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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:41:42 UTC

Update Date

2022-03-07 02:55:20 UTC

HMDB ID

HMDB0037445

Secondary Accession Numbers

HMDB37445

Metabolite Identification

Common Name

(S)-5,7-Dihydroxy-6-prenylflavanone

Description

(S)-5,7-Dihydroxy-6-prenylflavanone belongs to the class of organic compounds known as 6-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 6-position. Thus, (S)-5,7-dihydroxy-6-prenylflavanone is considered to be a flavonoid (S)-5,7-Dihydroxy-6-prenylflavanone has been detected, but not quantified in, several different foods, such as herbal tea, red tea, green tea, black tea, and herbs and spices. This could make (S)-5,7-dihydroxy-6-prenylflavanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (S)-5,7-Dihydroxy-6-prenylflavanone.

Structure

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

HMDB0037445
     RDKit          3D
(S)-5,7-Dihydroxy-6-prenylflavanone
 44 46  0  0  0  0  0  0  0  0999 V2000
   -6.3599   -0.7946   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3944    0.0877   -0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7397    1.5139    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2461   -0.3793    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3164    0.4834    1.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9559    0.5569    0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719    1.2585   -0.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5518    1.9891   -1.2338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659    1.2602   -0.9627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223    0.5552   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3479   -0.1683    0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9497   -0.1623    1.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3214   -0.8673    2.3667 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213   -0.9260    1.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243   -1.9204    2.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819   -0.3563    1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9524   -0.3346   -0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3518   -0.0491   -0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8412    1.2368   -0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1763    1.4944   -0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0257    0.4972   -1.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5379   -0.7925   -1.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2062   -1.0496   -0.9615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0372    0.5645   -0.7419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3776   -0.3470   -0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1612   -0.7732   -1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4183   -1.8032   -0.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1395    2.1556   -0.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7228    1.7899    1.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8145    1.6774   -0.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0120   -1.4437    0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7165    1.5325    1.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2285    0.2347    2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3311    2.5224   -2.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008    1.8349   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7820   -1.4007    2.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5552   -0.9426    1.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8219    0.7098    1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6451   -1.3649   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1585    2.0063   -0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5489    2.5032   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0658    0.6965   -1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2194   -1.5698   -1.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8349   -2.0555   -1.0282 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
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 17 18  1  0
 18 19  2  0
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 12  6  1  0
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M  END


  Mrv0541 05061309472D          

 24 26  0  0  0  0            999 V2000
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  8  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  8  2  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  2  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 17 11  1  0  0  0  0
 17 13  1  0  0  0  0
 18 10  1  0  0  0  0
 19 16  1  0  0  0  0
 19 18  2  0  0  0  0
 20 14  2  0  0  0  0
 20 19  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  2  0  0  0  0
 23 20  1  0  0  0  0
 24 17  1  0  0  0  0
 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037445

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O

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

> <INCHI_KEY>
UOWOIGNEFLTNAW-UHFFFAOYSA-N

> <FORMULA>
C20H20O4

> <MOLECULAR_WEIGHT>
324.3704

> <EXACT_MASS>
324.136159128

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.00003752400166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
4.867240371333333

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.47318811032918

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.73607218441128

> <JCHEM_PKA_STRONGEST_BASIC>
-3.913812961843294

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
93.55169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.95e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037445
     RDKit          3D
(S)-5,7-Dihydroxy-6-prenylflavanone
 44 46  0  0  0  0  0  0  0  0999 V2000
   -6.3599   -0.7946   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3944    0.0877   -0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7397    1.5139    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2461   -0.3793    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3164    0.4834    1.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9559    0.5569    0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719    1.2585   -0.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5518    1.9891   -1.2338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659    1.2602   -0.9627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223    0.5552   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3479   -0.1683    0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9497   -0.1623    1.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3214   -0.8673    2.3667 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213   -0.9260    1.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243   -1.9204    2.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819   -0.3563    1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9524   -0.3346   -0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3518   -0.0491   -0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8412    1.2368   -0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1763    1.4944   -0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0257    0.4972   -1.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5379   -0.7925   -1.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2062   -1.0496   -0.9615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0372    0.5645   -0.7419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3776   -0.3470   -0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1612   -0.7732   -1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4183   -1.8032   -0.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1395    2.1556   -0.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7228    1.7899    1.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8145    1.6774   -0.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0120   -1.4437    0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7165    1.5325    1.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2285    0.2347    2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3311    2.5224   -2.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008    1.8349   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7820   -1.4007    2.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5552   -0.9426    1.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8219    0.7098    1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6451   -1.3649   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1585    2.0063   -0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5489    2.5032   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0658    0.6965   -1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2194   -1.5698   -1.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8349   -2.0555   -1.0282 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  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 17 24  1  0
 12  6  1  0
 23 18  1  0
 24 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 13 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   13                                                       
CONECT    7    5   13                                                       
CONECT    8    9   12                                                       
CONECT    9    8   14                                                       
CONECT   10   15   18                                                       
CONECT   11   16   17                                                       
CONECT   12    1    2    8                                                  
CONECT   13    6    7   17                                                  
CONECT   14    9   15   20                                                  
CONECT   15   10   14   21                                                  
CONECT   16   11   19   22                                                  
CONECT   17   11   13   24                                                  
CONECT   18   10   19   24                                                  
CONECT   19   16   18   20                                                  
CONECT   20   14   19   23                                                  
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23   20                                                            
CONECT   24   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0037445
HETATM    1  C1  UNL     1      -6.360  -0.795  -0.788  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.394   0.088  -0.049  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.740   1.514   0.189  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.246  -0.379   0.411  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.316   0.483   1.125  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.956   0.557   0.577  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.572   1.258  -0.532  1.00  0.00           C  
HETATM    8  O1  UNL     1      -2.552   1.989  -1.234  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.266   1.260  -0.963  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.722   0.555  -0.300  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.348  -0.168   0.835  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.950  -0.162   1.254  1.00  0.00           C  
HETATM   13  O2  UNL     1      -1.321  -0.867   2.367  1.00  0.00           O  
HETATM   14  C12 UNL     1       1.421  -0.926   1.513  1.00  0.00           C  
HETATM   15  O3  UNL     1       1.124  -1.920   2.162  1.00  0.00           O  
HETATM   16  C13 UNL     1       2.782  -0.356   1.309  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.952  -0.335  -0.217  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.352  -0.049  -0.556  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.841   1.237  -0.475  1.00  0.00           C  
HETATM   20  C17 UNL     1       6.176   1.494  -0.801  1.00  0.00           C  
HETATM   21  C18 UNL     1       7.026   0.497  -1.204  1.00  0.00           C  
HETATM   22  C19 UNL     1       6.538  -0.793  -1.287  1.00  0.00           C  
HETATM   23  C20 UNL     1       5.206  -1.050  -0.962  1.00  0.00           C  
HETATM   24  O4  UNL     1       2.037   0.564  -0.742  1.00  0.00           O  
HETATM   25  H1  UNL     1      -7.378  -0.347  -0.642  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.161  -0.773  -1.861  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.418  -1.803  -0.343  1.00  0.00           H  
HETATM   28  H4  UNL     1      -5.139   2.156  -0.449  1.00  0.00           H  
HETATM   29  H5  UNL     1      -5.723   1.790   1.266  1.00  0.00           H  
HETATM   30  H6  UNL     1      -6.815   1.677  -0.120  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.012  -1.444   0.239  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.717   1.533   1.124  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.229   0.235   2.216  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.331   2.522  -2.053  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.001   1.835  -1.855  1.00  0.00           H  
HETATM   36  H12 UNL     1      -0.782  -1.401   2.963  1.00  0.00           H  
HETATM   37  H13 UNL     1       3.555  -0.943   1.801  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.822   0.710   1.621  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.645  -1.365  -0.557  1.00  0.00           H  
HETATM   40  H16 UNL     1       4.158   2.006  -0.156  1.00  0.00           H  
HETATM   41  H17 UNL     1       6.549   2.503  -0.734  1.00  0.00           H  
HETATM   42  H18 UNL     1       8.066   0.696  -1.459  1.00  0.00           H  
HETATM   43  H19 UNL     1       7.219  -1.570  -1.606  1.00  0.00           H  
HETATM   44  H20 UNL     1       4.835  -2.055  -1.028  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4    4
CONECT    3   28   29   30
CONECT    4    5   31
CONECT    5    6   32   33
CONECT    6    7    7   12
CONECT    7    8    9
CONECT    8   34
CONECT    9   10   10   35
CONECT   10   11   24
CONECT   11   12   12   14
CONECT   12   13
CONECT   13   36
CONECT   14   15   15   16
CONECT   16   17   37   38
CONECT   17   18   24   39
CONECT   18   19   19   23
CONECT   19   20   40
CONECT   20   21   21   41
CONECT   21   22   42
CONECT   22   23   23   43
CONECT   23   44
END

HMDB0037445
     RDKit          3D
(S)-5,7-Dihydroxy-6-prenylflavanone
 44 46  0  0  0  0  0  0  0  0999 V2000
   -6.3599   -0.7946   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3944    0.0877   -0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7397    1.5139    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2461   -0.3793    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3164    0.4834    1.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9559    0.5569    0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719    1.2585   -0.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5518    1.9891   -1.2338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659    1.2602   -0.9627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223    0.5552   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3479   -0.1683    0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9497   -0.1623    1.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3214   -0.8673    2.3667 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213   -0.9260    1.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243   -1.9204    2.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819   -0.3563    1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9524   -0.3346   -0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3518   -0.0491   -0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8412    1.2368   -0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1763    1.4944   -0.8009 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0257    0.4972   -1.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5379   -0.7925   -1.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2062   -1.0496   -0.9615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0372    0.5645   -0.7419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3776   -0.3470   -0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1612   -0.7732   -1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4183   -1.8032   -0.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1395    2.1556   -0.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7228    1.7899    1.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8145    1.6774   -0.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0120   -1.4437    0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7165    1.5325    1.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2285    0.2347    2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3311    2.5224   -2.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008    1.8349   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7820   -1.4007    2.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5552   -0.9426    1.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8219    0.7098    1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6451   -1.3649   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1585    2.0063   -0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5489    2.5032   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0658    0.6965   -1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2194   -1.5698   -1.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8349   -2.0555   -1.0282 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  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 17 24  1  0
 12  6  1  0
 23 18  1  0
 24 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 13 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Prenylpinocembrin	HMDB
Isoglabranin	HMDB

Chemical Formula

C₂₀H₂₀O₄

Average Molecular Weight

324.3704

Monoisotopic Molecular Weight

324.136159128

IUPAC Name

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

Traditional Name

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

CAS Registry Number

55051-77-9

SMILES

CC(C)=CCC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O

InChI Identifier

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

InChI Key

UOWOIGNEFLTNAW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

6-prenylated flavanones

Alternative Parents

Substituents

6-prenylated flavanone
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140166 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037445)

Cellular substructure

Membrane (HMDB: HMDB0037445)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037445)

Source

Exogenous

Food

Food (HMDB: HMDB0037445)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0037445)

Not Available

Nutrient (HMDB: HMDB0037445)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	212 - 214 °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	0.02 g/L	ALOGPS
logP	3.56	ALOGPS
logP	4.87	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	7.74	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.55 m³·mol⁻¹	ChemAxon
Polarizability	36 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
DarkChem	[M+H]+	178.847	31661259
DarkChem	[M-H]-	175.96	31661259
DeepCCS	[M+H]+	171.4	30932474
DeepCCS	[M-H]-	169.042	30932474
DeepCCS	[M-2H]-	202.812	30932474
DeepCCS	[M+Na]+	178.039	30932474
AllCCS	[M+H]+	180.7	32859911
AllCCS	[M+H-H2O]+	177.4	32859911
AllCCS	[M+NH4]+	183.9	32859911
AllCCS	[M+Na]+	184.8	32859911
AllCCS	[M-H]-	180.4	32859911
AllCCS	[M+Na-2H]-	180.0	32859911
AllCCS	[M+HCOO]-	179.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-5,7-Dihydroxy-6-prenylflavanone	CC(C)=CCC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O	3876.8	Standard polar	33892256
(S)-5,7-Dihydroxy-6-prenylflavanone	CC(C)=CCC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O	2830.3	Standard non polar	33892256
(S)-5,7-Dihydroxy-6-prenylflavanone	CC(C)=CCC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O	2748.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-5,7-Dihydroxy-6-prenylflavanone,1TMS,isomer #1	CC(C)=CCC1=C(O)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O[Si](C)(C)C	2864.6	Semi standard non polar	33892256
(S)-5,7-Dihydroxy-6-prenylflavanone,1TMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O	2869.2	Semi standard non polar	33892256
(S)-5,7-Dihydroxy-6-prenylflavanone,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O[Si](C)(C)C	2904.8	Semi standard non polar	33892256
(S)-5,7-Dihydroxy-6-prenylflavanone,1TBDMS,isomer #1	CC(C)=CCC1=C(O)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O[Si](C)(C)C(C)(C)C	3079.7	Semi standard non polar	33892256
(S)-5,7-Dihydroxy-6-prenylflavanone,1TBDMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O	3098.1	Semi standard non polar	33892256
(S)-5,7-Dihydroxy-6-prenylflavanone,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=CC=C3)CC(=O)C2=C1O[Si](C)(C)C(C)(C)C	3305.1	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 - (S)-5,7-Dihydroxy-6-prenylflavanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-8396000000-fced42ca67eac62e2f9d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone GC-MS (2 TMS) - 70eV, Positive	splash10-0zmj-7816900000-0891d37e8b85c24eed49	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone LC-ESI-qTof , Positive-QTOF	splash10-0gx3-0953000000-85e6abfd3e71f7e303f9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone , positive-QTOF	splash10-014i-0900000000-74fa9463fcd7c256ed8d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone 6V, Positive-QTOF	splash10-004r-0595000000-4b2b886a46a211902840	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone 6V, Negative-QTOF	splash10-00dr-1906000000-18088b4b32a2a265e96e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone 10V, Positive-QTOF	splash10-004i-0249000000-bde8832254f5c6db1131	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone 20V, Positive-QTOF	splash10-0690-5493000000-79cbdd6853fa774ee1ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone 40V, Positive-QTOF	splash10-066u-4920000000-fb5152f8d1e43f70b50a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone 10V, Negative-QTOF	splash10-00di-0109000000-aff2f8087503d62a3080	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone 20V, Negative-QTOF	splash10-00di-1659000000-0d5ef888f9f7c1ec98fe	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone 40V, Negative-QTOF	splash10-004i-3910000000-ba775eda89e4b8dea20f	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone 10V, Positive-QTOF	splash10-004i-0009000000-d9a4381be839f3255a4d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone 20V, Positive-QTOF	splash10-00fs-0496000000-fa361f8a1a38b10bb52d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone 40V, Positive-QTOF	splash10-00di-0190000000-0371bea8cea80705c406	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone 10V, Negative-QTOF	splash10-00di-0009000000-503adc4dafe30207b3ff	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone 20V, Negative-QTOF	splash10-00xr-0179000000-808e5e095600e67b1990	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-5,7-Dihydroxy-6-prenylflavanone 40V, Negative-QTOF	splash10-0udi-0910000000-441434a59a3224552a7d	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

FDB016503

KNApSAcK ID

C00008171

Chemspider ID

421847

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

480763

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (S)-5,7-Dihydroxy-6-prenylflavanone (HMDB0037445)

MOL for HMDB0037445 ((S)-5,7-Dihydroxy-6-prenylflavanone)

3D MOL for HMDB0037445 ((S)-5,7-Dihydroxy-6-prenylflavanone)

3D SDF for HMDB0037445 ((S)-5,7-Dihydroxy-6-prenylflavanone)

3D-SDF for HMDB0037445 ((S)-5,7-Dihydroxy-6-prenylflavanone)

PDB for HMDB0037445 ((S)-5,7-Dihydroxy-6-prenylflavanone)

3D PDB for HMDB0037445 ((S)-5,7-Dihydroxy-6-prenylflavanone)

SMILES for HMDB0037445 ((S)-5,7-Dihydroxy-6-prenylflavanone)

INCHI for HMDB0037445 ((S)-5,7-Dihydroxy-6-prenylflavanone)

Structure for HMDB0037445 ((S)-5,7-Dihydroxy-6-prenylflavanone)

3D Structure for HMDB0037445 ((S)-5,7-Dihydroxy-6-prenylflavanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra