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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 02:10:32 UTC

Update Date

2022-09-22 17:45:01 UTC

HMDB ID

HMDB0248730

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Aurin

Description

4-[bis(4-hydroxyphenyl)methylidene]cyclohexa-2,5-dien-1-one belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Based on a literature review very few articles have been published on 4-[bis(4-hydroxyphenyl)methylidene]cyclohexa-2,5-dien-1-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). Aurin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Aurin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0248730
     RDKit          3D
Aurin
 36 38  0  0  0  0  0  0  0  0999 V2000
    0.7802    5.4592    0.0744 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6037    4.1942    0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249    3.3083   -0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5376    1.9915   -0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2217    1.4501    0.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0747    0.1285    0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1975   -0.7706   -0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6876   -1.7057    0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7198   -2.5265    0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2610   -2.4348   -0.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2910   -3.2552   -1.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7485   -1.4823   -1.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7281   -0.6520   -1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2728   -0.3983    0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2889    0.0107   -0.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5485   -0.4476   -0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8645   -1.3185    0.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1758   -1.7537    0.8245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8936   -1.7385    1.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5880   -1.2547    1.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929    2.3446    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7214    3.6784    0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7140    3.6954   -0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096    1.3845   -0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232   -1.8157    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433   -3.2809    1.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2730   -2.9696   -1.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1419   -1.3643   -2.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3093    0.0946   -2.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0129    0.6926   -1.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -0.1057   -1.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8975   -1.4622    0.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1148   -2.4285    2.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8735   -1.6102    2.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8906    1.9853    0.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5361    4.3573    0.6360 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  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  5 21  1  0
 21 22  2  0
 22  2  1  0
 13  7  1  0
 20 14  1  0
  3 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
M  END


  Mrv1652309112104102D          

 22 24  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   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
   -2.1434   -0.4125    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
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248730

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C(C1=CC=C(O)C=C1)=C1C=CC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H14O3/c20-16-7-1-13(2-8-16)19(14-3-9-17(21)10-4-14)15-5-11-18(22)12-6-15/h1-12,20-21H

> <INCHI_KEY>
FYEHYMARPSSOBO-UHFFFAOYSA-N

> <FORMULA>
C19H14O3

> <MOLECULAR_WEIGHT>
290.318

> <EXACT_MASS>
290.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
30.888067077764042

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[bis(4-hydroxyphenyl)methylidene]cyclohexa-2,5-dien-1-one

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
3.8524214309999993

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.243521152971677

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.635548058675678

> <JCHEM_PKA_STRONGEST_BASIC>
-5.053769002332605

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
98.04310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aurin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248730
     RDKit          3D
Aurin
 36 38  0  0  0  0  0  0  0  0999 V2000
    0.7802    5.4592    0.0744 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6037    4.1942    0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249    3.3083   -0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5376    1.9915   -0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2217    1.4501    0.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0747    0.1285    0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1975   -0.7706   -0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6876   -1.7057    0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7198   -2.5265    0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2610   -2.4348   -0.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2910   -3.2552   -1.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7485   -1.4823   -1.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7281   -0.6520   -1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2728   -0.3983    0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2889    0.0107   -0.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5485   -0.4476   -0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8645   -1.3185    0.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1758   -1.7537    0.8245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8936   -1.7385    1.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5880   -1.2547    1.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929    2.3446    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7214    3.6784    0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7140    3.6954   -0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096    1.3845   -0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232   -1.8157    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433   -3.2809    1.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2730   -2.9696   -1.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1419   -1.3643   -2.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3093    0.0946   -2.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0129    0.6926   -1.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -0.1057   -1.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8975   -1.4622    0.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1148   -2.4285    2.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8735   -1.6102    2.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8906    1.9853    0.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5361    4.3573    0.6360 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  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  5 21  1  0
 21 22  2  0
 22  2  1  0
 13  7  1  0
 20 14  1  0
  3 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001  -0.770   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  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   12                                                            
CONECT   16    8   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0248730
HETATM    1  O1  UNL     1       0.780   5.459   0.074  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.604   4.194   0.102  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.725   3.308  -0.188  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.538   1.991  -0.159  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.222   1.450   0.160  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.075   0.129   0.188  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.197  -0.771  -0.092  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.688  -1.706   0.788  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.720  -2.526   0.354  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.261  -2.435  -0.910  1.00  0.00           C  
HETATM   11  O2  UNL     1       4.291  -3.255  -1.340  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.749  -1.482  -1.777  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.728  -0.652  -1.387  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.273  -0.398   0.380  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.289   0.011  -0.499  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.549  -0.448  -0.328  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.865  -1.319   0.702  1.00  0.00           C  
HETATM   18  O3  UNL     1      -5.176  -1.754   0.825  1.00  0.00           O  
HETATM   19  C16 UNL     1      -2.894  -1.738   1.580  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.588  -1.255   1.392  1.00  0.00           C  
HETATM   21  C18 UNL     1      -0.893   2.345   0.450  1.00  0.00           C  
HETATM   22  C19 UNL     1      -0.721   3.678   0.425  1.00  0.00           C  
HETATM   23  H1  UNL     1       2.714   3.695  -0.429  1.00  0.00           H  
HETATM   24  H2  UNL     1       2.410   1.385  -0.372  1.00  0.00           H  
HETATM   25  H3  UNL     1       1.323  -1.816   1.787  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.143  -3.281   1.005  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.273  -2.970  -1.202  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.142  -1.364  -2.797  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.309   0.095  -2.042  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.013   0.693  -1.299  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.319  -0.106  -1.036  1.00  0.00           H  
HETATM   32  H10 UNL     1      -5.897  -1.462   0.198  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.115  -2.428   2.406  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.873  -1.610   2.121  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.891   1.985   0.708  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.536   4.357   0.636  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   22
CONECT    3    4    4   23
CONECT    4    5   24
CONECT    5    6    6   21
CONECT    6    7   14
CONECT    7    8    8   13
CONECT    8    9   25
CONECT    9   10   10   26
CONECT   10   11   12
CONECT   11   27
CONECT   12   13   13   28
CONECT   13   29
CONECT   14   15   15   20
CONECT   15   16   30
CONECT   16   17   17   31
CONECT   17   18   19
CONECT   18   32
CONECT   19   20   20   33
CONECT   20   34
CONECT   21   22   22   35
CONECT   22   36
END

HMDB0248730
     RDKit          3D
Aurin
 36 38  0  0  0  0  0  0  0  0999 V2000
    0.7802    5.4592    0.0744 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6037    4.1942    0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249    3.3083   -0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5376    1.9915   -0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2217    1.4501    0.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0747    0.1285    0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1975   -0.7706   -0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6876   -1.7057    0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7198   -2.5265    0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2610   -2.4348   -0.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2910   -3.2552   -1.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7485   -1.4823   -1.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7281   -0.6520   -1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2728   -0.3983    0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2889    0.0107   -0.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5485   -0.4476   -0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8645   -1.3185    0.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1758   -1.7537    0.8245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8936   -1.7385    1.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5880   -1.2547    1.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929    2.3446    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7214    3.6784    0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7140    3.6954   -0.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096    1.3845   -0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232   -1.8157    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433   -3.2809    1.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2730   -2.9696   -1.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1419   -1.3643   -2.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3093    0.0946   -2.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0129    0.6926   -1.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -0.1057   -1.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8975   -1.4622    0.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1148   -2.4285    2.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8735   -1.6102    2.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8906    1.9853    0.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5361    4.3573    0.6360 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  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  5 21  1  0
 21 22  2  0
 22  2  1  0
 13  7  1  0
 20 14  1  0
  3 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Rosolic acid	MeSH

Chemical Formula

C₁₉H₁₄O₃

Average Molecular Weight

290.318

Monoisotopic Molecular Weight

290.094294311

IUPAC Name

4-[bis(4-hydroxyphenyl)methylidene]cyclohexa-2,5-dien-1-one

Traditional Name

aurin

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C(C1=CC=C(O)C=C1)=C1C=CC(=O)C=C1

InChI Identifier

InChI=1S/C19H14O3/c20-16-7-1-13(2-8-16)19(14-3-9-17(21)10-4-14)15-5-11-18(22)12-6-15/h1-12,20-21H

InChI Key

FYEHYMARPSSOBO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Quinomethane
P-quinomethane
1-hydroxy-2-unsubstituted benzenoid
Phenol
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

diarylmethane (CHEBI:34544 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.84	ALOGPS
logP	3.85	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	8.64	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.04 m³·mol⁻¹	ChemAxon
Polarizability	30.89 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]+	173.597	30932474
DeepCCS	[M-H]-	171.239	30932474
DeepCCS	[M-2H]-	205.001	30932474
DeepCCS	[M+Na]+	180.228	30932474
AllCCS	[M+H]+	169.0	32859911
AllCCS	[M+H-H2O]+	165.3	32859911
AllCCS	[M+NH4]+	172.3	32859911
AllCCS	[M+Na]+	173.3	32859911
AllCCS	[M-H]-	170.7	32859911
AllCCS	[M+Na-2H]-	169.9	32859911
AllCCS	[M+HCOO]-	169.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aurin	OC1=CC=C(C=C1)C(C1=CC=C(O)C=C1)=C1C=CC(=O)C=C1	4663.1	Standard polar	33892256
Aurin	OC1=CC=C(C=C1)C(C1=CC=C(O)C=C1)=C1C=CC(=O)C=C1	2901.5	Standard non polar	33892256
Aurin	OC1=CC=C(C=C1)C(C1=CC=C(O)C=C1)=C1C=CC(=O)C=C1	3353.7	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 - Aurin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-1190000000-6ffa8b919ef2cb99a011	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aurin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aurin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aurin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aurin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aurin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	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 - Aurin 10V, Positive-QTOF	splash10-0006-0090000000-7e372f98088a79afb4bb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurin 20V, Positive-QTOF	splash10-0006-0390000000-cfb17e45fcb54b44829d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurin 40V, Positive-QTOF	splash10-014j-0940000000-14a6e6fa280643de3851	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurin 10V, Negative-QTOF	splash10-000i-0090000000-9c70290ef613696ea2ac	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurin 20V, Negative-QTOF	splash10-000i-0090000000-9c70290ef613696ea2ac	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurin 40V, Negative-QTOF	splash10-0a4r-0090000000-454031af45ade3ad8be4	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4921

KEGG Compound ID

C14213

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Aurin (HMDB0248730)

MOL for HMDB0248730 (Aurin)

3D MOL for HMDB0248730 (Aurin)

3D SDF for HMDB0248730 (Aurin)

3D-SDF for HMDB0248730 (Aurin)

PDB for HMDB0248730 (Aurin)

3D PDB for HMDB0248730 (Aurin)

SMILES for HMDB0248730 (Aurin)

INCHI for HMDB0248730 (Aurin)

Structure for HMDB0248730 (Aurin)

3D Structure for HMDB0248730 (Aurin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra