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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:17:34 UTC

Update Date

2022-03-07 02:56:42 UTC

HMDB ID

HMDB0040716

Secondary Accession Numbers

HMDB40716

Metabolite Identification

Common Name

Irenolone

Description

Irenolone belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group. Irenolone has been detected, but not quantified in, a few different foods, such as bananas (Musa acuminata), french plantains (Musa X paradisiaca), and fruits. This could make irenolone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Irenolone.

Structure

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

HMDB0040716
     RDKit          3D
Irenolone
 34 37  0  0  0  0  0  0  0  0999 V2000
   -3.6458   -1.6881    2.1324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6769   -1.2024    1.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3176   -1.6712    1.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0353   -2.7097    2.5951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3044   -1.1369    1.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248   -0.0423    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5132    0.5448   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8629    0.0319   -0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8272    0.9120   -0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1254    0.4817    0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5153   -0.8324   -0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8280   -1.2526    0.0409 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4975   -1.6779   -0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1929   -1.2786   -0.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2185    1.5770   -1.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638    2.0389   -1.6206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1166    1.4684   -0.9388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3780    1.9671   -1.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4482    1.4117   -0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2104    0.3771    0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078   -0.1055    0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8300    0.4238   -0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731   -3.3476    2.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7203   -1.4911    1.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6367    1.9599    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8968    1.1891    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5076   -0.5693    0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7728   -2.7257   -0.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4379   -2.0123   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0068    2.0560   -1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2691    2.8655   -2.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    2.7800   -1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4660    1.7488   -0.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0097   -0.0900    0.9471 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
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  7 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  2  1  0
 22  6  2  0
 14  8  1  0
 22 17  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END


  Mrv0541 05061312042D          

 22 25  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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
    1.4289    0.8250    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
    1.4289    2.4750    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
    2.8579   -1.6500    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
    3.5724   -0.4125    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  6  2  0  0  0  0
 11  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  2  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15  3  2  0  0  0  0
 16 10  1  0  0  0  0
 16 14  2  0  0  0  0
 17 10  2  0  0  0  0
 18 12  2  0  0  0  0
 18 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20 13  1  0  0  0  0
 21 17  1  0  0  0  0
 22 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040716

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C1=C2C=C(O)C(=O)C3=CC=CC(C=C1)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C19H12O3/c20-13-7-4-11(5-8-13)14-9-6-12-2-1-3-15-18(12)16(14)10-17(21)19(15)22/h1-10,20-21H

> <INCHI_KEY>
UQMKPTIDKHEGFW-UHFFFAOYSA-N

> <FORMULA>
C19H12O3

> <MOLECULAR_WEIGHT>
288.2968

> <EXACT_MASS>
288.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.395106260838304

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-4-(4-hydroxyphenyl)-1H-phenalen-1-one

> <ALOGPS_LOGP>
3.67

> <JCHEM_LOGP>
3.7315586086666666

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.869455288952402

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.161551293154643

> <JCHEM_PKA_STRONGEST_BASIC>
-3.570373094738378

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
86.35369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.34e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-4-(4-hydroxyphenyl)phenalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040716
     RDKit          3D
Irenolone
 34 37  0  0  0  0  0  0  0  0999 V2000
   -3.6458   -1.6881    2.1324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6769   -1.2024    1.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3176   -1.6712    1.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0353   -2.7097    2.5951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3044   -1.1369    1.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248   -0.0423    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5132    0.5448   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8629    0.0319   -0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8272    0.9120   -0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1254    0.4817    0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5153   -0.8324   -0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8280   -1.2526    0.0409 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4975   -1.6779   -0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1929   -1.2786   -0.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2185    1.5770   -1.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638    2.0389   -1.6206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1166    1.4684   -0.9388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3780    1.9671   -1.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4482    1.4117   -0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2104    0.3771    0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078   -0.1055    0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8300    0.4238   -0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731   -3.3476    2.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7203   -1.4911    1.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6367    1.9599    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8968    1.1891    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5076   -0.5693    0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7728   -2.7257   -0.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4379   -2.0123   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0068    2.0560   -1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2691    2.8655   -2.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    2.7800   -1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4660    1.7488   -0.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0097   -0.0900    0.9471 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
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  7 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  2  1  0
 22  6  2  0
 14  8  1  0
 22 17  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  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       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1   12                                                       
CONECT    3    1   15                                                       
CONECT    4    7   11                                                       
CONECT    5    8   11                                                       
CONECT    6    9   12                                                       
CONECT    7    4   13                                                       
CONECT    8    5   13                                                       
CONECT    9    6   14                                                       
CONECT   10   16   17                                                       
CONECT   11    4    5   14                                                  
CONECT   12    2    6   18                                                  
CONECT   13    7    8   20                                                  
CONECT   14    9   11   16                                                  
CONECT   15    3   18   19                                                  
CONECT   16   10   14   18                                                  
CONECT   17   10   19   21                                                  
CONECT   18   12   15   16                                                  
CONECT   19   15   17   22                                                  
CONECT   20   13                                                            
CONECT   21   17                                                            
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0040716
HETATM    1  O1  UNL     1      -3.646  -1.688   2.132  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.677  -1.202   1.532  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.318  -1.671   1.716  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.035  -2.710   2.595  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.304  -1.137   1.065  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.525  -0.042   0.124  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.513   0.545  -0.571  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.863   0.032  -0.403  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.827   0.912  -0.019  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.125   0.482   0.123  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.515  -0.832  -0.107  1.00  0.00           C  
HETATM   12  O3  UNL     1       5.828  -1.253   0.041  1.00  0.00           O  
HETATM   13  C10 UNL     1       3.497  -1.678  -0.493  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.193  -1.279  -0.644  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.218   1.577  -1.431  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.064   2.039  -1.621  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.117   1.468  -0.939  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.378   1.967  -1.159  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.448   1.412  -0.481  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.210   0.377   0.394  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.908  -0.105   0.593  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.830   0.424  -0.066  1.00  0.00           C  
HETATM   23  H1  UNL     1      -1.773  -3.348   2.897  1.00  0.00           H  
HETATM   24  H2  UNL     1       0.720  -1.491   1.223  1.00  0.00           H  
HETATM   25  H3  UNL     1       2.637   1.960   0.187  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.897   1.189   0.431  1.00  0.00           H  
HETATM   27  H5  UNL     1       6.508  -0.569   0.326  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.773  -2.726  -0.683  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.438  -2.012  -0.962  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.007   2.056  -1.987  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.269   2.866  -2.314  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.582   2.780  -1.843  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.466   1.749  -0.602  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.010  -0.090   0.947  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4    5    5
CONECT    4   23
CONECT    5    6   24
CONECT    6    7   22   22
CONECT    7    8   15   15
CONECT    8    9    9   14
CONECT    9   10   25
CONECT   10   11   11   26
CONECT   11   12   13
CONECT   12   27
CONECT   13   14   14   28
CONECT   14   29
CONECT   15   16   30
CONECT   16   17   17   31
CONECT   17   18   22
CONECT   18   19   19   32
CONECT   19   20   33
CONECT   20   21   21   34
CONECT   21   22
END

HMDB0040716
     RDKit          3D
Irenolone
 34 37  0  0  0  0  0  0  0  0999 V2000
   -3.6458   -1.6881    2.1324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6769   -1.2024    1.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3176   -1.6712    1.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0353   -2.7097    2.5951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3044   -1.1369    1.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248   -0.0423    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5132    0.5448   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8629    0.0319   -0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8272    0.9120   -0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1254    0.4817    0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5153   -0.8324   -0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8280   -1.2526    0.0409 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4975   -1.6779   -0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1929   -1.2786   -0.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2185    1.5770   -1.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638    2.0389   -1.6206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1166    1.4684   -0.9388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3780    1.9671   -1.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4482    1.4117   -0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2104    0.3771    0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078   -0.1055    0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8300    0.4238   -0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731   -3.3476    2.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7203   -1.4911    1.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6367    1.9599    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8968    1.1891    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5076   -0.5693    0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7728   -2.7257   -0.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4379   -2.0123   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0068    2.0560   -1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2691    2.8655   -2.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    2.7800   -1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4660    1.7488   -0.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0097   -0.0900    0.9471 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
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  7 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  2  1  0
 22  6  2  0
 14  8  1  0
 22 17  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₁₂O₃

Average Molecular Weight

288.2968

Monoisotopic Molecular Weight

288.07864425

IUPAC Name

2-hydroxy-4-(4-hydroxyphenyl)-1H-phenalen-1-one

Traditional Name

2-hydroxy-4-(4-hydroxyphenyl)phenalen-1-one

CAS Registry Number

149184-19-0

SMILES

OC1=CC=C(C=C1)C1=C2C=C(O)C(=O)C3=CC=CC(C=C1)=C23

InChI Identifier

InChI=1S/C19H12O3/c20-13-7-4-11(5-8-13)14-9-6-12-2-1-3-15-18(12)16(14)10-17(21)19(15)22/h1-10,20-21H

InChI Key

UQMKPTIDKHEGFW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenylnaphthalene
Phenalen-1-one
Phenalen
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0040716)
Cell membrane (HMDB: HMDB0040716)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040716)

Source

Exogenous

Exogenous (HMDB: HMDB0040716)

Food

Food (HMDB: HMDB0040716)

Fruit

Tropical fruit

Banana (FooDB: FOOD00208)
French plantain (FooDB: FOOD00436)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0040716)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040716)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	285 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.48 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	0.0063 g/L	ALOGPS
logP	3.67	ALOGPS
logP	3.73	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	9.16	ChemAxon
pKa (Strongest Basic)	-3.6	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	1	ChemAxon
Refractivity	86.35 m³·mol⁻¹	ChemAxon
Polarizability	30.4 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
DeepCCS	[M-2H]-	201.933	30932474
DeepCCS	[M+Na]+	177.16	30932474
AllCCS	[M+H]+	167.9	32859911
AllCCS	[M+H-H2O]+	164.2	32859911
AllCCS	[M+NH4]+	171.3	32859911
AllCCS	[M+Na]+	172.3	32859911
AllCCS	[M-H]-	170.6	32859911
AllCCS	[M+Na-2H]-	169.4	32859911
AllCCS	[M+HCOO]-	168.3	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. Predicted by Afia on May 17, 2022.	7.99 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9319 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.24 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2277.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	390.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	183.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	217.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	408.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	655.1 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	521.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	99.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1224.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	493.3 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	1367.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	411.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	416.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	361.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	176.4 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	47.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Irenolone	OC1=CC=C(C=C1)C1=C2C=C(O)C(=O)C3=CC=CC(C=C1)=C23	4262.3	Standard polar	33892256
Irenolone	OC1=CC=C(C=C1)C1=C2C=C(O)C(=O)C3=CC=CC(C=C1)=C23	2754.0	Standard non polar	33892256
Irenolone	OC1=CC=C(C=C1)C1=C2C=C(O)C(=O)C3=CC=CC(C=C1)=C23	3184.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Irenolone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=CC=C3C=CC=C4C(=O)C(O)=CC2=C43)C=C1	3195.2	Semi standard non polar	33892256
Irenolone,1TMS,isomer #2	C[Si](C)(C)OC1=CC2=C3C(=CC=CC3=CC=C2C2=CC=C(O)C=C2)C1=O	3233.0	Semi standard non polar	33892256
Irenolone,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=C3C(=CC=CC3=CC=C2C2=CC=C(O[Si](C)(C)C)C=C2)C1=O	3194.1	Semi standard non polar	33892256
Irenolone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC=C3C=CC=C4C(=O)C(O)=CC2=C43)C=C1	3444.0	Semi standard non polar	33892256
Irenolone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=CC=CC3=CC=C2C2=CC=C(O)C=C2)C1=O	3472.5	Semi standard non polar	33892256
Irenolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=CC=CC3=CC=C2C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C1=O	3662.7	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 - Irenolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bu0-0090000000-3bc82c31952bf2ce22ac	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Irenolone GC-MS (2 TMS) - 70eV, Positive	splash10-00xr-9008600000-53c05c277181d05a2266	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Irenolone 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 - Irenolone 10V, Positive-QTOF	splash10-000i-0090000000-418fac8b530b8c6ab582	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irenolone 20V, Positive-QTOF	splash10-000i-0190000000-8c41e7434cef043fbdcd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irenolone 40V, Positive-QTOF	splash10-0kmj-0190000000-b82626098c30f1b83d1d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irenolone 10V, Negative-QTOF	splash10-000i-0090000000-8e165b5e31ea35c989a8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irenolone 20V, Negative-QTOF	splash10-000i-0090000000-96d79177be0638f92271	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irenolone 40V, Negative-QTOF	splash10-0apu-1090000000-1923029a02fe63ae8a22	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irenolone 10V, Negative-QTOF	splash10-000i-0090000000-ad76c01409fa18536a26	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irenolone 20V, Negative-QTOF	splash10-000i-0090000000-775291b18c312826c59b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irenolone 40V, Negative-QTOF	splash10-0a5i-0090000000-851d3b930599d858ab03	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irenolone 10V, Positive-QTOF	splash10-000i-0090000000-9b8c528cd946b073787c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irenolone 20V, Positive-QTOF	splash10-000i-0090000000-9b8c528cd946b073787c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irenolone 40V, Positive-QTOF	splash10-053r-0090000000-b06b840bb662e372fdf4	2021-09-25	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

FDB020523

KNApSAcK ID

C00037306

Chemspider ID

2035535

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2754650

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1885781

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 Irenolone (HMDB0040716)

MOL for HMDB0040716 (Irenolone)

3D MOL for HMDB0040716 (Irenolone)

3D SDF for HMDB0040716 (Irenolone)

3D-SDF for HMDB0040716 (Irenolone)

PDB for HMDB0040716 (Irenolone)

3D PDB for HMDB0040716 (Irenolone)

SMILES for HMDB0040716 (Irenolone)

INCHI for HMDB0040716 (Irenolone)

Structure for HMDB0040716 (Irenolone)

3D Structure for HMDB0040716 (Irenolone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra