MiMeDB: Showing metabocard for Isorhamnetin (MMDBc0033660)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:57:52 UTC

Update Date

2022-08-31 22:37:32 UTC

Metabolite ID

MMDBc0033660

Metabolite Identification

Common Name

Isorhamnetin

Description

Isorhamnetin is the methylated metabolite of quercetin. Quercetin is an important dietary flavonoid with in vitro antioxidant activity. However, it is found in human plasma as conjugates with glucuronic acid, sulfate or methyl groups, with no significant amounts of free quercetin present. Isorhamnetin prevents endothelial cell injuries from oxidized LDL via inhibition of lectin-like ox-LDL receptor-1 upregulation, interference of ox-LDL-mediated intracellular signaling pathway (p38MAPK activation, NF-kappaB nuclear translocation, eNOS expression) and the antioxidant activity of isorhamnetin. Isorhamnetin prevents endothelial dysfunction, superoxide production, and overexpression of p47phox induced by angiotensin II. Isorhamnetin appears to be a potent drug against esophageal cancer due to its in vitro potential to not only inhibit proliferation but also induce apoptosis of Eca-109 cells. (PMID: 15493462 , 17368593 , 17374653 , 16963021 ).

Structure

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

HMDB0002655
     RDKit          3D
Isorhamnetin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.3275   -2.3310   -1.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1001   -1.2638   -1.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4695   -0.2191   -0.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151   -0.2364   -0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638    0.8016    0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0184    0.7339    0.4511 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6115   -0.3220   -0.0725 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8971   -0.5202   -0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4661   -1.6620   -0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8163   -1.8965   -0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3700   -3.0497   -1.1369 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6153   -0.9864    0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0722    0.1743    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8809    1.0629    1.3035 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7133    0.4027    0.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0892    1.4952    1.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7568    2.3729    1.7715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941    1.6879    1.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1560    2.8208    1.6780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1916    1.8387    0.7940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5865    1.8654    0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1985    0.8347   -0.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5726    0.8259   -0.2469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6385   -2.7578   -1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0005   -3.0591   -2.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7113   -1.8833   -2.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4895   -1.0547   -0.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8097   -2.3706   -1.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6746   -3.0328   -2.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6920   -1.1245    0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8662    1.8823    1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828    3.5230    2.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7891    2.6745    1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793    2.6901    1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0126    0.0829   -0.7347 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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 18  6  2  0
 15  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 19 32  1  0
 20 33  1  0
 21 34  1  0
 23 35  1  0
M  END


  Mrv1652309272007452D          

 23 25  0  0  0  0            999 V2000
 9999.6614 9997.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0876 9998.5361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.805210002.2526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.232010001.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2367 9997.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.807810000.1927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.236710000.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5222 9999.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5221 9998.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2366 9998.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.517710001.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.803210001.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.088710001.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.088510000.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8030 9999.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.517710000.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.662310000.1883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9478 9999.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9478 9998.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6623 9998.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3768 9998.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3768 9999.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.091710002.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
  8  6  1  0  0  0  0
 10  5  1  0  0  0  0
 12  3  1  0  0  0  0
 11  4  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
  1 20  2  0  0  0  0
 22 14  1  0  0  0  0
 21  2  1  0  0  0  0
 18  7  2  0  0  0  0
 10 19  2  0  0  0  0
  3 23  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033660

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3

> <INCHI_KEY>
IZQSVPBOUDKVDZ-UHFFFAOYSA-N

> <FORMULA>
C16H12O7

> <MOLECULAR_WEIGHT>
316.2623

> <EXACT_MASS>
316.058302738

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.57793899979265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
1.96

> <JCHEM_LOGP>
2.30219352

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.911190018691145

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.381413988597494

> <JCHEM_PKA_STRONGEST_BASIC>
-3.954837655837035

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
81.34450000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isorhamnetin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002655
     RDKit          3D
Isorhamnetin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.3275   -2.3310   -1.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1001   -1.2638   -1.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4695   -0.2191   -0.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151   -0.2364   -0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638    0.8016    0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0184    0.7339    0.4511 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6115   -0.3220   -0.0725 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8971   -0.5202   -0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4661   -1.6620   -0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8163   -1.8965   -0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3700   -3.0497   -1.1369 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6153   -0.9864    0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0722    0.1743    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8809    1.0629    1.3035 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7133    0.4027    0.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0892    1.4952    1.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7568    2.3729    1.7715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941    1.6879    1.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1560    2.8208    1.6780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1916    1.8387    0.7940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5865    1.8654    0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1985    0.8347   -0.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5726    0.8259   -0.2469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6385   -2.7578   -1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0005   -3.0591   -2.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7113   -1.8833   -2.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4895   -1.0547   -0.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8097   -2.3706   -1.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6746   -3.0328   -2.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6920   -1.1245    0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8662    1.8823    1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828    3.5230    2.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7891    2.6745    1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793    2.6901    1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0126    0.0829   -0.7347 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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 18  6  2  0
 15  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 19 32  1  0
 20 33  1  0
 21 34  1  0
 23 35  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8666.0358662.387   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8668.6978663.934   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8670.0368670.872   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8672.7008669.332   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8663.3758662.387   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8660.7088667.026   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8663.3758667.018   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.0418666.248   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.0418664.708   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.3758663.938   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8671.3668668.565   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8670.0338669.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8668.6998668.565   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.6998667.025   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8670.0328666.255   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8671.3668667.025   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8666.0368667.018   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8664.7038666.248   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.7038664.708   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.0368663.938   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8667.3708664.708   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8667.3708666.248   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.7058671.645   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3   12   23                                                       
CONECT    4   11                                                            
CONECT    5   10                                                            
CONECT    6    8                                                            
CONECT    7    8   18                                                       
CONECT    8    7    9    6                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   19                                                  
CONECT   11   12   16    4                                                  
CONECT   12   11   13    3                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   18   22                                                       
CONECT   18   19   17    7                                                  
CONECT   19   18   20   10                                                  
CONECT   20   19   21    1                                                  
CONECT   21   20   22    2                                                  
CONECT   22   21   17   14                                                  
CONECT   23    3                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0002655
HETATM    1  C1  UNL     1      -3.328  -2.331  -1.763  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.100  -1.264  -1.252  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.469  -0.219  -0.565  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.115  -0.236  -0.392  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.464   0.802   0.295  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.018   0.734   0.451  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.612  -0.322  -0.072  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.897  -0.520  -0.013  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.466  -1.662  -0.594  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.816  -1.897  -0.547  1.00  0.00           C  
HETATM   11  O3  UNL     1       4.370  -3.050  -1.137  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.615  -0.986   0.086  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.072   0.174   0.682  1.00  0.00           C  
HETATM   14  O4  UNL     1       4.881   1.063   1.303  1.00  0.00           O  
HETATM   15  C11 UNL     1       2.713   0.403   0.630  1.00  0.00           C  
HETATM   16  C12 UNL     1       2.089   1.495   1.175  1.00  0.00           C  
HETATM   17  O5  UNL     1       2.757   2.373   1.772  1.00  0.00           O  
HETATM   18  C13 UNL     1       0.694   1.688   1.098  1.00  0.00           C  
HETATM   19  O6  UNL     1       0.156   2.821   1.678  1.00  0.00           O  
HETATM   20  C14 UNL     1      -2.192   1.839   0.794  1.00  0.00           C  
HETATM   21  C15 UNL     1      -3.586   1.865   0.621  1.00  0.00           C  
HETATM   22  C16 UNL     1      -4.199   0.835  -0.056  1.00  0.00           C  
HETATM   23  O7  UNL     1      -5.573   0.826  -0.247  1.00  0.00           O  
HETATM   24  H1  UNL     1      -2.638  -2.758  -1.010  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.001  -3.059  -2.217  1.00  0.00           H  
HETATM   26  H3  UNL     1      -2.711  -1.883  -2.596  1.00  0.00           H  
HETATM   27  H4  UNL     1      -1.490  -1.055  -0.779  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.810  -2.371  -1.092  1.00  0.00           H  
HETATM   29  H6  UNL     1       4.675  -3.033  -2.111  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.692  -1.124   0.152  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.866   1.882   1.774  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.683   3.523   2.154  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.789   2.675   1.330  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.179   2.690   1.016  1.00  0.00           H  
HETATM   35  H12 UNL     1      -6.013   0.083  -0.735  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   27
CONECT    5    6   20   20
CONECT    6    7   18   18
CONECT    7    8
CONECT    8    9    9   15
CONECT    9   10   28
CONECT   10   11   12   12
CONECT   11   29
CONECT   12   13   30
CONECT   13   14   15   15
CONECT   14   31
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   32
CONECT   20   21   33
CONECT   21   22   22   34
CONECT   22   23
CONECT   23   35
END

HMDB0002655
     RDKit          3D
Isorhamnetin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.3275   -2.3310   -1.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1001   -1.2638   -1.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4695   -0.2191   -0.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151   -0.2364   -0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638    0.8016    0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0184    0.7339    0.4511 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6115   -0.3220   -0.0725 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8971   -0.5202   -0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4661   -1.6620   -0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8163   -1.8965   -0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3700   -3.0497   -1.1369 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6153   -0.9864    0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0722    0.1743    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8809    1.0629    1.3035 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7133    0.4027    0.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0892    1.4952    1.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7568    2.3729    1.7715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941    1.6879    1.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1560    2.8208    1.6780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1916    1.8387    0.7940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5865    1.8654    0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1985    0.8347   -0.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5726    0.8259   -0.2469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6385   -2.7578   -1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0005   -3.0591   -2.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7113   -1.8833   -2.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4895   -1.0547   -0.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8097   -2.3706   -1.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6746   -3.0328   -2.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6920   -1.1245    0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8662    1.8823    1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828    3.5230    2.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7891    2.6745    1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793    2.6901    1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0126    0.0829   -0.7347 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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 18  6  2  0
 15  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 19 32  1  0
 20 33  1  0
 21 34  1  0
 23 35  1  0
M  END

Synonyms

Value	Source
3,5,7,4'-Tetrahydroxy-3'-methoxyflavone	ChEBI
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-benzopyran-4-one	ChEBI
3-Methylquercetin	ChEBI
Isorhamnetol	ChEBI
Quercetin 3'-methyl ether	ChEBI
3'-Methoxy-3,4',5,7-tetrahydroxyflavone	HMDB
3'-Methoxyquercetin	HMDB
3'-Methylquercetin	HMDB
3'-O-Methylquercetin	HMDB
3,4',5,7-Tetrahydroxy-3'-methoxy-flavone	HMDB, MeSH
3,4',5,7-Tetrahydroxy-3'-methoxyflavone	HMDB, MeSH
3-Methylquercetine	HMDB
4'-Methoxyquercetin	HMDB
4'-Methylquercetin	HMDB
4'-O-Methylquercetin	HMDB
3-O-Methylquercetin	MeSH, HMDB
iso-Rhamnetin	MeSH, HMDB
Isorhamnetine	MeSH, HMDB
3-Methyl-quercetin	MeSH, HMDB
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one	PhytoBank
3,4’,5,7-Tetrahydroxy-3’-methoxyflavone	PhytoBank
3’-Methoxyquercetin	PhytoBank
3’-Methylquercetin	PhytoBank
3’-O-Methylquercetin	PhytoBank
Quercetin 3’-methyl ether	PhytoBank

Molecular Formula

C₁₆H₁₂O₇

Average Mass

316.2623

Monoisotopic Mass

316.058302738

IUPAC Name

3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one

Traditional Name

isorhamnetin

CAS Registry Number

480-19-3

SMILES

COC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3

InChI Key

IZQSVPBOUDKVDZ-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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavone (CHEBI:6052 )
tetrahydroxyflavone (CHEBI:6052 )
7-hydroxyflavonol (CHEBI:6052 )
flavonols (C10084 )
Flavones and Flavonols (C10084 )
Flavones and Flavonols (LMPK12110002 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	1.96	ALOGPS
logP	2.3	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.34 m³·mol⁻¹	ChemAxon
Polarizability	30.58 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

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Fibroblasts
Intestine
Leukocyte
Liver
Neuron
Pancreas
Platelet
Prostate
Urine

Tissue Locations

Fibroblasts
Intestine
Leukocyte
Liver
Neuron
Pancreas
Platelet
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo_sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human	Detected and Quantified	0.00432				Adult (>18 years old)	Both	Normal	HMDB	21272408
Human	Detected and Quantified	0.02				Adult (>18 years old)	Both	Normal	HMDB	17426744
Human	Detected and Quantified	0.02				Adult (>18 years old)	Both	Normal	HMDB	17426744
Human	Detected and Quantified	0.0347				Adult (>18 years old)	Both	Normal	HMDB	27273479
Human	Detected and Quantified			0	0.157	Adult (>18 years old)	Both	Normal	HMDB	19747418
Human	Detected and Quantified	0.0065	0.0065			Adult (>18 years old)	Both	Normal	HMDB	16197573
Human	Detected and Quantified	0.019	0.0065			Adult (>18 years old)	Both	Normal	HMDB	16197573
Human	Detected and Quantified	0.0300	0.0300			Adult (>18 years old)	Both	Normal	HMDB	16870009
Human	Detected and Quantified	0.0333	0.0333			Adult (>18 years old)	Both	Normal	HMDB	16870009
Human	Detected and Quantified	0.0388	0.0454			Adult (>18 years old)	Both	Normal	HMDB	20851305
Human	Detected and Quantified	0.0399	0.0450			Adult (>18 years old)	Both	Normal	HMDB	19747418
Human	Detected and Quantified	0.043		0.040	0.046	Adult (>18 years old)	Not Specified	Normal	HMDB	16294501
Human	Detected and Quantified	0.0546	0.0420			Adult (>18 years old)	Both	Normal	HMDB	26814424
Human Fibroblasts	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Leukocyte	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0002655

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Isorhamnetin

METLIN ID

3445

PubChem Compound

5281654

PDB ID

Not Available

ChEBI ID

6052

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

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Miniscalco A, Lundahl J, Regardh CG, Edgar B, Eriksson UG: Inhibition of dihydropyridine metabolism in rat and human liver microsomes by flavonoids found in grapefruit juice. J Pharmacol Exp Ther. 1992 Jun;261(3):1195-9. [PubMed:1602384 ]
Ritter J, Kahl R, Hildebrandt AG: Effect of the antioxidant (+)-cyanidanol-3 on H2O2 formation and lipid peroxidation in liver microsomes. Res Commun Chem Pathol Pharmacol. 1985 Jan;47(1):48-58. [PubMed:3983470 ]
Lindahl M, Tagesson C: Flavonoids as phospholipase A2 inhibitors: importance of their structure for selective inhibition of group II phospholipase A2. Inflammation. 1997 Jun;21(3):347-56. doi: 10.1023/a:1027306118026. [PubMed:9246576 ]
Shoab SS, Porter JB, Scurr JH, Coleridge-Smith PD: Effect of oral micronized purified flavonoid fraction treatment on leukocyte adhesion molecule expression in patients with chronic venous disease: a pilot study. J Vasc Surg. 2000 Mar;31(3):456-61. [PubMed:10709057 ]
Meng Z, Zhou Y, Lu J, Sugahara K, Xu S, Kodama H: Effect of five flavonoid compounds isolated from Quercus dentata Thunb on superoxide generation in human neutrophils and phosphorylation of neutrophil proteins. Clin Chim Acta. 2001 Apr;306(1-2):97-102. doi: 10.1016/s0009-8981(01)00403-x. [PubMed:11282099 ]
Spencer JP, Schroeter H, Crossthwaithe AJ, Kuhnle G, Williams RJ, Rice-Evans C: Contrasting influences of glucuronidation and O-methylation of epicatechin on hydrogen peroxide-induced cell death in neurons and fibroblasts. Free Radic Biol Med. 2001 Nov 1;31(9):1139-46. doi: 10.1016/s0891-5849(01)00704-3. [PubMed:11677047 ]
Lu J, Feng X, Sun Q, Lu H, Manabe M, Sugahara K, Ma D, Sagara Y, Kodama H: Effect of six flavonoid compounds from Ixeris sonchifolia on stimulus-induced superoxide generation and tyrosyl phosphorylation in human neutrophils. Clin Chim Acta. 2002 Feb;316(1-2):95-9. doi: 10.1016/s0009-8981(01)00725-2. [PubMed:11750278 ]
Wenisch C, Biffignandi PM: Effect of bioflavonoids (trihydroxyethylrutin and disodium flavodate) in vitro on neutrophil reactive oxygen production and phagocytic ability assessed by flow cytometry. Curr Med Res Opin. 2001;17(2):123-7. [PubMed:11759181 ]
Chen G, Lu H, Wang C, Yamashita K, Manabe M, Meng Z, Xu S, Kodama H: Effect of five flavonoid compounds isolated from leaves of Diospyros kaki on stimulus-induced superoxide generation and tyrosyl phosphorylation of proteins in human neutrophils. Clin Chim Acta. 2002 Dec;326(1-2):169-75. doi: 10.1016/s0009-8981(02)00298-x. [PubMed:12417109 ]
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Engler MB, Engler MM, Chen CY, Malloy MJ, Browne A, Chiu EY, Kwak HK, Milbury P, Paul SM, Blumberg J, Mietus-Snyder ML: Flavonoid-rich dark chocolate improves endothelial function and increases plasma epicatechin concentrations in healthy adults. J Am Coll Nutr. 2004 Jun;23(3):197-204. doi: 10.1080/07315724.2004.10719361. [PubMed:15190043 ]
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Hubbard GP, Wolffram S, Lovegrove JA, Gibbins JM: Ingestion of quercetin inhibits platelet aggregation and essential components of the collagen-stimulated platelet activation pathway in humans. J Thromb Haemost. 2004 Dec;2(12):2138-45. doi: 10.1111/j.1538-7836.2004.01067.x. [PubMed:15613018 ]
Chen CY, Milbury PE, Lapsley K, Blumberg JB: Flavonoids from almond skins are bioavailable and act synergistically with vitamins C and E to enhance hamster and human LDL resistance to oxidation. J Nutr. 2005 Jun;135(6):1366-73. doi: 10.1093/jn/135.6.1366. [PubMed:15930439 ]
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Showing metabocard for Isorhamnetin (MMDBc0033660)

MOL for #<Metabolite:0x0000560bdfc6b4c0>

3D MOL for #<Metabolite:0x0000560bdfc6b4c0>

3D SDF for #<Metabolite:0x0000560bdfc6b4c0>

3D-SDF for #<Metabolite:0x0000560bdfc6b4c0>

PDB for #<Metabolite:0x0000560bdfc6b4c0>

3D PDB for #<Metabolite:0x0000560bdfc6b4c0>

SMILES for #<Metabolite:0x0000560bdfc6b4c0>

INCHI for #<Metabolite:0x0000560bdfc6b4c0>

Structure for #<Metabolite:0x0000560bdfc6b4c0>

3D Structure for #<Metabolite:0x0000560bdfc6b4c0>