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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:10:51 UTC

Update Date

2022-03-07 02:55:34 UTC

HMDB ID

HMDB0037922

Secondary Accession Numbers

HMDB37922

Metabolite Identification

Common Name

Phaseol

Description

Phaseol belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, phaseol is considered to be a flavonoid. Phaseol has been detected, but not quantified in, pulses and soy beans (Glycine max). This could make phaseol a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Phaseol.

Structure

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

HMDB0037922
     RDKit          3D
Phaseol
 41 44  0  0  0  0  0  0  0  0999 V2000
   -5.5127    0.2792   -0.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6806   -0.4292    0.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3879   -1.3576    1.7323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3869   -0.2487    0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6589    0.6480   -0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5674   -0.0118   -0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7573   -0.8224   -1.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0455   -1.0646   -2.3539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7072   -1.4172   -2.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5841   -1.1957   -2.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7963   -0.3913   -1.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2460    0.2024   -0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0211    0.9733    0.6293 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1968    1.2102    1.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4197    1.9555    2.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2742    0.6445    0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6383    0.7113    0.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609    1.3925    1.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7392    1.2776    1.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3302    0.4952    0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7108    0.3633    0.5824 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6049   -0.1752   -0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2351   -0.0675   -0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2775   -0.5818   -1.0996 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1129   -0.1756   -0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5998    0.1752    0.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2337    1.3697   -0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3378   -0.1873   -1.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5155   -2.3299    1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7654   -1.4952    2.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3676   -0.9102    1.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7790   -0.7802    1.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3059    1.1983   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2321    1.4724    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2543   -1.6468   -3.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8793   -2.0539   -3.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4465   -1.6331   -2.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8338    1.9743    2.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3322    1.8015    2.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2721    0.8348    1.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0763   -0.7923   -1.1026 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  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 12  6  1  0
 25 16  2  0
 25 11  1  0
 23 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 22 41  1  0
M  END


  Mrv0541 05061310052D          

 25 28  0  0  0  0            999 V2000
    5.3205    5.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5968    5.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4021    4.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    3.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5785    4.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466    3.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    2.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2891    2.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7731    5.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    2.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2075    3.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9407    3.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0128    2.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601    2.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014    2.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365    3.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838    3.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892    2.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    4.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2591    2.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4838    2.8924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548    4.8202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6731    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9312    4.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  2  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  2  0  0  0  0
 11  4  1  0  0  0  0
 11  9  2  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  2  0  0  0  0
 16  9  1  0  0  0  0
 16 13  2  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 18 14  2  0  0  0  0
 19 14  1  0  0  0  0
 19 17  2  0  0  0  0
 20 17  1  0  0  0  0
 21 11  1  0  0  0  0
 22 15  1  0  0  0  0
 23 20  2  0  0  0  0
 24 16  1  0  0  0  0
 24 19  1  0  0  0  0
 25 18  1  0  0  0  0
 25 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037922

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C1=C2OC2=C1C=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O5/c1-10(2)3-5-12-15(22)8-7-14-18(12)25-20(23)17-13-6-4-11(21)9-16(13)24-19(14)17/h3-4,6-9,21-22H,5H2,1-2H3

> <INCHI_KEY>
FRXPSBUCIWPZMH-UHFFFAOYSA-N

> <FORMULA>
C20H16O5

> <MOLECULAR_WEIGHT>
336.338

> <EXACT_MASS>
336.099773622

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.9896798274789

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,14-dihydroxy-6-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

> <ALOGPS_LOGP>
4.59

> <JCHEM_LOGP>
4.125888321666666

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.109957681263777

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.9225789415810315

> <JCHEM_PKA_STRONGEST_BASIC>
-4.325585151569688

> <JCHEM_POLAR_SURFACE_AREA>
79.9

> <JCHEM_REFRACTIVITY>
93.86229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phaseol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037922
     RDKit          3D
Phaseol
 41 44  0  0  0  0  0  0  0  0999 V2000
   -5.5127    0.2792   -0.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6806   -0.4292    0.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3879   -1.3576    1.7323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3869   -0.2487    0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6589    0.6480   -0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5674   -0.0118   -0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7573   -0.8224   -1.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0455   -1.0646   -2.3539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7072   -1.4172   -2.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5841   -1.1957   -2.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7963   -0.3913   -1.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2460    0.2024   -0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0211    0.9733    0.6293 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1968    1.2102    1.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4197    1.9555    2.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2742    0.6445    0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6383    0.7113    0.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609    1.3925    1.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7392    1.2776    1.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3302    0.4952    0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7108    0.3633    0.5824 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6049   -0.1752   -0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2351   -0.0675   -0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2775   -0.5818   -1.0996 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1129   -0.1756   -0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5998    0.1752    0.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2337    1.3697   -0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3378   -0.1873   -1.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5155   -2.3299    1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7654   -1.4952    2.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3676   -0.9102    1.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7790   -0.7802    1.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3059    1.1983   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2321    1.4724    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2543   -1.6468   -3.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8793   -2.0539   -3.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4465   -1.6331   -2.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8338    1.9743    2.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3322    1.8015    2.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2721    0.8348    1.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0763   -0.7923   -1.1026 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  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 12  6  1  0
 25 16  2  0
 25 11  1  0
 23 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 22 41  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.932  10.725   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.314   9.526   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.084   8.062   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.909   6.056   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.547   7.974   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.460   6.761   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.469   3.848   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.006   3.936   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.314   3.685   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.776   9.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.982   4.518   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.854   6.599   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.756   5.929   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.624   5.135   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.699   5.311   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.683   4.391   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.241   6.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.316   6.511   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.087   5.047   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.934   7.710   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.350   3.812   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.236   5.399   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.089   8.998   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.123   3.846   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.472   7.798   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3    5   10                                                       
CONECT    4    6   11                                                       
CONECT    5    3   12                                                       
CONECT    6    4   13                                                       
CONECT    7    8   14                                                       
CONECT    8    7   15                                                       
CONECT    9   11   16                                                       
CONECT   10    1    2    3                                                  
CONECT   11    4    9   21                                                  
CONECT   12    5   15   18                                                  
CONECT   13    6   16   17                                                  
CONECT   14    7   18   19                                                  
CONECT   15    8   12   22                                                  
CONECT   16    9   13   24                                                  
CONECT   17   13   19   20                                                  
CONECT   18   12   14   25                                                  
CONECT   19   14   17   24                                                  
CONECT   20   17   23   25                                                  
CONECT   21   11                                                            
CONECT   22   15                                                            
CONECT   23   20                                                            
CONECT   24   16   19                                                       
CONECT   25   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0037922
HETATM    1  C1  UNL     1      -5.513   0.279  -0.199  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.681  -0.429   0.794  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.388  -1.358   1.732  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.387  -0.249   0.846  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.659   0.648  -0.054  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.567  -0.012  -0.821  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.757  -0.822  -1.909  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.045  -1.065  -2.354  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.707  -1.417  -2.591  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.584  -1.196  -2.173  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.796  -0.391  -1.091  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.246   0.202  -0.410  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.021   0.973   0.629  1.00  0.00           O  
HETATM   14  C12 UNL     1       1.197   1.210   1.061  1.00  0.00           C  
HETATM   15  O3  UNL     1       1.420   1.956   2.066  1.00  0.00           O  
HETATM   16  C13 UNL     1       2.274   0.644   0.420  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.638   0.711   0.642  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.361   1.392   1.611  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.739   1.278   1.595  1.00  0.00           C  
HETATM   20  C17 UNL     1       6.330   0.495   0.621  1.00  0.00           C  
HETATM   21  O4  UNL     1       7.711   0.363   0.582  1.00  0.00           O  
HETATM   22  C18 UNL     1       5.605  -0.175  -0.335  1.00  0.00           C  
HETATM   23  C19 UNL     1       4.235  -0.068  -0.327  1.00  0.00           C  
HETATM   24  O5  UNL     1       3.277  -0.582  -1.100  1.00  0.00           O  
HETATM   25  C20 UNL     1       2.113  -0.176  -0.678  1.00  0.00           C  
HETATM   26  H1  UNL     1      -6.600   0.175   0.030  1.00  0.00           H  
HETATM   27  H2  UNL     1      -5.234   1.370  -0.215  1.00  0.00           H  
HETATM   28  H3  UNL     1      -5.338  -0.187  -1.189  1.00  0.00           H  
HETATM   29  H4  UNL     1      -5.516  -2.330   1.228  1.00  0.00           H  
HETATM   30  H5  UNL     1      -4.765  -1.495   2.646  1.00  0.00           H  
HETATM   31  H6  UNL     1      -6.368  -0.910   1.961  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.779  -0.780   1.591  1.00  0.00           H  
HETATM   33  H8  UNL     1      -3.306   1.198  -0.774  1.00  0.00           H  
HETATM   34  H9  UNL     1      -2.232   1.472   0.594  1.00  0.00           H  
HETATM   35  H10 UNL     1      -3.254  -1.647  -3.142  1.00  0.00           H  
HETATM   36  H11 UNL     1      -0.879  -2.054  -3.448  1.00  0.00           H  
HETATM   37  H12 UNL     1       1.446  -1.633  -2.666  1.00  0.00           H  
HETATM   38  H13 UNL     1       3.834   1.974   2.327  1.00  0.00           H  
HETATM   39  H14 UNL     1       6.332   1.802   2.345  1.00  0.00           H  
HETATM   40  H15 UNL     1       8.272   0.835   1.259  1.00  0.00           H  
HETATM   41  H16 UNL     1       6.076  -0.792  -1.103  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4    4
CONECT    3   29   30   31
CONECT    4    5   32
CONECT    5    6   33   34
CONECT    6    7    7   12
CONECT    7    8    9
CONECT    8   35
CONECT    9   10   10   36
CONECT   10   11   37
CONECT   11   12   12   25
CONECT   12   13
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17   25   25
CONECT   17   18   18   23
CONECT   18   19   38
CONECT   19   20   20   39
CONECT   20   21   22
CONECT   21   40
CONECT   22   23   23   41
CONECT   23   24
CONECT   24   25
END

HMDB0037922
     RDKit          3D
Phaseol
 41 44  0  0  0  0  0  0  0  0999 V2000
   -5.5127    0.2792   -0.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6806   -0.4292    0.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3879   -1.3576    1.7323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3869   -0.2487    0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6589    0.6480   -0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5674   -0.0118   -0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7573   -0.8224   -1.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0455   -1.0646   -2.3539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7072   -1.4172   -2.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5841   -1.1957   -2.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7963   -0.3913   -1.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2460    0.2024   -0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0211    0.9733    0.6293 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1968    1.2102    1.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4197    1.9555    2.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2742    0.6445    0.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6383    0.7113    0.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609    1.3925    1.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7392    1.2776    1.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3302    0.4952    0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7108    0.3633    0.5824 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6049   -0.1752   -0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2351   -0.0675   -0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2775   -0.5818   -1.0996 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1129   -0.1756   -0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5998    0.1752    0.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2337    1.3697   -0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3378   -0.1873   -1.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5155   -2.3299    1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7654   -1.4952    2.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3676   -0.9102    1.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7790   -0.7802    1.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3059    1.1983   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2321    1.4724    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2543   -1.6468   -3.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8793   -2.0539   -3.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4465   -1.6331   -2.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8338    1.9743    2.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3322    1.8015    2.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2721    0.8348    1.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0763   -0.7923   -1.1026 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  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 12  6  1  0
 25 16  2  0
 25 11  1  0
 23 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 22 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,9-Dihydroxy-4-(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-6-one, 9ci	HMDB
3,9-Dihydroxy-4-prenylcoumestan	HMDB
Phaseollidin hydrate	HMDB

Chemical Formula

C₂₀H₁₆O₅

Average Molecular Weight

336.338

Monoisotopic Molecular Weight

336.099773622

IUPAC Name

5,14-dihydroxy-6-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

Traditional Name

phaseol

CAS Registry Number

88478-02-8

SMILES

CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C1=C2OC2=C1C=CC(O)=C2

InChI Identifier

InChI=1S/C20H16O5/c1-10(2)3-5-12-15(22)8-7-14-18(12)25-20(23)17-13-6-4-11(21)9-16(13)24-19(14)17/h3-4,6-9,21-22H,5H2,1-2H3

InChI Key

FRXPSBUCIWPZMH-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090010 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037922)

Cellular substructure

Membrane (HMDB: HMDB0037922)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037922)

Source

Exogenous

Food

Food (HMDB: HMDB0037922)

Soy

Soy bean (FooDB: FOOD00085)

Pulse

Pulses (FooDB: FOOD00867)

Not Available

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

fungicide (HMDB: HMDB0037922)

Agriculture

Pesticide

Insecticide

pesticide (HMDB: HMDB0037922)

Biological role

fungicide (HMDB: HMDB0037922)

Nutrient

Nutrient (HMDB: HMDB0037922)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.98 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	0.068 g/L	ALOGPS
logP	4.59	ALOGPS
logP	4.13	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.92	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.86 m³·mol⁻¹	ChemAxon
Polarizability	35.99 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]+	182.174	31661259
DarkChem	[M-H]-	177.477	31661259
DeepCCS	[M+H]+	178.796	30932474
DeepCCS	[M-H]-	176.438	30932474
DeepCCS	[M-2H]-	210.347	30932474
DeepCCS	[M+Na]+	185.575	30932474
AllCCS	[M+H]+	180.1	32859911
AllCCS	[M+H-H2O]+	176.7	32859911
AllCCS	[M+NH4]+	183.2	32859911
AllCCS	[M+Na]+	184.1	32859911
AllCCS	[M-H]-	179.5	32859911
AllCCS	[M+Na-2H]-	178.6	32859911
AllCCS	[M+HCOO]-	177.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phaseol	CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C1=C2OC2=C1C=CC(O)=C2	4426.3	Standard polar	33892256
Phaseol	CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C1=C2OC2=C1C=CC(O)=C2	3185.5	Standard non polar	33892256
Phaseol	CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C1=C2OC2=C1C=CC(O)=C2	3384.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phaseol,1TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=CC2=C1OC(=O)C1=C2OC2=CC(O)=CC=C21	3334.8	Semi standard non polar	33892256
Phaseol,1TMS,isomer #2	CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C1=C2OC2=CC(O[Si](C)(C)C)=CC=C21	3376.7	Semi standard non polar	33892256
Phaseol,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=CC2=C1OC(=O)C1=C2OC2=CC(O[Si](C)(C)C)=CC=C21	3362.6	Semi standard non polar	33892256
Phaseol,1TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC(=O)C1=C2OC2=CC(O)=CC=C21	3546.8	Semi standard non polar	33892256
Phaseol,1TBDMS,isomer #2	CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C1=C2OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	3573.7	Semi standard non polar	33892256
Phaseol,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC(=O)C1=C2OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	3815.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phaseol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6u-4639000000-80b890faae18353528b2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phaseol GC-MS (2 TMS) - 70eV, Positive	splash10-06di-2021900000-3e59be6bbcc6090afaee	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phaseol 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 - Phaseol 10V, Positive-QTOF	splash10-000i-0029000000-1b21ebd042fe66990335	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseol 20V, Positive-QTOF	splash10-00li-4097000000-35d782407e35cb768a50	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseol 40V, Positive-QTOF	splash10-014i-9260000000-27ea8869c3ebf9c3c0a1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseol 10V, Negative-QTOF	splash10-000i-0029000000-28986ccf750fc3fb6f10	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseol 20V, Negative-QTOF	splash10-000i-0059000000-e7b1828b4645bc1745a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseol 40V, Negative-QTOF	splash10-05gl-3691000000-7607411fdffd4e8e40dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseol 10V, Negative-QTOF	splash10-000i-0009000000-dc81427ba733f47873d1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseol 20V, Negative-QTOF	splash10-000i-0029000000-3414aa7d4567ef62cdec	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseol 40V, Negative-QTOF	splash10-014l-1190000000-15d4a88f14d0d9d294cb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseol 10V, Positive-QTOF	splash10-0019-0049000000-ed20812eeada82c0cb68	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseol 20V, Positive-QTOF	splash10-001i-0090000000-30908eb5a1e79c21ebed	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phaseol 40V, Positive-QTOF	splash10-004i-0090000000-1053c919d8eb7822a572	2021-09-25	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

44257530

PDB ID

Not Available

ChEBI ID

17465

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1864231

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 Phaseol (HMDB0037922)

MOL for HMDB0037922 (Phaseol)

3D MOL for HMDB0037922 (Phaseol)

3D SDF for HMDB0037922 (Phaseol)

3D-SDF for HMDB0037922 (Phaseol)

PDB for HMDB0037922 (Phaseol)

3D PDB for HMDB0037922 (Phaseol)

SMILES for HMDB0037922 (Phaseol)

INCHI for HMDB0037922 (Phaseol)

Structure for HMDB0037922 (Phaseol)

3D Structure for HMDB0037922 (Phaseol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra