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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:35:39 UTC

Update Date

2022-03-07 02:53:52 UTC

HMDB ID

HMDB0033820

Secondary Accession Numbers

HMDB33820

Metabolite Identification

Common Name

Irilone

Description

Irilone, also known as irolone, belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, irilone is considered to be a flavonoid. Irilone has been detected, but not quantified in, several different foods, such as black tea, herbs and spices, green tea, red tea, and herbal tea. This could make irilone a potential biomarker for the consumption of these foods. Irilone 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 a significant number of articles have been published on Irilone.

Structure

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

HMDB0033820
     RDKit          3D
Irilone
 32 35  0  0  0  0  0  0  0  0999 V2000
    0.1986    0.1723    1.6017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0457    0.0384    0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038   -0.0582   -0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4075   -0.0128   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3265   -0.9180   -0.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6419   -0.8673   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1016    0.0748    0.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4298    0.0924    0.9954 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2153    0.9806    1.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    0.9145    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6709   -0.2052   -1.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5787   -0.2522   -2.2450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6115   -0.1647   -1.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9155   -0.2200   -1.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9568   -0.1208   -1.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7339    0.0272    0.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367    0.0799    0.7983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    0.2280    2.1401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -0.0159   -0.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9549    0.0967    0.9856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0133   -0.0581    0.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3234   -0.1413   -1.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -1.6438   -1.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3563   -1.5901   -0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7863    0.7765    1.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6022    1.7003    1.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819    1.6205    1.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -0.2864   -2.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1105   -0.3371   -2.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8191    0.3069    2.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5281   -1.0240    0.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7048    0.8067    0.0950 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  3 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 19  2  1  0
 10  4  1  0
 19 13  1  0
 22 15  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 14 29  1  0
 18 30  1  0
 21 31  1  0
 21 32  1  0
M  END

  Mrv0541 05061307232D          

 22 25  0  0  0  0            999 V2000
    6.9246    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683    2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532    2.0930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532    3.4279    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
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 11  5  2  0  0  0  0
 12  5  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  2  0  0  0  0
 16 12  2  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 14  2  0  0  0  0
 19 15  1  0  0  0  0
 20  6  1  0  0  0  0
 20 11  1  0  0  0  0
 21  7  1  0  0  0  0
 21 12  1  0  0  0  0
 22  7  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033820

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C1=COC2=CC3=C(OCO3)C(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O6/c17-9-3-1-8(2-4-9)10-6-20-11-5-12-16(22-7-21-12)15(19)13(11)14(10)18/h1-6,17,19H,7H2

> <INCHI_KEY>
NUGRQNBDTZWXTP-UHFFFAOYSA-N

> <FORMULA>
C16H10O6

> <MOLECULAR_WEIGHT>
298.247

> <EXACT_MASS>
298.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.092793441426416

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxy-7-(4-hydroxyphenyl)-2H,8H-[1,3]dioxolo[4,5-g]chromen-8-one

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
3.0036711789999995

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.258123892631746

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.649837450164254

> <JCHEM_PKA_STRONGEST_BASIC>
-4.389651421988771

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
75.4689

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
irilone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033820
     RDKit          3D
Irilone
 32 35  0  0  0  0  0  0  0  0999 V2000
    0.1986    0.1723    1.6017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0457    0.0384    0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038   -0.0582   -0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4075   -0.0128   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3265   -0.9180   -0.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6419   -0.8673   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1016    0.0748    0.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4298    0.0924    0.9954 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2153    0.9806    1.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    0.9145    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6709   -0.2052   -1.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5787   -0.2522   -2.2450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6115   -0.1647   -1.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9155   -0.2200   -1.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9568   -0.1208   -1.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7339    0.0272    0.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367    0.0799    0.7983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    0.2280    2.1401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -0.0159   -0.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9549    0.0967    0.9856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0133   -0.0581    0.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3234   -0.1413   -1.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -1.6438   -1.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3563   -1.5901   -0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7863    0.7765    1.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6022    1.7003    1.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819    1.6205    1.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -0.2864   -2.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1105   -0.3371   -2.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8191    0.3069    2.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5281   -1.0240    0.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7048    0.8067    0.0950 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  3 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 19  2  1  0
 10  4  1  0
 19 13  1  0
 22 15  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 14 29  1  0
 18 30  1  0
 21 31  1  0
 21 32  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      12.926   5.923   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.592   8.233   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.260   6.693   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.926   9.003   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.554   5.153   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.592   6.693   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.260   8.233   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.259   5.923   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      15.593   9.003   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.925   8.233   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.258   8.233   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.925   3.613   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.459   3.907   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.459   6.399   0.000  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2    9                                                       
CONECT    5   11   12                                                       
CONECT    6   10   20                                                       
CONECT    7   21   22                                                       
CONECT    8    1    2   10                                                  
CONECT    9    3    4   17                                                  
CONECT   10    6    8   14                                                  
CONECT   11    5   13   20                                                  
CONECT   12    5   16   21                                                  
CONECT   13   11   14   15                                                  
CONECT   14   10   13   18                                                  
CONECT   15   13   16   19                                                  
CONECT   16   12   15   22                                                  
CONECT   17    9                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20    6   11                                                       
CONECT   21    7   12                                                       
CONECT   22    7   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0033820
HETATM    1  O1  UNL     1       0.199   0.172   1.602  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.046   0.038   0.388  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.004  -0.058  -0.503  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.408  -0.013  -0.110  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.326  -0.918  -0.633  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.642  -0.867  -0.257  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.102   0.075   0.645  1.00  0.00           C  
HETATM    8  O2  UNL     1       6.430   0.092   0.995  1.00  0.00           O  
HETATM    9  C7  UNL     1       4.215   0.981   1.176  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.896   0.915   0.787  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.671  -0.205  -1.834  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.579  -0.252  -2.245  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.612  -0.165  -1.435  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.915  -0.220  -1.920  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.957  -0.121  -1.005  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.734   0.027   0.337  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.437   0.080   0.798  1.00  0.00           C  
HETATM   18  O4  UNL     1      -2.119   0.228   2.140  1.00  0.00           O  
HETATM   19  C15 UNL     1      -1.357  -0.016  -0.086  1.00  0.00           C  
HETATM   20  O5  UNL     1      -4.955   0.097   0.986  1.00  0.00           O  
HETATM   21  C16 UNL     1      -6.013  -0.058   0.060  1.00  0.00           C  
HETATM   22  O6  UNL     1      -5.323  -0.141  -1.173  1.00  0.00           O  
HETATM   23  H1  UNL     1       2.929  -1.644  -1.339  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.356  -1.590  -0.679  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.786   0.777   1.656  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.602   1.700   1.874  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.182   1.620   1.195  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.461  -0.286  -2.583  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.110  -0.337  -2.981  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.819   0.307   2.867  1.00  0.00           H  
HETATM   31  H9  UNL     1      -6.528  -1.024   0.214  1.00  0.00           H  
HETATM   32  H10 UNL     1      -6.705   0.807   0.095  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4   11   11
CONECT    4    5    5   10
CONECT    5    6   23
CONECT    6    7    7   24
CONECT    7    8    9
CONECT    8   25
CONECT    9   10   10   26
CONECT   10   27
CONECT   11   12   28
CONECT   12   13
CONECT   13   14   14   19
CONECT   14   15   29
CONECT   15   16   16   22
CONECT   16   17   20
CONECT   17   18   19   19
CONECT   18   30
CONECT   20   21
CONECT   21   22   31   32
END

HMDB0033820
     RDKit          3D
Irilone
 32 35  0  0  0  0  0  0  0  0999 V2000
    0.1986    0.1723    1.6017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0457    0.0384    0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038   -0.0582   -0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4075   -0.0128   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3265   -0.9180   -0.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6419   -0.8673   -0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1016    0.0748    0.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4298    0.0924    0.9954 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2153    0.9806    1.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    0.9145    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6709   -0.2052   -1.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5787   -0.2522   -2.2450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6115   -0.1647   -1.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9155   -0.2200   -1.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9568   -0.1208   -1.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7339    0.0272    0.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367    0.0799    0.7983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    0.2280    2.1401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -0.0159   -0.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9549    0.0967    0.9856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0133   -0.0581    0.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3234   -0.1413   -1.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -1.6438   -1.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3563   -1.5901   -0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7863    0.7765    1.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6022    1.7003    1.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819    1.6205    1.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -0.2864   -2.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1105   -0.3371   -2.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8191    0.3069    2.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5281   -1.0240    0.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7048    0.8067    0.0950 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  3 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 19  2  1  0
 10  4  1  0
 19 13  1  0
 22 15  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 14 29  1  0
 18 30  1  0
 21 31  1  0
 21 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,4'-Dihydroxy-6,7-methylenedioxyisoflavone	ChEBI
9-Hydroxy-7-(4-hydroxyphenyl)-8H-1,3-dioxolo[4,5-g]-1-benzopyran-8-one	ChEBI
Irolone	ChEBI
9-Hydroxy-7-(4-hydroxyphenyl)-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one, 9ci	HMDB

Chemical Formula

C₁₆H₁₀O₆

Average Molecular Weight

298.247

Monoisotopic Molecular Weight

298.047738052

IUPAC Name

9-hydroxy-7-(4-hydroxyphenyl)-2H,8H-[1,3]dioxolo[4,5-g]chromen-8-one

Traditional Name

irilone

CAS Registry Number

41653-81-0

SMILES

OC1=CC=C(C=C1)C1=COC2=CC3=C(OCO3)C(O)=C2C1=O

InChI Identifier

InChI=1S/C16H10O6/c17-9-3-1-8(2-4-9)10-6-20-11-5-12-16(22-7-21-12)15(19)13(11)14(10)18/h1-6,17,19H,7H2

InChI Key

NUGRQNBDTZWXTP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Isoflavone
Hydroxyisoflavonoid
Chromone
Benzopyran
1-benzopyran
Benzodioxole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Organoheterocyclic compound
Oxacycle
Acetal
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:5970 )
oxacycle (CHEBI:5970 )
hydroxyisoflavone (CHEBI:5970 )
isoflavones (C10467 )
Isoflavonoids (C10467 )
Isoflavonoids (LMPK12050383 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20067656)

Cellular substructure

Membrane (HMDB: HMDB0033820)
Cell membrane (HMDB: HMDB0033820)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033820)

Source

Exogenous

Exogenous (HMDB: HMDB0033820)

Food

Food (HMDB: HMDB0033820)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033820)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033820)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	231 °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	0.15 g/L	ALOGPS
logP	2.69	ALOGPS
logP	3	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.65	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.47 m³·mol⁻¹	ChemAxon
Polarizability	29.09 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]+	167.607	31661259
DarkChem	[M-H]-	168.671	31661259
DeepCCS	[M+H]+	164.442	30932474
DeepCCS	[M-H]-	162.084	30932474
DeepCCS	[M-2H]-	194.999	30932474
DeepCCS	[M+Na]+	170.535	30932474
AllCCS	[M+H]+	167.3	32859911
AllCCS	[M+H-H2O]+	163.6	32859911
AllCCS	[M+NH4]+	170.8	32859911
AllCCS	[M+Na]+	171.8	32859911
AllCCS	[M-H]-	168.7	32859911
AllCCS	[M+Na-2H]-	167.6	32859911
AllCCS	[M+HCOO]-	166.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Irilone	OC1=CC=C(C=C1)C1=COC2=CC3=C(OCO3)C(O)=C2C1=O	4172.2	Standard polar	33892256
Irilone	OC1=CC=C(C=C1)C1=COC2=CC3=C(OCO3)C(O)=C2C1=O	2859.8	Standard non polar	33892256
Irilone	OC1=CC=C(C=C1)C1=COC2=CC3=C(OCO3)C(O)=C2C1=O	3089.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Irilone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=COC3=CC4=C(OCO4)C(O)=C3C2=O)C=C1	3103.7	Semi standard non polar	33892256
Irilone,1TMS,isomer #2	C[Si](C)(C)OC1=C2OCOC2=CC2=C1C(=O)C(C1=CC=C(O)C=C1)=CO2	3073.0	Semi standard non polar	33892256
Irilone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=COC3=CC4=C(OCO4)C(O[Si](C)(C)C)=C3C2=O)C=C1	3091.5	Semi standard non polar	33892256
Irilone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC4=C(OCO4)C(O)=C3C2=O)C=C1	3348.7	Semi standard non polar	33892256
Irilone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C2OCOC2=CC2=C1C(=O)C(C1=CC=C(O)C=C1)=CO2	3324.2	Semi standard non polar	33892256
Irilone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC4=C(OCO4)C(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1	3577.2	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 - Irilone GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ba-1390000000-b494a4467a2db1f49eee	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Irilone GC-MS (2 TMS) - 70eV, Positive	splash10-00fr-7249800000-84c36396282e56e8d30e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Irilone 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 - Irilone 10V, Positive-QTOF	splash10-0002-0090000000-b44cb871bfc28f8fde72	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irilone 20V, Positive-QTOF	splash10-0002-0090000000-b545b4e6df93d5b33185	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irilone 40V, Positive-QTOF	splash10-0gi9-2690000000-ab0de57efffedc7b326c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irilone 10V, Negative-QTOF	splash10-0002-0090000000-2fcecda831e90d690d91	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irilone 20V, Negative-QTOF	splash10-0002-0090000000-31a3968aedc8b9457a8a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irilone 40V, Negative-QTOF	splash10-0gdi-3970000000-5113848d178494d72421	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irilone 10V, Positive-QTOF	splash10-0002-0090000000-0e40d1dc69d66b601127	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irilone 20V, Positive-QTOF	splash10-0002-0090000000-0e40d1dc69d66b601127	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irilone 40V, Positive-QTOF	splash10-00xv-0190000000-df8a7ab225c8b147533b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irilone 10V, Negative-QTOF	splash10-0002-0090000000-96de5c56a94c496da9f8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irilone 20V, Negative-QTOF	splash10-0002-0090000000-770719d4c04d25e0a9a8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irilone 40V, Negative-QTOF	splash10-00kb-0090000000-cae8ea16121f02ca455f	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 909	20067656	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

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Irilone

METLIN ID

Not Available

PubChem Compound

5281779

PDB ID

Not Available

ChEBI ID

5970

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 Irilone (HMDB0033820)

MOL for HMDB0033820 (Irilone)

3D MOL for HMDB0033820 (Irilone)

3D SDF for HMDB0033820 (Irilone)

3D-SDF for HMDB0033820 (Irilone)

PDB for HMDB0033820 (Irilone)

3D PDB for HMDB0033820 (Irilone)

SMILES for HMDB0033820 (Irilone)

INCHI for HMDB0033820 (Irilone)

Structure for HMDB0033820 (Irilone)

3D Structure for HMDB0033820 (Irilone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra