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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:54:28 UTC

Update Date

2022-03-07 02:55:02 UTC

HMDB ID

HMDB0036738

Secondary Accession Numbers

HMDB36738

Metabolite Identification

Common Name

Lettucenin A

Description

Lettucenin A belongs to the class of organic compounds known as cycloheptafurans. These are organic heterocyclic compounds containing a cycloheptane derivative fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Lettucenin A has been detected, but not quantified in, lettuces (Lactuca sativa) and romaine lettuces (Lactuca sativa L. var. longifolia). This could make lettucenin a a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Lettucenin A.

Structure

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

HMDB0036738
     RDKit          3D
Lettucenin A
 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.9063    3.0452   -0.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2600    1.9813   -0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4739    1.6993    0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6208    0.2075    0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -0.2994    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9898   -1.6556    0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1599   -2.5889    0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2680   -2.2110    0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5195   -1.6824   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8516   -0.3624   -0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1173    0.1564   -0.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3735   -0.6213   -0.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7195   -0.9897   -1.5726 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9590    1.5184   -0.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9250    2.3268   -0.5860 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6699    1.8304   -0.3065 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435    0.7755   -0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4457    0.7781   -0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5707    3.8915   -0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0153    3.1249   -1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2929    1.9798    1.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3614    2.2605    0.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9244   -0.2574    1.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3165   -0.0380   -0.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8991   -3.5685    0.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4886   -2.6828   -0.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9877   -2.1454    0.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2964   -3.2518    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3473   -2.3623   -0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9589   -0.8588    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18  2  1  0
 18  5  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  1  0
M  END


  Mrv0541 05061309182D          

 18 20  0  0  0  0            999 V2000
    4.6417    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1278    0.2666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  3  2  0  0  0  0
  8  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  2  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 10  8  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  2  0  0  0  0
 15 12  1  0  0  0  0
 16  7  2  0  0  0  0
 17 15  2  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036738

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2CCC(=C)C2=C2OC(=O)C(C=O)=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O3/c1-8-3-6-11-12(7-16)15(17)18-14(11)13-9(2)4-5-10(8)13/h3,6-7H,2,4-5H2,1H3

> <INCHI_KEY>
PATCUDSVUMFCMB-UHFFFAOYSA-N

> <FORMULA>
C15H12O3

> <MOLECULAR_WEIGHT>
240.254

> <EXACT_MASS>
240.07864425

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.478300149308158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-methyl-9-methylidene-2-oxo-2H,7H,8H,9H-azuleno[4,5-b]furan-3-carbaldehyde

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
1.205812489666667

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.202021137866186

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
70.71839999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-methyl-9-methylidene-2-oxo-7H,8H-azuleno[4,5-b]furan-3-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036738
     RDKit          3D
Lettucenin A
 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.9063    3.0452   -0.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2600    1.9813   -0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4739    1.6993    0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6208    0.2075    0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -0.2994    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9898   -1.6556    0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1599   -2.5889    0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2680   -2.2110    0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5195   -1.6824   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8516   -0.3624   -0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1173    0.1564   -0.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3735   -0.6213   -0.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7195   -0.9897   -1.5726 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9590    1.5184   -0.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9250    2.3268   -0.5860 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6699    1.8304   -0.3065 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435    0.7755   -0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4457    0.7781   -0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5707    3.8915   -0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0153    3.1249   -1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2929    1.9798    1.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3614    2.2605    0.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9244   -0.2574    1.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3165   -0.0380   -0.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8991   -3.5685    0.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4886   -2.6828   -0.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9877   -2.1454    0.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2964   -3.2518    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3473   -2.3623   -0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9589   -0.8588    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18  2  1  0
 18  5  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  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       8.665   3.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.616   1.186   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.239   0.498   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.766  -2.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    6    8                                                       
CONECT    4    5    9                                                       
CONECT    5    4   10                                                       
CONECT    6    3   11                                                       
CONECT    7   12   16                                                       
CONECT    8    1    3   10                                                  
CONECT    9    2    4   13                                                  
CONECT   10    5    8   13                                                  
CONECT   11    6   12   14                                                  
CONECT   12    7   11   15                                                  
CONECT   13    9   10   14                                                  
CONECT   14   11   13   18                                                  
CONECT   15   12   17   18                                                  
CONECT   16    7                                                            
CONECT   17   15                                                            
CONECT   18   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0036738
HETATM    1  C1  UNL     1      -0.906   3.045  -0.771  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.260   1.981  -0.097  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.474   1.699   0.697  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.621   0.207   0.577  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.267  -0.299   0.251  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.990  -1.656   0.234  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.160  -2.589   0.195  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.268  -2.211   0.250  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.519  -1.682  -0.041  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.852  -0.362  -0.171  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.117   0.156  -0.345  1.00  0.00           C  
HETATM   12  C12 UNL     1       4.374  -0.621  -0.425  1.00  0.00           C  
HETATM   13  O1  UNL     1       4.720  -0.990  -1.573  1.00  0.00           O  
HETATM   14  C13 UNL     1       2.959   1.518  -0.424  1.00  0.00           C  
HETATM   15  O2  UNL     1       3.925   2.327  -0.586  1.00  0.00           O  
HETATM   16  O3  UNL     1       1.670   1.830  -0.306  1.00  0.00           O  
HETATM   17  C14 UNL     1       0.943   0.776  -0.153  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.446   0.778  -0.003  1.00  0.00           C  
HETATM   19  H1  UNL     1      -1.571   3.891  -0.787  1.00  0.00           H  
HETATM   20  H2  UNL     1       0.015   3.125  -1.315  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.293   1.980   1.769  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.361   2.260   0.369  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.924  -0.257   1.545  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.316  -0.038  -0.250  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.899  -3.568   0.642  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.489  -2.683  -0.860  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.988  -2.145   0.777  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.296  -3.252   0.541  1.00  0.00           H  
HETATM   29  H11 UNL     1       2.347  -2.362  -0.187  1.00  0.00           H  
HETATM   30  H12 UNL     1       4.959  -0.859   0.448  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3   18
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6    6   18
CONECT    6    7    8
CONECT    7   25   26   27
CONECT    8    9    9   28
CONECT    9   10   29
CONECT   10   11   11   17
CONECT   11   12   14
CONECT   12   13   13   30
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   18   18
END

HMDB0036738
     RDKit          3D
Lettucenin A
 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.9063    3.0452   -0.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2600    1.9813   -0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4739    1.6993    0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6208    0.2075    0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -0.2994    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9898   -1.6556    0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1599   -2.5889    0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2680   -2.2110    0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5195   -1.6824   -0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8516   -0.3624   -0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1173    0.1564   -0.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3735   -0.6213   -0.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7195   -0.9897   -1.5726 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9590    1.5184   -0.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9250    2.3268   -0.5860 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6699    1.8304   -0.3065 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435    0.7755   -0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4457    0.7781   -0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5707    3.8915   -0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0153    3.1249   -1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2929    1.9798    1.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3614    2.2605    0.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9244   -0.2574    1.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3165   -0.0380   -0.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8991   -3.5685    0.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4886   -2.6828   -0.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9877   -2.1454    0.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2964   -3.2518    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3473   -2.3623   -0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9589   -0.8588    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18  2  1  0
 18  5  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 12 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₃

Average Molecular Weight

240.254

Monoisotopic Molecular Weight

240.07864425

IUPAC Name

6-methyl-9-methylidene-2-oxo-2H,7H,8H,9H-azuleno[4,5-b]furan-3-carbaldehyde

Traditional Name

6-methyl-9-methylidene-2-oxo-7H,8H-azuleno[4,5-b]furan-3-carbaldehyde

CAS Registry Number

97915-46-3

SMILES

CC1=C2CCC(=C)C2=C2OC(=O)C(C=O)=C2C=C1

InChI Identifier

InChI=1S/C15H12O3/c1-8-3-6-11-12(7-16)15(17)18-14(11)13-9(2)4-5-10(8)13/h3,6-7H,2,4-5H2,1H3

InChI Key

PATCUDSVUMFCMB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloheptafurans. These are organic heterocyclic compounds containing a cycloheptane derivative fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Cycloheptafurans

Sub Class

Not Available

Direct Parent

Cycloheptafurans

Alternative Parents

Substituents

Cycloheptafuran
Aryl-aldehyde
Heteroaromatic compound
Furan
Lactone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036738)

Source

Endogenous

Endogenous (HMDB: HMDB0036738)

Plant

Plant (HMDB: HMDB0036738)

Animal

Animal (HMDB: HMDB0036738)

Exogenous

Food

Food (HMDB: HMDB0036738)

Vegetable

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Romaine lettuce (FooDB: FOOD00888)

Exogenous (HMDB: HMDB0036738)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036738)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036738)

Lipid metabolism pathway (HMDB: HMDB0036738)

Cellular process

Cell signaling (HMDB: HMDB0036738)

Biochemical process

Lipid transport (HMDB: HMDB0036738)

Role

Biological role

Energy source (HMDB: HMDB0036738)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	175 - 176 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	852.8 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	2.6	ALOGPS
logP	1.21	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.72 m³·mol⁻¹	ChemAxon
Polarizability	25.48 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]+	153.39	31661259
DarkChem	[M-H]-	151.76	31661259
DeepCCS	[M+H]+	157.449	30932474
DeepCCS	[M-H]-	155.091	30932474
DeepCCS	[M-2H]-	188.048	30932474
DeepCCS	[M+Na]+	163.543	30932474
AllCCS	[M+H]+	152.5	32859911
AllCCS	[M+H-H2O]+	148.5	32859911
AllCCS	[M+NH4]+	156.2	32859911
AllCCS	[M+Na]+	157.2	32859911
AllCCS	[M-H]-	157.1	32859911
AllCCS	[M+Na-2H]-	156.5	32859911
AllCCS	[M+HCOO]-	155.9	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.	7.65 minutes	32390414
Predicted by Siyang on May 30, 2022	15.6609 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.93 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1871.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	486.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	190.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	291.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	234.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	617.9 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	781.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	120.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1337.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	469.2 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	1481.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	409.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	418.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	435.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	454.0 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	26.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lettucenin A	CC1=C2CCC(=C)C2=C2OC(=O)C(C=O)=C2C=C1	2843.4	Standard polar	33892256
Lettucenin A	CC1=C2CCC(=C)C2=C2OC(=O)C(C=O)=C2C=C1	2227.1	Standard non polar	33892256
Lettucenin A	CC1=C2CCC(=C)C2=C2OC(=O)C(C=O)=C2C=C1	2436.2	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 - Lettucenin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-0590000000-bd5e07314e9598974438	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lettucenin A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lettucenin A 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 - Lettucenin A 10V, Positive-QTOF	splash10-0006-0090000000-1a929286d10e341e8c7a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lettucenin A 20V, Positive-QTOF	splash10-0006-0690000000-5b95d271fceefa1219bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lettucenin A 40V, Positive-QTOF	splash10-0gbc-3900000000-69e2312015f2721c9a7a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lettucenin A 10V, Negative-QTOF	splash10-000i-0090000000-27996a84f77db7517926	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lettucenin A 20V, Negative-QTOF	splash10-000i-0290000000-c96e565799c498b12564	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lettucenin A 40V, Negative-QTOF	splash10-014i-1900000000-387fe0ef6f6c911c3596	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lettucenin A 10V, Negative-QTOF	splash10-000i-0090000000-68ba9ba0c5a355ceefe4	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lettucenin A 20V, Negative-QTOF	splash10-01p9-0090000000-55248e35dfc1da037741	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lettucenin A 40V, Negative-QTOF	splash10-05mo-0950000000-6ed4031fd727a817dba7	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lettucenin A 10V, Positive-QTOF	splash10-0006-0090000000-250f7f03bbf18e8fd5e6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lettucenin A 20V, Positive-QTOF	splash10-0006-0090000000-55f8da2cb86438a6ef5b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lettucenin A 40V, Positive-QTOF	splash10-0gbi-1920000000-67126ca0cc7382fbb370	2021-09-25	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

FDB015675

KNApSAcK ID

C00020829

Chemspider ID

155799

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

178999

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1856841

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Lettucenin A (HMDB0036738)

MOL for HMDB0036738 (Lettucenin A)

3D MOL for HMDB0036738 (Lettucenin A)

3D SDF for HMDB0036738 (Lettucenin A)

3D-SDF for HMDB0036738 (Lettucenin A)

PDB for HMDB0036738 (Lettucenin A)

3D PDB for HMDB0036738 (Lettucenin A)

SMILES for HMDB0036738 (Lettucenin A)

INCHI for HMDB0036738 (Lettucenin A)

Structure for HMDB0036738 (Lettucenin A)

3D Structure for HMDB0036738 (Lettucenin A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra