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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:25:18 UTC

Update Date

2022-03-07 02:53:48 UTC

HMDB ID

HMDB0033669

Secondary Accession Numbers

HMDB33669

Metabolite Identification

Common Name

Phaseollidin

Description

Phaseollidin 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. Phaseollidin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, phaseollidin has been detected, but not quantified in, several different foods, such as fruits, cowpea, yellow wax beans, common beans, and lima beans. This could make phaseollidin a potential biomarker for the consumption of these foods.

Structure

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

HMDB0033669
     RDKit          3D
Phaseollidin
 44 47  0  0  0  0  0  0  0  0999 V2000
   -4.0034    1.9110   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5021    0.5861   -0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9624    0.3507   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6248   -0.3543   -0.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1920   -0.0831   -0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4541   -0.9541    0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063   -1.8823    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4734   -2.0689    0.8861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3651   -2.6549    1.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0030   -2.4917    1.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6420   -1.5626    1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0647   -0.7728    0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042    0.0932   -0.4244 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0660   -0.5882   -0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1819    0.3020   -0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702    0.4255   -1.9882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7298    1.2633   -2.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3010    1.9874   -1.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3703    2.8309   -1.6082 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8392    1.8868   -0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7684    1.0357    0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710    0.9042    1.5709 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2682   -0.0065    1.9571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0760   -1.1432    0.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4401    2.4249   -0.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8536    2.5873    0.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3553    1.8271    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4452    0.4700    0.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2278   -0.6417   -1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4495    1.1413   -1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0176   -1.3255   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0298    0.9864   -0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7638   -0.1862   -1.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9562   -2.7425    1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7944   -3.4102    2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6111   -3.1025    2.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432   -1.4046   -1.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2300   -0.1376   -2.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1073    1.3531   -3.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3074    2.4525   -1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2774    2.4502    0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5345   -0.3585    2.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3154    0.5782    1.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7643   -1.9758    1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 12  6  1  0
 24 14  1  0
 24 11  1  0
 21 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
 23 42  1  0
 23 43  1  0
 24 44  1  0
M  END


  Mrv0541 05061307162D          

 24 27  0  0  0  0            999 V2000
    1.0647   -5.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3626   -5.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4099   -3.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -2.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431   -3.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -2.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -0.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3707   -4.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743   -1.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548   -1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -2.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -2.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -2.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980   -1.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156   -2.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -2.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -1.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450   -2.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453   -0.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872   -2.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  2  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  3  2  0  0  0  0
 12  4  1  0  0  0  0
 12  9  2  0  0  0  0
 13  7  1  0  0  0  0
 14  5  1  0  0  0  0
 15  6  1  0  0  0  0
 16 10  1  0  0  0  0
 16 13  1  0  0  0  0
 17  8  1  0  0  0  0
 17 14  2  0  0  0  0
 18  9  1  0  0  0  0
 18 15  2  0  0  0  0
 19 13  2  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21 12  1  0  0  0  0
 22 17  1  0  0  0  0
 23 10  1  0  0  0  0
 23 18  1  0  0  0  0
 24 19  1  0  0  0  0
 24 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033669

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O4/c1-11(2)3-5-14-17(22)8-7-13-16-10-23-18-9-12(21)4-6-15(18)20(16)24-19(13)14/h3-4,6-9,16,20-22H,5,10H2,1-2H3

> <INCHI_KEY>
OFWYIUYVHYPQNX-UHFFFAOYSA-N

> <FORMULA>
C20H20O4

> <MOLECULAR_WEIGHT>
324.3704

> <EXACT_MASS>
324.136159128

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.417263812334625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
4.0918963396666665

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.692192330220221

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.087967623887911

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5922456624626555

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
92.82159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033669
     RDKit          3D
Phaseollidin
 44 47  0  0  0  0  0  0  0  0999 V2000
   -4.0034    1.9110   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5021    0.5861   -0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9624    0.3507   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6248   -0.3543   -0.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1920   -0.0831   -0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4541   -0.9541    0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063   -1.8823    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4734   -2.0689    0.8861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3651   -2.6549    1.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0030   -2.4917    1.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6420   -1.5626    1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0647   -0.7728    0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042    0.0932   -0.4244 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0660   -0.5882   -0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1819    0.3020   -0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702    0.4255   -1.9882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7298    1.2633   -2.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3010    1.9874   -1.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3703    2.8309   -1.6082 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8392    1.8868   -0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7684    1.0357    0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710    0.9042    1.5709 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2682   -0.0065    1.9571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0760   -1.1432    0.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4401    2.4249   -0.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8536    2.5873    0.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3553    1.8271    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4452    0.4700    0.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2278   -0.6417   -1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4495    1.1413   -1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0176   -1.3255   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0298    0.9864   -0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7638   -0.1862   -1.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9562   -2.7425    1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7944   -3.4102    2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6111   -3.1025    2.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432   -1.4046   -1.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2300   -0.1376   -2.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1073    1.3531   -3.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3074    2.4525   -1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2774    2.4502    0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5345   -0.3585    2.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3154    0.5782    1.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7643   -1.9758    1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 12  6  1  0
 24 14  1  0
 24 11  1  0
 21 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
 23 42  1  0
 23 43  1  0
 24 44  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       1.987  -9.836   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.677  -9.709   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.765  -7.466   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.899  -4.971   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.134  -6.760   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.362  -5.059   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.353  -2.145   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.985  -2.851   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.747  -2.308   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.827  -1.196   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.692  -9.004   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.592  -3.595   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.649  -2.978   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.207  -5.221   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.517  -3.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.135  -2.572   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.911  -4.389   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.210  -2.396   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.576  -4.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.979  -3.859   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.129  -3.507   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.457  -5.095   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.365  -1.108   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.016  -5.061   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3    5   11                                                       
CONECT    4    6   12                                                       
CONECT    5    3   14                                                       
CONECT    6    4   15                                                       
CONECT    7    8   13                                                       
CONECT    8    7   17                                                       
CONECT    9   12   18                                                       
CONECT   10   16   23                                                       
CONECT   11    1    2    3                                                  
CONECT   12    4    9   21                                                  
CONECT   13    7   16   19                                                  
CONECT   14    5   17   19                                                  
CONECT   15    6   18   20                                                  
CONECT   16   10   13   20                                                  
CONECT   17    8   14   22                                                  
CONECT   18    9   15   23                                                  
CONECT   19   13   14   24                                                  
CONECT   20   15   16   24                                                  
CONECT   21   12                                                            
CONECT   22   17                                                            
CONECT   23   10   18                                                       
CONECT   24   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0033669
HETATM    1  C1  UNL     1      -4.003   1.911  -0.117  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.502   0.586  -0.567  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.962   0.351  -0.654  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.625  -0.354  -0.880  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.192  -0.083  -0.780  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.454  -0.954   0.177  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.106  -1.882   0.946  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.473  -2.069   0.886  1.00  0.00           O  
HETATM    9  C8  UNL     1      -1.365  -2.655   1.809  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.003  -2.492   1.893  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.642  -1.563   1.122  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.065  -0.773   0.247  1.00  0.00           C  
HETATM   13  O2  UNL     1       0.804   0.093  -0.424  1.00  0.00           O  
HETATM   14  C12 UNL     1       2.066  -0.588  -0.422  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.182   0.302  -0.707  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.670   0.425  -1.988  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.730   1.263  -2.299  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.301   1.987  -1.286  1.00  0.00           C  
HETATM   19  O3  UNL     1       6.370   2.831  -1.608  1.00  0.00           O  
HETATM   20  C17 UNL     1       4.839   1.887  -0.005  1.00  0.00           C  
HETATM   21  C18 UNL     1       3.768   1.036   0.290  1.00  0.00           C  
HETATM   22  O4  UNL     1       3.271   0.904   1.571  1.00  0.00           O  
HETATM   23  C19 UNL     1       2.268  -0.006   1.957  1.00  0.00           C  
HETATM   24  C20 UNL     1       2.076  -1.143   0.982  1.00  0.00           C  
HETATM   25  H1  UNL     1      -3.440   2.425  -0.912  1.00  0.00           H  
HETATM   26  H2  UNL     1      -4.854   2.587   0.157  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.355   1.827   0.800  1.00  0.00           H  
HETATM   28  H4  UNL     1      -6.445   0.470   0.360  1.00  0.00           H  
HETATM   29  H5  UNL     1      -6.228  -0.642  -1.020  1.00  0.00           H  
HETATM   30  H6  UNL     1      -6.450   1.141  -1.293  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.018  -1.325  -1.218  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.030   0.986  -0.513  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.764  -0.186  -1.815  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.956  -2.742   1.441  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.794  -3.410   2.451  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.611  -3.102   2.578  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.943  -1.405  -1.176  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.230  -0.138  -2.789  1.00  0.00           H  
HETATM   39  H15 UNL     1       5.107   1.353  -3.316  1.00  0.00           H  
HETATM   40  H16 UNL     1       7.307   2.453  -1.564  1.00  0.00           H  
HETATM   41  H17 UNL     1       5.277   2.450   0.807  1.00  0.00           H  
HETATM   42  H18 UNL     1       2.534  -0.358   2.983  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.315   0.578   1.995  1.00  0.00           H  
HETATM   44  H20 UNL     1       2.764  -1.976   1.124  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4    4
CONECT    3   28   29   30
CONECT    4    5   31
CONECT    5    6   32   33
CONECT    6    7    7   12
CONECT    7    8    9
CONECT    8   34
CONECT    9   10   10   35
CONECT   10   11   36
CONECT   11   12   12   24
CONECT   12   13
CONECT   13   14
CONECT   14   15   24   37
CONECT   15   16   16   21
CONECT   16   17   38
CONECT   17   18   18   39
CONECT   18   19   20
CONECT   19   40
CONECT   20   21   21   41
CONECT   21   22
CONECT   22   23
CONECT   23   24   42   43
CONECT   24   44
END

HMDB0033669
     RDKit          3D
Phaseollidin
 44 47  0  0  0  0  0  0  0  0999 V2000
   -4.0034    1.9110   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5021    0.5861   -0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9624    0.3507   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6248   -0.3543   -0.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1920   -0.0831   -0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4541   -0.9541    0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063   -1.8823    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4734   -2.0689    0.8861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3651   -2.6549    1.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0030   -2.4917    1.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6420   -1.5626    1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0647   -0.7728    0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042    0.0932   -0.4244 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0660   -0.5882   -0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1819    0.3020   -0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702    0.4255   -1.9882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7298    1.2633   -2.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3010    1.9874   -1.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3703    2.8309   -1.6082 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8392    1.8868   -0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7684    1.0357    0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710    0.9042    1.5709 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2682   -0.0065    1.9571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0760   -1.1432    0.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4401    2.4249   -0.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8536    2.5873    0.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3553    1.8271    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4452    0.4700    0.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2278   -0.6417   -1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4495    1.1413   -1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0176   -1.3255   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0298    0.9864   -0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7638   -0.1862   -1.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9562   -2.7425    1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7944   -3.4102    2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6111   -3.1025    2.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432   -1.4046   -1.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2300   -0.1376   -2.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1073    1.3531   -3.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3074    2.4525   -1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2774    2.4502    0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5345   -0.3585    2.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3154    0.5782    1.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7643   -1.9758    1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 12  6  1  0
 24 14  1  0
 24 11  1  0
 21 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
 23 42  1  0
 23 43  1  0
 24 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Phaseollidin	HMDB
6a,11a-Dihydro-10-(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-3,9-diol, 9ci	HMDB

Chemical Formula

C₂₀H₂₀O₄

Average Molecular Weight

324.3704

Monoisotopic Molecular Weight

324.136159128

IUPAC Name

15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol

Traditional Name

15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol

CAS Registry Number

37831-70-2

SMILES

CC(C)=CCC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2

InChI Identifier

InChI=1S/C20H20O4/c1-11(2)3-5-14-17(22)8-7-13-16-10-23-18-9-12(21)4-6-15(18)20(16)24-19(13)14/h3-4,6-9,16,20-22H,5,10H2,1-2H3

InChI Key

OFWYIUYVHYPQNX-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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a pterocarpan (CPD-4885 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033669)

Cowpea (FooDB: FOOD00202)

Pulses (FooDB: FOOD00867)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

fungicide (HMDB: HMDB0033669)

Agriculture

Pesticide

Insecticide

pesticide (HMDB: HMDB0033669)

Biological role

fungicide (HMDB: HMDB0033669)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	67 - 69 °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	0.028 g/L	ALOGPS
logP	3.79	ALOGPS
logP	4.09	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.09	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.82 m³·mol⁻¹	ChemAxon
Polarizability	35.42 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]+	178.216	31661259
DarkChem	[M-H]-	173.517	31661259
DeepCCS	[M+H]+	174.374	30932474
DeepCCS	[M-H]-	172.016	30932474
DeepCCS	[M-2H]-	205.039	30932474
DeepCCS	[M+Na]+	180.467	30932474
AllCCS	[M+H]+	179.6	32859911
AllCCS	[M+H-H2O]+	176.3	32859911
AllCCS	[M+NH4]+	182.8	32859911
AllCCS	[M+Na]+	183.6	32859911
AllCCS	[M-H]-	182.8	32859911
AllCCS	[M+Na-2H]-	182.2	32859911
AllCCS	[M+HCOO]-	181.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phaseollidin	CC(C)=CCC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2	3753.8	Standard polar	33892256
Phaseollidin	CC(C)=CCC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2	2845.5	Standard non polar	33892256
Phaseollidin	CC(C)=CCC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2	3104.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phaseollidin,1TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=CC2=C1OC1C3=CC=C(O)C=C3OCC21	2887.0	Semi standard non polar	33892256
Phaseollidin,1TMS,isomer #2	CC(C)=CCC1=C(O)C=CC2=C1OC1C3=CC=C(O[Si](C)(C)C)C=C3OCC21	2924.6	Semi standard non polar	33892256
Phaseollidin,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=CC2=C1OC1C3=CC=C(O[Si](C)(C)C)C=C3OCC21	2906.5	Semi standard non polar	33892256
Phaseollidin,1TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC1C3=CC=C(O)C=C3OCC21	3107.9	Semi standard non polar	33892256
Phaseollidin,1TBDMS,isomer #2	CC(C)=CCC1=C(O)C=CC2=C1OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OCC21	3141.8	Semi standard non polar	33892256
Phaseollidin,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OCC21	3331.3	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 - Phaseollidin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-6594000000-8b5b4b73f84f06975696	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phaseollidin GC-MS (2 TMS) - 70eV, Positive	splash10-0udi-4233900000-c266017f6caebe727b88	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phaseollidin 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 - Phaseollidin 10V, Positive-QTOF	splash10-004i-1139000000-0516bafeac70b7f3307b	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollidin 20V, Positive-QTOF	splash10-016r-4395000000-3bab6345ec8bef02793d	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollidin 40V, Positive-QTOF	splash10-014j-9220000000-7b01887f18b52a30201c	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollidin 10V, Negative-QTOF	splash10-00di-0009000000-e5c925628b63acda0106	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollidin 20V, Negative-QTOF	splash10-00di-0049000000-f683037041131d6a52a1	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollidin 40V, Negative-QTOF	splash10-0a6u-3960000000-8b4bbee7eb29375ba3dd	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollidin 10V, Positive-QTOF	splash10-00or-0049000000-6580c60f6dd0e6b63190	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollidin 20V, Positive-QTOF	splash10-014i-0090000000-eb92797fe0707b76f151	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollidin 40V, Positive-QTOF	splash10-0002-0971000000-08a716e4b2b1d884d720	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollidin 10V, Negative-QTOF	splash10-00di-0009000000-b64caba2598a2db6662e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollidin 20V, Negative-QTOF	splash10-00di-0019000000-343d2223aac4f6903527	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollidin 40V, Negative-QTOF	splash10-0a59-1790000000-46dc90f67cf109ca5e89	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5117820

PDB ID

Not Available

ChEBI ID

17556

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

Phaseollidin → 3,4,5-trihydroxy-6-{[14-hydroxy-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-yl]oxy}oxane-2-carboxylic acid	details
Phaseollidin → 3,4,5-trihydroxy-6-{[5-hydroxy-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-14-yl]oxy}oxane-2-carboxylic acid	details

Showing metabocard for Phaseollidin (HMDB0033669)

MOL for HMDB0033669 (Phaseollidin)

3D MOL for HMDB0033669 (Phaseollidin)

3D SDF for HMDB0033669 (Phaseollidin)

3D-SDF for HMDB0033669 (Phaseollidin)

PDB for HMDB0033669 (Phaseollidin)

3D PDB for HMDB0033669 (Phaseollidin)

SMILES for HMDB0033669 (Phaseollidin)

INCHI for HMDB0033669 (Phaseollidin)

Structure for HMDB0033669 (Phaseollidin)

3D Structure for HMDB0033669 (Phaseollidin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions