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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:09:01 UTC

Update Date

2022-03-07 02:57:01 UTC

HMDB ID

HMDB0041463

Secondary Accession Numbers

HMDB41463

Metabolite Identification

Common Name

2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one

Description

2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 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. 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one has been detected, but not quantified in, fruits. This could make 2,3-dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one.

Structure

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

HMDB0041463
     RDKit          3D
2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one
 40 43  0  0  0  0  0  0  0  0999 V2000
    6.2047    0.7360    1.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4873    0.7105    0.0182 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1319    0.3372    0.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5249    0.0096    1.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009   -0.3518    1.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293   -0.4012    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0434   -0.8232    0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1180   -2.1031    0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776   -2.6124    1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4961   -1.9052    0.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7631   -2.4040    0.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8947   -1.6958    0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7430   -0.4425   -0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4572    0.0674   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3276   -0.6424    0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0624   -0.1078   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8589    1.2251   -0.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7892    1.2076   -2.0454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0489    2.1348   -0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9893    3.3357   -1.0302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2991    1.4168   -0.7663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1645    1.8808   -1.5213 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0188   -0.0800   -1.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3645    0.2875   -1.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1391   -0.2197    1.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7013    1.5297    1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2458    1.0368    1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1514    0.0553    2.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7926   -0.5962    2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7232   -2.6992    1.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5476   -3.5997    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9033   -3.3923    1.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8987   -2.0661    0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5605    0.1726   -0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0615    1.6733   -0.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2188    1.9424   -2.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063    2.3242    0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9357    3.6232   -1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4819   -0.1122   -1.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8578    0.5483   -1.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  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  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
  6 23  1  0
 23 24  2  0
 24  3  1  0
 16  7  1  0
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  1 27  1  0
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  8 30  1  0
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 17 35  1  0
 18 36  1  0
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 20 38  1  0
 23 39  1  0
 24 40  1  0
M  END

  Mrv0541 05061312412D          

 24 27  0  0  0  0            999 V2000
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    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   -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
    1.4289   -4.1250    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
    2.8579   -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
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
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 19 17  1  0  0  0  0
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 21 18  2  0  0  0  0
 22 19  1  0  0  0  0
 23 20  1  0  0  0  0
 24  1  1  0  0  0  0
 24 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041463

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C=C1)C1=C2C(O)C(O)C(=O)C3=CC=CC(C=C1)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O4/c1-24-13-8-5-11(6-9-13)14-10-7-12-3-2-4-15-16(12)17(14)19(22)20(23)18(15)21/h2-10,19-20,22-23H,1H3

> <INCHI_KEY>
GMMBTTCHJJMJKQ-UHFFFAOYSA-N

> <FORMULA>
C20H16O4

> <MOLECULAR_WEIGHT>
320.3386

> <EXACT_MASS>
320.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.53479285278461

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-dihydroxy-4-(4-methoxyphenyl)-2,3-dihydro-1H-phenalen-1-one

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
2.525524788666667

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.280368371616994

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.156213921264923

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4830920295540695

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
90.47499999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dihydroxy-4-(4-methoxyphenyl)-2,3-dihydrophenalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041463
     RDKit          3D
2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one
 40 43  0  0  0  0  0  0  0  0999 V2000
    6.2047    0.7360    1.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4873    0.7105    0.0182 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1319    0.3372    0.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5249    0.0096    1.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009   -0.3518    1.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293   -0.4012    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0434   -0.8232    0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1180   -2.1031    0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776   -2.6124    1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4961   -1.9052    0.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7631   -2.4040    0.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8947   -1.6958    0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7430   -0.4425   -0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4572    0.0674   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3276   -0.6424    0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0624   -0.1078   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8589    1.2251   -0.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7892    1.2076   -2.0454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0489    2.1348   -0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9893    3.3357   -1.0302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2991    1.4168   -0.7663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1645    1.8808   -1.5213 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0188   -0.0800   -1.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3645    0.2875   -1.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1391   -0.2197    1.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7013    1.5297    1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2458    1.0368    1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1514    0.0553    2.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7926   -0.5962    2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7232   -2.6992    1.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5476   -3.5997    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9033   -3.3923    1.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8987   -2.0661    0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5605    0.1726   -0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0615    1.6733   -0.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2188    1.9424   -2.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063    2.3242    0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9357    3.6232   -1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4819   -0.1122   -1.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8578    0.5483   -1.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  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  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
  6 23  1  0
 23 24  2  0
 24  3  1  0
 16  7  1  0
 15 10  1  0
 21 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 23 39  1  0
 24 40  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 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
CONECT    1   24                                                            
CONECT    2    3    4                                                       
CONECT    3    2   12                                                       
CONECT    4    2   15                                                       
CONECT    5    8   11                                                       
CONECT    6    9   11                                                       
CONECT    7   10   12                                                       
CONECT    8    5   13                                                       
CONECT    9    6   13                                                       
CONECT   10    7   14                                                       
CONECT   11    5    6   14                                                  
CONECT   12    3    7   16                                                  
CONECT   13    8    9   24                                                  
CONECT   14   10   11   17                                                  
CONECT   15    4   16   18                                                  
CONECT   16   12   15   17                                                  
CONECT   17   14   16   19                                                  
CONECT   18   15   20   21                                                  
CONECT   19   17   20   22                                                  
CONECT   20   18   19   23                                                  
CONECT   21   18                                                            
CONECT   22   19                                                            
CONECT   23   20                                                            
CONECT   24    1   13                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0041463
HETATM    1  C1  UNL     1       6.205   0.736   1.237  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.487   0.711   0.018  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.132   0.337   0.081  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.525   0.010   1.277  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.201  -0.352   1.318  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.429  -0.401   0.170  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.043  -0.823   0.313  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.118  -2.103   0.882  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.378  -2.612   1.061  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.496  -1.905   0.701  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.763  -2.404   0.883  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.895  -1.696   0.530  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.743  -0.442  -0.024  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.457   0.067  -0.210  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.328  -0.642   0.141  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.062  -0.108  -0.051  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.859   1.225  -0.652  1.00  0.00           C  
HETATM   18  O2  UNL     1      -0.789   1.208  -2.045  1.00  0.00           O  
HETATM   19  C17 UNL     1      -2.049   2.135  -0.348  1.00  0.00           C  
HETATM   20  O3  UNL     1      -1.989   3.336  -1.030  1.00  0.00           O  
HETATM   21  C18 UNL     1      -3.299   1.417  -0.766  1.00  0.00           C  
HETATM   22  O4  UNL     1      -4.165   1.881  -1.521  1.00  0.00           O  
HETATM   23  C19 UNL     1       2.019  -0.080  -1.019  1.00  0.00           C  
HETATM   24  C20 UNL     1       3.364   0.288  -1.060  1.00  0.00           C  
HETATM   25  H1  UNL     1       6.139  -0.220   1.795  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.701   1.530   1.863  1.00  0.00           H  
HETATM   27  H3  UNL     1       7.246   1.037   1.094  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.151   0.055   2.169  1.00  0.00           H  
HETATM   29  H5  UNL     1       1.793  -0.596   2.297  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.723  -2.699   1.183  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.548  -3.600   1.497  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.903  -3.392   1.319  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.899  -2.066   0.663  1.00  0.00           H  
HETATM   34  H10 UNL     1      -5.561   0.173  -0.325  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.062   1.673  -0.267  1.00  0.00           H  
HETATM   36  H12 UNL     1      -0.219   1.942  -2.335  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.106   2.324   0.738  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.936   3.623  -1.181  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.482  -0.112  -1.973  1.00  0.00           H  
HETATM   40  H16 UNL     1       3.858   0.548  -1.992  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   24
CONECT    4    5   28
CONECT    5    6    6   29
CONECT    6    7   23
CONECT    7    8    8   16
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11   15
CONECT   11   12   12   32
CONECT   12   13   33
CONECT   13   14   14   34
CONECT   14   15   21
CONECT   15   16   16
CONECT   16   17
CONECT   17   18   19   35
CONECT   18   36
CONECT   19   20   21   37
CONECT   20   38
CONECT   21   22   22
CONECT   23   24   24   39
CONECT   24   40
END

HMDB0041463
     RDKit          3D
2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one
 40 43  0  0  0  0  0  0  0  0999 V2000
    6.2047    0.7360    1.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4873    0.7105    0.0182 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1319    0.3372    0.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5249    0.0096    1.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009   -0.3518    1.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293   -0.4012    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0434   -0.8232    0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1180   -2.1031    0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776   -2.6124    1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4961   -1.9052    0.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7631   -2.4040    0.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8947   -1.6958    0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7430   -0.4425   -0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4572    0.0674   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3276   -0.6424    0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0624   -0.1078   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8589    1.2251   -0.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7892    1.2076   -2.0454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0489    2.1348   -0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9893    3.3357   -1.0302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2991    1.4168   -0.7663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1645    1.8808   -1.5213 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0188   -0.0800   -1.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3645    0.2875   -1.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1391   -0.2197    1.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7013    1.5297    1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2458    1.0368    1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1514    0.0553    2.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7926   -0.5962    2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7232   -2.6992    1.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5476   -3.5997    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9033   -3.3923    1.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8987   -2.0661    0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5605    0.1726   -0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0615    1.6733   -0.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2188    1.9424   -2.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063    2.3242    0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9357    3.6232   -1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4819   -0.1122   -1.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8578    0.5483   -1.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  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  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
  6 23  1  0
 23 24  2  0
 24  3  1  0
 16  7  1  0
 15 10  1  0
 21 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 23 39  1  0
 24 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₁₆O₄

Average Molecular Weight

320.3386

Monoisotopic Molecular Weight

320.104859

IUPAC Name

2,3-dihydroxy-4-(4-methoxyphenyl)-2,3-dihydro-1H-phenalen-1-one

Traditional Name

2,3-dihydroxy-4-(4-methoxyphenyl)-2,3-dihydrophenalen-1-one

CAS Registry Number

159853-37-9

SMILES

COC1=CC=C(C=C1)C1=C2C(O)C(O)C(=O)C3=CC=CC(C=C1)=C23

InChI Identifier

InChI=1S/C20H16O4/c1-24-13-8-5-11(6-9-13)14-10-7-12-3-2-4-15-16(12)17(14)19(22)20(23)18(15)21/h2-10,19-20,22-23H,1H3

InChI Key

GMMBTTCHJJMJKQ-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
Phenalane
Anisole
Phenoxy compound
Phenol ether
Aryl ketone
Aryl alkyl ketone
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Ketone
Secondary alcohol
1,2-diol
Ether
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041463)
Cell membrane (HMDB: HMDB0041463)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041463)

Source

Exogenous

Exogenous (HMDB: HMDB0041463)

Food

Food (HMDB: HMDB0041463)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0041463)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041463)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	175 - 177 °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	0.028 g/L	ALOGPS
logP	2.81	ALOGPS
logP	2.53	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	12.16	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	90.48 m³·mol⁻¹	ChemAxon
Polarizability	33.53 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]+	176.667	31661259
DarkChem	[M-H]-	176.655	31661259
DeepCCS	[M-2H]-	208.677	30932474
DeepCCS	[M+Na]+	183.904	30932474
AllCCS	[M+H]+	177.6	32859911
AllCCS	[M+H-H2O]+	174.2	32859911
AllCCS	[M+NH4]+	180.7	32859911
AllCCS	[M+Na]+	181.6	32859911
AllCCS	[M-H]-	180.2	32859911
AllCCS	[M+Na-2H]-	179.5	32859911
AllCCS	[M+HCOO]-	178.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one	COC1=CC=C(C=C1)C1=C2C(O)C(O)C(=O)C3=CC=CC(C=C1)=C23	4522.9	Standard polar	33892256
2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one	COC1=CC=C(C=C1)C1=C2C(O)C(O)C(=O)C3=CC=CC(C=C1)=C23	3053.4	Standard non polar	33892256
2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one	COC1=CC=C(C=C1)C1=C2C(O)C(O)C(=O)C3=CC=CC(C=C1)=C23	3165.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one,1TMS,isomer #1	COC1=CC=C(C2=CC=C3C=CC=C4C(=O)C(O)C(O[Si](C)(C)C)C2=C43)C=C1	3328.7	Semi standard non polar	33892256
2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one,1TMS,isomer #2	COC1=CC=C(C2=CC=C3C=CC=C4C(=O)C(O[Si](C)(C)C)C(O)C2=C43)C=C1	3306.5	Semi standard non polar	33892256
2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one,2TMS,isomer #1	COC1=CC=C(C2=CC=C3C=CC=C4C(=O)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2=C43)C=C1	3213.0	Semi standard non polar	33892256
2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one,1TBDMS,isomer #1	COC1=CC=C(C2=CC=C3C=CC=C4C(=O)C(O)C(O[Si](C)(C)C(C)(C)C)C2=C43)C=C1	3557.9	Semi standard non polar	33892256
2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one,1TBDMS,isomer #2	COC1=CC=C(C2=CC=C3C=CC=C4C(=O)C(O[Si](C)(C)C(C)(C)C)C(O)C2=C43)C=C1	3538.7	Semi standard non polar	33892256
2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one,2TBDMS,isomer #1	COC1=CC=C(C2=CC=C3C=CC=C4C(=O)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2=C43)C=C1	3655.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-0091000000-02f61bb1f090cdeabea8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one GC-MS (2 TMS) - 70eV, Positive	splash10-00ba-9007600000-a1de6ec19cc942808b3e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 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 - 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 10V, Positive-QTOF	splash10-00di-0009000000-b1f7643f376102856552	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 20V, Positive-QTOF	splash10-0fkc-0196000000-ea799ecb53c6731ba58d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 40V, Positive-QTOF	splash10-053r-0290000000-ffa7b5228edf6df82df7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 10V, Negative-QTOF	splash10-014i-0009000000-a667c9f5ac25df2c8720	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 20V, Negative-QTOF	splash10-014i-0019000000-090ee94726aa4517f4cd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 40V, Negative-QTOF	splash10-0h0r-0091000000-f170c5ceb5d177738f71	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 10V, Negative-QTOF	splash10-014i-0019000000-a1aea4ed35ba102950b7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 20V, Negative-QTOF	splash10-014i-0098000000-45004691d7b710f36f71	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 40V, Negative-QTOF	splash10-007t-0090000000-48b15c318604fca9bcd4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 10V, Positive-QTOF	splash10-00di-0009000000-8e34f689cbc3cfca8822	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 20V, Positive-QTOF	splash10-00di-0069000000-efa19ef50b09b314fa8a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 40V, Positive-QTOF	splash10-001r-0090000000-9a5f6eabe88107016e42	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021420

KNApSAcK ID

C00054884

Chemspider ID

8556766

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10381323

PDB ID

Not Available

ChEBI ID

142247

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 2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one (HMDB0041463)

MOL for HMDB0041463 (2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

3D MOL for HMDB0041463 (2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

3D SDF for HMDB0041463 (2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

3D-SDF for HMDB0041463 (2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

PDB for HMDB0041463 (2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

3D PDB for HMDB0041463 (2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

SMILES for HMDB0041463 (2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

INCHI for HMDB0041463 (2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

Structure for HMDB0041463 (2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

3D Structure for HMDB0041463 (2,3-Dihydro-2,3-dihydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra