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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-01-22 22:39:32 UTC

Update Date

2022-03-07 02:49:29 UTC

HMDB ID

HMDB0005800

Secondary Accession Numbers

HMDB05800

Metabolite Identification

Common Name

Luteolin

Description

Luteolin is a naturally occurring flavonoid. (PMID:17168665 ). The flavonoids are polyphenolic compounds found as integral components of the human diet. They are universally present as constituents of flowering plants, particularly of food plants. The flavonoids are phenyl substituted chromones (benzopyran derivatives) consisting of a 15-carbon basic skeleton (C6-C3-C6), composed of a chroman (C6-C3) nucleus (the benzo ring A and the heterocyclic ring C), also shared by the tocopherols, with a phenyl (the aromatic ring B) substitution usually at the 2-position. Different substitutions can typically occur in the rings, A and B. Several plants and spices containing flavonoid derivatives have found application as disease preventive and therapeutic agents in traditional medicine in Asia for thousands of years. The selection of a particular food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. The much lower risk of colon, prostate and breast cancers in Asians, who consume more vegetables, fruits and tea than populations in the Western hemisphere do, raises the question of whether flavonoid components mediate the protective effects of diets rich in these foodstuffs by acting as natural chemopreventive and anticancer agents. An impressive body of information exists on the antitumoral action of plant flavonoids. In vitro work has concentrated on the direct and indirect actions of flavonoids on tumor cells, and has found a variety of anticancer effects such as cell growth and kinase activity inhibition, apoptosis induction, suppression of the secretion of matrix metalloproteinases and of tumor invasive behavior. Furthermore, some studies have reported the impairment of in vivo angiogenesis by dietary flavonoids. Experimental animal studies indicate that certain dietary flavonoids possess antitumoral activity. The hydroxylation pattern of the B ring of the flavones and flavonols, such as luteolin seems to critically influence their activities, especially the inhibition of protein kinase activity and antiproliferation. The different mechanisms underlying the potential anticancer action of plant flavonoids await further elucidation. Certain dietary flavonols and flavones targeting cell surface signal transduction enzymes, such as protein tyrosine and focal adhesion kinases, and the processes of angiogenesis appear to be promising candidates as anticancer agents. Further in vivo studies of these bioactive constituents is deemed necessary in order to develop flavonoid-based anticancer strategies. In view of the increasing interest in the association between dietary flavonoids and cancer initiation and progression, this important field is likely to witness expanded effort and to attract and stimulate further vigorous investigations (PMID:16097445 ).

Structure

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

HMDB0005800
     RDKit          3D
Luteolin
 31 33  0  0  0  0  0  0  0  0999 V2000
    2.2961    2.3283    1.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358    1.4002    1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499    1.4062    1.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3214    0.4160    0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781    0.4383    0.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5696    1.4458    0.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9558    1.4350    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5402    0.3914   -0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9099    0.3401   -0.3799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7676   -0.6487   -0.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3948   -1.6807   -1.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4150   -0.5909   -0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3947   -0.5669   -0.0949 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7067   -0.6282    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3859   -1.7109   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7517   -1.7888   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4043   -2.8833   -0.9273 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4798   -0.8359    0.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8290    0.2768    0.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5661    1.2197    1.4846 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4519    0.3488    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558    2.2555    1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1158    2.2643    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5328    2.2519    0.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5480    1.0338   -0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9258   -2.4598   -1.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8047   -1.3788   -0.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072   -2.4813   -1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7120   -2.7578   -1.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5537   -0.8653    0.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3107    2.0252    1.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21  2  1  0
 12  5  1  0
 21 14  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  1  0
M  END


  Mrv1652309272007352D          

 21 23  0  0  0  0            999 V2000
   15.8257    2.1216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1103    0.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1091   -0.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8231   -0.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8213    0.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5359    0.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5394   -0.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2577   -0.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9774   -0.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9739    0.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2509    0.8831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2600   -1.6053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8217   -1.6048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3965    0.8699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6861    0.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4041    0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1161    0.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1139    1.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3940    2.1160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6849    1.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3884    2.9401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  5  2  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  8 12  2  0  0  0  0
  4 13  1  0  0  0  0
  2 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2  3  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  3  4  1  0  0  0  0
 18 19  1  0  0  0  0
  4  7  2  0  0  0  0
 19 20  2  0  0  0  0
 20 15  1  0  0  0  0
 19 21  1  0  0  0  0
 18  1  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005800

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H

> <INCHI_KEY>
IQPNAANSBPBGFQ-UHFFFAOYSA-N

> <FORMULA>
C15H10O6

> <MOLECULAR_WEIGHT>
286.2363

> <EXACT_MASS>
286.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.727516971367624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
2.4031238119999996

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.069737468610946

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.574503413930256

> <JCHEM_PKA_STRONGEST_BASIC>
-5.382358240962719

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
74.8948

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
luteolin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005800
     RDKit          3D
Luteolin
 31 33  0  0  0  0  0  0  0  0999 V2000
    2.2961    2.3283    1.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358    1.4002    1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499    1.4062    1.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3214    0.4160    0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781    0.4383    0.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5696    1.4458    0.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9558    1.4350    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5402    0.3914   -0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9099    0.3401   -0.3799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7676   -0.6487   -0.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3948   -1.6807   -1.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4150   -0.5909   -0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3947   -0.5669   -0.0949 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7067   -0.6282    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3859   -1.7109   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7517   -1.7888   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4043   -2.8833   -0.9273 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4798   -0.8359    0.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8290    0.2768    0.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5661    1.2197    1.4846 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4519    0.3488    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558    2.2555    1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1158    2.2643    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5328    2.2519    0.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5480    1.0338   -0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9258   -2.4598   -1.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8047   -1.3788   -0.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072   -2.4813   -1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7120   -2.7578   -1.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5537   -0.8653    0.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3107    2.0252    1.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21  2  1  0
 12  5  1  0
 21 14  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  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      29.541   3.960   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      18.873   0.855   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.870  -0.688   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.203  -1.457   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.200   1.625   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.534   0.862   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.540  -0.691   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.881  -1.458   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.225  -0.680   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.218   0.873   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      22.868   1.648   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      22.885  -2.997   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      20.200  -2.996   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      17.540   1.624   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      25.547   1.646   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.888   0.873   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.217   1.645   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.213   3.185   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.869   3.950   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.545   3.174   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      26.858   5.488   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    5   14    3                                                  
CONECT    3    2    4                                                       
CONECT    4   13    3    7                                                  
CONECT    5    6    2                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11    6   10                                                       
CONECT   12    8                                                            
CONECT   13    4                                                            
CONECT   14    2                                                            
CONECT   15   10   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19    1                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   15                                                       
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0005800
HETATM    1  O1  UNL     1       2.296   2.328   1.838  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.736   1.400   1.225  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.350   1.406   1.049  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.321   0.416   0.385  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.778   0.438   0.211  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.570   1.446   0.695  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.956   1.435   0.510  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.540   0.391  -0.173  1.00  0.00           C  
HETATM    9  O2  UNL     1      -5.910   0.340  -0.380  1.00  0.00           O  
HETATM   10  C8  UNL     1      -3.768  -0.649  -0.680  1.00  0.00           C  
HETATM   11  O3  UNL     1      -4.395  -1.681  -1.362  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.415  -0.591  -0.471  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.395  -0.567  -0.095  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.707  -0.628   0.039  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.386  -1.711  -0.505  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.752  -1.789  -0.374  1.00  0.00           C  
HETATM   17  O5  UNL     1       4.404  -2.883  -0.927  1.00  0.00           O  
HETATM   18  C13 UNL     1       4.480  -0.836   0.276  1.00  0.00           C  
HETATM   19  C14 UNL     1       3.829   0.277   0.840  1.00  0.00           C  
HETATM   20  O6  UNL     1       4.566   1.220   1.485  1.00  0.00           O  
HETATM   21  C15 UNL     1       2.452   0.349   0.704  1.00  0.00           C  
HETATM   22  H1  UNL     1      -0.156   2.255   1.479  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.116   2.264   1.231  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.533   2.252   0.912  1.00  0.00           H  
HETATM   25  H4  UNL     1      -6.548   1.034  -0.058  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.926  -2.460  -1.755  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.805  -1.379  -0.852  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.807  -2.481  -1.028  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.712  -2.758  -1.903  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.554  -0.865   0.397  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.311   2.025   1.921  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4    4   22
CONECT    4    5   13
CONECT    5    6    6   12
CONECT    6    7   23
CONECT    7    8    8   24
CONECT    8    9   10
CONECT    9   25
CONECT   10   11   12   12
CONECT   11   26
CONECT   12   27
CONECT   13   14
CONECT   14   15   15   21
CONECT   15   16   28
CONECT   16   17   18   18
CONECT   17   29
CONECT   18   19   30
CONECT   19   20   21   21
CONECT   20   31
END

HMDB0005800
     RDKit          3D
Luteolin
 31 33  0  0  0  0  0  0  0  0999 V2000
    2.2961    2.3283    1.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358    1.4002    1.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3499    1.4062    1.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3214    0.4160    0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781    0.4383    0.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5696    1.4458    0.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9558    1.4350    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5402    0.3914   -0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9099    0.3401   -0.3799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7676   -0.6487   -0.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3948   -1.6807   -1.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4150   -0.5909   -0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3947   -0.5669   -0.0949 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7067   -0.6282    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3859   -1.7109   -0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7517   -1.7888   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4043   -2.8833   -0.9273 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4798   -0.8359    0.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8290    0.2768    0.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5661    1.2197    1.4846 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4519    0.3488    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558    2.2555    1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1158    2.2643    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5328    2.2519    0.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5480    1.0338   -0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9258   -2.4598   -1.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8047   -1.3788   -0.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072   -2.4813   -1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7120   -2.7578   -1.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5537   -0.8653    0.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3107    2.0252    1.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21  2  1  0
 12  5  1  0
 21 14  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-benzopyrone	ChEBI
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one	ChEBI
3',4',5,7-Tetrahydroxyflavone	ChEBI
5,7,3',4'-Tetrahydroxyflavone	ChEBI
Digitoflavone	ChEBI
Flacitran	ChEBI
Luteolol	ChEBI
Salifazide	ChEBI
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyrone-4-one	HMDB
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one	HMDB
Luteoline	MeSH, HMDB
3',4',5,7-Tetrahydroxy-flavone	MeSH, HMDB
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-one	PhytoBank
3’,4’,5,7-Tetrahydroxyflavone	PhytoBank
5,7,3’,4’-Tetrahydroxyflavone	PhytoBank
Cyanidenon	PhytoBank

Chemical Formula

C₁₅H₁₀O₆

Average Molecular Weight

286.2363

Monoisotopic Molecular Weight

286.047738052

IUPAC Name

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

Traditional Name

luteolin

CAS Registry Number

491-70-3

SMILES

OC1=CC2=C(C(O)=C1)C(=O)C=C(O2)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H

InChI Key

IQPNAANSBPBGFQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydroxyflavone (CHEBI:15864 )
3'-hydroxyflavonoid (CHEBI:15864 )
flavones (C01514 )
Flavones and Flavonols (C01514 )
Flavones and Flavonols (LMPK12110006 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	329.5 °C	Not Available
Boiling Point	616.00 to 617.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	387.5 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.53	PERRISSOUD,D & TESTA,B (1986)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.73	ALOGPS
logP	2.4	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.57	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.89 m³·mol⁻¹	ChemAxon
Polarizability	27.73 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]+	166.587	30932474
DeepCCS	[M-H]-	164.229	30932474
DeepCCS	[M-2H]-	197.719	30932474
DeepCCS	[M+Na]+	172.946	30932474
AllCCS	[M+H]+	164.5	32859911
AllCCS	[M+H-H2O]+	160.7	32859911
AllCCS	[M+NH4]+	168.0	32859911
AllCCS	[M+Na]+	169.1	32859911
AllCCS	[M-H]-	163.4	32859911
AllCCS	[M+Na-2H]-	162.7	32859911
AllCCS	[M+HCOO]-	162.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.11 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4383 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.61 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1908.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	276.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	113.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	160.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	449.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	540.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	444.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	190.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	784.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	376.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1384.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	311.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	342.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	528.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	247.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	242.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Luteolin	OC1=CC2=C(C(O)=C1)C(=O)C=C(O2)C1=CC=C(O)C(O)=C1	5101.5	Standard polar	33892256
Luteolin	OC1=CC2=C(C(O)=C1)C(=O)C=C(O2)C1=CC=C(O)C(O)=C1	3118.6	Standard non polar	33892256
Luteolin	OC1=CC2=C(C(O)=C1)C(=O)C=C(O2)C1=CC=C(O)C(O)=C1	3285.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Luteolin,1TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C(O)=C3)OC2=C1	3321.5	Semi standard non polar	33892256
Luteolin,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C=C(C1=CC=C(O)C(O)=C1)O2	3267.0	Semi standard non polar	33892256
Luteolin,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O	3339.1	Semi standard non polar	33892256
Luteolin,1TMS,isomer #4	C[Si](C)(C)OC1=CC(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O	3316.9	Semi standard non polar	33892256
Luteolin,2TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C(O)=C3)OC2=C1	3228.0	Semi standard non polar	33892256
Luteolin,2TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C)C(O)=C3)OC2=C1	3318.8	Semi standard non polar	33892256
Luteolin,2TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3286.4	Semi standard non polar	33892256
Luteolin,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1O	3223.0	Semi standard non polar	33892256
Luteolin,2TMS,isomer #5	C[Si](C)(C)OC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC=C1O	3190.1	Semi standard non polar	33892256
Luteolin,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C	3181.9	Semi standard non polar	33892256
Luteolin,3TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C)C(O)=C3)OC2=C1	3235.5	Semi standard non polar	33892256
Luteolin,3TMS,isomer #2	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3200.6	Semi standard non polar	33892256
Luteolin,3TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3097.9	Semi standard non polar	33892256
Luteolin,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1O[Si](C)(C)C	3045.5	Semi standard non polar	33892256
Luteolin,4TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3159.3	Semi standard non polar	33892256
Luteolin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C(O)=C3)OC2=C1	3594.4	Semi standard non polar	33892256
Luteolin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C=C(C1=CC=C(O)C(O)=C1)O2	3534.3	Semi standard non polar	33892256
Luteolin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O	3594.6	Semi standard non polar	33892256
Luteolin,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O	3572.9	Semi standard non polar	33892256
Luteolin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C(O)=C3)OC2=C1	3797.4	Semi standard non polar	33892256
Luteolin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C1	3860.3	Semi standard non polar	33892256
Luteolin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3834.2	Semi standard non polar	33892256
Luteolin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C1O	3797.1	Semi standard non polar	33892256
Luteolin,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC=C1O	3745.5	Semi standard non polar	33892256
Luteolin,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C	3780.0	Semi standard non polar	33892256
Luteolin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C1	4000.9	Semi standard non polar	33892256
Luteolin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3972.2	Semi standard non polar	33892256
Luteolin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3940.9	Semi standard non polar	33892256
Luteolin,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C	3863.4	Semi standard non polar	33892256
Luteolin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4067.2	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0999 +/- 0.0977 uM	Adult (>18 years old)	Both	Normal	19747418	details
Blood	Detected and Quantified	0.101 +/- 0.0985 uM	Adult (>18 years old)	Both	Normal	20851305	details
Blood	Detected and Quantified	0-0.288 uM	Adult (>18 years old)	Both	Normal	19747418	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

5734-TETRAHYDROXYFLAVONE

BiGG ID

Not Available

Wikipedia Link

Luteolin

METLIN ID

Not Available

PubChem Compound

5280445

PDB ID

LU2

ChEBI ID

15864

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1504531

References

Synthesis Reference

Hutchins, W. A.; Wheeler, T. S. Chalcones: A new synthesis of chrysin, apigenin and luteolin. Journal of the Chemical Society (1939), 91-4.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Lupu R, Menendez JA: Pharmacological inhibitors of Fatty Acid Synthase (FASN)--catalyzed endogenous fatty acid biogenesis: a new family of anti-cancer agents? Curr Pharm Biotechnol. 2006 Dec;7(6):483-93. [PubMed:17168665 ]
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 ]

Enzymes

Enzyme Details

1. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

Reactions

Luteolin → Chrysoeriol	details

Enzyme Details

2. 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

Luteolin → 6-{[2-(3,4-dihydroxyphenyl)-7-hydroxy-4-oxo-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Luteolin → 6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Luteolin → 6-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Luteolin → 6-[4-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

3. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

Luteolin → [5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]oxidanesulfonic acid	details

Showing metabocard for Luteolin (HMDB0005800)

MOL for HMDB0005800 (Luteolin)

3D MOL for HMDB0005800 (Luteolin)

3D SDF for HMDB0005800 (Luteolin)

3D-SDF for HMDB0005800 (Luteolin)

PDB for HMDB0005800 (Luteolin)

3D PDB for HMDB0005800 (Luteolin)

SMILES for HMDB0005800 (Luteolin)

INCHI for HMDB0005800 (Luteolin)

Structure for HMDB0005800 (Luteolin)

3D Structure for HMDB0005800 (Luteolin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions

Reactions