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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:10:48 UTC

Update Date

2022-03-07 02:55:33 UTC

HMDB ID

HMDB0037921

Secondary Accession Numbers

HMDB37921

Metabolite Identification

Common Name

Aureol

Description

Aureol belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, aureol is considered to be a flavonoid. Aureol has been detected, but not quantified in, several different foods, such as gram beans (Vigna mungo), mung beans (Vigna radiata), pulses, and scarlet beans (Phaseolus coccineus). This could make aureol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Aureol.

Structure

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

HMDB0037921
     RDKit          3D
Aureol
 29 32  0  0  0  0  0  0  0  0999 V2000
    0.2042   -3.2765    0.3364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3429   -2.1347    0.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6580   -2.0311    0.2792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617   -0.8695    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516   -0.8003    0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3123    0.4040    0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6931    0.4342    0.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6413    1.5925    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2394    1.5411    0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5651    2.7194   -0.0133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5845    0.3283    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1961    0.2280    0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7482    1.1242    0.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9437    0.5927    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2159    1.1565    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3023    0.3166    0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5885    0.8901    0.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1332   -1.0344    0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8841   -1.6118    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8003   -0.7859    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4405   -1.0048    0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1691   -1.7533    0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3010   -0.3474    0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1502    2.5589    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6108    2.8311   -0.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2887    2.2353   -0.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0707    1.0572   -0.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0204   -1.6756    0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7366   -2.6849    0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21  2  1  0
 11  4  1  0
 21 12  2  0
 20 14  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 15 26  1  0
 17 27  1  0
 18 28  1  0
 19 29  1  0
M  END


  Mrv0541 05061310052D          

 21 24  0  0  0  0            999 V2000
    2.3400    0.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0733    0.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1158    1.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9948    1.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0341    0.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3008    1.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4868    1.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7673    0.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2921    1.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7281    1.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2105    0.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5632    0.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8395    1.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0158    1.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9342   -0.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5675    1.9223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3104    1.0719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9211    2.6399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4815   -0.8559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4997    1.9041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7578   -0.2133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  1  1  0  0  0  0
  6  4  2  0  0  0  0
  7  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  2  0  0  0  0
 11  5  2  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 16  6  1  0  0  0  0
 17  7  1  0  0  0  0
 18  9  1  0  0  0  0
 19 15  2  0  0  0  0
 20 10  1  0  0  0  0
 20 14  1  0  0  0  0
 21 11  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037921

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(C=C1)C1=C(O2)C2=C(O)C=C(O)C=C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H8O6/c16-6-1-2-8-10(4-6)20-14-12(8)15(19)21-11-5-7(17)3-9(18)13(11)14/h1-5,16-18H

> <INCHI_KEY>
WIRRQLQRDSREEG-UHFFFAOYSA-N

> <FORMULA>
C15H8O6

> <MOLECULAR_WEIGHT>
284.2204

> <EXACT_MASS>
284.032087988

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.21812016094573

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,14-trihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
2.0937560006666662

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.9973398646044185

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.601309026166093

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4714762804537855

> <JCHEM_POLAR_SURFACE_AREA>
100.13

> <JCHEM_REFRACTIVITY>
71.6004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aureol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037921
     RDKit          3D
Aureol
 29 32  0  0  0  0  0  0  0  0999 V2000
    0.2042   -3.2765    0.3364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3429   -2.1347    0.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6580   -2.0311    0.2792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617   -0.8695    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516   -0.8003    0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3123    0.4040    0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6931    0.4342    0.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6413    1.5925    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2394    1.5411    0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5651    2.7194   -0.0133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5845    0.3283    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1961    0.2280    0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7482    1.1242    0.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9437    0.5927    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2159    1.1565    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3023    0.3166    0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5885    0.8901    0.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1332   -1.0344    0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8841   -1.6118    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8003   -0.7859    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4405   -1.0048    0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1691   -1.7533    0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3010   -0.3474    0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1502    2.5589    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6108    2.8311   -0.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2887    2.2353   -0.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0707    1.0572   -0.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0204   -1.6756    0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7366   -2.6849    0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21  2  1  0
 11  4  1  0
 21 12  2  0
 20 14  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 15 26  1  0
 17 27  1  0
 18 28  1  0
 19 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       4.368   1.344   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.737   0.639   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.283   3.464   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.590   3.715   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.130   0.801   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.295   2.883   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.975   2.089   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.032   1.471   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.745   3.552   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.959   3.009   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.593   0.889   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.518   1.065   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.900   2.265   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.363   2.353   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.211  -0.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.926   3.588   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      15.513   2.001   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      11.053   4.928   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.365  -1.598   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.399   3.554   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.748  -0.398   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    8                                                       
CONECT    3    7    9                                                       
CONECT    4    6   10                                                       
CONECT    5    7   11                                                       
CONECT    6    1    4   16                                                  
CONECT    7    3    5   17                                                  
CONECT    8    2   10   12                                                  
CONECT    9    3   13   18                                                  
CONECT   10    4    8   20                                                  
CONECT   11    5   13   21                                                  
CONECT   12    8   14   15                                                  
CONECT   13    9   11   14                                                  
CONECT   14   12   13   20                                                  
CONECT   15   12   19   21                                                  
CONECT   16    6                                                            
CONECT   17    7                                                            
CONECT   18    9                                                            
CONECT   19   15                                                            
CONECT   20   10   14                                                       
CONECT   21   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0037921
HETATM    1  O1  UNL     1       0.204  -3.277   0.336  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.343  -2.135   0.272  1.00  0.00           C  
HETATM    3  O2  UNL     1      -1.658  -2.031   0.279  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.262  -0.870   0.214  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.652  -0.800   0.224  1.00  0.00           C  
HETATM    6  C4  UNL     1      -4.312   0.404   0.157  1.00  0.00           C  
HETATM    7  O3  UNL     1      -5.693   0.434   0.169  1.00  0.00           O  
HETATM    8  C5  UNL     1      -3.641   1.593   0.077  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.239   1.541   0.066  1.00  0.00           C  
HETATM   10  O4  UNL     1      -1.565   2.719  -0.013  1.00  0.00           O  
HETATM   11  C7  UNL     1      -1.585   0.328   0.134  1.00  0.00           C  
HETATM   12  C8  UNL     1      -0.196   0.228   0.126  1.00  0.00           C  
HETATM   13  O5  UNL     1       0.748   1.124   0.061  1.00  0.00           O  
HETATM   14  C9  UNL     1       1.944   0.593   0.081  1.00  0.00           C  
HETATM   15  C10 UNL     1       3.216   1.157   0.033  1.00  0.00           C  
HETATM   16  C11 UNL     1       4.302   0.317   0.074  1.00  0.00           C  
HETATM   17  O6  UNL     1       5.589   0.890   0.025  1.00  0.00           O  
HETATM   18  C12 UNL     1       4.133  -1.034   0.158  1.00  0.00           C  
HETATM   19  C13 UNL     1       2.884  -1.612   0.207  1.00  0.00           C  
HETATM   20  C14 UNL     1       1.800  -0.786   0.167  1.00  0.00           C  
HETATM   21  C15 UNL     1       0.440  -1.005   0.195  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.169  -1.753   0.288  1.00  0.00           H  
HETATM   23  H2  UNL     1      -6.301  -0.347   0.224  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.150   2.559   0.023  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.611   2.831  -0.030  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.289   2.235  -0.034  1.00  0.00           H  
HETATM   27  H6  UNL     1       6.071   1.057  -0.837  1.00  0.00           H  
HETATM   28  H7  UNL     1       5.020  -1.676   0.189  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.737  -2.685   0.274  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4
CONECT    4    5    5   11
CONECT    5    6   22
CONECT    6    7    8    8
CONECT    7   23
CONECT    8    9   24
CONECT    9   10   11   11
CONECT   10   25
CONECT   11   12
CONECT   12   13   21   21
CONECT   13   14
CONECT   14   15   15   20
CONECT   15   16   26
CONECT   16   17   18   18
CONECT   17   27
CONECT   18   19   28
CONECT   19   20   20   29
CONECT   20   21
END

HMDB0037921
     RDKit          3D
Aureol
 29 32  0  0  0  0  0  0  0  0999 V2000
    0.2042   -3.2765    0.3364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3429   -2.1347    0.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6580   -2.0311    0.2792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617   -0.8695    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6516   -0.8003    0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3123    0.4040    0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6931    0.4342    0.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6413    1.5925    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2394    1.5411    0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5651    2.7194   -0.0133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5845    0.3283    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1961    0.2280    0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7482    1.1242    0.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9437    0.5927    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2159    1.1565    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3023    0.3166    0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5885    0.8901    0.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1332   -1.0344    0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8841   -1.6118    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8003   -0.7859    0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4405   -1.0048    0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1691   -1.7533    0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3010   -0.3474    0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1502    2.5589    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6108    2.8311   -0.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2887    2.2353   -0.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0707    1.0572   -0.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0204   -1.6756    0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7366   -2.6849    0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21  2  1  0
 11  4  1  0
 21 12  2  0
 20 14  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 15 26  1  0
 17 27  1  0
 18 28  1  0
 19 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3,9-Trihydroxy-6H-benzofuro[3,2-c]benzopyran-6-one, 9ci	HMDB
Aureol?	HMDB

Chemical Formula

C₁₅H₈O₆

Average Molecular Weight

284.2204

Monoisotopic Molecular Weight

284.032087988

IUPAC Name

3,5,14-trihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

Traditional Name

aureol

CAS Registry Number

88478-03-9

SMILES

OC1=CC2=C(C=C1)C1=C(O2)C2=C(O)C=C(O)C=C2OC1=O

InChI Identifier

InChI=1S/C15H8O6/c16-6-1-2-8-10(4-6)20-14-12(8)15(19)21-11-5-7(17)3-9(18)13(11)14/h1-5,16-18H

InChI Key

WIRRQLQRDSREEG-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Angular furanocoumarin
Furanocoumarin
Coumarin
Benzopyran
1-benzopyran
Benzofuran
Furopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Furan
Heteroaromatic compound
Lactone
Polyol
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090039 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037921)

Cellular substructure

Membrane (HMDB: HMDB0037921)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037921)

Source

Exogenous

Food

Food (HMDB: HMDB0037921)

Pulse

Bean

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0037921)
Fabaceae (HMDB: HMDB0037921)

Not Available

Nutrient (HMDB: HMDB0037921)

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	522 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	0.8 g/L	ALOGPS
logP	2.64	ALOGPS
logP	2.09	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.6	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.6 m³·mol⁻¹	ChemAxon
Polarizability	27.22 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	161.307	31661259
DarkChem	[M-H]-	161.693	31661259
DeepCCS	[M+H]+	167.96	30932474
DeepCCS	[M-H]-	165.603	30932474
DeepCCS	[M-2H]-	198.489	30932474
DeepCCS	[M+Na]+	174.054	30932474
AllCCS	[M+H]+	162.9	32859911
AllCCS	[M+H-H2O]+	159.1	32859911
AllCCS	[M+NH4]+	166.4	32859911
AllCCS	[M+Na]+	167.5	32859911
AllCCS	[M-H]-	163.2	32859911
AllCCS	[M+Na-2H]-	162.0	32859911
AllCCS	[M+HCOO]-	160.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aureol	OC1=CC2=C(C=C1)C1=C(O2)C2=C(O)C=C(O)C=C2OC1=O	4560.0	Standard polar	33892256
Aureol	OC1=CC2=C(C=C1)C1=C(O2)C2=C(O)C=C(O)C=C2OC1=O	2630.0	Standard non polar	33892256
Aureol	OC1=CC2=C(C=C1)C1=C(O2)C2=C(O)C=C(O)C=C2OC1=O	3188.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aureol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC(O)=C21	3170.5	Semi standard non polar	33892256
Aureol,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC2=C1C1=C(C(=O)O2)C2=CC=C(O)C=C2O1	3128.5	Semi standard non polar	33892256
Aureol,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC=C21	3172.5	Semi standard non polar	33892256
Aureol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC(O[Si](C)(C)C)=C21	3174.9	Semi standard non polar	33892256
Aureol,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C)=CC(O)=C21	3253.2	Semi standard non polar	33892256
Aureol,2TMS,isomer #3	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC=C21	3176.4	Semi standard non polar	33892256
Aureol,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C21	3321.9	Semi standard non polar	33892256
Aureol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC(O)=C21	3374.4	Semi standard non polar	33892256
Aureol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C1=C(C(=O)O2)C2=CC=C(O)C=C2O1	3339.4	Semi standard non polar	33892256
Aureol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC=C21	3380.9	Semi standard non polar	33892256
Aureol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C21	3626.5	Semi standard non polar	33892256
Aureol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C21	3697.0	Semi standard non polar	33892256
Aureol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC=C21	3623.4	Semi standard non polar	33892256
Aureol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C21	3991.3	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 - Aureol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0536-0090000000-3a0135632b41aafb912d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aureol GC-MS (3 TMS) - 70eV, Positive	splash10-00g0-3041900000-4e9caaf096a595555177	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aureol 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 - Aureol 10V, Positive-QTOF	splash10-000i-0090000000-3486b0a460d737859445	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aureol 20V, Positive-QTOF	splash10-000i-0090000000-5eab173630209e9ac172	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aureol 40V, Positive-QTOF	splash10-014i-2290000000-3ffe39b45053ac1c5d39	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aureol 10V, Negative-QTOF	splash10-001i-0090000000-7923569b9bdcb0b46d47	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aureol 20V, Negative-QTOF	splash10-001i-0090000000-068016fc39adcf62bf2f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aureol 40V, Negative-QTOF	splash10-014s-1790000000-d127a211a68b1ba2333a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aureol 10V, Positive-QTOF	splash10-000i-0090000000-3896d645ce486a1e32ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aureol 20V, Positive-QTOF	splash10-000i-0090000000-3896d645ce486a1e32ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aureol 40V, Positive-QTOF	splash10-0ap3-0090000000-7fa7de3ad6d37cc4085f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aureol 10V, Negative-QTOF	splash10-001i-0090000000-279002154c712db975df	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aureol 20V, Negative-QTOF	splash10-001i-0090000000-279002154c712db975df	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aureol 40V, Negative-QTOF	splash10-0ikc-0090000000-835dab1c475ad6e70fdb	2021-09-23	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

FDB017078

KNApSAcK ID

C00010048

Chemspider ID

4590624

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5491648

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1864221

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Aureol → 6-({5,14-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Aureol → 6-({3,5-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-14-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Aureol → 6-({3,14-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for Aureol (HMDB0037921)

MOL for HMDB0037921 (Aureol)

3D MOL for HMDB0037921 (Aureol)

3D SDF for HMDB0037921 (Aureol)

3D-SDF for HMDB0037921 (Aureol)

PDB for HMDB0037921 (Aureol)

3D PDB for HMDB0037921 (Aureol)

SMILES for HMDB0037921 (Aureol)

INCHI for HMDB0037921 (Aureol)

Structure for HMDB0037921 (Aureol)

3D Structure for HMDB0037921 (Aureol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions