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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:49:03 UTC

Update Date

2022-03-07 02:53:57 UTC

HMDB ID

HMDB0034042

Secondary Accession Numbers

HMDB34042

Metabolite Identification

Common Name

Lucernol

Description

Glycerol 1,2-di-(9Z-octadecenoate) belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. Glycerol 1,2-di-(9Z-octadecenoate) is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0034042
     RDKit          3D
Lucernol
 29 32  0  0  0  0  0  0  0  0999 V2000
   -0.9329    0.6022   -3.2271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657    0.3904   -2.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1426    0.4365   -2.3400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9566    0.2239   -1.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3388    0.2818   -1.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1558    0.0483   -0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5388    0.0970   -0.5111 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6294   -0.2418    0.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4878   -0.4720    1.9233 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2719   -0.3027    1.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4658   -0.0653   -0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0901   -0.1271    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6450   -0.3752    1.1113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9128   -0.3215    0.7789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0160   -0.5255    1.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535   -0.4099    0.9943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3668   -0.6152    1.8175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3745   -0.1093   -0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2434    0.0902   -1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0109   -0.0233   -0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    0.1051   -1.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395    0.5087   -2.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1495   -0.0668    0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1276   -0.6838    2.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8239   -0.5264    1.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8983   -0.7620    2.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7219    0.2279    2.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3419   -0.0261   -0.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3132    0.3270   -2.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21  2  1  0
 11  4  1  0
 21 12  2  0
 20 14  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 15 26  1  0
 17 27  1  0
 18 28  1  0
 19 29  1  0
M  END


  Mrv0541 05061307312D          

 21 24  0  0  0  0            999 V2000
   -0.4867    3.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466    3.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    2.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2075    3.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    2.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9407    3.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0128    2.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2891    2.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601    2.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014    2.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838    3.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365    3.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892    2.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    4.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2591    2.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7418    1.4187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4838    2.8924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548    4.8202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6731    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9312    4.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  1  1  0  0  0  0
  6  3  2  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  9  4  2  0  0  0  0
 10  5  2  0  0  0  0
 10  9  1  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 12  5  1  0  0  0  0
 12  8  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
 16  6  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 15  2  0  0  0  0
 20 11  1  0  0  0  0
 20 14  1  0  0  0  0
 21 12  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034042

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H8O6/c16-6-1-2-7-11(3-6)20-14-8-4-9(17)10(18)5-12(8)21-15(19)13(7)14/h1-5,16-18H

> <INCHI_KEY>
CJPXZAMCIOOMNF-UHFFFAOYSA-N

> <FORMULA>
C15H8O6

> <MOLECULAR_WEIGHT>
284.2204

> <EXACT_MASS>
284.032087988

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.388073617054577

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5,14-trihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
2.0937560006666662

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.111782818630248

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.216304423819977

> <JCHEM_PKA_STRONGEST_BASIC>
-4.351480868608245

> <JCHEM_POLAR_SURFACE_AREA>
100.13

> <JCHEM_REFRACTIVITY>
71.60040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5,14-trihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034042
     RDKit          3D
Lucernol
 29 32  0  0  0  0  0  0  0  0999 V2000
   -0.9329    0.6022   -3.2271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657    0.3904   -2.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1426    0.4365   -2.3400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9566    0.2239   -1.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3388    0.2818   -1.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1558    0.0483   -0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5388    0.0970   -0.5111 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6294   -0.2418    0.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4878   -0.4720    1.9233 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2719   -0.3027    1.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4658   -0.0653   -0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0901   -0.1271    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6450   -0.3752    1.1113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9128   -0.3215    0.7789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0160   -0.5255    1.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535   -0.4099    0.9943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3668   -0.6152    1.8175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3745   -0.1093   -0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2434    0.0902   -1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0109   -0.0233   -0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    0.1051   -1.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395    0.5087   -2.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1495   -0.0668    0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1276   -0.6838    2.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8239   -0.5264    1.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8983   -0.7620    2.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7219    0.2279    2.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3419   -0.0261   -0.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3132    0.3270   -2.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21  2  1  0
 11  4  1  0
 21 12  2  0
 20 14  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 15 26  1  0
 17 27  1  0
 18 28  1  0
 19 29  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      -0.909   6.056   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.460   6.761   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.314   3.685   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.469   3.848   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.854   6.599   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.982   4.518   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.756   5.929   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.624   5.135   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.006   3.936   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.699   5.311   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.683   4.391   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.316   6.511   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.241   6.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.087   5.047   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.934   7.710   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.350   3.812   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.851   2.648   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.236   5.399   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.089   8.998   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.123   3.846   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.472   7.798   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    7                                                       
CONECT    3    6   11                                                       
CONECT    4    8    9                                                       
CONECT    5   10   12                                                       
CONECT    6    1    3   16                                                  
CONECT    7    2   11   13                                                  
CONECT    8    4   12   14                                                  
CONECT    9    4   10   17                                                  
CONECT   10    5    9   18                                                  
CONECT   11    3    7   20                                                  
CONECT   12    5    8   21                                                  
CONECT   13    7   14   15                                                  
CONECT   14    8   13   20                                                  
CONECT   15   13   19   21                                                  
CONECT   16    6                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   15                                                            
CONECT   20   11   14                                                       
CONECT   21   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0034042
HETATM    1  O1  UNL     1      -0.933   0.602  -3.227  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.166   0.390  -2.234  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.143   0.437  -2.340  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.957   0.224  -1.340  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.339   0.282  -1.492  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.156   0.048  -0.400  1.00  0.00           C  
HETATM    7  O3  UNL     1       5.539   0.097  -0.511  1.00  0.00           O  
HETATM    8  C5  UNL     1       3.629  -0.242   0.842  1.00  0.00           C  
HETATM    9  O4  UNL     1       4.488  -0.472   1.923  1.00  0.00           O  
HETATM   10  C6  UNL     1       2.272  -0.303   1.009  1.00  0.00           C  
HETATM   11  C7  UNL     1       1.466  -0.065  -0.099  1.00  0.00           C  
HETATM   12  C8  UNL     1       0.090  -0.127   0.071  1.00  0.00           C  
HETATM   13  O5  UNL     1      -0.645  -0.375   1.111  1.00  0.00           O  
HETATM   14  C9  UNL     1      -1.913  -0.321   0.779  1.00  0.00           C  
HETATM   15  C10 UNL     1      -3.016  -0.525   1.597  1.00  0.00           C  
HETATM   16  C11 UNL     1      -4.253  -0.410   0.994  1.00  0.00           C  
HETATM   17  O6  UNL     1      -5.367  -0.615   1.818  1.00  0.00           O  
HETATM   18  C12 UNL     1      -4.375  -0.109  -0.343  1.00  0.00           C  
HETATM   19  C13 UNL     1      -3.243   0.090  -1.139  1.00  0.00           C  
HETATM   20  C14 UNL     1      -2.011  -0.023  -0.545  1.00  0.00           C  
HETATM   21  C15 UNL     1      -0.721   0.105  -1.016  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.740   0.509  -2.464  1.00  0.00           H  
HETATM   23  H2  UNL     1       6.150  -0.067   0.258  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.128  -0.684   2.832  1.00  0.00           H  
HETATM   25  H4  UNL     1       1.824  -0.526   1.964  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.898  -0.762   2.651  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.722   0.228   2.274  1.00  0.00           H  
HETATM   28  H7  UNL     1      -5.342  -0.026  -0.783  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.313   0.327  -2.190  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4
CONECT    4    5    5   11
CONECT    5    6   22
CONECT    6    7    8    8
CONECT    7   23
CONECT    8    9   10
CONECT    9   24
CONECT   10   11   11   25
CONECT   11   12
CONECT   12   13   21   21
CONECT   13   14
CONECT   14   15   15   20
CONECT   15   16   26
CONECT   16   17   18   18
CONECT   17   27
CONECT   18   19   28
CONECT   19   20   20   29
CONECT   20   21
END

HMDB0034042
     RDKit          3D
Lucernol
 29 32  0  0  0  0  0  0  0  0999 V2000
   -0.9329    0.6022   -3.2271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657    0.3904   -2.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1426    0.4365   -2.3400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9566    0.2239   -1.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3388    0.2818   -1.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1558    0.0483   -0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5388    0.0970   -0.5111 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6294   -0.2418    0.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4878   -0.4720    1.9233 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2719   -0.3027    1.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4658   -0.0653   -0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0901   -0.1271    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6450   -0.3752    1.1113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9128   -0.3215    0.7789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0160   -0.5255    1.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535   -0.4099    0.9943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3668   -0.6152    1.8175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3745   -0.1093   -0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2434    0.0902   -1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0109   -0.0233   -0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    0.1051   -1.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395    0.5087   -2.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1495   -0.0668    0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1276   -0.6838    2.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8239   -0.5264    1.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8983   -0.7620    2.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7219    0.2279    2.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3419   -0.0261   -0.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3132    0.3270   -2.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21  2  1  0
 11  4  1  0
 21 12  2  0
 20 14  1  0
  5 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 15 26  1  0
 17 27  1  0
 18 28  1  0
 19 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Glycerol 1,2-di-(9Z-octadecenoic acid)	Generator
2,3,9-Trihydroxy-6H-benzofuro(3,2-c)(1)benzopyran-6-one	HMDB
2,3,9-Trihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one, 9ci	HMDB
2,3-Dimethoxy-alpha-methyl-benzeneethanamine	HMDB
6,7,12-Trihydroxycoumestan	HMDB

Chemical Formula

C₁₅H₈O₆

Average Molecular Weight

284.2204

Monoisotopic Molecular Weight

284.032087988

IUPAC Name

4,5,14-trihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

Traditional Name

4,5,14-trihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

CAS Registry Number

15402-22-9

SMILES

OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C(O)=C2

InChI Identifier

InChI=1S/C15H8O6/c16-6-1-2-7-11(3-6)20-14-8-4-9(17)10(18)5-12(8)21-15(19)13(7)14/h1-5,16-18H

InChI Key

CJPXZAMCIOOMNF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Diradylglycerols

Direct Parent

1,2-diacylglycerols

Alternative Parents

Substituents

1,2-acyl-sn-glycerol
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0034042)

Cellular substructure

Membrane (HMDB: HMDB0034042)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034042)

Source

Exogenous

Food

Food (HMDB: HMDB0034042)

Herb and spice

Herb

Alfalfa (FooDB: FOOD00286)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0034042)
Fabaceae (HMDB: HMDB0034042)

Not Available

Nutrient (HMDB: HMDB0034042)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	350 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.79 g/L	ALOGPS
logP	2.68	ALOGPS
logP	2.09	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.22	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.6 m³·mol⁻¹	ChemAxon
Polarizability	27.39 Å³	ChemAxon
Number of Rings	4	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]+	162.442	31661259
DarkChem	[M-H]-	162.127	31661259
DeepCCS	[M+H]+	166.927	30932474
DeepCCS	[M-H]-	164.569	30932474
DeepCCS	[M-2H]-	197.876	30932474
DeepCCS	[M+Na]+	173.103	30932474
AllCCS	[M+H]+	162.8	32859911
AllCCS	[M+H-H2O]+	159.0	32859911
AllCCS	[M+NH4]+	166.4	32859911
AllCCS	[M+Na]+	167.4	32859911
AllCCS	[M-H]-	162.9	32859911
AllCCS	[M+Na-2H]-	161.8	32859911
AllCCS	[M+HCOO]-	160.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lucernol	OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C(O)=C2	4418.5	Standard polar	33892256
Lucernol	OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C(O)=C2	2947.3	Standard non polar	33892256
Lucernol	OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C(O)=C2	3153.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lucernol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=C(O)C=C21	3194.2	Semi standard non polar	33892256
Lucernol,1TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=C1O)C1=C(C(=O)O2)C2=CC=C(O)C=C2O1	3189.0	Semi standard non polar	33892256
Lucernol,1TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C=C1O)OC(=O)C1=C2OC2=CC(O)=CC=C21	3164.9	Semi standard non polar	33892256
Lucernol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=C(O[Si](C)(C)C)C=C21	3289.4	Semi standard non polar	33892256
Lucernol,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C)=C(O)C=C21	3295.2	Semi standard non polar	33892256
Lucernol,2TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)C1=C(C(=O)O2)C2=CC=C(O)C=C2O1	3133.3	Semi standard non polar	33892256
Lucernol,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C21	3272.0	Semi standard non polar	33892256
Lucernol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=C(O)C=C21	3387.9	Semi standard non polar	33892256
Lucernol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)C1=C(C(=O)O2)C2=CC=C(O)C=C2O1	3400.5	Semi standard non polar	33892256
Lucernol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)OC(=O)C1=C2OC2=CC(O)=CC=C21	3374.9	Semi standard non polar	33892256
Lucernol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C21	3738.0	Semi standard non polar	33892256
Lucernol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C21	3742.2	Semi standard non polar	33892256
Lucernol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1=C(C(=O)O2)C2=CC=C(O)C=C2O1	3625.3	Semi standard non polar	33892256
Lucernol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C21	3965.9	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 - Lucernol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ac3-0290000000-490add647a516af40030	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lucernol GC-MS (3 TMS) - 70eV, Positive	splash10-0109-3143900000-70e72686245c2ab072c2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lucernol 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 - Lucernol 10V, Positive-QTOF	splash10-000i-0090000000-970c7dc3bfdf907374e5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucernol 20V, Positive-QTOF	splash10-000i-0090000000-e96e1332ac342e95a4c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucernol 40V, Positive-QTOF	splash10-05mo-1390000000-85a3101defc1543edc9c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucernol 10V, Negative-QTOF	splash10-001i-0090000000-e33e03a4d2dee4f0bd0b	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucernol 20V, Negative-QTOF	splash10-001i-0090000000-6ea3c5a5902c921c073a	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucernol 40V, Negative-QTOF	splash10-01q3-0390000000-7738ed36b3907a963288	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucernol 10V, Positive-QTOF	splash10-000i-0090000000-3896d645ce486a1e32ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucernol 20V, Positive-QTOF	splash10-000i-0090000000-3896d645ce486a1e32ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucernol 40V, Positive-QTOF	splash10-0ar9-0090000000-3f59b3ef30e10083f467	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucernol 10V, Negative-QTOF	splash10-001i-0090000000-279002154c712db975df	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucernol 20V, Negative-QTOF	splash10-001i-0090000000-279002154c712db975df	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lucernol 40V, Negative-QTOF	splash10-001r-0090000000-fd747db13c238936914b	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB003000

KNApSAcK ID

Not Available

Chemspider ID

Not Available

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

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

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Lucernol → 6-({5,14-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Lucernol → 6-({4,5-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Lucernol → 6-({4,14-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for Lucernol (HMDB0034042)

MOL for HMDB0034042 (Lucernol)

3D MOL for HMDB0034042 (Lucernol)

3D SDF for HMDB0034042 (Lucernol)

3D-SDF for HMDB0034042 (Lucernol)

PDB for HMDB0034042 (Lucernol)

3D PDB for HMDB0034042 (Lucernol)

SMILES for HMDB0034042 (Lucernol)

INCHI for HMDB0034042 (Lucernol)

Structure for HMDB0034042 (Lucernol)

3D Structure for HMDB0034042 (Lucernol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions