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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:17:36 UTC

Update Date

2022-03-07 02:54:06 UTC

HMDB ID

HMDB0034449

Secondary Accession Numbers

HMDB34449

Metabolite Identification

Common Name

Hydroxyanigorufone

Description

Hydroxyanigorufone 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. Hydroxyanigorufone 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 hydroxyanigorufone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Hydroxyanigorufone.

Structure

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

HMDB0034449
     RDKit          3D
Hydroxyanigorufone
 34 37  0  0  0  0  0  0  0  0999 V2000
   -0.6212    2.1634    0.3431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    1.5272    0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7015    2.2755    0.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5910    3.6493    0.8663 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660    1.6592    0.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636    0.2223    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2108   -0.3850    0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3349   -1.7447    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2180   -2.5006    0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9895   -1.8806    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8647   -2.6322   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612   -2.0184   -0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5449   -0.6411   -0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8814   -0.0668   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8606   -0.4603    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1469    0.0072    0.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5114    0.8780   -0.4324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8383    1.3430   -0.5118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5585    1.2744   -1.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2728    0.7988   -1.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751    0.1011    0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309   -0.5124    0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0049    4.2350    0.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7878    2.2229    0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1172    0.1886    0.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3348   -2.1854    0.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3358   -3.5754   -0.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9756   -3.7157   -0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2580   -2.5957   -0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5927   -1.1439    1.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8925   -0.3239    1.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4648    0.7611   -1.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8497    1.9651   -2.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5130    1.1100   -1.9634 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 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
 13 21  2  0
 21 22  1  0
 21  2  1  0
 22  6  2  0
 22 10  1  0
 20 14  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 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 05061307492D          

 22 25  0  0  0  0            999 V2000
    0.7145   -0.4125    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    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
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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
    3.5724   -2.8875    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    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
    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
    2.8579   -1.6500    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
    5.7158   -4.1250    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  3  2  0  0  0  0
 13 10  1  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 11  1  0  0  0  0
 16 10  2  0  0  0  0
 17 12  2  0  0  0  0
 17 13  1  0  0  0  0
 18 15  2  0  0  0  0
 18 17  1  0  0  0  0
 19 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20 14  1  0  0  0  0
 21 16  1  0  0  0  0
 22 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034449

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C1=C2C(=O)C(O)=CC3=CC=CC(C=C1)=C23

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

> <INCHI_KEY>
HTELDEYOMOTOBI-UHFFFAOYSA-N

> <FORMULA>
C19H12O3

> <MOLECULAR_WEIGHT>
288.2968

> <EXACT_MASS>
288.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.337606422988195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-9-(4-hydroxyphenyl)-1H-phenalen-1-one

> <ALOGPS_LOGP>
3.62

> <JCHEM_LOGP>
3.7315586086666666

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.774108031605222

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.115199717694452

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5524693931614566

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
86.35369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-9-(4-hydroxyphenyl)phenalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034449
     RDKit          3D
Hydroxyanigorufone
 34 37  0  0  0  0  0  0  0  0999 V2000
   -0.6212    2.1634    0.3431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    1.5272    0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7015    2.2755    0.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5910    3.6493    0.8663 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660    1.6592    0.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636    0.2223    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2108   -0.3850    0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3349   -1.7447    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2180   -2.5006    0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9895   -1.8806    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8647   -2.6322   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612   -2.0184   -0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5449   -0.6411   -0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8814   -0.0668   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8606   -0.4603    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1469    0.0072    0.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5114    0.8780   -0.4324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8383    1.3430   -0.5118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5585    1.2744   -1.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2728    0.7988   -1.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751    0.1011    0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309   -0.5124    0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0049    4.2350    0.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7878    2.2229    0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1172    0.1886    0.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3348   -2.1854    0.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3358   -3.5754   -0.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9756   -3.7157   -0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2580   -2.5957   -0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5927   -1.1439    1.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8925   -0.3239    1.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4648    0.7611   -1.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8497    1.9651   -2.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5130    1.1100   -1.9634 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 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
 13 21  2  0
 21 22  1  0
 21  2  1  0
 22  6  2  0
 22 10  1  0
 20 14  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -5.390   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       6.668  -5.390   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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -3.080   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      10.669  -7.700   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   13                                                       
CONECT    4    7   11                                                       
CONECT    5    8   11                                                       
CONECT    6    9   12                                                       
CONECT    7    4   14                                                       
CONECT    8    5   14                                                       
CONECT    9    6   15                                                       
CONECT   10   13   16                                                       
CONECT   11    4    5   15                                                  
CONECT   12    2    6   17                                                  
CONECT   13    3   10   17                                                  
CONECT   14    7    8   20                                                  
CONECT   15    9   11   18                                                  
CONECT   16   10   19   21                                                  
CONECT   17   12   13   18                                                  
CONECT   18   15   17   19                                                  
CONECT   19   16   18   22                                                  
CONECT   20   14                                                            
CONECT   21   16                                                            
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0034449
HETATM    1  O1  UNL     1      -0.621   2.163   0.343  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.466   1.527   0.375  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.702   2.275   0.656  1.00  0.00           C  
HETATM    4  O2  UNL     1       1.591   3.649   0.866  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.866   1.659   0.705  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.964   0.222   0.484  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.211  -0.385   0.554  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.335  -1.745   0.358  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.218  -2.501   0.091  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.990  -1.881   0.026  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.865  -2.632  -0.233  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.361  -2.018  -0.294  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.545  -0.641  -0.103  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.881  -0.067  -0.243  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.861  -0.460   0.668  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.147   0.007   0.568  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.511   0.878  -0.432  1.00  0.00           C  
HETATM   18  O3  UNL     1      -5.838   1.343  -0.512  1.00  0.00           O  
HETATM   19  C16 UNL     1      -3.559   1.274  -1.337  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.273   0.799  -1.227  1.00  0.00           C  
HETATM   21  C18 UNL     1       0.575   0.101   0.155  1.00  0.00           C  
HETATM   22  C19 UNL     1       1.831  -0.512   0.218  1.00  0.00           C  
HETATM   23  H1  UNL     1       2.005   4.235   0.129  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.788   2.223   0.916  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.117   0.189   0.764  1.00  0.00           H  
HETATM   26  H4  UNL     1       5.335  -2.185   0.421  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.336  -3.575  -0.061  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.976  -3.716  -0.387  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.258  -2.596  -0.497  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.593  -1.144   1.461  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.893  -0.324   1.304  1.00  0.00           H  
HETATM   32  H10 UNL     1      -6.465   0.761  -1.086  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.850   1.965  -2.130  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.513   1.110  -1.963  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    8   25
CONECT    8    9   26
CONECT    9   10   10   27
CONECT   10   11   22
CONECT   11   12   12   28
CONECT   12   13   29
CONECT   13   14   21   21
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
END

HMDB0034449
     RDKit          3D
Hydroxyanigorufone
 34 37  0  0  0  0  0  0  0  0999 V2000
   -0.6212    2.1634    0.3431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    1.5272    0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7015    2.2755    0.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5910    3.6493    0.8663 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660    1.6592    0.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636    0.2223    0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2108   -0.3850    0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3349   -1.7447    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2180   -2.5006    0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9895   -1.8806    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8647   -2.6322   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612   -2.0184   -0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5449   -0.6411   -0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8814   -0.0668   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8606   -0.4603    0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1469    0.0072    0.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5114    0.8780   -0.4324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8383    1.3430   -0.5118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5585    1.2744   -1.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2728    0.7988   -1.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751    0.1011    0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309   -0.5124    0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0049    4.2350    0.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7878    2.2229    0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1172    0.1886    0.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3348   -2.1854    0.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3358   -3.5754   -0.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9756   -3.7157   -0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2580   -2.5957   -0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5927   -1.1439    1.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8925   -0.3239    1.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4648    0.7611   -1.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8497    1.9651   -2.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5130    1.1100   -1.9634 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 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
 13 21  2  0
 21 22  1  0
 21  2  1  0
 22  6  2  0
 22 10  1  0
 20 14  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 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

Value	Source
2-Hydroxy-9-(4-hydroxyphenyl)-1H-phenalen-1-one	HMDB
Emenolone	HMDB

Chemical Formula

C₁₉H₁₂O₃

Average Molecular Weight

288.2968

Monoisotopic Molecular Weight

288.07864425

IUPAC Name

2-hydroxy-9-(4-hydroxyphenyl)-1H-phenalen-1-one

Traditional Name

2-hydroxy-9-(4-hydroxyphenyl)phenalen-1-one

CAS Registry Number

56252-02-9

SMILES

OC1=CC=C(C=C1)C1=C2C(=O)C(O)=CC3=CC=CC(C=C1)=C23

InChI Identifier

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

InChI Key

HTELDEYOMOTOBI-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: HMDB0034449)
Cell membrane (HMDB: HMDB0034449)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034449)

Source

Exogenous

Exogenous (HMDB: HMDB0034449)

Food

Food (HMDB: HMDB0034449)

Fruit

Tropical fruit

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

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0034449)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034449)
Phytoalexin (HMDB: HMDB0034449)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	238 - 242 °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	0.0072 g/L	ALOGPS
logP	3.62	ALOGPS
logP	3.73	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.12	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	30.34 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]-	198.026	30932474
DeepCCS	[M+Na]+	173.254	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	13.9304 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.26 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2332.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	388.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	184.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	215.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	402.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	653.8 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	512.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	118.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1216.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	495.8 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	1377.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	405.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	416.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	384.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	193.9 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	48.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxyanigorufone	OC1=CC=C(C=C1)C1=C2C(=O)C(O)=CC3=CC=CC(C=C1)=C23	4346.2	Standard polar	33892256
Hydroxyanigorufone	OC1=CC=C(C=C1)C1=C2C(=O)C(O)=CC3=CC=CC(C=C1)=C23	2739.3	Standard non polar	33892256
Hydroxyanigorufone	OC1=CC=C(C=C1)C1=C2C(=O)C(O)=CC3=CC=CC(C=C1)=C23	3237.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxyanigorufone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=CC=C3C=CC=C4C=C(O)C(=O)C2=C43)C=C1	3132.5	Semi standard non polar	33892256
Hydroxyanigorufone,1TMS,isomer #2	C[Si](C)(C)OC1=CC2=C3C(=C(C4=CC=C(O)C=C4)C=CC3=CC=C2)C1=O	3182.8	Semi standard non polar	33892256
Hydroxyanigorufone,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=C3C(=C(C4=CC=C(O[Si](C)(C)C)C=C4)C=CC3=CC=C2)C1=O	3157.9	Semi standard non polar	33892256
Hydroxyanigorufone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC=C3C=CC=C4C=C(O)C(=O)C2=C43)C=C1	3394.5	Semi standard non polar	33892256
Hydroxyanigorufone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=C(C4=CC=C(O)C=C4)C=CC3=CC=C2)C1=O	3426.8	Semi standard non polar	33892256
Hydroxyanigorufone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=C(C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4)C=CC3=CC=C2)C1=O	3620.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyanigorufone GC-MS (Non-derivatized) - 70eV, Positive	splash10-06si-0090000000-c11b8fe90b80cc465057	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyanigorufone GC-MS (2 TMS) - 70eV, Positive	splash10-00xr-8009600000-beea274403311f7afbaa	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxyanigorufone 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 - Hydroxyanigorufone 10V, Positive-QTOF	splash10-000i-0090000000-418fac8b530b8c6ab582	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyanigorufone 20V, Positive-QTOF	splash10-000i-0190000000-e0d9ecfd2b17558333b0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyanigorufone 40V, Positive-QTOF	splash10-0kna-1290000000-0d52bcc3132f0f2bcb74	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyanigorufone 10V, Negative-QTOF	splash10-000i-0090000000-24ce8ed5137f02c12763	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyanigorufone 20V, Negative-QTOF	splash10-000i-0090000000-a2a574a007f55cef2452	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyanigorufone 40V, Negative-QTOF	splash10-0apu-1090000000-cf88458c5b15d92d2590	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyanigorufone 10V, Positive-QTOF	splash10-000i-0090000000-9b8c528cd946b073787c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyanigorufone 20V, Positive-QTOF	splash10-000i-0090000000-9b8c528cd946b073787c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyanigorufone 40V, Positive-QTOF	splash10-001i-0090000000-c1d5123bb4f59375695f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyanigorufone 10V, Negative-QTOF	splash10-000i-0090000000-ad76c01409fa18536a26	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyanigorufone 20V, Negative-QTOF	splash10-000i-0090000000-ad76c01409fa18536a26	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxyanigorufone 40V, Negative-QTOF	splash10-0540-0090000000-49ce443ca6ba2e165d1e	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012856

KNApSAcK ID

C00037288

Chemspider ID

9646582

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11471752

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1842941

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 Hydroxyanigorufone (HMDB0034449)

MOL for HMDB0034449 (Hydroxyanigorufone)

3D MOL for HMDB0034449 (Hydroxyanigorufone)

3D SDF for HMDB0034449 (Hydroxyanigorufone)

3D-SDF for HMDB0034449 (Hydroxyanigorufone)

PDB for HMDB0034449 (Hydroxyanigorufone)

3D PDB for HMDB0034449 (Hydroxyanigorufone)

SMILES for HMDB0034449 (Hydroxyanigorufone)

INCHI for HMDB0034449 (Hydroxyanigorufone)

Structure for HMDB0034449 (Hydroxyanigorufone)

3D Structure for HMDB0034449 (Hydroxyanigorufone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra