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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:47:03 UTC

Update Date

2022-03-07 02:53:57 UTC

HMDB ID

HMDB0034009

Secondary Accession Numbers

HMDB34009

Metabolite Identification

Common Name

Trifolian

Description

Trifolian belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, trifolian is considered to be a flavonoid. Trifolian has been detected, but not quantified in, several different foods, such as herbal tea, black tea, herbs and spices, red tea, and green tea. This could make trifolian a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Trifolian.

Structure

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

HMDB0034009
     RDKit          3D
Trifolian
 38 42  0  0  0  0  0  0  0  0999 V2000
   -5.1070   -1.8924   -1.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7741   -0.5173   -1.3050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7862    0.1058   -0.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1240    0.7472    0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4484    0.7625    1.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1542    1.3533    1.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8107    1.3287    1.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802    0.6898   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4672    0.0781   -0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1073   -0.5609   -2.0779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0735    0.6481   -0.5687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4490   -0.6705   -0.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8148   -0.5688   -0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7891   -1.5195   -0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1228   -1.2196   -0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4701    0.0089    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4740    0.9389    0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1556    0.6704    0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8730    1.4490    0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4868    1.4169    1.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8273    1.9336    1.7990 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8672    0.0339    0.2279 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3757   -1.2910    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2993   -1.9194   -0.6009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1671   -2.0641   -1.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9358   -2.1712   -0.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4670   -2.5659   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8072    1.1981    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3904    1.8656    2.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1342   -0.5648   -2.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0441    1.0881   -1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5853   -2.4853   -1.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7366    1.9057    0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0101    2.4870   -0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5474    0.3598    2.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2025    1.9899    2.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2705   -1.2607   -0.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5761   -1.7879    1.0131 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 16 22  1  0
 22 23  1  0
 23 24  1  0
  9  3  1  0
 19 11  1  0
 21  7  1  0
 18 13  1  0
 24 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
 10 30  1  0
 11 31  1  0
 14 32  1  0
 17 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 23 37  1  0
 23 38  1  0
M  END


  Mrv0541 05061307302D          

 24 28  0  0  0  0            999 V2000
   -0.3164    2.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0288    0.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0671    0.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0867    2.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1743    0.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0405    1.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292    1.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361    1.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6059    1.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3582    2.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7573    1.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7863    2.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8901    0.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519    1.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7908    2.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0749    1.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9678    2.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171    1.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1526    3.1328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5066    3.0181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513    0.2819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5325    0.9754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5794    2.3094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5830    2.4147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  2  2  0  0  0  0
  8  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  3  2  0  0  0  0
 10  4  2  0  0  0  0
 10  7  1  0  0  0  0
 11  2  1  0  0  0  0
 12  4  1  0  0  0  0
 12 11  2  0  0  0  0
 13  3  1  0  0  0  0
 14 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16  8  1  0  0  0  0
 16 14  1  0  0  0  0
 17  9  1  0  0  0  0
 17 15  2  0  0  0  0
 18  9  1  0  0  0  0
 19 15  1  0  0  0  0
 20  1  1  0  0  0  0
 20 17  1  0  0  0  0
 21  5  1  0  0  0  0
 21 13  1  0  0  0  0
 22  6  1  0  0  0  0
 22 11  1  0  0  0  0
 23  6  1  0  0  0  0
 23 12  1  0  0  0  0
 24 10  1  0  0  0  0
 24 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034009

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C2=C(OCC3C2OC2=CC4=C(OCO4)C=C32)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O7/c1-20-17-9(18)3-13-14(15(17)19)16-8(5-21-13)7-2-11-12(23-6-22-11)4-10(7)24-16/h2-4,8,16,18-19H,5-6H2,1H3

> <INCHI_KEY>
PCVFSIAOIHIYNK-UHFFFAOYSA-N

> <FORMULA>
C17H14O7

> <MOLECULAR_WEIGHT>
330.2889

> <EXACT_MASS>
330.073952802

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
32.5686610504794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaene-14,16-diol

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
1.8288915423333325

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.86615986758286

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.41445805463211

> <JCHEM_PKA_STRONGEST_BASIC>
-4.252881497300357

> <JCHEM_POLAR_SURFACE_AREA>
86.61000000000001

> <JCHEM_REFRACTIVITY>
80.80890000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trifolian

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034009
     RDKit          3D
Trifolian
 38 42  0  0  0  0  0  0  0  0999 V2000
   -5.1070   -1.8924   -1.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7741   -0.5173   -1.3050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7862    0.1058   -0.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1240    0.7472    0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4484    0.7625    1.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1542    1.3533    1.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8107    1.3287    1.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802    0.6898   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4672    0.0781   -0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1073   -0.5609   -2.0779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0735    0.6481   -0.5687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4490   -0.6705   -0.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8148   -0.5688   -0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7891   -1.5195   -0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1228   -1.2196   -0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4701    0.0089    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4740    0.9389    0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1556    0.6704    0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8730    1.4490    0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4868    1.4169    1.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8273    1.9336    1.7990 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8672    0.0339    0.2279 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3757   -1.2910    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2993   -1.9194   -0.6009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1671   -2.0641   -1.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9358   -2.1712   -0.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4670   -2.5659   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8072    1.1981    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3904    1.8656    2.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1342   -0.5648   -2.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0441    1.0881   -1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5853   -2.4853   -1.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7366    1.9057    0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0101    2.4870   -0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5474    0.3598    2.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2025    1.9899    2.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2705   -1.2607   -0.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5761   -1.7879    1.0131 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 16 22  1  0
 22 23  1  0
 23 24  1  0
  9  3  1  0
 19 11  1  0
 21  7  1  0
 18 13  1  0
 24 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
 10 30  1  0
 11 31  1  0
 14 32  1  0
 17 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 23 37  1  0
 23 38  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      -0.591   5.527   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.387   1.625   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.992   1.696   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.495   4.703   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.925   0.633   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.142   3.034   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.081   2.441   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.601   2.017   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.131   2.973   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.135   3.980   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.747   2.348   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.801   3.887   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.528   1.803   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.204   3.187   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.343   4.464   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.740   3.294   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.807   4.357   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.405   2.866   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.018   5.848   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.946   5.634   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.389   0.526   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.194   1.821   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      12.282   4.311   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.688   4.507   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    7   11                                                       
CONECT    3    9   13                                                       
CONECT    4   10   12                                                       
CONECT    5    8   21                                                       
CONECT    6   22   23                                                       
CONECT    7    2    8   10                                                  
CONECT    8    5    7   16                                                  
CONECT    9    3   17   18                                                  
CONECT   10    4    7   24                                                  
CONECT   11    2   12   22                                                  
CONECT   12    4   11   23                                                  
CONECT   13    3   14   21                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   17   19                                                  
CONECT   16    8   14   24                                                  
CONECT   17    9   15   20                                                  
CONECT   18    9                                                            
CONECT   19   15                                                            
CONECT   20    1   17                                                       
CONECT   21    5   13                                                       
CONECT   22    6   11                                                       
CONECT   23    6   12                                                       
CONECT   24   10   16                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0034009
HETATM    1  C1  UNL     1      -5.107  -1.892  -1.076  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.774  -0.517  -1.305  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.786   0.106  -0.512  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.124   0.747   0.660  1.00  0.00           C  
HETATM    5  O2  UNL     1      -5.448   0.763   1.033  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.154   1.353   1.429  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.811   1.329   1.036  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.480   0.690  -0.130  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.467   0.078  -0.904  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.107  -0.561  -2.078  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.073   0.648  -0.569  1.00  0.00           C  
HETATM   12  O4  UNL     1       0.449  -0.671  -0.628  1.00  0.00           O  
HETATM   13  C9  UNL     1       1.815  -0.569  -0.442  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.789  -1.520  -0.712  1.00  0.00           C  
HETATM   15  C11 UNL     1       4.123  -1.220  -0.452  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.470   0.009   0.069  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.474   0.939   0.328  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.156   0.670   0.081  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.873   1.449   0.250  1.00  0.00           C  
HETATM   20  C16 UNL     1       0.487   1.417   1.713  1.00  0.00           C  
HETATM   21  O5  UNL     1      -0.827   1.934   1.799  1.00  0.00           O  
HETATM   22  O6  UNL     1       5.867   0.034   0.228  1.00  0.00           O  
HETATM   23  C17 UNL     1       6.376  -1.291   0.044  1.00  0.00           C  
HETATM   24  O7  UNL     1       5.299  -1.919  -0.601  1.00  0.00           O  
HETATM   25  H1  UNL     1      -6.167  -2.064  -1.317  1.00  0.00           H  
HETATM   26  H2  UNL     1      -4.936  -2.171  -0.012  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.467  -2.566  -1.681  1.00  0.00           H  
HETATM   28  H4  UNL     1      -5.807   1.198   1.863  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.390   1.866   2.356  1.00  0.00           H  
HETATM   30  H6  UNL     1      -1.134  -0.565  -2.341  1.00  0.00           H  
HETATM   31  H7  UNL     1      -0.044   1.088  -1.612  1.00  0.00           H  
HETATM   32  H8  UNL     1       2.585  -2.485  -1.114  1.00  0.00           H  
HETATM   33  H9  UNL     1       3.737   1.906   0.736  1.00  0.00           H  
HETATM   34  H10 UNL     1       1.010   2.487  -0.056  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.547   0.360   2.043  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.203   1.990   2.320  1.00  0.00           H  
HETATM   37  H13 UNL     1       7.271  -1.261  -0.606  1.00  0.00           H  
HETATM   38  H14 UNL     1       6.576  -1.788   1.013  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5    6
CONECT    5   28
CONECT    6    7    7   29
CONECT    7    8   21
CONECT    8    9    9   11
CONECT    9   10
CONECT   10   30
CONECT   11   12   19   31
CONECT   12   13
CONECT   13   14   14   18
CONECT   14   15   32
CONECT   15   16   16   24
CONECT   16   17   22
CONECT   17   18   18   33
CONECT   18   19
CONECT   19   20   34
CONECT   20   21   35   36
CONECT   22   23
CONECT   23   24   37   38
END

HMDB0034009
     RDKit          3D
Trifolian
 38 42  0  0  0  0  0  0  0  0999 V2000
   -5.1070   -1.8924   -1.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7741   -0.5173   -1.3050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7862    0.1058   -0.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1240    0.7472    0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4484    0.7625    1.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1542    1.3533    1.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8107    1.3287    1.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802    0.6898   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4672    0.0781   -0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1073   -0.5609   -2.0779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0735    0.6481   -0.5687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4490   -0.6705   -0.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8148   -0.5688   -0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7891   -1.5195   -0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1228   -1.2196   -0.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4701    0.0089    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4740    0.9389    0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1556    0.6704    0.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8730    1.4490    0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4868    1.4169    1.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8273    1.9336    1.7990 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8672    0.0339    0.2279 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3757   -1.2910    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2993   -1.9194   -0.6009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1671   -2.0641   -1.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9358   -2.1712   -0.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4670   -2.5659   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8072    1.1981    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3904    1.8656    2.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1342   -0.5648   -2.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0441    1.0881   -1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5853   -2.4853   -1.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7366    1.9057    0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0101    2.4870   -0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5474    0.3598    2.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2025    1.9899    2.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2705   -1.2607   -0.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5761   -1.7879    1.0131 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 16 22  1  0
 22 23  1  0
 23 24  1  0
  9  3  1  0
 19 11  1  0
 21  7  1  0
 18 13  1  0
 24 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
 10 30  1  0
 11 31  1  0
 14 32  1  0
 17 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 23 37  1  0
 23 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3-Dihydroxy-2-methoxy-8,9-methylenedioxypterocarpan	HMDB

Chemical Formula

C₁₇H₁₄O₇

Average Molecular Weight

330.2889

Monoisotopic Molecular Weight

330.073952802

IUPAC Name

15-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaene-14,16-diol

Traditional Name

trifolian

CAS Registry Number

73520-83-9

SMILES

COC1=C(O)C2=C(OCC3C2OC2=CC4=C(OCO4)C=C32)C=C1O

InChI Identifier

InChI=1S/C17H14O7/c1-20-17-9(18)3-13-14(15(17)19)16-8(5-21-13)7-2-11-12(23-6-22-11)4-10(7)24-16/h2-4,8,16,18-19H,5-6H2,1H3

InChI Key

PCVFSIAOIHIYNK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Pterocarpan
Isoflavanol
Isoflavan
1-benzopyran
Chromane
Benzopyran
Coumaran
Benzodioxole
Benzofuran
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070106 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	132 - 134 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	46.86 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	0.73 g/L	ALOGPS
logP	2.2	ALOGPS
logP	1.83	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.41	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.61 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.81 m³·mol⁻¹	ChemAxon
Polarizability	32.57 Å³	ChemAxon
Number of Rings	5	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]+	176.478	31661259
DarkChem	[M-H]-	176.256	31661259
DeepCCS	[M-2H]-	207.631	30932474
DeepCCS	[M+Na]+	182.858	30932474
AllCCS	[M+H]+	175.9	32859911
AllCCS	[M+H-H2O]+	172.6	32859911
AllCCS	[M+NH4]+	179.1	32859911
AllCCS	[M+Na]+	180.0	32859911
AllCCS	[M-H]-	179.2	32859911
AllCCS	[M+Na-2H]-	178.4	32859911
AllCCS	[M+HCOO]-	177.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trifolian	COC1=C(O)C2=C(OCC3C2OC2=CC4=C(OCO4)C=C32)C=C1O	4381.1	Standard polar	33892256
Trifolian	COC1=C(O)C2=C(OCC3C2OC2=CC4=C(OCO4)C=C32)C=C1O	2802.9	Standard non polar	33892256
Trifolian	COC1=C(O)C2=C(OCC3C2OC2=CC4=C(OCO4)C=C32)C=C1O	2977.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Trifolian,1TMS,isomer #1	COC1=C(O)C=C2OCC3C4=CC5=C(C=C4OC3C2=C1O[Si](C)(C)C)OCO5	3006.1	Semi standard non polar	33892256
Trifolian,1TMS,isomer #2	COC1=C(O[Si](C)(C)C)C=C2OCC3C4=CC5=C(C=C4OC3C2=C1O)OCO5	3008.7	Semi standard non polar	33892256
Trifolian,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=C2OCC3C4=CC5=C(C=C4OC3C2=C1O[Si](C)(C)C)OCO5	3015.0	Semi standard non polar	33892256
Trifolian,1TBDMS,isomer #1	COC1=C(O)C=C2OCC3C4=CC5=C(C=C4OC3C2=C1O[Si](C)(C)C(C)(C)C)OCO5	3260.0	Semi standard non polar	33892256
Trifolian,1TBDMS,isomer #2	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OCC3C4=CC5=C(C=C4OC3C2=C1O)OCO5	3249.6	Semi standard non polar	33892256
Trifolian,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OCC3C4=CC5=C(C=C4OC3C2=C1O[Si](C)(C)C(C)(C)C)OCO5	3480.5	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 - Trifolian GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w29-0469000000-140934f14ddf25c3bc83	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trifolian GC-MS (2 TMS) - 70eV, Positive	splash10-0r6r-3302900000-08b1ba9de58a9d76c5bf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trifolian GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trifolian 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 - Trifolian 10V, Positive-QTOF	splash10-001i-0009000000-6e8e7d679d840cad72fc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifolian 20V, Positive-QTOF	splash10-001i-0119000000-a38e216c2ea4d5c5ffca	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifolian 40V, Positive-QTOF	splash10-0fml-5891000000-92963a5fbd83082e701a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifolian 10V, Negative-QTOF	splash10-004i-0009000000-d2032607a11eb21f8c83	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifolian 20V, Negative-QTOF	splash10-004i-0069000000-86069b5084e79ad6918e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifolian 40V, Negative-QTOF	splash10-05i0-3391000000-efcc5867c523c74ec4c4	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifolian 10V, Negative-QTOF	splash10-004i-0009000000-8e9d1a384717180cd0e2	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifolian 20V, Negative-QTOF	splash10-004i-0019000000-3631fa029ef4aa6e4a31	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifolian 40V, Negative-QTOF	splash10-00os-0391000000-dd2b2a9883903bc24672	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifolian 10V, Positive-QTOF	splash10-001i-0009000000-931b28fcfeb1b8f804fe	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifolian 20V, Positive-QTOF	splash10-001i-0009000000-da625d60a25b903108a4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trifolian 40V, Positive-QTOF	splash10-0pdi-0295000000-220779a38e51fc28188f	2021-09-25	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

FDB012245

KNApSAcK ID

C00009632

Chemspider ID

24843036

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257476

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1839761

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 Trifolian (HMDB0034009)

MOL for HMDB0034009 (Trifolian)

3D MOL for HMDB0034009 (Trifolian)

3D SDF for HMDB0034009 (Trifolian)

3D-SDF for HMDB0034009 (Trifolian)

PDB for HMDB0034009 (Trifolian)

3D PDB for HMDB0034009 (Trifolian)

SMILES for HMDB0034009 (Trifolian)

INCHI for HMDB0034009 (Trifolian)

Structure for HMDB0034009 (Trifolian)

3D Structure for HMDB0034009 (Trifolian)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra