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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:55:51 UTC

Update Date

2021-09-26 23:13:24 UTC

HMDB ID

HMDB0257193

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Rhamnocitrin

Description

Rhamnocitrin belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, rhamnocitrin is considered to be a flavonoid. Rhamnocitrin has been detected, but not quantified in, cloves (Syzygium aromaticum) and lemon balms (Melissa officinalis). This could make rhamnocitrin a potential biomarker for the consumption of these foods. Rhamnocitrin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Rhamnocitrin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Rhamnocitrin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Rhamnocitrin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0257193
     RDKit          3D
Rhamnocitrin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.6525   -1.8232    0.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2622   -2.0254    0.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3769   -0.9772    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525    0.2767   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9039    1.2963   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3826    2.5267   -0.5340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5498    1.0432   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6023    2.0186   -0.4261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9141    3.1891   -0.6693 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7472    1.6358   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6388    2.6574   -0.5566 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1371    0.3618   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5354   -0.0490    0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8108   -1.4000    0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0888   -1.8755    0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1502   -1.0345    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4415   -1.5269    0.3160 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9451    0.2946   -0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6239    0.7549   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1796   -0.5268    0.1028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0948   -0.2499    0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0387   -1.2542    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0494   -1.2939    1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1403   -2.8279    0.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9711   -1.2557   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9071    0.4772   -0.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0473    3.4000   -0.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3946    3.6094   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9480   -2.0689    0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2809   -2.9336    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2275   -0.9310    0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7768    0.9689   -0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5180    1.8002   -0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6986   -2.2569    0.4601 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 12 20  1  0
 20 21  1  0
 21 22  2  0
 22  3  1  0
 21  7  1  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 11 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 22 34  1  0
M  END


  Mrv0541 02241221172D          

 22 24  0  0  0  0            999 V2000
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    1.4289    0.0000    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
    2.8579    0.8250    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 18 21  1  0  0  0  0
  5 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257193

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=C2C(=O)C(O)=C(OC2=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-21-10-6-11(18)13-12(7-10)22-16(15(20)14(13)19)8-2-4-9(17)5-3-8/h2-7,17-18,20H,1H3

> <INCHI_KEY>
MQSZRBPYXNEFHF-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.69954373836079

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
2.6057588416666664

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.753755347396933

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.05331932150105

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8876054530339195

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
79.3636

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rhamnocitrin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257193
     RDKit          3D
Rhamnocitrin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.6525   -1.8232    0.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2622   -2.0254    0.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3769   -0.9772    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525    0.2767   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9039    1.2963   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3826    2.5267   -0.5340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5498    1.0432   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6023    2.0186   -0.4261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9141    3.1891   -0.6693 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7472    1.6358   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6388    2.6574   -0.5566 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1371    0.3618   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5354   -0.0490    0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8108   -1.4000    0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0888   -1.8755    0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1502   -1.0345    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4415   -1.5269    0.3160 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9451    0.2946   -0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6239    0.7549   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1796   -0.5268    0.1028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0948   -0.2499    0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0387   -1.2542    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0494   -1.2939    1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1403   -2.8279    0.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9711   -1.2557   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9071    0.4772   -0.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0473    3.4000   -0.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3946    3.6094   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9480   -2.0689    0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2809   -2.9336    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2275   -0.9310    0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7768    0.9689   -0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5180    1.8002   -0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6986   -2.2569    0.4601 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 12 20  1  0
 20 21  1  0
 21 22  2  0
 22  3  1  0
 21  7  1  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 11 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 22 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   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  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12                                                            
CONECT   14   11                                                            
CONECT   15   10   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   18                                                            
CONECT   22    5                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0257193
HETATM    1  C1  UNL     1      -5.653  -1.823   0.367  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.262  -2.025   0.410  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.377  -0.977   0.193  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.852   0.277  -0.068  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.904   1.296  -0.278  1.00  0.00           C  
HETATM    6  O2  UNL     1      -3.383   2.527  -0.534  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.550   1.043  -0.225  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.602   2.019  -0.426  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.914   3.189  -0.669  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.747   1.636  -0.345  1.00  0.00           C  
HETATM   11  O4  UNL     1       1.639   2.657  -0.557  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.137   0.362  -0.081  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.535  -0.049   0.006  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.811  -1.400   0.286  1.00  0.00           C  
HETATM   15  C11 UNL     1       4.089  -1.876   0.386  1.00  0.00           C  
HETATM   16  C12 UNL     1       5.150  -1.034   0.213  1.00  0.00           C  
HETATM   17  O5  UNL     1       6.442  -1.527   0.316  1.00  0.00           O  
HETATM   18  C13 UNL     1       4.945   0.295  -0.063  1.00  0.00           C  
HETATM   19  C14 UNL     1       3.624   0.755  -0.160  1.00  0.00           C  
HETATM   20  O6  UNL     1       0.180  -0.527   0.103  1.00  0.00           O  
HETATM   21  C15 UNL     1      -1.095  -0.250   0.044  1.00  0.00           C  
HETATM   22  C16 UNL     1      -2.039  -1.254   0.252  1.00  0.00           C  
HETATM   23  H1  UNL     1      -6.049  -1.294   1.247  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.140  -2.828   0.317  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.971  -1.256  -0.538  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.907   0.477  -0.110  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.047   3.400  -0.715  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.395   3.609  -0.754  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.948  -2.069   0.424  1.00  0.00           H  
HETATM   30  H8  UNL     1       4.281  -2.934   0.606  1.00  0.00           H  
HETATM   31  H9  UNL     1       7.227  -0.931   0.193  1.00  0.00           H  
HETATM   32  H10 UNL     1       5.777   0.969  -0.202  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.518   1.800  -0.377  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.699  -2.257   0.460  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   26
CONECT    5    6    7    7
CONECT    6   27
CONECT    7    8   21
CONECT    8    9    9   10
CONECT   10   11   12   12
CONECT   11   28
CONECT   12   13   20
CONECT   13   14   14   19
CONECT   14   15   29
CONECT   15   16   16   30
CONECT   16   17   18
CONECT   17   31
CONECT   18   19   19   32
CONECT   19   33
CONECT   20   21
CONECT   21   22   22
CONECT   22   34
END

HMDB0257193
     RDKit          3D
Rhamnocitrin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.6525   -1.8232    0.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2622   -2.0254    0.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3769   -0.9772    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525    0.2767   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9039    1.2963   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3826    2.5267   -0.5340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5498    1.0432   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6023    2.0186   -0.4261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9141    3.1891   -0.6693 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7472    1.6358   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6388    2.6574   -0.5566 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1371    0.3618   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5354   -0.0490    0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8108   -1.4000    0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0888   -1.8755    0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1502   -1.0345    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4415   -1.5269    0.3160 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9451    0.2946   -0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6239    0.7549   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1796   -0.5268    0.1028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0948   -0.2499    0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0387   -1.2542    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0494   -1.2939    1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1403   -2.8279    0.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9711   -1.2557   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9071    0.4772   -0.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0473    3.4000   -0.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3946    3.6094   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9480   -2.0689    0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2809   -2.9336    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2275   -0.9310    0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7768    0.9689   -0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5180    1.8002   -0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6986   -2.2569    0.4601 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 12 20  1  0
 20 21  1  0
 21 22  2  0
 22  3  1  0
 21  7  1  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 11 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4',5-Trihydroxy-7-methoxyflavone	ChEBI
7-Methylkaempferol	ChEBI
Kaempferol-7-methyl ether	MeSH

Chemical Formula

C₁₆H₁₂O₆

Average Molecular Weight

300.2629

Monoisotopic Molecular Weight

300.063388116

IUPAC Name

3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one

Traditional Name

rhamnocitrin

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C(O)=C(OC2=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H12O6/c1-21-10-6-11(18)13-12(7-10)22-16(15(20)14(13)19)8-2-4-9(17)5-3-8/h2-7,17-18,20H,1H3

InChI Key

MQSZRBPYXNEFHF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

7-methoxyflavonoid-skeleton
3-hydroxyflavone
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavone (CHEBI:80897 )
trihydroxyflavone (CHEBI:80897 )
flavonols (CHEBI:80897 )
Flavones and Flavonols (C17059 )
Flavones and Flavonols (LMPK12112589 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cloves (FooDB: FOOD00179)

Herb

Lemon balm (FooDB: FOOD00108)

Not Available

EC 1.1.1.21 (aldehyde reductase) inhibitor (HMDB: HMDB0257193)

Industrial application

Agriculture

Pesticide

Insecticide

pesticide (HMDB: HMDB0257193)

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
logP	2.34	ALOGPS
logP	2.61	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.05	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.36 m³·mol⁻¹	ChemAxon
Polarizability	29.7 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
DeepCCS	[M+H]+	172.555	30932474
DeepCCS	[M-H]-	170.197	30932474
DeepCCS	[M-2H]-	204.279	30932474
DeepCCS	[M+Na]+	179.506	30932474
AllCCS	[M+H]+	168.5	32859911
AllCCS	[M+H-H2O]+	164.8	32859911
AllCCS	[M+NH4]+	171.9	32859911
AllCCS	[M+Na]+	172.9	32859911
AllCCS	[M-H]-	168.6	32859911
AllCCS	[M+Na-2H]-	167.9	32859911
AllCCS	[M+HCOO]-	167.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rhamnocitrin	COC1=CC(O)=C2C(=O)C(O)=C(OC2=C1)C1=CC=C(O)C=C1	4586.8	Standard polar	33892256
Rhamnocitrin	COC1=CC(O)=C2C(=O)C(O)=C(OC2=C1)C1=CC=C(O)C=C1	2995.7	Standard non polar	33892256
Rhamnocitrin	COC1=CC(O)=C2C(=O)C(O)=C(OC2=C1)C1=CC=C(O)C=C1	3069.1	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 - Rhamnocitrin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0790000000-19a24af81092fdb06258	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnocitrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnocitrin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnocitrin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnocitrin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnocitrin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnocitrin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnocitrin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnocitrin GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnocitrin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnocitrin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnocitrin GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnocitrin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnocitrin GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnocitrin GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rhamnocitrin GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	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 - Rhamnocitrin 10V, Positive-QTOF	splash10-0udi-0029000000-768cdf795b8d46e4211b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnocitrin 20V, Positive-QTOF	splash10-0udi-0069000000-c73cfb69e78d92d7288f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnocitrin 40V, Positive-QTOF	splash10-0v6r-3590000000-6a4dcd114c7614798cd3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnocitrin 10V, Negative-QTOF	splash10-0002-0090000000-d961904801166b3dbf71	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnocitrin 20V, Negative-QTOF	splash10-0002-0190000000-3517bc11de5b376dc6a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rhamnocitrin 40V, Negative-QTOF	splash10-00lr-3790000000-8c9a9d4d548458d70ec6	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

80897

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Rhamnocitrin (HMDB0257193)

MOL for HMDB0257193 (Rhamnocitrin)

3D MOL for HMDB0257193 (Rhamnocitrin)

3D SDF for HMDB0257193 (Rhamnocitrin)

3D-SDF for HMDB0257193 (Rhamnocitrin)

PDB for HMDB0257193 (Rhamnocitrin)

3D PDB for HMDB0257193 (Rhamnocitrin)

SMILES for HMDB0257193 (Rhamnocitrin)

INCHI for HMDB0257193 (Rhamnocitrin)

Structure for HMDB0257193 (Rhamnocitrin)

3D Structure for HMDB0257193 (Rhamnocitrin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra