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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:56:04 UTC

Update Date

2022-03-07 02:54:00 UTC

HMDB ID

HMDB0034139

Secondary Accession Numbers

HMDB34139

Metabolite Identification

Common Name

Trifoliol

Description

Trifoliol belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, trifoliol is considered to be a flavonoid. Trifoliol has been detected, but not quantified in, several different foods, such as herbal tea, alfalfas (Medicago sativa), black tea, herbs and spices, and teas (Camellia sinensis). This could make trifoliol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Trifoliol.

Structure

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

HMDB0034139
     RDKit          3D
Trifoliol
 32 35  0  0  0  0  0  0  0  0999 V2000
    5.8024   -1.1575   -0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5981   -1.6832    0.4666 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -1.0171    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3923    0.1376   -0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1988    0.8094   -0.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2027    1.9604   -1.5381 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0362    0.2996   -0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0274   -0.8745    0.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2381   -1.5010    0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2000   -1.1456    0.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0300   -0.2582    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3912   -0.0816    0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1948   -0.9403    1.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5717   -0.7734    1.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1423    0.3211    0.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5068    0.5513    0.7083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3196    1.2080   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9632    1.0050   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2092    1.8645   -0.8021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9179    1.7448   -0.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2865    2.5795   -1.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2856    0.6807   -0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8354   -0.0823    0.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7864   -1.1823   -1.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7031   -1.6256    0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2992    0.5499   -0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0756    2.3177   -1.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2156   -2.4134    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7430   -1.7945    1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2077   -1.4569    1.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0738   -0.1069    1.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7908    2.0650   -0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  9  3  1  0
 22 11  2  0
 22  7  1  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  9 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
M  END


  Mrv0541 05061307362D          

 22 25  0  0  0  0            999 V2000
   -1.9532    2.4880    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
    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
   -0.4867    3.2441    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
    4.6601    2.8453    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
    3.0128    2.7510    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
    3.3838    3.4879    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
    0.9407    3.1762    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
    5.4838    2.8924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    4.4463    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
   -1.2591    2.0420    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
  3  2  2  0  0  0  0
  7  2  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
 10  5  1  0  0  0  0
 11  4  1  0  0  0  0
 11  9  2  0  0  0  0
 12  6  2  0  0  0  0
 13 10  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16 14  1  0  0  0  0
 17  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 16  2  0  0  0  0
 20  1  1  0  0  0  0
 20  8  1  0  0  0  0
 21 12  1  0  0  0  0
 21 15  1  0  0  0  0
 22 11  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034139

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O6/c1-20-8-5-10(18)13-12(6-8)21-15-9-3-2-7(17)4-11(9)22-16(19)14(13)15/h2-6,17-18H,1H3

> <INCHI_KEY>
YFVNQUXNYCREJW-UHFFFAOYSA-N

> <FORMULA>
C16H10O6

> <MOLECULAR_WEIGHT>
298.247

> <EXACT_MASS>
298.047738052

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.3887073250744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,12-dihydroxy-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.239650056666666

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.976468872581998

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.076151283140327

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8894800369498364

> <JCHEM_POLAR_SURFACE_AREA>
89.13000000000001

> <JCHEM_REFRACTIVITY>
76.0827

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trifoliol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034139
     RDKit          3D
Trifoliol
 32 35  0  0  0  0  0  0  0  0999 V2000
    5.8024   -1.1575   -0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5981   -1.6832    0.4666 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -1.0171    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3923    0.1376   -0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1988    0.8094   -0.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2027    1.9604   -1.5381 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0362    0.2996   -0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0274   -0.8745    0.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2381   -1.5010    0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2000   -1.1456    0.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0300   -0.2582    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3912   -0.0816    0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1948   -0.9403    1.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5717   -0.7734    1.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1423    0.3211    0.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5068    0.5513    0.7083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3196    1.2080   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9632    1.0050   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2092    1.8645   -0.8021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9179    1.7448   -0.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2865    2.5795   -1.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2856    0.6807   -0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8354   -0.0823    0.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7864   -1.1823   -1.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7031   -1.6256    0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2992    0.5499   -0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0756    2.3177   -1.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2156   -2.4134    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7430   -1.7945    1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2077   -1.4569    1.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0738   -0.1069    1.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7908    2.0650   -0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  9  3  1  0
 22 11  2  0
 22  7  1  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  9 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  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      -3.646   4.644   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.006   3.936   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.469   3.848   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.854   6.599   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.909   6.056   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.314   3.685   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.699   5.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.982   4.518   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.624   5.135   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.460   6.761   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.316   6.511   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.683   4.391   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.756   5.929   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.241   6.335   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.087   5.047   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.934   7.710   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.236   5.399   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.533   8.300   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      -2.350   3.812   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.123   3.846   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.472   7.798   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    3    7                                                       
CONECT    3    2    9                                                       
CONECT    4    7   11                                                       
CONECT    5    8   10                                                       
CONECT    6    8   12                                                       
CONECT    7    2    4   17                                                  
CONECT    8    5    6   20                                                  
CONECT    9    3   11   15                                                  
CONECT   10    5   13   18                                                  
CONECT   11    4    9   22                                                  
CONECT   12    6   13   21                                                  
CONECT   13   10   12   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15    9   14   21                                                  
CONECT   16   14   19   22                                                  
CONECT   17    7                                                            
CONECT   18   10                                                            
CONECT   19   16                                                            
CONECT   20    1    8                                                       
CONECT   21   12   15                                                       
CONECT   22   11   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0034139
HETATM    1  C1  UNL     1       5.802  -1.157  -0.059  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.598  -1.683   0.467  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.423  -1.017   0.213  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.392   0.138  -0.534  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.199   0.809  -0.789  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.203   1.960  -1.538  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.036   0.300  -0.280  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.027  -0.874   0.486  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.238  -1.501   0.708  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.200  -1.146   0.849  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.030  -0.258   0.399  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.391  -0.082   0.492  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.195  -0.940   1.173  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.572  -0.773   1.275  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.142   0.321   0.650  1.00  0.00           C  
HETATM   16  O4  UNL     1      -6.507   0.551   0.708  1.00  0.00           O  
HETATM   17  C13 UNL     1      -4.320   1.208  -0.053  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.963   1.005  -0.128  1.00  0.00           C  
HETATM   19  O5  UNL     1      -2.209   1.865  -0.802  1.00  0.00           O  
HETATM   20  C15 UNL     1      -0.918   1.745  -0.921  1.00  0.00           C  
HETATM   21  O6  UNL     1      -0.286   2.580  -1.561  1.00  0.00           O  
HETATM   22  C16 UNL     1      -0.286   0.681  -0.326  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.835  -0.082   0.247  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.786  -1.182  -1.162  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.703  -1.626   0.382  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.299   0.550  -0.941  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.076   2.318  -1.904  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.216  -2.413   1.305  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.743  -1.795   1.660  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.208  -1.457   1.817  1.00  0.00           H  
HETATM   31  H9  UNL     1      -7.074  -0.107   1.223  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.791   2.065  -0.538  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   26
CONECT    5    6    7    7
CONECT    6   27
CONECT    7    8   22
CONECT    8    9    9   10
CONECT    9   28
CONECT   10   11
CONECT   11   12   22   22
CONECT   12   13   13   18
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   16   17
CONECT   16   31
CONECT   17   18   18   32
CONECT   18   19
CONECT   19   20
CONECT   20   21   21   22
END

HMDB0034139
     RDKit          3D
Trifoliol
 32 35  0  0  0  0  0  0  0  0999 V2000
    5.8024   -1.1575   -0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5981   -1.6832    0.4666 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -1.0171    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3923    0.1376   -0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1988    0.8094   -0.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2027    1.9604   -1.5381 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0362    0.2996   -0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0274   -0.8745    0.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2381   -1.5010    0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2000   -1.1456    0.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0300   -0.2582    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3912   -0.0816    0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1948   -0.9403    1.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5717   -0.7734    1.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1423    0.3211    0.6498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5068    0.5513    0.7083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3196    1.2080   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9632    1.0050   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2092    1.8645   -0.8021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9179    1.7448   -0.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2865    2.5795   -1.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2856    0.6807   -0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8354   -0.0823    0.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7864   -1.1823   -1.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7031   -1.6256    0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2992    0.5499   -0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0756    2.3177   -1.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2156   -2.4134    1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7430   -1.7945    1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2077   -1.4569    1.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0738   -0.1069    1.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7908    2.0650   -0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  9  3  1  0
 22 11  2  0
 22  7  1  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  9 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,7-Dihydroxy-9-methoxycoumestan	HMDB
7,10-Dihydroxy-12-methoxycoumestan	HMDB

Chemical Formula

C₁₆H₁₀O₆

Average Molecular Weight

298.247

Monoisotopic Molecular Weight

298.047738052

IUPAC Name

5,12-dihydroxy-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one

Traditional Name

trifoliol

CAS Registry Number

1857-26-7

SMILES

COC1=CC(O)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1

InChI Identifier

InChI=1S/C16H10O6/c1-20-8-5-10(18)13-12(6-8)21-15-9-3-2-7(17)4-11(9)22-16(19)14(13)15/h2-6,17-18H,1H3

InChI Key

YFVNQUXNYCREJW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Angular furanocoumarin
Furanocoumarin
Coumarin
Benzopyran
1-benzopyran
Benzofuran
Furopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Furan
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090030 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034139)
Cytoplasm (HMDB: HMDB0034139)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034139)

Source

Exogenous

Food

Food (HMDB: HMDB0034139)

Herb and spice

Herb

Alfalfa (FooDB: FOOD00286)

Herbs and Spices (FooDB: FOOD00866)

Tea

Pulse

Pulses (FooDB: FOOD00867)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0034139)
Fabaceae (HMDB: HMDB0034139)

Not Available

Nutrient (HMDB: HMDB0034139)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	332 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	143.6 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	0.33 g/L	ALOGPS
logP	2.5	ALOGPS
logP	2.24	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.08	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.08 m³·mol⁻¹	ChemAxon
Polarizability	29.39 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]+	168.131	31661259
DarkChem	[M-H]-	169.537	31661259
DeepCCS	[M+H]+	174.206	30932474
DeepCCS	[M-H]-	171.848	30932474
DeepCCS	[M-2H]-	205.724	30932474
DeepCCS	[M+Na]+	180.952	30932474
AllCCS	[M+H]+	166.9	32859911
AllCCS	[M+H-H2O]+	163.2	32859911
AllCCS	[M+NH4]+	170.3	32859911
AllCCS	[M+Na]+	171.3	32859911
AllCCS	[M-H]-	168.2	32859911
AllCCS	[M+Na-2H]-	167.1	32859911
AllCCS	[M+HCOO]-	166.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trifoliol	COC1=CC(O)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1	4434.1	Standard polar	33892256
Trifoliol	COC1=CC(O)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1	2923.4	Standard non polar	33892256
Trifoliol	COC1=CC(O)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1	3059.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Trifoliol,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC=C21	3121.4	Semi standard non polar	33892256
Trifoliol,1TMS,isomer #2	COC1=CC(O)=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C)=CC=C21	3211.1	Semi standard non polar	33892256
Trifoliol,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C)=CC=C21	3269.1	Semi standard non polar	33892256
Trifoliol,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC=C21	3299.8	Semi standard non polar	33892256
Trifoliol,1TBDMS,isomer #2	COC1=CC(O)=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	3419.1	Semi standard non polar	33892256
Trifoliol,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	3681.4	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 - Trifoliol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00sj-0090000000-df8f664ac0e17dc464ae	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trifoliol GC-MS (2 TMS) - 70eV, Positive	splash10-00ur-2619400000-1b9aa84dbc60e18c71a4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trifoliol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trifoliol 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 - Trifoliol 10V, Positive-QTOF	splash10-0002-0090000000-c92bdeecc53adf4c130f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifoliol 20V, Positive-QTOF	splash10-0002-0090000000-a1bb6f82879248140c64	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifoliol 40V, Positive-QTOF	splash10-0690-0090000000-3b49f0557f326ebea97a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifoliol 10V, Negative-QTOF	splash10-0002-0090000000-e29c1d4cf2cb4c86f35e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifoliol 20V, Negative-QTOF	splash10-0002-0090000000-1b28a987b752c154092a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifoliol 40V, Negative-QTOF	splash10-0h3r-0090000000-47b60f160152f4ae4264	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifoliol 10V, Positive-QTOF	splash10-0002-0090000000-0e40d1dc69d66b601127	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifoliol 20V, Positive-QTOF	splash10-0002-0090000000-0e40d1dc69d66b601127	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifoliol 40V, Positive-QTOF	splash10-0pi0-0190000000-5c1d67af5ecd2c9e1785	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifoliol 10V, Negative-QTOF	splash10-0002-0090000000-96de5c56a94c496da9f8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifoliol 20V, Negative-QTOF	splash10-000t-0090000000-9dac957f14d6a8a59c77	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifoliol 40V, Negative-QTOF	splash10-0hh0-0090000000-a344c048803f4783cb1d	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB012414

KNApSAcK ID

C00009762

Chemspider ID

4589482

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5487671

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1840741

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

Trifoliol → 3,4,5-trihydroxy-6-({5-hydroxy-14-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-12-yl}oxy)oxane-2-carboxylic acid	details
Trifoliol → 3,4,5-trihydroxy-6-({12-hydroxy-14-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-5-yl}oxy)oxane-2-carboxylic acid	details

Showing metabocard for Trifoliol (HMDB0034139)

MOL for HMDB0034139 (Trifoliol)

3D MOL for HMDB0034139 (Trifoliol)

3D SDF for HMDB0034139 (Trifoliol)

3D-SDF for HMDB0034139 (Trifoliol)

PDB for HMDB0034139 (Trifoliol)

3D PDB for HMDB0034139 (Trifoliol)

SMILES for HMDB0034139 (Trifoliol)

INCHI for HMDB0034139 (Trifoliol)

Structure for HMDB0034139 (Trifoliol)

3D Structure for HMDB0034139 (Trifoliol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions