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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:54:03 UTC

Update Date

2022-03-07 02:53:36 UTC

HMDB ID

HMDB0033153

Secondary Accession Numbers

HMDB33153

Metabolite Identification

Common Name

(Z)-4',6-Dihydroxyaurone

Description

(Z)-4',6-Dihydroxyaurone belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus) (Z)-4',6-Dihydroxyaurone has been detected, but not quantified in, pulses and soy beans (Glycine max). This could make (Z)-4',6-dihydroxyaurone a potential biomarker for the consumption of these foods (Z)-4',6-Dihydroxyaurone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on (Z)-4',6-Dihydroxyaurone.

Structure

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

HMDB0033153
     RDKit          3D
(Z)-4',6-Dihydroxyaurone
 29 31  0  0  0  0  0  0  0  0999 V2000
    1.6115    2.6009    1.6460 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5055    1.5334    1.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2378    0.9886    0.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9477    1.5757    0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1103    0.8985    0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1487    0.3341   -1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2751   -0.3172   -1.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4236   -0.4434   -0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5737   -1.0995   -1.3148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3926    0.1229    0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2708    0.7713    0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5835   -0.1923   -0.1053 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690   -0.4216   -0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7854   -1.4419   -0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1466   -1.4501   -0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9351   -2.5200   -0.7742 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7294   -0.4118    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9518    0.6199    0.8688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5870    0.6119    0.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0406    2.5348    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726    0.4105   -1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3049   -0.7657   -2.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3259   -0.6202   -1.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2952    0.0302    1.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2362    1.2237    1.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3274   -2.2595   -1.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0550   -3.3027   -0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8082   -0.4526    0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3845    1.4424    1.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  3 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19  2  1  0
 11  5  1  0
 19 13  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 14 26  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
M  END


  Mrv0541 05061306572D          

 19 21  0  0  0  0            999 V2000
   -0.7676   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  6  5  2  0  0  0  0
  9  1  2  0  0  0  0
  9  2  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  2  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  2  0  0  0  0
 14  7  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 15  2  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033153

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(\C=C2/OC3=C(C=CC(O)=C3)C2=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)7-14-15(18)12-6-5-11(17)8-13(12)19-14/h1-8,16-17H/b14-7-

> <INCHI_KEY>
KEZLDSPIRVZOKZ-AUWJEWJLSA-N

> <FORMULA>
C15H10O4

> <MOLECULAR_WEIGHT>
254.2375

> <EXACT_MASS>
254.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.22198930553707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-6-hydroxy-2-[(4-hydroxyphenyl)methylidene]-2,3-dihydro-1-benzofuran-3-one

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
2.595143673

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.84931004892162

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.623914244852833

> <JCHEM_PKA_STRONGEST_BASIC>
-5.464243810201438

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
71.00810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hispidol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033153
     RDKit          3D
(Z)-4',6-Dihydroxyaurone
 29 31  0  0  0  0  0  0  0  0999 V2000
    1.6115    2.6009    1.6460 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5055    1.5334    1.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2378    0.9886    0.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9477    1.5757    0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1103    0.8985    0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1487    0.3341   -1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2751   -0.3172   -1.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4236   -0.4434   -0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5737   -1.0995   -1.3148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3926    0.1229    0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2708    0.7713    0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5835   -0.1923   -0.1053 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690   -0.4216   -0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7854   -1.4419   -0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1466   -1.4501   -0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9351   -2.5200   -0.7742 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7294   -0.4118    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9518    0.6199    0.8688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5870    0.6119    0.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0406    2.5348    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726    0.4105   -1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3049   -0.7657   -2.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3259   -0.6202   -1.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2952    0.0302    1.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2362    1.2237    1.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3274   -2.2595   -1.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0550   -3.3027   -0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8082   -0.4526    0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3845    1.4424    1.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  3 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19  2  1  0
 11  5  1  0
 19 13  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 14 26  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.433  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.877  -1.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.203  -1.897   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.107  -3.231   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.877   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.107  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.433  -3.231   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.203  -4.565   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    3    9                                                       
CONECT    2    4    9                                                       
CONECT    3    1   10                                                       
CONECT    4    2   10                                                       
CONECT    5    6   11                                                       
CONECT    6    5   12                                                       
CONECT    7    9   14                                                       
CONECT    8   11   13                                                       
CONECT    9    1    2    7                                                  
CONECT   10    3    4   16                                                  
CONECT   11    5    8   17                                                  
CONECT   12    6   13   15                                                  
CONECT   13    8   12   19                                                  
CONECT   14    7   15   19                                                  
CONECT   15   12   14   18                                                  
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   15                                                            
CONECT   19   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0033153
HETATM    1  O1  UNL     1       1.612   2.601   1.646  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.506   1.533   1.019  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.238   0.989   0.517  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.948   1.576   0.677  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.110   0.898   0.118  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.149   0.334  -1.139  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.275  -0.317  -1.610  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.424  -0.443  -0.857  1.00  0.00           C  
HETATM    9  O2  UNL     1      -5.574  -1.100  -1.315  1.00  0.00           O  
HETATM   10  C8  UNL     1      -4.393   0.123   0.411  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.271   0.771   0.880  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.583  -0.192  -0.105  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.969  -0.422  -0.028  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.785  -1.442  -0.487  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.147  -1.450  -0.283  1.00  0.00           C  
HETATM   16  O4  UNL     1       4.935  -2.520  -0.774  1.00  0.00           O  
HETATM   17  C13 UNL     1       4.729  -0.412   0.399  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.952   0.620   0.869  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.587   0.612   0.656  1.00  0.00           C  
HETATM   20  H1  UNL     1      -1.041   2.535   1.210  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.273   0.410  -1.771  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.305  -0.766  -2.606  1.00  0.00           H  
HETATM   23  H4  UNL     1      -6.326  -0.620  -1.820  1.00  0.00           H  
HETATM   24  H5  UNL     1      -5.295   0.030   1.016  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.236   1.224   1.879  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.327  -2.259  -1.029  1.00  0.00           H  
HETATM   27  H8  UNL     1       5.055  -3.303  -0.114  1.00  0.00           H  
HETATM   28  H9  UNL     1       5.808  -0.453   0.544  1.00  0.00           H  
HETATM   29  H10 UNL     1       4.385   1.442   1.409  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4    4   12
CONECT    4    5   20
CONECT    5    6    6   11
CONECT    6    7   21
CONECT    7    8    8   22
CONECT    8    9   10
CONECT    9   23
CONECT   10   11   11   24
CONECT   11   25
CONECT   12   13
CONECT   13   14   14   19
CONECT   14   15   26
CONECT   15   16   17   17
CONECT   16   27
CONECT   17   18   28
CONECT   18   19   19   29
END

HMDB0033153
     RDKit          3D
(Z)-4',6-Dihydroxyaurone
 29 31  0  0  0  0  0  0  0  0999 V2000
    1.6115    2.6009    1.6460 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5055    1.5334    1.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2378    0.9886    0.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9477    1.5757    0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1103    0.8985    0.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1487    0.3341   -1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2751   -0.3172   -1.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4236   -0.4434   -0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5737   -1.0995   -1.3148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3926    0.1229    0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2708    0.7713    0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5835   -0.1923   -0.1053 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690   -0.4216   -0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7854   -1.4419   -0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1466   -1.4501   -0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9351   -2.5200   -0.7742 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7294   -0.4118    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9518    0.6199    0.8688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5870    0.6119    0.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0406    2.5348    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726    0.4105   -1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3049   -0.7657   -2.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3259   -0.6202   -1.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2952    0.0302    1.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2362    1.2237    1.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3274   -2.2595   -1.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0550   -3.3027   -0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8082   -0.4526    0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3845    1.4424    1.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  3 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19  2  1  0
 11  5  1  0
 19 13  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 14 26  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2Z)-6-Hydroxy-2-(4-hydroxybenzylidene)-1-benzofuran-3(2H)-one	MeSH
Hispidol	HMDB

Chemical Formula

C₁₅H₁₀O₄

Average Molecular Weight

254.2375

Monoisotopic Molecular Weight

254.057908808

IUPAC Name

(2Z)-6-hydroxy-2-[(4-hydroxyphenyl)methylidene]-2,3-dihydro-1-benzofuran-3-one

Traditional Name

hispidol

CAS Registry Number

5786-54-9

SMILES

OC1=CC=C(\C=C2/OC3=C(C=CC(O)=C3)C2=O)C=C1

InChI Identifier

InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)7-14-15(18)12-6-5-11(17)8-13(12)19-14/h1-8,16-17H/b14-7-

InChI Key

KEZLDSPIRVZOKZ-AUWJEWJLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Aurone flavonoids

Sub Class

Not Available

Direct Parent

Aurone flavonoids

Alternative Parents

Substituents

Aurone
Benzofuran
Coumaran
Aryl ketone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Ketone
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyaurone (CHEBI:5731 )
aurones (C08644 )
Aurone flavonoids (C08644 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033153)
Cell membrane (HMDB: HMDB0033153)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033153)

Source

Exogenous

Exogenous (HMDB: HMDB0033153)

Food

Food (HMDB: HMDB0033153)

Soy

Soy bean (FooDB: FOOD00085)

Pulse

Pulses (FooDB: FOOD00867)

Not Available

Nutrient (HMDB: HMDB0033153)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	288 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	568.4 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	0.067 g/L	ALOGPS
logP	3.4	ALOGPS
logP	2.6	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.62	ChemAxon
pKa (Strongest Basic)	-5.5	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	1	ChemAxon
Refractivity	71.01 m³·mol⁻¹	ChemAxon
Polarizability	26.22 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
DeepCCS	[M+H]+	163.873	30932474
DeepCCS	[M-H]-	161.515	30932474
DeepCCS	[M-2H]-	194.401	30932474
DeepCCS	[M+Na]+	169.966	30932474
AllCCS	[M+H]+	158.6	32859911
AllCCS	[M+H-H2O]+	154.5	32859911
AllCCS	[M+NH4]+	162.3	32859911
AllCCS	[M+Na]+	163.4	32859911
AllCCS	[M-H]-	159.0	32859911
AllCCS	[M+Na-2H]-	158.3	32859911
AllCCS	[M+HCOO]-	157.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	6.55 minutes	32390414
Predicted by Siyang on May 30, 2022	11.7114 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.34 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1905.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	322.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	150.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	190.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	311.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	572.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	457.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	116.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1082.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	405.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1223.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	360.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	357.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	381.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	245.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	110.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(Z)-4',6-Dihydroxyaurone	OC1=CC=C(\C=C2/OC3=C(C=CC(O)=C3)C2=O)C=C1	4340.0	Standard polar	33892256
(Z)-4',6-Dihydroxyaurone	OC1=CC=C(\C=C2/OC3=C(C=CC(O)=C3)C2=O)C=C1	2679.0	Standard non polar	33892256
(Z)-4',6-Dihydroxyaurone	OC1=CC=C(\C=C2/OC3=C(C=CC(O)=C3)C2=O)C=C1	2895.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(Z)-4',6-Dihydroxyaurone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C2\OC3=CC(O)=CC=C3C2=O)C=C1	2754.5	Semi standard non polar	33892256
(Z)-4',6-Dihydroxyaurone,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C(=O)/C(=C/C3=CC=C(O)C=C3)OC2=C1	2734.0	Semi standard non polar	33892256
(Z)-4',6-Dihydroxyaurone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C2\OC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C=C1	2805.0	Semi standard non polar	33892256
(Z)-4',6-Dihydroxyaurone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C2\OC3=CC(O)=CC=C3C2=O)C=C1	3007.5	Semi standard non polar	33892256
(Z)-4',6-Dihydroxyaurone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=O)/C(=C/C3=CC=C(O)C=C3)OC2=C1	2974.1	Semi standard non polar	33892256
(Z)-4',6-Dihydroxyaurone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C2\OC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=C1	3301.1	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 - (Z)-4',6-Dihydroxyaurone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fi9-0590000000-770f11e6492946f4a141	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-4',6-Dihydroxyaurone GC-MS (2 TMS) - 70eV, Positive	splash10-00gi-5429000000-d4f5fdbb62061eaeabe4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-4',6-Dihydroxyaurone 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 - (Z)-4',6-Dihydroxyaurone 10V, Positive-QTOF	splash10-0a4i-0090000000-22ad14d4f84dbb69afe3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4',6-Dihydroxyaurone 20V, Positive-QTOF	splash10-052r-0790000000-8cbdd07a0860cb4eb125	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4',6-Dihydroxyaurone 40V, Positive-QTOF	splash10-000i-8930000000-e43c45ab5496af027917	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4',6-Dihydroxyaurone 10V, Negative-QTOF	splash10-0udi-0090000000-028540604acffdb10589	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4',6-Dihydroxyaurone 20V, Negative-QTOF	splash10-0udi-0090000000-063381aa384e6baff38d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4',6-Dihydroxyaurone 40V, Negative-QTOF	splash10-014r-3950000000-cbbd7f8f514b5613d8bc	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4',6-Dihydroxyaurone 10V, Positive-QTOF	splash10-0a4i-0090000000-88382720cb3b98a4d462	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4',6-Dihydroxyaurone 20V, Positive-QTOF	splash10-0a4i-0390000000-d1bb1eda2ef5192af08d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4',6-Dihydroxyaurone 40V, Positive-QTOF	splash10-08i1-2970000000-16ee7be17fe10d97e912	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4',6-Dihydroxyaurone 10V, Negative-QTOF	splash10-0udi-0090000000-ff2e7266db5d933feb85	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4',6-Dihydroxyaurone 20V, Negative-QTOF	splash10-0udi-0090000000-5316d246daa20d7ef4f2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4',6-Dihydroxyaurone 40V, Negative-QTOF	splash10-0002-2930000000-68e0af310692bd4615f2	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281254

PDB ID

Not Available

ChEBI ID

5731

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1833491

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 (Z)-4',6-Dihydroxyaurone (HMDB0033153)

MOL for HMDB0033153 ((Z)-4',6-Dihydroxyaurone)

3D MOL for HMDB0033153 ((Z)-4',6-Dihydroxyaurone)

3D SDF for HMDB0033153 ((Z)-4',6-Dihydroxyaurone)

3D-SDF for HMDB0033153 ((Z)-4',6-Dihydroxyaurone)

PDB for HMDB0033153 ((Z)-4',6-Dihydroxyaurone)

3D PDB for HMDB0033153 ((Z)-4',6-Dihydroxyaurone)

SMILES for HMDB0033153 ((Z)-4',6-Dihydroxyaurone)

INCHI for HMDB0033153 ((Z)-4',6-Dihydroxyaurone)

Structure for HMDB0033153 ((Z)-4',6-Dihydroxyaurone)

3D Structure for HMDB0033153 ((Z)-4',6-Dihydroxyaurone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra