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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:50:15 UTC

Update Date

2022-03-07 02:54:38 UTC

HMDB ID

HMDB0035814

Secondary Accession Numbers

HMDB35814

Metabolite Identification

Common Name

Lactucin

Description

Lactucin 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. Lactucin has been detected, but not quantified in, several different foods, such as herbs and spices, green vegetables, lettuces (Lactuca sativa), robusta coffees (Coffea canephora), and coffee and coffee products. This could make lactucin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Lactucin.

Structure

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

HMDB0035814
     RDKit          3D
Lactucin
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.7216    1.6250   -0.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5606    1.1260   -0.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8434    1.0117   -1.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3686    1.2508   -3.0020 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5195    0.6018   -1.6055 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3324    0.9952   -0.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9057    0.5814    0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454    1.1947   -0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3973    2.6386   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7046    2.7934   -0.8069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0695    0.2767   -0.2132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615   -1.0365    0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2287   -2.1268    0.1165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1821   -0.8303    0.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4151   -1.8634    0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9879   -3.2020    0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0159   -1.7178    1.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7576   -0.9760    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0812   -1.3924    0.1575 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6049    0.4898    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0662    1.6046    0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4049    2.0804   -1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3940    2.1066   -0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8061    0.9643    1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2256    3.2500    0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6969    3.0316   -1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8098    2.1833   -1.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1107    0.4380   -0.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8232   -3.1932    1.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2421   -3.9487    1.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3715   -3.5503   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1674   -1.2428    2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4556   -2.7356    1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496   -1.2216   -0.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2606   -2.0310   -0.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7796    0.8243    1.3769 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
  8 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20  2  1  0
 20  6  1  0
 14  7  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END

lactucin
  Mrv1572001071617122D          

 20 22  0  0  0  0            999 V2000
    3.6754    3.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    3.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    2.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    1.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    0.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    2.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    2.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    2.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    3.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988    3.7963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    3.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    0.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882   -0.2656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    2.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749    2.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  2 14  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035814

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2C(C3OC(=O)C(=C)C3C(O)C1)C(CO)=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3

> <INCHI_KEY>
VJQAFLAZRVKAKM-UHFFFAOYSA-N

> <FORMULA>
C15H16O5

> <MOLECULAR_WEIGHT>
276.288

> <EXACT_MASS>
276.099773615

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.9208870492323

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.28

> <JCHEM_LOGP>
-0.017741119666666097

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.72776069066077

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.003862645150448

> <JCHEM_PKA_STRONGEST_BASIC>
-2.760564152181555

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
71.8651

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lactucin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035814
     RDKit          3D
Lactucin
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.7216    1.6250   -0.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5606    1.1260   -0.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8434    1.0117   -1.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3686    1.2508   -3.0020 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5195    0.6018   -1.6055 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3324    0.9952   -0.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9057    0.5814    0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454    1.1947   -0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3973    2.6386   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7046    2.7934   -0.8069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0695    0.2767   -0.2132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615   -1.0365    0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2287   -2.1268    0.1165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1821   -0.8303    0.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4151   -1.8634    0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9879   -3.2020    0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0159   -1.7178    1.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7576   -0.9760    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0812   -1.3924    0.1575 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6049    0.4898    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0662    1.6046    0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4049    2.0804   -1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3940    2.1066   -0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8061    0.9643    1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2256    3.2500    0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6969    3.0316   -1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8098    2.1833   -1.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1107    0.4380   -0.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8232   -3.1932    1.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2421   -3.9487    1.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3715   -3.5503   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1674   -1.2428    2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4556   -2.7356    1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496   -1.2216   -0.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2606   -2.0310   -0.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7796    0.8243    1.3769 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
  8 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20  2  1  0
 20  6  1  0
 14  7  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: lactucin                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       6.861   7.086   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.657   6.126   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.999   4.625   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.039   3.421   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.499   3.421   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.651   2.136   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.166   2.545   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.038   1.585   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.097   4.084   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.188   4.932   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.539   4.625   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.882   6.126   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.678   7.086   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.269   6.794   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.888   2.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.347   0.694   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.325  -0.496   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.372   2.545   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.441   4.084   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.726   4.932   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    2                                                       
CONECT   15    4   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18    3   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0035814
HETATM    1  C1  UNL     1       3.722   1.625  -0.309  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.561   1.126  -0.623  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.843   1.012  -1.886  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.369   1.251  -3.002  1.00  0.00           O  
HETATM    5  O2  UNL     1       0.519   0.602  -1.605  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.332   0.995  -0.264  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.906   0.581   0.400  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.145   1.195  -0.076  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.397   2.639  -0.382  1.00  0.00           C  
HETATM   10  O3  UNL     1      -3.705   2.793  -0.807  1.00  0.00           O  
HETATM   11  C8  UNL     1      -3.070   0.277  -0.213  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.561  -1.036   0.144  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.229  -2.127   0.116  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.182  -0.830   0.523  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.415  -1.863   0.874  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.988  -3.202   0.909  1.00  0.00           C  
HETATM   17  C13 UNL     1       1.016  -1.718   1.213  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.758  -0.976   0.122  1.00  0.00           C  
HETATM   19  O5  UNL     1       3.081  -1.392   0.157  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.605   0.490   0.362  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.066   1.605   0.714  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.405   2.080  -1.016  1.00  0.00           H  
HETATM   23  H3  UNL     1       0.394   2.107  -0.252  1.00  0.00           H  
HETATM   24  H4  UNL     1      -0.806   0.964   1.480  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.226   3.250   0.544  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.697   3.032  -1.134  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.810   2.183  -1.604  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.111   0.438  -0.553  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.823  -3.193   1.650  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.242  -3.949   1.220  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.372  -3.550  -0.080  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.167  -1.243   2.183  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.456  -2.736   1.254  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.350  -1.222  -0.872  1.00  0.00           H  
HETATM   35  H15 UNL     1       3.261  -2.031  -0.564  1.00  0.00           H  
HETATM   36  H16 UNL     1       1.780   0.824   1.377  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3   20
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   20   23
CONECT    7    8   14   24
CONECT    8    9   11   11
CONECT    9   10   25   26
CONECT   10   27
CONECT   11   12   28
CONECT   12   13   13   14
CONECT   14   15   15
CONECT   15   16   17
CONECT   16   29   30   31
CONECT   17   18   32   33
CONECT   18   19   20   34
CONECT   19   35
CONECT   20   36
END

HMDB0035814
     RDKit          3D
Lactucin
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.7216    1.6250   -0.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5606    1.1260   -0.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8434    1.0117   -1.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3686    1.2508   -3.0020 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5195    0.6018   -1.6055 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3324    0.9952   -0.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9057    0.5814    0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454    1.1947   -0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3973    2.6386   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7046    2.7934   -0.8069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0695    0.2767   -0.2132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615   -1.0365    0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2287   -2.1268    0.1165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1821   -0.8303    0.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4151   -1.8634    0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9879   -3.2020    0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0159   -1.7178    1.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7576   -0.9760    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0812   -1.3924    0.1575 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6049    0.4898    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0662    1.6046    0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4049    2.0804   -1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3940    2.1066   -0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8061    0.9643    1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2256    3.2500    0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6969    3.0316   -1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8098    2.1833   -1.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1107    0.4380   -0.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8232   -3.1932    1.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2421   -3.9487    1.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3715   -3.5503   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1674   -1.2428    2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4556   -2.7356    1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496   -1.2216   -0.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2606   -2.0310   -0.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7796    0.8243    1.3769 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
  8 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20  2  1  0
 20  6  1  0
 14  7  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
11beta,13-Dihydrolactucin	HMDB
Lactucin	MeSH

Chemical Formula

C₁₅H₁₆O₅

Average Molecular Weight

276.288

Monoisotopic Molecular Weight

276.099773615

IUPAC Name

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

Traditional Name

lactucin

CAS Registry Number

1891-29-8

SMILES

CC1=C2C(C3OC(=O)C(=C)C3C(O)C1)C(CO)=CC2=O

InChI Identifier

InChI=1S/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3

InChI Key

VJQAFLAZRVKAKM-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
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Carbonyl group
Primary alcohol
Organooxygen compound
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
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: HMDB0035814)

Source

Endogenous

Endogenous (HMDB: HMDB0035814)

Plant

Plant (HMDB: HMDB0035814)
Coffea (HMDB: HMDB0035814)

Exogenous

Food

Food (HMDB: HMDB0035814)

Vegetable

Leaf vegetable

Root vegetable

Chicory (FooDB: FOOD00049)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0035814)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0035814)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	224 - 228 °C	Not Available
Boiling Point	575.60 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	71070 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.330 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.84 g/L	ALOGPS
logP	-0.28	ALOGPS
logP	-0.018	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	13	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.87 m³·mol⁻¹	ChemAxon
Polarizability	27.92 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	165.103	31661259
DarkChem	[M-H]-	160.868	31661259
DeepCCS	[M+H]+	163.193	30932474
DeepCCS	[M-H]-	160.835	30932474
DeepCCS	[M-2H]-	194.052	30932474
DeepCCS	[M+Na]+	169.286	30932474
AllCCS	[M+H]+	163.0	32859911
AllCCS	[M+H-H2O]+	159.4	32859911
AllCCS	[M+NH4]+	166.2	32859911
AllCCS	[M+Na]+	167.2	32859911
AllCCS	[M-H]-	165.1	32859911
AllCCS	[M+Na-2H]-	164.7	32859911
AllCCS	[M+HCOO]-	164.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.29 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1442 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.06 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1705.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	220.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	116.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	55.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	275.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	388.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	125.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	712.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	323.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1105.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	225.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	275.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	377.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	212.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	150.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lactucin	CC1=C2C(C3OC(=O)C(=C)C3C(O)C1)C(CO)=CC2=O	3899.4	Standard polar	33892256
Lactucin	CC1=C2C(C3OC(=O)C(=C)C3C(O)C1)C(CO)=CC2=O	2437.1	Standard non polar	33892256
Lactucin	CC1=C2C(C3OC(=O)C(=C)C3C(O)C1)C(CO)=CC2=O	2743.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lactucin,1TMS,isomer #1	C=C1C(=O)OC2C3C(CO)=CC(=O)C3=C(C)CC(O[Si](C)(C)C)C12	2583.4	Semi standard non polar	33892256
Lactucin,1TMS,isomer #2	C=C1C(=O)OC2C3C(CO[Si](C)(C)C)=CC(=O)C3=C(C)CC(O)C12	2593.9	Semi standard non polar	33892256
Lactucin,2TMS,isomer #1	C=C1C(=O)OC2C3C(CO[Si](C)(C)C)=CC(=O)C3=C(C)CC(O[Si](C)(C)C)C12	2620.4	Semi standard non polar	33892256
Lactucin,1TBDMS,isomer #1	C=C1C(=O)OC2C3C(CO)=CC(=O)C3=C(C)CC(O[Si](C)(C)C(C)(C)C)C12	2789.7	Semi standard non polar	33892256
Lactucin,1TBDMS,isomer #2	C=C1C(=O)OC2C3C(CO[Si](C)(C)C(C)(C)C)=CC(=O)C3=C(C)CC(O)C12	2809.3	Semi standard non polar	33892256
Lactucin,2TBDMS,isomer #1	C=C1C(=O)OC2C3C(CO[Si](C)(C)C(C)(C)C)=CC(=O)C3=C(C)CC(O[Si](C)(C)C(C)(C)C)C12	3020.6	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 - Lactucin GC-MS (Non-derivatized) - 70eV, Positive	splash10-052b-5790000000-b95d08ba5457bf6b2069	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lactucin GC-MS (2 TMS) - 70eV, Positive	splash10-0ab9-2139000000-fe4b945f22fd4dcc8988	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lactucin 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 - Lactucin 10V, Positive-QTOF	splash10-0a6r-0090000000-adba28495fd27a848006	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactucin 20V, Positive-QTOF	splash10-052u-0490000000-fb65751d00ebf7cfc048	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactucin 40V, Positive-QTOF	splash10-0f76-5950000000-cc2ba0ae124168adaaa1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactucin 10V, Negative-QTOF	splash10-004i-0090000000-aa9e3a2cce7827efdc3a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactucin 20V, Negative-QTOF	splash10-057i-0090000000-48ae893a3deee473fadb	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactucin 40V, Negative-QTOF	splash10-00dl-2910000000-9062473d504431458708	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactucin 10V, Positive-QTOF	splash10-0a4i-0090000000-5eee9e278d85992a4bc3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactucin 20V, Positive-QTOF	splash10-0a6u-0090000000-a5e6ac486e245f455cda	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactucin 40V, Positive-QTOF	splash10-00bd-0960000000-d62be5c7a1ff74131be2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactucin 10V, Negative-QTOF	splash10-004i-0090000000-aa99d0f367d18fe63c0c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactucin 20V, Negative-QTOF	splash10-0a6r-0090000000-9caf2622ff8214727496	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactucin 40V, Negative-QTOF	splash10-004r-0290000000-3d238649ddfe7d1c32b0	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lactucin

METLIN ID

Not Available

PubChem Compound

3756497

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1699961

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 Lactucin (HMDB0035814)

MOL for HMDB0035814 (Lactucin)

3D MOL for HMDB0035814 (Lactucin)

3D SDF for HMDB0035814 (Lactucin)

3D-SDF for HMDB0035814 (Lactucin)

PDB for HMDB0035814 (Lactucin)

3D PDB for HMDB0035814 (Lactucin)

SMILES for HMDB0035814 (Lactucin)

INCHI for HMDB0035814 (Lactucin)

Structure for HMDB0035814 (Lactucin)

3D Structure for HMDB0035814 (Lactucin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra