MiMeDB: Showing metabocard for Isorhamnetin (MMDBc0033660)

Not Available

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:57:52 UTC

Update Date

2024-09-27 20:42:48 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

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-2219000000-20feeef38553ee7cdd29	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-2219000000-20feeef38553ee7cdd29	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0591000000-2e1f6e28bf0d47d5e240	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-001u-0041090000-7e13d91dc4b2bd93fc17	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0udi-0394000000-f903b8df9b79e6a94f44	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-0udi-0956000000-6286c6784746c9eba0e8	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0gb9-0219000000-c620190cc3878a4242f9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0zfr-1941000000-10313269e61a0584f37f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0gb9-0109000000-082620470bd7fd8a6897	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ufr-0491000000-da6ec11ed89cc64a7972	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0139000000-141b68c1e564685b35ce	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0139000000-8fa57905e16cdfcc4e9e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0udi-0493000000-2b88769e97319b5f076c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0udi-1940000000-51e0d426523f81faa98b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0gb9-0009000000-caca1c7784ed9828dfb4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-0233e63233dadf52ffc5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0zfr-0952000000-13e1d438b3f800cfc18a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0gb9-0209000000-89d7fc697d82018c1228	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0gb9-0209000000-405d086d8e4de2b975b1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Negative	splash10-0a4i-1910000000-170b80b866f2075e44e9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-0029000000-a9da21c499e339f09ac6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0udi-0493000000-14bbb49d59d91543a76e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0029000000-3458ddb4f7ba64eb81c8	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0019000000-bb7cbcffdd9f296b6b9b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0079000000-c73663231834b1b1b79a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uds-3790000000-3b8ca78684ffcba51bf1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-57dd2505d869c8f411dc	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0169000000-38b50b4081dff638023b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0frb-3890000000-3525a3f4676b6a964b71	2016-08-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum

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

Metabolic Reactions

Not Available

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; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal		Eucheuma	FooDB	34893796
Food			FooDB	Phenol Explorer
Food			FooDB	Phenol Explorer
Food			FooDB	Phenol Explorer
Plant		Solanum lycopersicum	FooDB	Manually Annotated
Plant		Solanum melongena	FooDB	34893796
Plant		Rorippa nasturtium-aquaticum	FooDB	Phenol Explorer
Plant	Leaves	Pastinaca sativa	FooDB	DUKE
Plant	Plant	Anethum graveolens	FooDB	DUKE
Plant	Fruit	Ribes nigrum	FooDB	34893796
Plant		Cucurbita	FooDB	34893796
Plant	Fruit	Citrus limon	FooDB	Phenol Explorer
Plant	Fruit	Prunus cerasus	FooDB	34893796
Plant	Fruit	Hippophae rhamnoides	FooDB	DUKE
Plant		Petroselinum crispum	FooDB	Phenol Explorer
Plant		Allium cepa	FooDB	Manually Annotated
Plant	Leave	Eruca vesicaria ssp. sativa	FooDB	DUKE
Plant	Stalk	Apium graveolens var. dulce	FooDB	Phenol Explorer
Plant	Fruit	Prunus cerasus	FooDB	34893796
Plant		Allium cepa	FooDB	Manually Annotated
Plant		Psidium guajava	FooDB	24285751
Plant	Fruit	Prunus cerasus	FooDB	34893796
Plant		Thymus vulgaris	FooDB	Phenol Explorer
Plant		Ipomoea aquatica	FooDB	34893796
Plant		Allium sativum	FooDB	Manually Annotated
Plant		Allium sativum	FooDB	Manually Annotated
Plant			FooDB	DFC codes
Plant	Juice	Hippophae rhamnoides	FooDB	Phenol Explorer
Plant		Prunus dulcis	FooDB	34893796
Plant		Fragaria x ananassa	FooDB	34893796
Plant		Daucus carota	FooDB	34893796
Plant		Melissa officinalis	FooDB	Phenol Explorer
Plant	Fruit	Hippophae rhamnoides	FooDB	24285751
Plant		Allium cepa var. cepa	FooDB	Phenol Explorer
Plant		Allium cepa var. cepa	FooDB	Phenol Explorer
Plant		Melissa officinalis	FooDB	34893796
Plant	Leaves	Foeniculum vulgare	FooDB	Phenol Explorer
Plant		Solanum lycopersicum	FooDB	34893796
Plant		Hippophae rhamnoides	FooDB	34893796
Plant		Pyrus communis	FooDB	34893796
Plant	Fruit	Rubus arcticus	FooDB	34893796
Plant		Abelmoschus esculentus	FooDB	34893796
Plant	Leaves	Moringa oleifera	FooDB	34893796
Plant		Allium cepa var. cepa	FooDB	Phenol Explorer
Plant	Flower	Taraxacum officinale	FooDB	DUKE
Plant		Eruca vesicaria ssp. sativa	FooDB	34893796
Plant		Allium cepa var. cepa	FooDB	Phenol Explorer
Plant		Allium cepa var. cepa	FooDB	Phenol Explorer
Plant		Eruca vesicaria ssp. sativa	FooDB	34893796
Plant		Petroselinum crispum	FooDB	34893796
Plant		Zingiber officinale	FooDB	34893796
Plant		Brassica juncea	FooDB	34893796
Plant		Rorippa nasturtium-aquaticum	FooDB	34893796
Plant		Thymus vulgaris	FooDB	34893796
Plant	Fruit	Citrus sinensis	FooDB	Phenol Explorer
Plant	Plant	Matricaria recutita	FooDB	DUKE
Plant		Medicago sativa	FooDB	24285751
Plant		Petroselinum crispum	FooDB	34893796
Plant		Allium cepa var. cepa	FooDB	34893796
Plant		Allium cepa var. cepa	FooDB	34893796
Plant		Vigna unguiculata	FooDB	34893796
Plant	Fruit	Malus pumila	FooDB	Phenol Explorer
Plant	Shoot	Asparagus officinalis	FooDB	34893796
Plant	Fruit	Solanum lycopersicum var. cerasiforme	FooDB	Phenol Explorer
Plant		Rosmarinus officinalis	FooDB	Phenol Explorer
Plant		Levisticum officinale	FooDB	Phenol Explorer
Plant		Rosmarinus officinalis	FooDB	34893796
Plant		Foeniculum vulgare	FooDB	34893796
Plant		Levisticum officinale	FooDB	34893796
Plant		Lepidium sativum	FooDB	Phenol Explorer
Plant		Anethum graveolens	FooDB	34893796
Plant		Origanum x majoricum	FooDB	34893796
Plant		Lepidium sativum	FooDB	34893796
Plant	Plant	Artemisia dracunculus	FooDB	DUKE
Plant		Allium cepa	FooDB	DFC codes
Plant		Trigonella foenum-graecum	FooDB	24285751
Plant		Anethum graveolens	FooDB	Phenol Explorer
Plant		Allium	FooDB	34893796
Plant		Allium	FooDB	34893796
Plant	Fruit	Rubus chamaemorus	FooDB	34893796
Plant		Brassica napus	FooDB	34893796
Plant	Seed	Phaseolus lunatus	FooDB	34893796
Plant		Pastinaca sativa	FooDB	Manually Annotated
Plant		Pastinaca sativa	FooDB	Manually Annotated
Plant		Artemisia dracunculus	FooDB	Phenol Explorer
Plant		Artemisia dracunculus	FooDB	34893796
Plant		Brassica oleracea var. viridis	FooDB	34893796
Plant		Coriandrum sativum	FooDB	Phenol Explorer
Plant		Cucumis sativus	FooDB	Manually Annotated
Plant		Cucumis sativus	FooDB	Manually Annotated
Plant	Leaves	Allium schoenoprasum	FooDB	Phenol Explorer
Plant		Brassica oleracea	FooDB	34893796
Plant		Lactuca sativa l. var. longifolia	FooDB	Manually Annotated
Plant		Musa acuminata	FooDB	34893796
Plant		Lactuca sativa l. var. longifolia	FooDB	Manually Annotated
Plant		Ipomoea batatas	FooDB	34893796
Plant		Rumex	FooDB	34893796
Plant		Musa acuminata	FooDB	34893796
Plant		Portulaca oleracea	FooDB	34893796
Plant		Cucumis sativus	FooDB	34893796
Plant		Allium fistulosum	FooDB	DFC codes
Plant	Fruit	Sambucus	FooDB	34893796
Plant		Ocimum basilicum	FooDB	34893796
Plant		Brassica oleracea var. italica	FooDB	Phenol Explorer
Plant	Meat	Cocos nucifera	FooDB	34893796
Plant		Capsicum annuum	FooDB	Manually Annotated
Plant		Capsicum annuum	FooDB	Manually Annotated
Plant		Mentha x piperita	FooDB	34893796
Plant	Fruit	Solanum lycopersicum var. lycopersicum	FooDB	Phenol Explorer
Plant		Papaver	FooDB	34893796
Plant		Brassica rapa	FooDB	34893796
Plant		Ocimum basilicum	FooDB	Phenol Explorer
Plant		Lactuca sativa	FooDB	Phenol Explorer
Plant	Bulb	Allium cepa	FooDB	DUKE
Plant	Leaves	Ginkgo biloba	FooDB	DUKE
Plant		Lactuca sativa	FooDB	Phenol Explorer
Plant	Fruit	Prunus avium	FooDB	34893796
Plant		Artocarpus heterophyllus	FooDB	34893796
Plant	Fruit	Momordica charantia	FooDB	34893796
Plant		Salvia officinalis	FooDB	Phenol Explorer
Plant		Anethum graveolens	FooDB	Manually Annotated
Plant		Anethum graveolens	FooDB	Manually Annotated
Plant		Allium schoenoprasum	FooDB	34893796
Plant		Daucus carota ssp. sativus	FooDB	Manually Annotated
Plant		Daucus carota ssp. sativus	FooDB	Manually Annotated
Plant		Origanum vulgare	FooDB	Phenol Explorer
Plant		Prunus dulcis	FooDB	Phenol Explorer
Plant		Coriandrum sativum	FooDB	34893796
Plant		Phaseolus vulgaris	FooDB	Manually Annotated
Plant		Cicer arietinum	FooDB	24285751
Plant		Phaseolus vulgaris	FooDB	Manually Annotated
Plant		Manihot esculenta	FooDB	34893796
Plant	Fruit	Vaccinium vitis-idaea	FooDB	Phenol Explorer
Plant		Solanum melongena	FooDB	Manually Annotated
Plant		Photinia melanocarpa	FooDB	34893796
Plant		Solanum melongena	FooDB	Manually Annotated
Plant	Nut	Cocos nucifera	FooDB	34893796
Plant		Capsicum annuum	FooDB	Manually Annotated
Plant		Capsicum annuum	FooDB	Manually Annotated
Plant		Daucus carota ssp. sativus	FooDB	34893796
Plant	Fruit	Opuntia	FooDB	34893796
Plant	Flower	Citrus limon	FooDB	DUKE
Plant		Petroselinum crispum	FooDB	Phenol Explorer
Plant		Colocasia esculenta	FooDB	34893796
Plant		Solanum lycopersicum	FooDB	Manually Annotated

Source Type	Activity	Data Source	Reference
Not Available	Antioxidant	U.S. Environmental Protection Agency	CompTox
General Exposome	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.00432				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	21272408
Human Urine	Detected and Quantified	0.02				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	17426744
Human Urine	Detected and Quantified	0.02				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	17426744
Human Urine	Detected and Quantified	0.0347				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	27273479
Human Blood	Detected and Quantified			0	0.157	uM	Adult (>18 years old)	Both	Normal	HMDB	19747418
Human Urine	Detected and Quantified	0.0065	0.0065			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.019	0.0065			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.0300	0.0300			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16870009
Human Urine	Detected and Quantified	0.0333	0.0333			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16870009
Human Blood	Detected and Quantified	0.0388	0.0454			uM	Adult (>18 years old)	Both	Normal	HMDB	20851305
Human Blood	Detected and Quantified	0.0399	0.0450			uM	Adult (>18 years old)	Both	Normal	HMDB	19747418
Human Blood	Detected and Quantified	0.043		0.040	0.046	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	16294501
Human Urine	Detected and Quantified	0.0546	0.0420			umol/mmol creatinine	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

References

Synthesis Reference

Not Available

General References

Chanoine JP, Braverman LE: The role of transthyretin in the transport of thyroid hormone to cerebrospinal fluid and brain. Acta Med Austriaca. 1992;19 Suppl 1:25-8. [PubMed:1519447 ]
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 ]
Lin N, Sato T, Takayama Y, Mimaki Y, Sashida Y, Yano M, Ito A: Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Biochem Pharmacol. 2003 Jun 15;65(12):2065-71. doi: 10.1016/s0006-2952(03)00203-x. [PubMed:12787887 ]
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 ]
Sheu JR, Hsiao G, Chou PH, Shen MY, Chou DS: Mechanisms involved in the antiplatelet activity of rutin, a glycoside of the flavonol quercetin, in human platelets. J Agric Food Chem. 2004 Jul 14;52(14):4414-8. doi: 10.1021/jf040059f. [PubMed:15237945 ]
Janisch KM, Williamson G, Needs P, Plumb GW: Properties of quercetin conjugates: modulation of LDL oxidation and binding to human serum albumin. Free Radic Res. 2004 Aug;38(8):877-84. doi: 10.1080/10715760410001728415. [PubMed:15493462 ]
Brusselmans K, Vrolix R, Verhoeven G, Swinnen JV: Induction of cancer cell apoptosis by flavonoids is associated with their ability to inhibit fatty acid synthase activity. J Biol Chem. 2005 Feb 18;280(7):5636-45. doi: 10.1074/jbc.M408177200. Epub 2004 Nov 8. [PubMed:15533929 ]
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 ]
Kandaswami C, Lee LT, Lee PP, Hwang JJ, Ke FC, Huang YT, Lee MT: The antitumor activities of flavonoids. In Vivo. 2005 Sep-Oct;19(5):895-909. [PubMed:16097445 ]
Ito H, Gonthier MP, Manach C, Morand C, Mennen L, Remesy C, Scalbert A: Polyphenol levels in human urine after intake of six different polyphenol-rich beverages. Br J Nutr. 2005 Oct;94(4):500-9. doi: 10.1079/bjn20051522. [PubMed:16197573 ]
Young JM, Shand BI, McGregor PM, Scott RS, Frampton CM: Comparative effects of enzogenol and vitamin C supplementation versus vitamin C alone on endothelial function and biochemical markers of oxidative stress and inflammation in chronic smokers. Free Radic Res. 2006 Jan;40(1):85-94. doi: 10.1080/10715760500329788. [PubMed:16298763 ]
Lee HJ, Noh YH, Lee DY, Kim YS, Kim KY, Chung YH, Lee WB, Kim SS: Baicalein attenuates 6-hydroxydopamine-induced neurotoxicity in SH-SY5Y cells. Eur J Cell Biol. 2005 Nov;84(11):897-905. doi: 10.1016/j.ejcb.2005.07.003. [PubMed:16323286 ]
Bao M, Lou Y: Isorhamnetin prevent endothelial cell injuries from oxidized LDL via activation of p38MAPK. Eur J Pharmacol. 2006 Oct 10;547(1-3):22-30. doi: 10.1016/j.ejphar.2006.07.021. Epub 2006 Jul 22. [PubMed:16963021 ]
Ma G, Yang C, Qu Y, Wei H, Zhang T, Zhang N: The flavonoid component isorhamnetin in vitro inhibits proliferation and induces apoptosis in Eca-109 cells. Chem Biol Interact. 2007 Apr 25;167(2):153-60. doi: 10.1016/j.cbi.2007.02.006. Epub 2007 Feb 20. [PubMed:17368593 ]
Sanchez M, Lodi F, Vera R, Villar IC, Cogolludo A, Jimenez R, Moreno L, Romero M, Tamargo J, Perez-Vizcaino F, Duarte J: Quercetin and isorhamnetin prevent endothelial dysfunction, superoxide production, and overexpression of p47phox induced by angiotensin II in rat aorta. J Nutr. 2007 Apr;137(4):910-5. doi: 10.1093/jn/137.4.910. [PubMed:17374653 ]

Showing metabocard for Isorhamnetin (MMDBc0033660)

MOL for #<Metabolite:0x00007fdb4d2efa10>

3D MOL for #<Metabolite:0x00007fdb4d2efa10>

3D SDF for #<Metabolite:0x00007fdb4d2efa10>

3D-SDF for #<Metabolite:0x00007fdb4d2efa10>

PDB for #<Metabolite:0x00007fdb4d2efa10>

3D PDB for #<Metabolite:0x00007fdb4d2efa10>

SMILES for #<Metabolite:0x00007fdb4d2efa10>

INCHI for #<Metabolite:0x00007fdb4d2efa10>

Structure for #<Metabolite:0x00007fdb4d2efa10>

3D Structure for #<Metabolite:0x00007fdb4d2efa10>