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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:01 UTC

Update Date

2022-03-07 02:49:16 UTC

HMDB ID

HMDB0002655

Secondary Accession Numbers

HMDB02655

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>
HMDB0002655

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

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

Chemical Formula

C₁₆H₁₂O₇

Average Molecular Weight

316.2623

Monoisotopic Molecular Weight

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 )

Ontology

Physiological effect

Organoleptic effect

Odor

bitter

Platelet (HMDB: HMDB0002655)

Fibroblast

Fibroblast (HMDB: HMDB0002655)

Organ

Biofluid or Excreta

Non-excretory biofluid

Blood (PMID: 16294501)

Excreta

Urine (PMID: 16197573)

Urine (HMDB: HMDB0002655)
Blood (HMDB: HMDB0002655)

Cellular substructure

Membrane (HMDB: HMDB0002655)

Cellular element

Platelet (HMDB: HMDB0002655)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002655)

Source

Exogenous

Food

Food (HMDB: HMDB0002655)
Legumes (HMDB: HMDB0002655)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Cabbage

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)
Rocket salad (FooDB: FOOD00244)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)
Vegetables (HMDB: HMDB0002655)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Bilberry (FooDB: FOOD00193)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Peach (FooDB: FOOD00149)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruits (HMDB: HMDB0002655)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Soy sauce (FooDB: FOOD00694)
Miso (FooDB: FOOD00695)
Tofu (FooDB: FOOD00696)
Soy milk (FooDB: FOOD00736)
Soy cream (FooDB: FOOD00784)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Nuts (HMDB: HMDB0002655)

Cereal and cereal product

Cereal

Cereal product

Pasta (FooDB: FOOD00273)
Bulgur (FooDB: FOOD00741)
Semolina (FooDB: FOOD00745)
Flour (FooDB: FOOD00799)
Whole grain cereal products (HMDB: HMDB0002655)

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Chayote (FooDB: FOOD00325)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee product

Coffee products (HMDB: HMDB0002655)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Ground meat

Sausage (FooDB: FOOD00652)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0002655)

Fat and oil

Olive oil (HMDB: HMDB0002655)

Confectionery

Other confectionery

Honey (FooDB: FOOD00626)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0002655)

Fortified wines

Sherry (FooDB: FOOD00632)

Fermented beverage

Grape wine (FooDB: FOOD00612)

Aquatic origin

Seaweed

Agar (FooDB: FOOD00284)

Endogenous

Plant

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Flavone and Flavonol Biosynthesis (PathBank: SMP0012025)

Role

Biological role

anti inflammatory (HMDB: HMDB0002655)
anti bacterial (HMDB: HMDB0002655)
anti histaminic (HMDB: HMDB0002655)
Antioxidant (HMDB: HMDB0002655)
anti spasmodic (HMDB: HMDB0002655)
cancer preventive (HMDB: HMDB0002655)
hepatoprotective (HMDB: HMDB0002655)
quinone-reductase inducer (HMDB: HMDB0002655)
Rna component (HMDB: HMDB0002655)

Modulator

Inhibitor

Enzyme inhibitor

monoamine-oxidase inhibitor (HMDB: HMDB0002655)
EC 1.14.18.1 (tyrosinase) inhibitor (HMDB: HMDB0002655)

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

anticoagulant (HMDB: HMDB0002655)
vasodilator agent (HMDB: HMDB0002655)

Agriculture

Pesticide

Insecticide

pesticide (HMDB: HMDB0002655)

Pharmaceutical industry

Biomarker

Fruits Consumption (MarkerDB: MDB00000395)
Vegetables Consumption (MarkerDB: MDB00000395)
Apple Consumption (MarkerDB: MDB00000395)
Peach Consumption (MarkerDB: MDB00000395)
Berries Consumption (MarkerDB: MDB00000395)
Fruit Juices Consumption (MarkerDB: MDB00000395)
Onion Consumption (MarkerDB: MDB00000395)
Black Tea Consumption (MarkerDB: MDB00000395)
Herbal Tea Consumption (MarkerDB: MDB00000395)

Indirect biological role

antioxidant (HMDB: HMDB0002655)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	311 - 314 °C	Not Available
Boiling Point	599.40 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1122 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.760 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	174.6	30932474
[M+H]+	Baker	172.958	30932474
[M-H]-	Not Available	174.6	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001936
[M+H]+	Not Available	172.958	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001936

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	174.174	30932474
DeepCCS	[M-H]-	171.816	30932474
DeepCCS	[M-2H]-	205.55	30932474
DeepCCS	[M+Na]+	180.777	30932474
AllCCS	[M+H]+	171.6	32859911
AllCCS	[M+H-H2O]+	168.0	32859911
AllCCS	[M+NH4]+	175.0	32859911
AllCCS	[M+Na]+	175.9	32859911
AllCCS	[M-H]-	171.1	32859911
AllCCS	[M+Na-2H]-	170.5	32859911
AllCCS	[M+HCOO]-	170.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isorhamnetin	COC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1	5088.9	Standard polar	33892256
Isorhamnetin	COC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1	3146.5	Standard non polar	33892256
Isorhamnetin	COC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1	3216.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isorhamnetin,1TMS,isomer #1	COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C	3248.4	Semi standard non polar	33892256
Isorhamnetin,1TMS,isomer #2	COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O	3225.5	Semi standard non polar	33892256
Isorhamnetin,1TMS,isomer #3	COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC=C1O	3259.6	Semi standard non polar	33892256
Isorhamnetin,1TMS,isomer #4	COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O	3311.4	Semi standard non polar	33892256
Isorhamnetin,2TMS,isomer #1	COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C	3185.4	Semi standard non polar	33892256
Isorhamnetin,2TMS,isomer #2	COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C	3138.4	Semi standard non polar	33892256
Isorhamnetin,2TMS,isomer #3	COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C	3116.3	Semi standard non polar	33892256
Isorhamnetin,2TMS,isomer #4	COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O	3146.7	Semi standard non polar	33892256
Isorhamnetin,2TMS,isomer #5	COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC=C1O	3117.3	Semi standard non polar	33892256
Isorhamnetin,2TMS,isomer #6	COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O	3248.7	Semi standard non polar	33892256
Isorhamnetin,3TMS,isomer #1	COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C	3136.9	Semi standard non polar	33892256
Isorhamnetin,3TMS,isomer #2	COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C	3059.1	Semi standard non polar	33892256
Isorhamnetin,3TMS,isomer #3	COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C	3033.4	Semi standard non polar	33892256
Isorhamnetin,3TMS,isomer #4	COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O	3139.4	Semi standard non polar	33892256
Isorhamnetin,4TMS,isomer #1	COC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C	3129.8	Semi standard non polar	33892256
Isorhamnetin,1TBDMS,isomer #1	COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3524.5	Semi standard non polar	33892256
Isorhamnetin,1TBDMS,isomer #2	COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O	3527.1	Semi standard non polar	33892256
Isorhamnetin,1TBDMS,isomer #3	COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC=C1O	3534.1	Semi standard non polar	33892256
Isorhamnetin,1TBDMS,isomer #4	COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O	3580.7	Semi standard non polar	33892256
Isorhamnetin,2TBDMS,isomer #1	COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3724.7	Semi standard non polar	33892256
Isorhamnetin,2TBDMS,isomer #2	COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3678.6	Semi standard non polar	33892256
Isorhamnetin,2TBDMS,isomer #3	COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3658.8	Semi standard non polar	33892256
Isorhamnetin,2TBDMS,isomer #4	COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O	3696.5	Semi standard non polar	33892256
Isorhamnetin,2TBDMS,isomer #5	COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC=C1O	3661.8	Semi standard non polar	33892256
Isorhamnetin,2TBDMS,isomer #6	COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O	3766.6	Semi standard non polar	33892256
Isorhamnetin,3TBDMS,isomer #1	COC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3917.0	Semi standard non polar	33892256
Isorhamnetin,3TBDMS,isomer #2	COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3820.8	Semi standard non polar	33892256
Isorhamnetin,3TBDMS,isomer #3	COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3791.0	Semi standard non polar	33892256
Isorhamnetin,3TBDMS,isomer #4	COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O	3893.1	Semi standard non polar	33892256
Isorhamnetin,4TBDMS,isomer #1	COC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	4022.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Isorhamnetin EI-B (Non-derivatized)	splash10-014i-2219000000-20feeef38553ee7cdd29	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isorhamnetin EI-B (Non-derivatized)	splash10-014i-2219000000-20feeef38553ee7cdd29	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isorhamnetin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0591000000-2e1f6e28bf0d47d5e240	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isorhamnetin GC-MS (4 TMS) - 70eV, Positive	splash10-001u-0041090000-7e13d91dc4b2bd93fc17	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isorhamnetin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin DI-ESI-qTof , Positive-QTOF	splash10-0udi-0394000000-f903b8df9b79e6a94f44	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin DI-ESI-qTof , Negative-QTOF	splash10-0udi-0956000000-6286c6784746c9eba0e8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin LC-ESI-QTOF , negative-QTOF	splash10-0gb9-0219000000-c620190cc3878a4242f9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin LC-ESI-QTOF , negative-QTOF	splash10-0zfr-1941000000-10313269e61a0584f37f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin LC-ESI-QTOF , negative-QTOF	splash10-0gb9-0109000000-082620470bd7fd8a6897	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin LC-ESI-QTOF , positive-QTOF	splash10-0ufr-0491000000-da6ec11ed89cc64a7972	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin LC-ESI-QTOF , positive-QTOF	splash10-014i-0139000000-141b68c1e564685b35ce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin LC-ESI-QTOF , positive-QTOF	splash10-014i-0139000000-8fa57905e16cdfcc4e9e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin 30V, Positive-QTOF	splash10-0udi-0493000000-2b88769e97319b5f076c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin 50V, Positive-QTOF	splash10-0udi-1940000000-51e0d426523f81faa98b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin 35V, Negative-QTOF	splash10-0gb9-0009000000-caca1c7784ed9828dfb4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin 10V, Negative-QTOF	splash10-014i-0009000000-0233e63233dadf52ffc5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin 30V, Negative-QTOF	splash10-0zfr-0952000000-13e1d438b3f800cfc18a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin 10V, Negative-QTOF	splash10-0gb9-0209000000-89d7fc697d82018c1228	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin 6V, Positive-QTOF	splash10-0gb9-0209000000-405d086d8e4de2b975b1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin 50V, Negative-QTOF	splash10-0a4i-1910000000-170b80b866f2075e44e9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin 6V, Positive-QTOF	splash10-014i-0029000000-a9da21c499e339f09ac6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin 6V, Positive-QTOF	splash10-0udi-0493000000-14bbb49d59d91543a76e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isorhamnetin 10V, Positive-QTOF	splash10-014i-0029000000-3458ddb4f7ba64eb81c8	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhamnetin 10V, Positive-QTOF	splash10-014i-0019000000-bb7cbcffdd9f296b6b9b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhamnetin 20V, Positive-QTOF	splash10-014i-0079000000-c73663231834b1b1b79a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhamnetin 40V, Positive-QTOF	splash10-0uds-3790000000-3b8ca78684ffcba51bf1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhamnetin 10V, Negative-QTOF	splash10-014i-0009000000-57dd2505d869c8f411dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhamnetin 20V, Negative-QTOF	splash10-014i-0169000000-38b50b4081dff638023b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isorhamnetin 40V, Negative-QTOF	splash10-0frb-3890000000-3525a3f4676b6a964b71	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Fibroblasts
Intestine
Leukocyte
Liver
Neuron
Pancreas
Platelet
Prostate

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0388 +/- 0.0454 uM	Adult (>18 years old)	Both	Normal	20851305	details
Blood	Detected and Quantified	0.0399 +/- 0.0450 uM	Adult (>18 years old)	Both	Normal	19747418	details
Blood	Detected and Quantified	0.043 (0.040-0.046) uM	Adult (>18 years old)	Not Specified	Normal	16294501	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0-0.157 uM	Adult (>18 years old)	Both	Normal	19747418	details
Urine	Detected and Quantified	0.00432 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	21272408	details
Urine	Detected and Quantified	0.0300 +/- 0.0300 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Detected and Quantified	0.0333 +/- 0.0333 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.02 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17426744	details
Urine	Detected and Quantified	0.02 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17426744	details
Urine	Detected and Quantified	0.0065 +/- 0.0065 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.019 +/- 0.0065 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 318	14969553	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 318	16197573	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 318	15595664	details
Urine	Detected and Quantified	0.0347 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	0.0546 +/- 0.0420 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	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

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

VMH ID

Not Available

MarkerDB ID

MDB00000395

Good Scents ID

rw1486311

References

Synthesis Reference

Heap, Tom; Robinson, Robert. Synthesis of kaempferide and of isorhamnetin. Journal of the Chemical Society (1926), 2336-44.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. [PubMed:11677047 ]
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. [PubMed:15237945 ]
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 ]
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 ]
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 ]
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. [PubMed:16323286 ]
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. [PubMed:15930439 ]
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. [PubMed:9246576 ]
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 ]
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. [PubMed:15613018 ]
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 ]
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. [PubMed:11750278 ]
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 ]
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. [PubMed:15190043 ]
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. Epub 2004 Nov 8. [PubMed:15533929 ]
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. [PubMed:12417109 ]
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. [PubMed:16298763 ]
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. [PubMed:11282099 ]
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. [PubMed:16197573 ]
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. [PubMed:12787887 ]
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. [PubMed:15493462 ]
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. 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. [PubMed:17374653 ]
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. Epub 2006 Jul 22. [PubMed:16963021 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Isorhamnetin → 6-{[3,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Isorhamnetin → 6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Isorhamnetin → 3,4,5-trihydroxy-6-[2-methoxy-4-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]oxane-2-carboxylic acid	details

Showing metabocard for Isorhamnetin (HMDB0002655)

MOL for HMDB0002655 (Isorhamnetin)

3D MOL for HMDB0002655 (Isorhamnetin)

3D SDF for HMDB0002655 (Isorhamnetin)

3D-SDF for HMDB0002655 (Isorhamnetin)

PDB for HMDB0002655 (Isorhamnetin)

3D PDB for HMDB0002655 (Isorhamnetin)

SMILES for HMDB0002655 (Isorhamnetin)

INCHI for HMDB0002655 (Isorhamnetin)

Structure for HMDB0002655 (Isorhamnetin)

3D Structure for HMDB0002655 (Isorhamnetin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions