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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:26:04 UTC

Update Date

2022-03-07 02:54:51 UTC

HMDB ID

HMDB0036305

Secondary Accession Numbers

HMDB36305

Metabolite Identification

Common Name

Isotrifoliol

Description

Isotrifoliol 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. Isotrifoliol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, isotrifoliol has been detected, but not quantified in, herbs and spices. This could make isotrifoliol a potential biomarker for the consumption of these foods.

Structure

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

HMDB0036305
     RDKit          3D
Isotrifoliol
 32 35  0  0  0  0  0  0  0  0999 V2000
   -2.4700    3.1168   -0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6537    1.9730   -0.0778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1382    0.6882   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5033    0.5013   -0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9886   -0.7941   -0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3712   -1.0389   -0.2585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1157   -1.8588   -0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7315   -1.6850   -0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9170   -2.7084   -0.0617 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3867   -2.5967   -0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1889   -3.5619    0.0311 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9128   -1.3229    0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2117   -0.8156    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4377   -1.4458    0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5821   -0.6882    0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5456    0.6905    0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7196    1.4512    0.2562 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3014    1.2842    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1230    0.5610    0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481    0.8809    0.0321 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1088   -0.2024   -0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2754   -0.3853   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7516    3.4079   -1.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3481    2.9796    0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8681    3.9447    0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2282    1.3010   -0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9030   -1.1292    0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4702   -2.8790   -0.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4395   -2.5287    0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5361   -1.2004    0.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1147    1.6830   -0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2769    2.3777    0.1484 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  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22  3  1  0
 22  8  2  0
 21 12  2  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
M  END


  Mrv0541 05061309032D          

 22 25  0  0  0  0            999 V2000
    5.0975    2.6871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3400    0.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0733    0.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9948    1.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1158    1.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0341    0.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3008    1.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4868    1.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7673    0.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7281    1.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2921    1.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2105    0.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5632    0.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8395    1.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0158    1.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9342   -0.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5675    1.9223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3104    1.0719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4815   -0.8559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9211    2.6399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4997    1.9041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7578   -0.2133    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  4  1  0  0  0  0
 10  9  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 13  9  1  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 13  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19 16  2  0  0  0  0
 20  1  1  0  0  0  0
 20 11  1  0  0  0  0
 21 10  1  0  0  0  0
 21 15  1  0  0  0  0
 22 12  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036305

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2C3=C(C4=C(O3)C=C(O)C=C4)C(=O)OC2=CC(O)=C1

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

> <INCHI_KEY>
OVLUQDOJWGTPHA-UHFFFAOYSA-N

> <FORMULA>
C16H10O6

> <MOLECULAR_WEIGHT>
298.247

> <EXACT_MASS>
298.047738052

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.11242794321625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,14-dihydroxy-3-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
2.239650056666666

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.10990417007712

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.21050370441412

> <JCHEM_PKA_STRONGEST_BASIC>
-4.334132902620373

> <JCHEM_POLAR_SURFACE_AREA>
89.13000000000001

> <JCHEM_REFRACTIVITY>
76.0827

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,14-dihydroxy-3-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036305
     RDKit          3D
Isotrifoliol
 32 35  0  0  0  0  0  0  0  0999 V2000
   -2.4700    3.1168   -0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6537    1.9730   -0.0778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1382    0.6882   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5033    0.5013   -0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9886   -0.7941   -0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3712   -1.0389   -0.2585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1157   -1.8588   -0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7315   -1.6850   -0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9170   -2.7084   -0.0617 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3867   -2.5967   -0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1889   -3.5619    0.0311 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9128   -1.3229    0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2117   -0.8156    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4377   -1.4458    0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5821   -0.6882    0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5456    0.6905    0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7196    1.4512    0.2562 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3014    1.2842    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1230    0.5610    0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481    0.8809    0.0321 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1088   -0.2024   -0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2754   -0.3853   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7516    3.4079   -1.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3481    2.9796    0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8681    3.9447    0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2282    1.3010   -0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9030   -1.1292    0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4702   -2.8790   -0.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4395   -2.5287    0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5361   -1.2004    0.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1147    1.6830   -0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2769    2.3777    0.1484 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  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22  3  1  0
 22  8  2  0
 21 12  2  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 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       9.515   5.016   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.368   1.344   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.737   0.639   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.590   3.715   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.283   3.464   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.130   0.801   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.295   2.883   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.975   2.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.032   1.471   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.959   3.009   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.745   3.552   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.593   0.889   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.518   1.065   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.900   2.265   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.363   2.353   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.211  -0.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.926   3.588   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      15.513   2.001   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.365  -1.598   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.053   4.928   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.399   3.554   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.748  -0.398   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    3    7                                                       
CONECT    3    2    9                                                       
CONECT    4    7   10                                                       
CONECT    5    8   11                                                       
CONECT    6    8   12                                                       
CONECT    7    2    4   17                                                  
CONECT    8    5    6   18                                                  
CONECT    9    3   10   13                                                  
CONECT   10    4    9   21                                                  
CONECT   11    5   14   20                                                  
CONECT   12    6   14   22                                                  
CONECT   13    9   15   16                                                  
CONECT   14   11   12   15                                                  
CONECT   15   13   14   21                                                  
CONECT   16   13   19   22                                                  
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19   16                                                            
CONECT   20    1   11                                                       
CONECT   21   10   15                                                       
CONECT   22   12   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0036305
HETATM    1  C1  UNL     1      -2.470   3.117  -0.111  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.654   1.973  -0.078  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.138   0.688  -0.105  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.503   0.501  -0.168  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.989  -0.794  -0.195  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.371  -1.039  -0.258  1.00  0.00           O  
HETATM    7  C5  UNL     1      -3.116  -1.859  -0.159  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.731  -1.685  -0.095  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.917  -2.708  -0.062  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.387  -2.597  -0.002  1.00  0.00           C  
HETATM   11  O4  UNL     1       1.189  -3.562   0.031  1.00  0.00           O  
HETATM   12  C8  UNL     1       0.913  -1.323   0.027  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.212  -0.816   0.088  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.438  -1.446   0.141  1.00  0.00           C  
HETATM   15  C11 UNL     1       4.582  -0.688   0.196  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.546   0.691   0.200  1.00  0.00           C  
HETATM   17  O5  UNL     1       5.720   1.451   0.256  1.00  0.00           O  
HETATM   18  C13 UNL     1       3.301   1.284   0.145  1.00  0.00           C  
HETATM   19  C14 UNL     1       2.123   0.561   0.089  1.00  0.00           C  
HETATM   20  O6  UNL     1       0.848   0.881   0.032  1.00  0.00           O  
HETATM   21  C15 UNL     1       0.109  -0.202  -0.006  1.00  0.00           C  
HETATM   22  C16 UNL     1      -1.275  -0.385  -0.069  1.00  0.00           C  
HETATM   23  H1  UNL     1      -2.752   3.408  -1.143  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.348   2.980   0.557  1.00  0.00           H  
HETATM   25  H3  UNL     1      -1.868   3.945   0.355  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.228   1.301  -0.198  1.00  0.00           H  
HETATM   27  H5  UNL     1      -5.903  -1.129   0.609  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.470  -2.879  -0.179  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.440  -2.529   0.137  1.00  0.00           H  
HETATM   30  H8  UNL     1       5.536  -1.200   0.238  1.00  0.00           H  
HETATM   31  H9  UNL     1       6.115   1.683  -0.665  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.277   2.378   0.148  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   26
CONECT    5    6    7    7
CONECT    6   27
CONECT    7    8   28
CONECT    8    9   22   22
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   21   21
CONECT   13   14   14   19
CONECT   14   15   29
CONECT   15   16   16   30
CONECT   16   17   18
CONECT   17   31
CONECT   18   19   19   32
CONECT   19   20
CONECT   20   21
CONECT   21   22
END

HMDB0036305
     RDKit          3D
Isotrifoliol
 32 35  0  0  0  0  0  0  0  0999 V2000
   -2.4700    3.1168   -0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6537    1.9730   -0.0778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1382    0.6882   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5033    0.5013   -0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9886   -0.7941   -0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3712   -1.0389   -0.2585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1157   -1.8588   -0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7315   -1.6850   -0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9170   -2.7084   -0.0617 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3867   -2.5967   -0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1889   -3.5619    0.0311 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9128   -1.3229    0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2117   -0.8156    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4377   -1.4458    0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5821   -0.6882    0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5456    0.6905    0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7196    1.4512    0.2562 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3014    1.2842    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1230    0.5610    0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481    0.8809    0.0321 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1088   -0.2024   -0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2754   -0.3853   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7516    3.4079   -1.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3481    2.9796    0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8681    3.9447    0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2282    1.3010   -0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9030   -1.1292    0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4702   -2.8790   -0.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4395   -2.5287    0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5361   -1.2004    0.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1147    1.6830   -0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2769    2.3777    0.1484 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  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22  3  1  0
 22  8  2  0
 21 12  2  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,9-Dihydroxy-1-methoxycoumestan	HMDB
Isotrifoliol	MeSH

Chemical Formula

C₁₆H₁₀O₆

Average Molecular Weight

298.247

Monoisotopic Molecular Weight

298.047738052

IUPAC Name

5,14-dihydroxy-3-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

Traditional Name

5,14-dihydroxy-3-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

CAS Registry Number

Not Available

SMILES

COC1=C2C3=C(C4=C(O3)C=C(O)C=C4)C(=O)OC2=CC(O)=C1

InChI Identifier

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

InChI Key

OVLUQDOJWGTPHA-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

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0036305)

Membrane (HMDB: HMDB0036305)
Cell membrane (HMDB: HMDB0036305)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036305)

Source

Exogenous

Food

Food (HMDB: HMDB0036305)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0036305)

Not Available

Nutrient (HMDB: HMDB0036305)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	2.54	ALOGPS
logP	2.24	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.21	ChemAxon
pKa (Strongest Basic)	-4.3	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	29.11 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]+	168.122	31661259
DarkChem	[M-H]-	170.0	31661259
DeepCCS	[M+H]+	178.051	30932474
DeepCCS	[M-H]-	175.693	30932474
DeepCCS	[M-2H]-	209.978	30932474
DeepCCS	[M+Na]+	185.573	30932474
AllCCS	[M+H]+	166.5	32859911
AllCCS	[M+H-H2O]+	162.8	32859911
AllCCS	[M+NH4]+	169.9	32859911
AllCCS	[M+Na]+	170.9	32859911
AllCCS	[M-H]-	168.0	32859911
AllCCS	[M+Na-2H]-	166.9	32859911
AllCCS	[M+HCOO]-	165.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isotrifoliol	COC1=C2C3=C(C4=C(O3)C=C(O)C=C4)C(=O)OC2=CC(O)=C1	4318.3	Standard polar	33892256
Isotrifoliol	COC1=C2C3=C(C4=C(O3)C=C(O)C=C4)C(=O)OC2=CC(O)=C1	2853.2	Standard non polar	33892256
Isotrifoliol	COC1=C2C3=C(C4=C(O3)C=C(O)C=C4)C(=O)OC2=CC(O)=C1	3241.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isotrifoliol,1TMS,isomer #1	COC1=CC(O)=CC2=C1C1=C(C(=O)O2)C2=CC=C(O[Si](C)(C)C)C=C2O1	3149.1	Semi standard non polar	33892256
Isotrifoliol,1TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=CC2=C1C1=C(C(=O)O2)C2=CC=C(O)C=C2O1	3155.5	Semi standard non polar	33892256
Isotrifoliol,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC2=C1C1=C(C(=O)O2)C2=CC=C(O[Si](C)(C)C)C=C2O1	3315.8	Semi standard non polar	33892256
Isotrifoliol,1TBDMS,isomer #1	COC1=CC(O)=CC2=C1C1=C(C(=O)O2)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O1	3346.8	Semi standard non polar	33892256
Isotrifoliol,1TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C1=C(C(=O)O2)C2=CC=C(O)C=C2O1	3349.5	Semi standard non polar	33892256
Isotrifoliol,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1C1=C(C(=O)O2)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O1	3734.0	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 - Isotrifoliol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00sj-0190000000-97e135336bc2f4ee0092	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isotrifoliol GC-MS (2 TMS) - 70eV, Positive	splash10-05i1-4249500000-f771aa9c2acd65afb780	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isotrifoliol 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 - Isotrifoliol 10V, Positive-QTOF	splash10-0002-0090000000-3a1c73a243f500d29415	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrifoliol 20V, Positive-QTOF	splash10-0002-0090000000-a4db415efa2c378cc979	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrifoliol 40V, Positive-QTOF	splash10-016r-0190000000-3617bac350efb170dbf5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrifoliol 10V, Negative-QTOF	splash10-0002-0090000000-4f72c19c40413a4bee27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrifoliol 20V, Negative-QTOF	splash10-0002-0090000000-12af3276a21593dee63b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrifoliol 40V, Negative-QTOF	splash10-02u0-0490000000-b377712d4067c24811d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrifoliol 10V, Negative-QTOF	splash10-0002-0090000000-96de5c56a94c496da9f8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrifoliol 20V, Negative-QTOF	splash10-0002-0090000000-e7ef826f53a0bc5194e7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrifoliol 40V, Negative-QTOF	splash10-014i-0090000000-94d9dcfbfc7563b044fd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrifoliol 10V, Positive-QTOF	splash10-0002-0090000000-0e40d1dc69d66b601127	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrifoliol 20V, Positive-QTOF	splash10-0002-0090000000-0e40d1dc69d66b601127	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrifoliol 40V, Positive-QTOF	splash10-000i-0790000000-c00035bd45f07039ae68	2021-09-24	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

FDB015173

KNApSAcK ID

C00018990

Chemspider ID

4477198

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318679

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.. .

Showing metabocard for Isotrifoliol (HMDB0036305)

MOL for HMDB0036305 (Isotrifoliol)

3D MOL for HMDB0036305 (Isotrifoliol)

3D SDF for HMDB0036305 (Isotrifoliol)

3D-SDF for HMDB0036305 (Isotrifoliol)

PDB for HMDB0036305 (Isotrifoliol)

3D PDB for HMDB0036305 (Isotrifoliol)

SMILES for HMDB0036305 (Isotrifoliol)

INCHI for HMDB0036305 (Isotrifoliol)

Structure for HMDB0036305 (Isotrifoliol)

3D Structure for HMDB0036305 (Isotrifoliol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra