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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 03:51:22 UTC

Update Date

2021-09-23 03:51:22 UTC

HMDB ID

HMDB0301942

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(+)-Dihydrowighteone

Description

(+)-dihydrowighteone is a member of the class of compounds known as isoflavanones. Isoflavanones are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4. Thus, (+)-dihydrowighteone is considered to be a flavonoid lipid molecule (+)-dihydrowighteone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (+)-dihydrowighteone can be found in adzuki bean, which makes (+)-dihydrowighteone a potential biomarker for the consumption of this food product.

Structure

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

HMDB0301942
     RDKit          3D
(+)-Dihydrowighteone
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.2088    2.6050   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    1.4741    0.8090 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010    1.7423    2.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1959    0.2432    0.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6484   -0.1741   -0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3797   -0.9213   -0.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3865   -2.2289   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5595   -2.8996    0.0010 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829   -2.9084    0.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278   -2.2921   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0367   -0.9667   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1502   -0.2870   -0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0186    1.0190   -1.2166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3173   -0.2843   -0.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3223    0.9617   -0.8618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5303   -1.1435   -0.7332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7777   -0.3416   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6956   -0.4692   -1.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8524    0.2774   -1.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0848    1.1352   -0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2471    1.8815   -0.5238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1362    1.2386    0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9768    0.4926    0.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3945   -2.0946    0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545   -2.9103    0.1446 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3888    2.3956   -1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7628    3.5353    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1293    2.9060    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1468    1.9487    2.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7296    2.5793    2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4784    0.7996    2.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3888   -0.5749    1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5059    0.6511   -1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3212   -0.9084   -1.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4490   -2.4979   -0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1979   -3.9409    0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833    1.6234   -1.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915   -1.7811   -1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5094   -1.1572   -2.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5541    0.1652   -2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3044    2.8063   -0.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3023    1.9145    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2486    0.6058    1.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1329   -1.4869    1.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2698   -2.7328    0.5794 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
 11 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
 16 24  1  0
 24 25  1  0
 12  6  1  0
 23 17  1  0
 25 10  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
 13 37  1  0
 16 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 24 45  1  0
M  END

  Mrv0541 02241212132D          

 25 27  0  0  0  0            999 V2000
   -3.7714    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4859    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4859    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7714    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0570    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0570    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3425    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3425    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6280    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6280    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9136    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1991    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9136   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1991   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7714   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3425   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9148   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9149   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6293   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 11  2  0  0  0  0
 11 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 17  1  0  0  0  0
  4 18  1  0  0  0  0
  8 19  2  0  0  0  0
 15 20  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301942

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C2=C(OCC(C2=O)C2=CC=C(O)C=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O5/c1-11(2)3-8-14-16(22)9-17-18(19(14)23)20(24)15(10-25-17)12-4-6-13(21)7-5-12/h3-7,9,15,21-23H,8,10H2,1-2H3

> <INCHI_KEY>
UYDQKAKPHFFLDY-UHFFFAOYSA-N

> <FORMULA>
C20H20O5

> <MOLECULAR_WEIGHT>
340.3698

> <EXACT_MASS>
340.13107375

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
35.90976298536516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
4.456225113333334

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.454908929322874

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.7135139759240205

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9173470558691994

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
95.91929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-dihydrowighteone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301942
     RDKit          3D
(+)-Dihydrowighteone
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.2088    2.6050   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    1.4741    0.8090 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010    1.7423    2.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1959    0.2432    0.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6484   -0.1741   -0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3797   -0.9213   -0.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3865   -2.2289   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5595   -2.8996    0.0010 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829   -2.9084    0.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278   -2.2921   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0367   -0.9667   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1502   -0.2870   -0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0186    1.0190   -1.2166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3173   -0.2843   -0.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3223    0.9617   -0.8618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5303   -1.1435   -0.7332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7777   -0.3416   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6956   -0.4692   -1.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8524    0.2774   -1.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0848    1.1352   -0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2471    1.8815   -0.5238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1362    1.2386    0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9768    0.4926    0.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3945   -2.0946    0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545   -2.9103    0.1446 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3888    2.3956   -1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7628    3.5353    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1293    2.9060    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1468    1.9487    2.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7296    2.5793    2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4784    0.7996    2.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3888   -0.5749    1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5059    0.6511   -1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3212   -0.9084   -1.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4490   -2.4979   -0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1979   -3.9409    0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833    1.6234   -1.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915   -1.7811   -1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5094   -1.1572   -2.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5541    0.1652   -2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3044    2.8063   -0.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3023    1.9145    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2486    0.6058    1.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1329   -1.4869    1.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2698   -2.7328    0.5794 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
 11 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
 16 24  1  0
 24 25  1  0
 12  6  1  0
 23 17  1  0
 25 10  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
 13 37  1  0
 16 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 24 45  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.040   4.235   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.374   3.465   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.374   1.925   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.040   1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.706   1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.706   3.465   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.373   4.235   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.373   1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.039   1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.039   3.465   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.705   1.155   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.372   1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.705  -0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.372  -1.155   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.962  -0.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.962   1.155   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -9.707   4.235   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -7.040  -0.385   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.373  -0.385   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.296  -1.155   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -9.707   1.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.707  -0.385   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -11.041  -1.155   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -11.041  -2.695   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -12.375  -0.385   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   19                                                  
CONECT    9    8   10   11                                                  
CONECT   10    7    9                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11   16                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   12   15                                                       
CONECT   17    2                                                            
CONECT   18    4                                                            
CONECT   19    8                                                            
CONECT   20   15                                                            
CONECT   21    3   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0301942
HETATM    1  C1  UNL     1       4.209   2.605  -0.103  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.454   1.474   0.809  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.001   1.742   2.161  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.196   0.243   0.441  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.648  -0.174  -0.874  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.380  -0.921  -0.614  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.386  -2.229  -0.184  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.560  -2.900   0.001  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.183  -2.908   0.075  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.028  -2.292  -0.094  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.037  -0.967  -0.531  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.150  -0.287  -0.789  1.00  0.00           C  
HETATM   13  O2  UNL     1       1.019   1.019  -1.217  1.00  0.00           O  
HETATM   14  C12 UNL     1      -1.317  -0.284  -0.722  1.00  0.00           C  
HETATM   15  O3  UNL     1      -1.322   0.962  -0.862  1.00  0.00           O  
HETATM   16  C13 UNL     1      -2.530  -1.144  -0.733  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.778  -0.342  -0.674  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.696  -0.469  -1.689  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.852   0.277  -1.631  1.00  0.00           C  
HETATM   20  C17 UNL     1      -6.085   1.135  -0.576  1.00  0.00           C  
HETATM   21  O4  UNL     1      -7.247   1.882  -0.524  1.00  0.00           O  
HETATM   22  C18 UNL     1      -5.136   1.239   0.431  1.00  0.00           C  
HETATM   23  C19 UNL     1      -3.977   0.493   0.376  1.00  0.00           C  
HETATM   24  C20 UNL     1      -2.395  -2.095   0.443  1.00  0.00           C  
HETATM   25  O5  UNL     1      -1.255  -2.910   0.145  1.00  0.00           O  
HETATM   26  H1  UNL     1       4.389   2.396  -1.155  1.00  0.00           H  
HETATM   27  H2  UNL     1       4.763   3.535   0.238  1.00  0.00           H  
HETATM   28  H3  UNL     1       3.129   2.906   0.039  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.147   1.949   2.838  1.00  0.00           H  
HETATM   30  H5  UNL     1       5.730   2.579   2.163  1.00  0.00           H  
HETATM   31  H6  UNL     1       5.478   0.800   2.558  1.00  0.00           H  
HETATM   32  H7  UNL     1       4.389  -0.575   1.153  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.506   0.651  -1.582  1.00  0.00           H  
HETATM   34  H9  UNL     1       4.321  -0.908  -1.375  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.449  -2.498  -0.172  1.00  0.00           H  
HETATM   36  H11 UNL     1       1.198  -3.941   0.415  1.00  0.00           H  
HETATM   37  H12 UNL     1       1.783   1.623  -1.440  1.00  0.00           H  
HETATM   38  H13 UNL     1      -2.491  -1.781  -1.646  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.509  -1.157  -2.536  1.00  0.00           H  
HETATM   40  H15 UNL     1      -6.554   0.165  -2.429  1.00  0.00           H  
HETATM   41  H16 UNL     1      -7.304   2.806  -0.936  1.00  0.00           H  
HETATM   42  H17 UNL     1      -5.302   1.915   1.277  1.00  0.00           H  
HETATM   43  H18 UNL     1      -3.249   0.606   1.199  1.00  0.00           H  
HETATM   44  H19 UNL     1      -2.133  -1.487   1.326  1.00  0.00           H  
HETATM   45  H20 UNL     1      -3.270  -2.733   0.579  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   25
CONECT   11   12   12   14
CONECT   12   13
CONECT   13   37
CONECT   14   15   15   16
CONECT   16   17   24   38
CONECT   17   18   18   23
CONECT   18   19   39
CONECT   19   20   20   40
CONECT   20   21   22
CONECT   21   41
CONECT   22   23   23   42
CONECT   23   43
CONECT   24   25   44   45
END

HMDB0301942
     RDKit          3D
(+)-Dihydrowighteone
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.2088    2.6050   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    1.4741    0.8090 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010    1.7423    2.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1959    0.2432    0.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6484   -0.1741   -0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3797   -0.9213   -0.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3865   -2.2289   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5595   -2.8996    0.0010 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829   -2.9084    0.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278   -2.2921   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0367   -0.9667   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1502   -0.2870   -0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0186    1.0190   -1.2166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3173   -0.2843   -0.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3223    0.9617   -0.8618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5303   -1.1435   -0.7332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7777   -0.3416   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6956   -0.4692   -1.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8524    0.2774   -1.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0848    1.1352   -0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2471    1.8815   -0.5238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1362    1.2386    0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9768    0.4926    0.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3945   -2.0946    0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545   -2.9103    0.1446 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3888    2.3956   -1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7628    3.5353    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1293    2.9060    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1468    1.9487    2.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7296    2.5793    2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4784    0.7996    2.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3888   -0.5749    1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5059    0.6511   -1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3212   -0.9084   -1.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4490   -2.4979   -0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1979   -3.9409    0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833    1.6234   -1.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915   -1.7811   -1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5094   -1.1572   -2.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5541    0.1652   -2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3044    2.8063   -0.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3023    1.9145    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2486    0.6058    1.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1329   -1.4869    1.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2698   -2.7328    0.5794 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
 11 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
 16 24  1  0
 24 25  1  0
 12  6  1  0
 23 17  1  0
 25 10  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
 13 37  1  0
 16 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 24 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₀O₅

Average Molecular Weight

340.3698

Monoisotopic Molecular Weight

340.13107375

IUPAC Name

5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(+)-dihydrowighteone

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C2=C(OCC(C2=O)C2=CC=C(O)C=C2)C=C1O

InChI Identifier

InChI=1S/C20H20O5/c1-11(2)3-8-14-16(22)9-17-18(19(14)23)20(24)15(10-25-17)12-4-6-13(21)7-5-12/h3-7,9,15,21-23H,8,10H2,1-2H3

InChI Key

UYDQKAKPHFFLDY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanones

Alternative Parents

Substituents

Isoflavanone
Isoflavanol
Hydroxyisoflavonoid
Chromone
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050473 )

Ontology

Not Available

Exogenous (HMDB: HMDB0301942)

Food

Pulse

Bean

Adzuki bean (FooDB: FOOD00198)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.16	ALOGPS
logP	4.46	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	7.71	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.92 m³·mol⁻¹	ChemAxon
Polarizability	35.91 Å³	ChemAxon
Number of Rings	3	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
AllCCS	[M+H]+	182.649	32859911
AllCCS	[M+H-H2O]+	179.392	32859911
AllCCS	[M+Na]+	186.53	32859911
AllCCS	[M+NH4]+	185.664	32859911
AllCCS	[M-H]-	183.689	32859911
AllCCS	[M+Na-2H]-	183.342	32859911
AllCCS	[M+HCOO]-	183.115	32859911
DeepCCS	[M+H]+	179.37	30932474
DeepCCS	[M-H]-	177.012	30932474
DeepCCS	[M-2H]-	210.959	30932474
DeepCCS	[M+Na]+	186.187	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dihydrowighteone 10V, Positive-QTOF	splash10-0006-0249000000-9b05b110222a96c9fa27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dihydrowighteone 20V, Positive-QTOF	splash10-060c-3795000000-968831545e2483003434	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dihydrowighteone 40V, Positive-QTOF	splash10-01b9-4911000000-56b3cfb2acab10c66423	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dihydrowighteone 10V, Negative-QTOF	splash10-000i-0109000000-459c045be6a1849f01cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dihydrowighteone 20V, Negative-QTOF	splash10-000i-1859000000-847c0a8700092e858484	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dihydrowighteone 40V, Negative-QTOF	splash10-00kf-2910000000-ecd2f6ad5f703efb0af6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dihydrowighteone 10V, Positive-QTOF	splash10-000i-0091000000-528bf6adac1b7f973556	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dihydrowighteone 20V, Positive-QTOF	splash10-000i-0393000000-f3d010564c78b5c0db9d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dihydrowighteone 40V, Positive-QTOF	splash10-014i-0940000000-9cec2185a4f415dc29bc	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dihydrowighteone 10V, Negative-QTOF	splash10-000i-0009000000-fd63e399cebf431bd289	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dihydrowighteone 20V, Negative-QTOF	splash10-01bi-1903000000-fbdfce12853eebd7d727	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dihydrowighteone 40V, Negative-QTOF	splash10-0gbc-3941000000-1b30ec50765e88202f32	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB001653

KNApSAcK ID

Not Available

Chemspider ID

24842916

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for (+)-Dihydrowighteone (HMDB0301942)

MOL for HMDB0301942 ((+)-Dihydrowighteone)

3D MOL for HMDB0301942 ((+)-Dihydrowighteone)

3D SDF for HMDB0301942 ((+)-Dihydrowighteone)

3D-SDF for HMDB0301942 ((+)-Dihydrowighteone)

PDB for HMDB0301942 ((+)-Dihydrowighteone)

3D PDB for HMDB0301942 ((+)-Dihydrowighteone)

SMILES for HMDB0301942 ((+)-Dihydrowighteone)

INCHI for HMDB0301942 ((+)-Dihydrowighteone)

Structure for HMDB0301942 ((+)-Dihydrowighteone)

3D Structure for HMDB0301942 ((+)-Dihydrowighteone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra