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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:20:25 UTC

Update Date

2022-03-07 02:55:11 UTC

HMDB ID

HMDB0037096

Secondary Accession Numbers

HMDB37096

Metabolite Identification

Common Name

Pilosin

Description

Pilosin belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Pilosin has been detected, but not quantified in, herbs and spices. This could make pilosin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Pilosin.

Structure

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

HMDB0037096
     RDKit          3D
Pilosin
 38 40  0  0  0  0  0  0  0  0999 V2000
   -7.1620   -0.2222   -0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1495    0.5823   -0.8582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8113    0.3185   -0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8343    1.1154   -1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4831    0.8833   -0.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0951   -0.1688   -0.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6547   -0.4015    0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1975   -1.4146    0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1644   -1.5820    1.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5971   -2.5162    1.7986 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0516   -0.7185    0.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4222   -0.8178    0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0017   -1.7765    1.3415 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2846    0.0875   -0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6680   -0.0364    0.1000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2416    0.6774    1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7216    1.0760   -0.8191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5799    1.9879   -1.4703 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3633    1.1880   -0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7676    2.1626   -1.7190 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5140    0.2799   -0.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211    0.3795   -0.4402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0791   -0.9465    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4224   -0.7301    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1286    0.2867   -0.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0537   -0.2915    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1520   -1.2480   -0.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1365    1.9473   -1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7147    1.5228   -1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8441   -2.1025    1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6526   -2.4908    1.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3235    0.8570    1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7491    1.6657    1.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0079    0.0746    2.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2633    2.7317   -2.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3081    2.8433   -2.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006   -1.7716    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1842   -1.3759    0.6571 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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
  6 23  1  0
 23 24  2  0
 24  3  1  0
 22  7  1  0
 21 11  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
 13 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 20 36  1  0
 23 37  1  0
 24 38  1  0
M  END

  Mrv0541 05061309342D          

 24 26  0  0  0  0            999 V2000
   -5.0013    2.0625    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    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    0.0000    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    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
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 15 14  2  0  0  0  0
 16 12  2  0  0  0  0
 16 14  1  0  0  0  0
 17 13  2  0  0  0  0
 17 15  1  0  0  0  0
 18 10  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22  1  1  0  0  0  0
 22  9  1  0  0  0  0
 23  2  1  0  0  0  0
 23 17  1  0  0  0  0
 24 11  1  0  0  0  0
 24 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037096

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(O)=C(O)C(OC)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O7/c1-22-9-5-3-8(4-6-9)11-7-10(18)12-13(19)17(23-2)15(21)14(20)16(12)24-11/h3-7,19-21H,1-2H3

> <INCHI_KEY>
ASAOSMVQLGTAQO-UHFFFAOYSA-N

> <FORMULA>
C17H14O7

> <MOLECULAR_WEIGHT>
330.2889

> <EXACT_MASS>
330.073952802

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
32.79347810963612

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7,8-trihydroxy-6-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
2.391346602333333

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.398963110987744

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.482432197100065

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2372153972999635

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
85.8403

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7,8-trihydroxy-6-methoxy-2-(4-methoxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037096
     RDKit          3D
Pilosin
 38 40  0  0  0  0  0  0  0  0999 V2000
   -7.1620   -0.2222   -0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1495    0.5823   -0.8582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8113    0.3185   -0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8343    1.1154   -1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4831    0.8833   -0.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0951   -0.1688   -0.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6547   -0.4015    0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1975   -1.4146    0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1644   -1.5820    1.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5971   -2.5162    1.7986 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0516   -0.7185    0.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4222   -0.8178    0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0017   -1.7765    1.3415 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2846    0.0875   -0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6680   -0.0364    0.1000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2416    0.6774    1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7216    1.0760   -0.8191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5799    1.9879   -1.4703 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3633    1.1880   -0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7676    2.1626   -1.7190 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5140    0.2799   -0.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211    0.3795   -0.4402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0791   -0.9465    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4224   -0.7301    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1286    0.2867   -0.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0537   -0.2915    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1520   -1.2480   -0.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1365    1.9473   -1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7147    1.5228   -1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8441   -2.1025    1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6526   -2.4908    1.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3235    0.8570    1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7491    1.6657    1.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0079    0.0746    2.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2633    2.7317   -2.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3081    2.8433   -2.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006   -1.7716    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1842   -1.3759    0.6571 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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
  6 23  1  0
 23 24  2  0
 24  3  1  0
 22  7  1  0
 21 11  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
 13 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 20 36  1  0
 23 37  1  0
 24 38  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      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   3.850   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      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   23                                                            
CONECT    3    5    8                                                       
CONECT    4    6    8                                                       
CONECT    5    3    9                                                       
CONECT    6    4    9                                                       
CONECT    7   10   11                                                       
CONECT    8    3    4   11                                                  
CONECT    9    5    6   22                                                  
CONECT   10    7   12   18                                                  
CONECT   11    7    8   24                                                  
CONECT   12   10   13   16                                                  
CONECT   13   12   17   19                                                  
CONECT   14   15   16   20                                                  
CONECT   15   14   17   21                                                  
CONECT   16   12   14   24                                                  
CONECT   17   13   15   23                                                  
CONECT   18   10                                                            
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22    1    9                                                       
CONECT   23    2   17                                                       
CONECT   24   11   16                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0037096
HETATM    1  C1  UNL     1      -7.162  -0.222  -0.294  1.00  0.00           C  
HETATM    2  O1  UNL     1      -6.150   0.582  -0.858  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.811   0.318  -0.604  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.834   1.115  -1.163  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.483   0.883  -0.932  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.095  -0.169  -0.124  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.655  -0.401   0.112  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.198  -1.415   0.894  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.164  -1.582   1.077  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.597  -2.516   1.799  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.052  -0.718   0.463  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.422  -0.818   0.595  1.00  0.00           C  
HETATM   13  O3  UNL     1       4.002  -1.776   1.341  1.00  0.00           O  
HETATM   14  C11 UNL     1       4.285   0.087  -0.051  1.00  0.00           C  
HETATM   15  O4  UNL     1       5.668  -0.036   0.100  1.00  0.00           O  
HETATM   16  C12 UNL     1       6.242   0.677   1.188  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.722   1.076  -0.819  1.00  0.00           C  
HETATM   18  O5  UNL     1       4.580   1.988  -1.470  1.00  0.00           O  
HETATM   19  C14 UNL     1       2.363   1.188  -0.960  1.00  0.00           C  
HETATM   20  O6  UNL     1       1.768   2.163  -1.719  1.00  0.00           O  
HETATM   21  C15 UNL     1       1.514   0.280  -0.311  1.00  0.00           C  
HETATM   22  O7  UNL     1       0.221   0.380  -0.440  1.00  0.00           O  
HETATM   23  C16 UNL     1      -3.079  -0.946   0.421  1.00  0.00           C  
HETATM   24  C17 UNL     1      -4.422  -0.730   0.202  1.00  0.00           C  
HETATM   25  H1  UNL     1      -8.129   0.287  -0.473  1.00  0.00           H  
HETATM   26  H2  UNL     1      -7.054  -0.292   0.820  1.00  0.00           H  
HETATM   27  H3  UNL     1      -7.152  -1.248  -0.732  1.00  0.00           H  
HETATM   28  H4  UNL     1      -4.137   1.947  -1.803  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.715   1.523  -1.382  1.00  0.00           H  
HETATM   30  H6  UNL     1      -0.844  -2.103   1.385  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.653  -2.491   1.865  1.00  0.00           H  
HETATM   32  H8  UNL     1       7.323   0.857   1.055  1.00  0.00           H  
HETATM   33  H9  UNL     1       5.749   1.666   1.262  1.00  0.00           H  
HETATM   34  H10 UNL     1       6.008   0.075   2.098  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.263   2.732  -2.044  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.308   2.843  -2.209  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.801  -1.772   1.054  1.00  0.00           H  
HETATM   38  H14 UNL     1      -5.184  -1.376   0.657  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   22
CONECT    8    9   30
CONECT    9   10   10   11
CONECT   11   12   12   21
CONECT   12   13   14
CONECT   13   31
CONECT   14   15   17   17
CONECT   15   16
CONECT   16   32   33   34
CONECT   17   18   19
CONECT   18   35
CONECT   19   20   21   21
CONECT   20   36
CONECT   21   22
CONECT   23   24   24   37
CONECT   24   38
END

HMDB0037096
     RDKit          3D
Pilosin
 38 40  0  0  0  0  0  0  0  0999 V2000
   -7.1620   -0.2222   -0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1495    0.5823   -0.8582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8113    0.3185   -0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8343    1.1154   -1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4831    0.8833   -0.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0951   -0.1688   -0.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6547   -0.4015    0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1975   -1.4146    0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1644   -1.5820    1.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5971   -2.5162    1.7986 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0516   -0.7185    0.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4222   -0.8178    0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0017   -1.7765    1.3415 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2846    0.0875   -0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6680   -0.0364    0.1000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2416    0.6774    1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7216    1.0760   -0.8191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5799    1.9879   -1.4703 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3633    1.1880   -0.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7676    2.1626   -1.7190 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5140    0.2799   -0.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211    0.3795   -0.4402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0791   -0.9465    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4224   -0.7301    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1286    0.2867   -0.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0537   -0.2915    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1520   -1.2480   -0.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1365    1.9473   -1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7147    1.5228   -1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8441   -2.1025    1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6526   -2.4908    1.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3235    0.8570    1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7491    1.6657    1.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0079    0.0746    2.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2633    2.7317   -2.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3081    2.8433   -2.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006   -1.7716    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1842   -1.3759    0.6571 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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
  6 23  1  0
 23 24  2  0
 24  3  1  0
 22  7  1  0
 21 11  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
 13 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 20 36  1  0
 23 37  1  0
 24 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,7,8-Trihydroxy-4',6-dimethoxyflavone	HMDB

Chemical Formula

C₁₇H₁₄O₇

Average Molecular Weight

330.2889

Monoisotopic Molecular Weight

330.073952802

IUPAC Name

5,7,8-trihydroxy-6-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

5,7,8-trihydroxy-6-methoxy-2-(4-methoxyphenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(O)=C(O)C(OC)=C2O

InChI Identifier

InChI=1S/C17H14O7/c1-22-9-5-3-8(4-6-9)11-7-10(18)12-13(19)17(23-2)15(21)14(20)16(12)24-11/h3-7,19-21H,1-2H3

InChI Key

ASAOSMVQLGTAQO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

6-O-methylated flavonoids

Alternative Parents

Substituents

4p-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
5-hydroxyflavonoid
Flavone
7-hydroxyflavonoid
Hydroxyflavonoid
8-hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
Pyranone
Alkyl aryl ether
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0037096)
Cell membrane (HMDB: HMDB0037096)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037096)

Source

Exogenous

Exogenous (HMDB: HMDB0037096)

Food

Food (HMDB: HMDB0037096)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0037096)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037096)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.081 g/L	ALOGPS
logP	2.99	ALOGPS
logP	2.39	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.48	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.84 m³·mol⁻¹	ChemAxon
Polarizability	32.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	177.917	31661259
DarkChem	[M-H]-	178.749	31661259
DeepCCS	[M+H]+	174.903	30932474
DeepCCS	[M-H]-	172.545	30932474
DeepCCS	[M-2H]-	206.629	30932474
DeepCCS	[M+Na]+	182.115	30932474
AllCCS	[M+H]+	176.3	32859911
AllCCS	[M+H-H2O]+	172.9	32859911
AllCCS	[M+NH4]+	179.5	32859911
AllCCS	[M+Na]+	180.4	32859911
AllCCS	[M-H]-	176.4	32859911
AllCCS	[M+Na-2H]-	175.9	32859911
AllCCS	[M+HCOO]-	175.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pilosin	COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(O)=C(O)C(OC)=C2O	5060.7	Standard polar	33892256
Pilosin	COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(O)=C(O)C(OC)=C2O	3294.1	Standard non polar	33892256
Pilosin	COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(O)=C(O)C(OC)=C2O	3176.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pilosin,1TMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O)C(OC)=C(O)C(O[Si](C)(C)C)=C3O2)C=C1	3349.8	Semi standard non polar	33892256
Pilosin,1TMS,isomer #2	COC1=CC=C(C2=CC(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C)C(O)=C3O2)C=C1	3339.0	Semi standard non polar	33892256
Pilosin,1TMS,isomer #3	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O)C(O)=C3O2)C=C1	3328.1	Semi standard non polar	33892256
Pilosin,2TMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O)C(O[Si](C)(C)C)=C3O2)C=C1	3297.2	Semi standard non polar	33892256
Pilosin,2TMS,isomer #2	COC1=CC=C(C2=CC(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3O2)C=C1	3304.2	Semi standard non polar	33892256
Pilosin,2TMS,isomer #3	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O[Si](C)(C)C)C(O)=C3O2)C=C1	3292.9	Semi standard non polar	33892256
Pilosin,3TMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C(OC)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3O2)C=C1	3210.7	Semi standard non polar	33892256
Pilosin,1TBDMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O)C(OC)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3O2)C=C1	3553.6	Semi standard non polar	33892256
Pilosin,1TBDMS,isomer #2	COC1=CC=C(C2=CC(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C(C)(C)C)C(O)=C3O2)C=C1	3539.3	Semi standard non polar	33892256
Pilosin,1TBDMS,isomer #3	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O)C(O)=C3O2)C=C1	3565.2	Semi standard non polar	33892256
Pilosin,2TBDMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3O2)C=C1	3747.0	Semi standard non polar	33892256
Pilosin,2TBDMS,isomer #2	COC1=CC=C(C2=CC(=O)C3=C(O)C(OC)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3O2)C=C1	3740.9	Semi standard non polar	33892256
Pilosin,2TBDMS,isomer #3	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O[Si](C)(C)C(C)(C)C)C(O)=C3O2)C=C1	3729.7	Semi standard non polar	33892256
Pilosin,3TBDMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C(OC)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3O2)C=C1	3861.7	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 - Pilosin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uyi-0549000000-e3ad4b86eabdeaa61975	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pilosin GC-MS (3 TMS) - 70eV, Positive	splash10-0089-2405970000-4baea018b12e29582afc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pilosin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pilosin 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 - Pilosin 10V, Positive-QTOF	splash10-001i-0009000000-e41b9fa02607ac4e3b2b	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilosin 20V, Positive-QTOF	splash10-001i-0039000000-815c31962d9f2684b3ac	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilosin 40V, Positive-QTOF	splash10-00xr-1791000000-5a246299149929a2871a	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilosin 10V, Negative-QTOF	splash10-004i-0009000000-23f2329677e0bf67bcb7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilosin 20V, Negative-QTOF	splash10-004i-0029000000-0af978d570f36526c18c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilosin 40V, Negative-QTOF	splash10-001i-2592000000-2d7eade23f212b123155	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilosin 10V, Positive-QTOF	splash10-001i-0009000000-871818988e70af3e8641	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilosin 20V, Positive-QTOF	splash10-001i-0009000000-cf8f22452f527423b387	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilosin 40V, Positive-QTOF	splash10-000i-0193000000-87d82fe44ad04c8fa5ab	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilosin 10V, Negative-QTOF	splash10-004i-0009000000-c990e475bc0cf06f28db	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilosin 20V, Negative-QTOF	splash10-03di-0009000000-d3e0fe093b1e3fddfd2f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pilosin 40V, Negative-QTOF	splash10-004i-0529000000-cb2d885659e681e97e9f	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

FDB016086

KNApSAcK ID

C00002356

Chemspider ID

29338177

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12085264

PDB ID

Not Available

ChEBI ID

174456

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 Pilosin (HMDB0037096)

MOL for HMDB0037096 (Pilosin)

3D MOL for HMDB0037096 (Pilosin)

3D SDF for HMDB0037096 (Pilosin)

3D-SDF for HMDB0037096 (Pilosin)

PDB for HMDB0037096 (Pilosin)

3D PDB for HMDB0037096 (Pilosin)

SMILES for HMDB0037096 (Pilosin)

INCHI for HMDB0037096 (Pilosin)

Structure for HMDB0037096 (Pilosin)

3D Structure for HMDB0037096 (Pilosin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra