro-8-deoxylactucin)

PDB for HMDB0303142 ((11S,13)-Dihydro-8-deoxylactucin)

3D PDB for HMDB0303142 ((11S,13)-Dihydro-8-deoxylactucin)

SMILES for HMDB0303142 ((11S,13)-Dihydro-8-deoxylactucin)

INCHI for HMDB0303142 ((11S,13)-Dihydro-8-deoxylactucin)

Structure for HMDB0303142 ((11S,13)-Dihydro-8-deoxylactucin)

3D Structure for HMDB0303142 ((11S,13)-Dihydro-8-deoxylactucin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra