Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:57:59 UTC

Update Date

2022-03-07 02:54:00 UTC

HMDB ID

HMDB0034173

Secondary Accession Numbers

HMDB34173

Metabolite Identification

Common Name

Phaseollin

Description

Phaseollin 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. Phaseollin has been detected, but not quantified in, several different foods, such as common beans (Phaseolus vulgaris), green beans (Phaseolus vulgaris), cowpeas (Vigna unguiculata), yellow wax beans (Phaseolus vulgaris), and scarlet beans (Phaseolus coccineus). This could make phaseollin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Phaseollin.

Structure

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

HMDB0034173
     RDKit          3D
Phaseollin
 42 46  0  0  0  0  0  0  0  0999 V2000
   -5.3685    0.4394    1.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4980   -0.2719    0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3996   -1.2514   -0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5165   -1.0724    1.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2310   -0.9830    1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7149   -0.0584    0.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6133    0.7030   -0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0997    1.5847   -1.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7332    1.6861   -1.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1390    0.9201   -1.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3342    0.0296   -0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7672   -0.6325    0.4334 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8083    0.3218    0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1653   -0.2261    0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5545   -1.3596    1.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8861   -1.7762    0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8353   -1.0554    0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.5111    0.2499 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4311    0.1078   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159    0.5238   -0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7552    1.6972   -0.9880 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3837    2.0390   -1.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5929    0.7956   -1.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9741    0.6113   -0.4784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9872   -0.3575    1.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9843    1.2209    1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6683    0.8162    2.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9640   -1.4963   -1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3575   -0.7009   -0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5081   -2.1376    0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8995   -1.7679    1.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5532   -1.5929    1.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7999    2.1946   -2.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253    2.3851   -2.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6755    1.1585    1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141   -1.9298    1.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1733   -2.6960    1.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8444   -1.2616    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2010    0.6496   -0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0271    2.7791   -0.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2761    2.4850   -2.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9400   -0.0371   -1.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  7 24  1  0
 24  2  1  0
 11  6  1  0
 23 13  1  0
 23 10  1  0
 20 14  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
  8 33  1  0
  9 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
M  END


  Mrv0541 05061307382D          

 24 28  0  0  0  0            999 V2000
    7.3066    2.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5271    1.4342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1740    2.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9810    2.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749   -0.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4818    0.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4397    2.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2466    2.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8769    1.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7458   -0.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220    1.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1228    0.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2359    1.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1847    1.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2978    0.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7368    0.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6839    0.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3778    1.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    1.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7987    1.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1850    1.9931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388    0.0808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7103    1.7919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5437    1.0369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
  8  7  2  0  0  0  0
 11  3  1  0  0  0  0
 11  9  2  0  0  0  0
 12  5  1  0  0  0  0
 13  4  1  0  0  0  0
 14  7  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16  6  1  0  0  0  0
 16 14  2  0  0  0  0
 17  9  1  0  0  0  0
 17 13  2  0  0  0  0
 18 12  2  0  0  0  0
 18 14  1  0  0  0  0
 19 13  1  0  0  0  0
 19 15  1  0  0  0  0
 20  1  1  0  0  0  0
 20  2  1  0  0  0  0
 20  8  1  0  0  0  0
 21 11  1  0  0  0  0
 22 10  1  0  0  0  0
 22 17  1  0  0  0  0
 23 18  1  0  0  0  0
 23 19  1  0  0  0  0
 24 16  1  0  0  0  0
 24 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034173

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)OC2=C(C=C1)C1=C(C=C2)C2COC3=C(C=CC(O)=C3)C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O4/c1-20(2)8-7-14-16(24-20)6-5-12-15-10-22-17-9-11(21)3-4-13(17)19(15)23-18(12)14/h3-9,15,19,21H,10H2,1-2H3

> <INCHI_KEY>
LWTDZKXXJRRKDG-UHFFFAOYSA-N

> <FORMULA>
C20H18O4

> <MOLECULAR_WEIGHT>
322.3545

> <EXACT_MASS>
322.120509064

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.66484454859216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17,17-dimethyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-1(13),5(10),6,8,14(19),15,20-heptaen-7-ol

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
3.5675180639999997

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.420753775274274

> <JCHEM_PKA_STRONGEST_BASIC>
-4.422821908958812

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
90.99130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17,17-dimethyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-1(13),5(10),6,8,14(19),15,20-heptaen-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034173
     RDKit          3D
Phaseollin
 42 46  0  0  0  0  0  0  0  0999 V2000
   -5.3685    0.4394    1.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4980   -0.2719    0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3996   -1.2514   -0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5165   -1.0724    1.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2310   -0.9830    1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7149   -0.0584    0.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6133    0.7030   -0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0997    1.5847   -1.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7332    1.6861   -1.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1390    0.9201   -1.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3342    0.0296   -0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7672   -0.6325    0.4334 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8083    0.3218    0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1653   -0.2261    0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5545   -1.3596    1.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8861   -1.7762    0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8353   -1.0554    0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.5111    0.2499 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4311    0.1078   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159    0.5238   -0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7552    1.6972   -0.9880 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3837    2.0390   -1.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5929    0.7956   -1.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9741    0.6113   -0.4784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9872   -0.3575    1.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9843    1.2209    1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6683    0.8162    2.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9640   -1.4963   -1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3575   -0.7009   -0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5081   -2.1376    0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8995   -1.7679    1.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5532   -1.5929    1.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7999    2.1946   -2.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253    2.3851   -2.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6755    1.1585    1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141   -1.9298    1.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1733   -2.6960    1.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8444   -1.2616    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2010    0.6496   -0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0271    2.7791   -0.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2761    2.4850   -2.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9400   -0.0371   -1.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  7 24  1  0
 24  2  1  0
 11  6  1  0
 23 13  1  0
 23 10  1  0
 20 14  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
  8 33  1  0
  9 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  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      13.639   4.614   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.051   2.677   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.191   4.545   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.698   4.224   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.726  -0.169   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.233   0.151   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.154   4.224   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.660   4.545   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.637   1.936   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.125  -0.169   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.161   3.400   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.696   0.975   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.174   2.760   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.678   2.760   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.156   0.975   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.709   1.615   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.143   1.615   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.172   2.440   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.680   2.440   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.691   3.400   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.345   3.720   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.619   0.151   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.926   3.345   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      12.215   1.936   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   20                                                            
CONECT    3    4   11                                                       
CONECT    4    3   13                                                       
CONECT    5    6   12                                                       
CONECT    6    5   16                                                       
CONECT    7    8   14                                                       
CONECT    8    7   20                                                       
CONECT    9   11   17                                                       
CONECT   10   15   22                                                       
CONECT   11    3    9   21                                                  
CONECT   12    5   15   18                                                  
CONECT   13    4   17   19                                                  
CONECT   14    7   16   18                                                  
CONECT   15   10   12   19                                                  
CONECT   16    6   14   24                                                  
CONECT   17    9   13   22                                                  
CONECT   18   12   14   23                                                  
CONECT   19   13   15   23                                                  
CONECT   20    1    2    8   24                                             
CONECT   21   11                                                            
CONECT   22   10   17                                                       
CONECT   23   18   19                                                       
CONECT   24   16   20                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0034173
HETATM    1  C1  UNL     1      -5.369   0.439   1.492  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.498  -0.272   0.457  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.400  -1.251  -0.305  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.516  -1.072   1.197  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.231  -0.983   1.011  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.715  -0.058   0.034  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.613   0.703  -0.672  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.100   1.585  -1.606  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.733   1.686  -1.810  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.139   0.920  -1.098  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.334   0.030  -0.158  1.00  0.00           C  
HETATM   12  O1  UNL     1       0.767  -0.632   0.433  1.00  0.00           O  
HETATM   13  C12 UNL     1       1.808   0.322   0.364  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.165  -0.226   0.387  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.555  -1.360   1.020  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.886  -1.776   0.965  1.00  0.00           C  
HETATM   17  C16 UNL     1       5.835  -1.055   0.274  1.00  0.00           C  
HETATM   18  O2  UNL     1       7.145  -1.511   0.250  1.00  0.00           O  
HETATM   19  C17 UNL     1       5.431   0.108  -0.374  1.00  0.00           C  
HETATM   20  C18 UNL     1       4.116   0.524  -0.323  1.00  0.00           C  
HETATM   21  O3  UNL     1       3.755   1.697  -0.988  1.00  0.00           O  
HETATM   22  C19 UNL     1       2.384   2.039  -1.244  1.00  0.00           C  
HETATM   23  C20 UNL     1       1.593   0.796  -1.087  1.00  0.00           C  
HETATM   24  O4  UNL     1      -3.974   0.611  -0.478  1.00  0.00           O  
HETATM   25  H1  UNL     1      -5.987  -0.358   1.960  1.00  0.00           H  
HETATM   26  H2  UNL     1      -5.984   1.221   1.041  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.668   0.816   2.268  1.00  0.00           H  
HETATM   28  H4  UNL     1      -4.964  -1.496  -1.287  1.00  0.00           H  
HETATM   29  H5  UNL     1      -6.358  -0.701  -0.470  1.00  0.00           H  
HETATM   30  H6  UNL     1      -5.508  -2.138   0.329  1.00  0.00           H  
HETATM   31  H7  UNL     1      -3.899  -1.768   1.931  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.553  -1.593   1.580  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.800   2.195  -2.173  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.325   2.385  -2.550  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.675   1.159   1.071  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.814  -1.930   1.564  1.00  0.00           H  
HETATM   37  H13 UNL     1       5.173  -2.696   1.486  1.00  0.00           H  
HETATM   38  H14 UNL     1       7.844  -1.262   0.920  1.00  0.00           H  
HETATM   39  H15 UNL     1       6.201   0.650  -0.907  1.00  0.00           H  
HETATM   40  H16 UNL     1       2.027   2.779  -0.499  1.00  0.00           H  
HETATM   41  H17 UNL     1       2.276   2.485  -2.268  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.940  -0.037  -1.736  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4   24
CONECT    3   28   29   30
CONECT    4    5    5   31
CONECT    5    6   32
CONECT    6    7    7   11
CONECT    7    8   24
CONECT    8    9    9   33
CONECT    9   10   34
CONECT   10   11   11   23
CONECT   11   12
CONECT   12   13
CONECT   13   14   23   35
CONECT   14   15   15   20
CONECT   15   16   36
CONECT   16   17   17   37
CONECT   17   18   19
CONECT   18   38
CONECT   19   20   20   39
CONECT   20   21
CONECT   21   22
CONECT   22   23   40   41
CONECT   23   42
END

HMDB0034173
     RDKit          3D
Phaseollin
 42 46  0  0  0  0  0  0  0  0999 V2000
   -5.3685    0.4394    1.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4980   -0.2719    0.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3996   -1.2514   -0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5165   -1.0724    1.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2310   -0.9830    1.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7149   -0.0584    0.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6133    0.7030   -0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0997    1.5847   -1.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7332    1.6861   -1.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1390    0.9201   -1.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3342    0.0296   -0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7672   -0.6325    0.4334 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8083    0.3218    0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1653   -0.2261    0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5545   -1.3596    1.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8861   -1.7762    0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8353   -1.0554    0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.5111    0.2499 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4311    0.1078   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159    0.5238   -0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7552    1.6972   -0.9880 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3837    2.0390   -1.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5929    0.7956   -1.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9741    0.6113   -0.4784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9872   -0.3575    1.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9843    1.2209    1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6683    0.8162    2.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9640   -1.4963   -1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3575   -0.7009   -0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5081   -2.1376    0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8995   -1.7679    1.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5532   -1.5929    1.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7999    2.1946   -2.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253    2.3851   -2.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6755    1.1585    1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141   -1.9298    1.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1733   -2.6960    1.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8444   -1.2616    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2010    0.6496   -0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0271    2.7791   -0.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2761    2.4850   -2.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9400   -0.0371   -1.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  7 24  1  0
 24  2  1  0
 11  6  1  0
 23 13  1  0
 23 10  1  0
 20 14  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
  8 33  1  0
  9 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Phaseollin	HMDB
6b,12b-dihydro-3,3-Dimethyl-3H,7H-furo[3,2-c:5,4-F]bis[1]benzopyran-10-ol, 9ci	HMDB
Phaseolin	HMDB
Phaseolin fungicide	HMDB

Chemical Formula

C₂₀H₁₈O₄

Average Molecular Weight

322.3545

Monoisotopic Molecular Weight

322.120509064

IUPAC Name

17,17-dimethyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-1(13),5(10),6,8,14(19),15,20-heptaen-7-ol

Traditional Name

17,17-dimethyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-1(13),5(10),6,8,14(19),15,20-heptaen-7-ol

CAS Registry Number

13401-40-6

SMILES

CC1(C)OC2=C(C=C1)C1=C(C=C2)C2COC3=C(C=CC(O)=C3)C2O1

InChI Identifier

InChI=1S/C20H18O4/c1-20(2)8-7-14-16(24-20)6-5-12-15-10-22-17-9-11(21)3-4-13(17)19(15)23-18(12)14/h3-9,15,19,21H,10H2,1-2H3

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a pterocarpan (CPD-4884 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034173)
Cell membrane (HMDB: HMDB0034173)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034173)

Source

Exogenous

Exogenous (HMDB: HMDB0034173)

Food

Food (HMDB: HMDB0034173)

Pulse

Bean

Pea

Cowpea (FooDB: FOOD00202)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Not Available

Industrial application

Agriculture

Pesticide

Fungicide (HMDB: HMDB0034173)

Pesticide (HMDB: HMDB0034173)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	177 - 178 °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	0.007 g/L	ALOGPS
logP	4.14	ALOGPS
logP	3.57	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	9.42	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.99 m³·mol⁻¹	ChemAxon
Polarizability	34.66 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]+	174.332	31661259
DarkChem	[M-H]-	174.523	31661259
DeepCCS	[M+H]+	181.799	30932474
DeepCCS	[M-H]-	179.441	30932474
DeepCCS	[M-2H]-	213.662	30932474
DeepCCS	[M+Na]+	188.889	30932474
AllCCS	[M+H]+	179.0	32859911
AllCCS	[M+H-H2O]+	175.5	32859911
AllCCS	[M+NH4]+	182.2	32859911
AllCCS	[M+Na]+	183.2	32859911
AllCCS	[M-H]-	184.0	32859911
AllCCS	[M+Na-2H]-	183.3	32859911
AllCCS	[M+HCOO]-	182.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phaseollin	CC1(C)OC2=C(C=C1)C1=C(C=C2)C2COC3=C(C=CC(O)=C3)C2O1	3808.3	Standard polar	33892256
Phaseollin	CC1(C)OC2=C(C=C1)C1=C(C=C2)C2COC3=C(C=CC(O)=C3)C2O1	2754.2	Standard non polar	33892256
Phaseollin	CC1(C)OC2=C(C=C1)C1=C(C=C2)C2COC3=C(C=CC(O)=C3)C2O1	2964.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phaseollin,1TMS,isomer #1	CC1(C)C=CC2=C(C=CC3=C2OC2C4=CC=C(O[Si](C)(C)C)C=C4OCC32)O1	2822.4	Semi standard non polar	33892256
Phaseollin,1TBDMS,isomer #1	CC1(C)C=CC2=C(C=CC3=C2OC2C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4OCC32)O1	3087.6	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 - Phaseollin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pba-0986000000-ef26fd9f571cb19c6da7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phaseollin GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-4659000000-30489c44cd92abec518c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phaseollin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phaseollin 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 - Phaseollin 10V, Positive-QTOF	splash10-00di-1019000000-4bbab45d581bac2b73b0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollin 20V, Positive-QTOF	splash10-01b9-1095000000-dc691a3331d87151164d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollin 40V, Positive-QTOF	splash10-014i-7390000000-d3aa381d2d66b3ecd240	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollin 10V, Negative-QTOF	splash10-00di-0009000000-eee8d60ede6b3ee25d06	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollin 20V, Negative-QTOF	splash10-00di-0069000000-190ffcf697fb9f20069b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollin 40V, Negative-QTOF	splash10-000i-0190000000-a6a942d005a9696cc3be	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollin 10V, Negative-QTOF	splash10-00di-0009000000-a4f58630e05faac231a5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollin 20V, Negative-QTOF	splash10-00fr-0098000000-6433a047af8ecc8e05c1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollin 40V, Negative-QTOF	splash10-0a6r-1982000000-aef35370b06f5bbbb8e3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollin 10V, Positive-QTOF	splash10-00di-0009000000-17eb34705e2ef23f703b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollin 20V, Positive-QTOF	splash10-00di-0029000000-9d0ae020608ee5e985d1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseollin 40V, Positive-QTOF	splash10-0avj-0932000000-f87d4a45a8e512e4f272	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phaseolin (pterocarpan)

METLIN ID

Not Available

PubChem Compound

4063834

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1840901

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 Phaseollin (HMDB0034173)

MOL for HMDB0034173 (Phaseollin)

3D MOL for HMDB0034173 (Phaseollin)

3D SDF for HMDB0034173 (Phaseollin)

3D-SDF for HMDB0034173 (Phaseollin)

PDB for HMDB0034173 (Phaseollin)

3D PDB for HMDB0034173 (Phaseollin)

SMILES for HMDB0034173 (Phaseollin)

INCHI for HMDB0034173 (Phaseollin)

Structure for HMDB0034173 (Phaseollin)

3D Structure for HMDB0034173 (Phaseollin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra