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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

Physiological effect

Organoleptic effect

Odor

bitter

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0005800)

Membrane (HMDB: HMDB0005800)
Cell membrane (HMDB: HMDB0005800)

Biofluid or Excreta

Non-excretory biofluid

Blood (PMID: 19747418)

Excreta

Feces (PMID: 25037050)
Urine (PMID: 32966057)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0005800)

Source

Exogenous

Food

Food (HMDB: HMDB0005800)
Legumes (HMDB: HMDB0005800)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Nut

Pistachio (FooDB: FOOD00140)
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)
Hickory nut (FooDB: FOOD00377)
Hazelnut (FooDB: FOOD00376)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Nuts (HMDB: HMDB0005800)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Mixed nuts (FooDB: FOOD00771)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Common hazelnut (FooDB: FOOD00062)

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

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

Lentil

Lentils (FooDB: FOOD00098)

Fruit

Drupe

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

Tropical fruit

Pome

Berry

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)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Common grape (FooDB: FOOD00204)
Muscadine grape (FooDB: FOOD00203)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Canada blueberry (FooDB: FOOD00211)
Elliott's blueberry (FooDB: FOOD00210)
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)
Fox grape (FooDB: FOOD00228)
Summer grape (FooDB: FOOD00227)
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)
Strawberry (FooDB: FOOD00083)
Black mulberry (FooDB: FOOD00117)
Sea-buckthornberry (FooDB: FOOD00087)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)

Citrus

Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Pummelo (FooDB: FOOD00055)
Citrus (FooDB: FOOD00859)

Other fruit

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

Fruits (HMDB: HMDB0005800)

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)
Orange bell pepper (FooDB: FOOD00879)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)
Avocado (FooDB: FOOD00130)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)

Tuber

Leaf vegetable

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)
New Zealand spinach (FooDB: FOOD00415)
Malabar spinach (FooDB: FOOD00404)
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)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Common beet (FooDB: FOOD00025)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

Onion-family vegetable

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

Cabbage

Shoot vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Okra (FooDB: FOOD00420)
Nopal (FooDB: FOOD00416)
Sesbania flower (FooDB: FOOD00469)
Narrowleaf cattail (FooDB: FOOD00564)
Agave (FooDB: FOOD00563)
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: HMDB0005800)

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Cereal

Dough

Sourdough (FooDB: FOOD00275)

Cereal product

Pasta (FooDB: FOOD00273)
Semolina (FooDB: FOOD00745)
Bulgur (FooDB: FOOD00741)
Flour (FooDB: FOOD00799)
Biscuit (FooDB: FOOD00274)
Breakfast cereal (FooDB: FOOD00270)
Whole grain cereal products (HMDB: HMDB0005800)
Other cereal product (FooDB: FOOD00272)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Cereals and cereal products (FooDB: FOOD00858)

Gourd

Winter squash (FooDB: FOOD00283)
Calabash (FooDB: FOOD00318)
Butternut squash (FooDB: FOOD00317)
Chayote (FooDB: FOOD00325)
Wax gourd (FooDB: FOOD00499)
Towel gourd (FooDB: FOOD00492)
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)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)

Soy

Soy product

Soy bean (FooDB: FOOD00085)

Tea

Herbal tea

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

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Dish

Other dish

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

Ground meat

Sausage (FooDB: FOOD00652)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Alcoholic beverage

Red wine (HMDB: HMDB0005800)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Coffee and coffee product

Coffee

Coffee product

Coffee products (HMDB: HMDB0005800)

Fat and oil

Olive oil (HMDB: HMDB0005800)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0005800)

Cocoa product

Hot chocolate (FooDB: FOOD00688)

Cocoa

Cocoa bean (FooDB: FOOD00182)

Confectionery

Other confectionery

Honey (FooDB: FOOD00626)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0005800)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Flavone and Flavonol Biosynthesis (PathBank: SMP0012025)

EC 1.1.1.21 (aldehyde reductase) inhibitor (HMDB: HMDB0005800)
angiogenesis inhibitor (HMDB: HMDB0005800)
EC 1.14.14.14 (aromatase) inhibitor (HMDB: HMDB0005800)
beta-glucuronidase inhibitor (HMDB: HMDB0005800)
deiodinase inhibitor (HMDB: HMDB0005800)
hyaluronidase inhibitor (HMDB: HMDB0005800)
ICAM-1 inhibitor (HMDB: HMDB0005800)
IKK inhibitor (HMDB: HMDB0005800)
iNOS inhibitor (HMDB: HMDB0005800)
iodothyronine-deiodinase inhibitor (HMDB: HMDB0005800)
lipoxygenase inhibitor (HMDB: HMDB0005800)
mitogen-activated-protein-kinase inhibitor (HMDB: HMDB0005800)
metalloproteinase inhibitor (HMDB: HMDB0005800)
matrix metalloproteinase inhibitor (HMDB: HMDB0005800)
matrix-metalloproteinase-9 inhibitor (HMDB: HMDB0005800)
EC 3.4.24.* (metalloendopeptidase) inhibitor (HMDB: HMDB0005800)
neutral-endopeptidase inhibitor (HMDB: HMDB0005800)
NF-kappa-B inhibitor (HMDB: HMDB0005800)
nitric-oxide inhibitor (HMDB: HMDB0005800)
EC 2.7.11.13 (protein kinase C) inhibitor (HMDB: HMDB0005800)
prostaglandin-synthetase inhibitor (HMDB: HMDB0005800)
protein-tyrosine-kinase inhibitor (HMDB: HMDB0005800)
succinoxidase inhibitor (HMDB: HMDB0005800)
TNF-alpha inhibitor (HMDB: HMDB0005800)
EC 5.99.1.2 (DNA topoisomerase) inhibitor (HMDB: HMDB0005800)
VEGF inhibitor (HMDB: HMDB0005800)
EC 1.17.3.2 (xanthine oxidase) inhibitor (HMDB: HMDB0005800)

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

anti-allergic agent (HMDB: HMDB0005800)
antiviral agent (HMDB: HMDB0005800)
antineoplastic agent (HMDB: HMDB0005800)
diuretic (HMDB: HMDB0005800)
vasodilator agent (HMDB: HMDB0005800)

Agriculture

Pesticide

Insecticide

pesticide (HMDB: HMDB0005800)

Indirect biological role

antioxidant (HMDB: HMDB0005800)

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 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

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Luteolin GC-MS (4 TMS)	splash10-0bt9-0000190000-f355e064b0e4a8fee2a8	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Luteolin GC-MS (Non-derivatized)	splash10-0bt9-0001290000-3a6e4f4a889b4b595e3e	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Luteolin GC-MS (Non-derivatized)	splash10-0bt9-0000190000-f355e064b0e4a8fee2a8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Luteolin GC-MS (Non-derivatized)	splash10-0bt9-0001290000-3a6e4f4a889b4b595e3e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Luteolin GC-EI-TOF (Non-derivatized)	splash10-00dj-1735900000-66504e5cc81bcf3dd0a2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Luteolin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aou-0290000000-c72aa0a44afb34434ad5	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Luteolin GC-MS (4 TMS) - 70eV, Positive	splash10-0zmi-2040190000-5d0acf5ba2153f12546d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Luteolin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Luteolin 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 - Luteolin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive-QTOF	splash10-000i-0090000000-c8d8c5048f03b4f9ad5e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-000i-0490000000-b23f87f7af1af38d9686	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0f79-1940000000-006d75dee56e7481a44f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-000i-0290000000-e0e08b588cde4ec7d7c8	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-000i-0190000000-f142e0417f0f94a4623b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOF	splash10-0f79-1920000000-42c47240052ab59116f7	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-000i-0690000000-74dbeef56be77f266f6e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative-QTOF	splash10-001i-0900000000-4b5589ca157de0b5885b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin LC-ESI-ITTOF (LCMS-IT-TOF) , Positive-QTOF	splash10-000i-0090000000-7b507d1551bc27fa6952	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin LC-ESI-ITTOF (LCMS-IT-TOF) , Negative-QTOF	splash10-0079-0090080000-787383a28d957fc65a9e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin ESI-TOF , Negative-QTOF	splash10-000i-0090000000-03ffb3e4764e7236f82d	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin ESI-TOF 30V, Negative-QTOF	splash10-0a4i-0190000000-7f42ffe76ed9c3f69f11	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin ESI-TOF , Negative-QTOF	splash10-000i-0090000000-03ffb3e4764e7236f82d	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin ESI-TOF 30V, Negative-QTOF	splash10-0a4i-0190000000-7f42ffe76ed9c3f69f11	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin DI-ESI-qTof , Negative-QTOF	splash10-000i-0790000000-814cdaf9d50189cf2f2a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin DI-ESI-qTof , Positive-QTOF	splash10-0udr-0930000000-ad4b17e3762693841171	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin LC-ESI-QTOF , negative-QTOF	splash10-000i-0490000000-b23f87f7af1af38d9686	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin LC-ESI-QTOF , negative-QTOF	splash10-000i-0690000000-4135ff68dafc65e9f339	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Luteolin LC-ESI-QTOF , negative-QTOF	splash10-001i-0900000000-4b5589ca157de0b5885b	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 10V, Positive-QTOF	splash10-000i-0090000000-1682faadbefced000a71	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 20V, Positive-QTOF	splash10-000i-0090000000-fd32d917fb0b393a99aa	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 40V, Positive-QTOF	splash10-1000-5690000000-407bf2d6b008427648fa	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 10V, Negative-QTOF	splash10-000i-0090000000-c5cbc6ffe79c8cd57604	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 20V, Negative-QTOF	splash10-000i-0090000000-147d7dcca6436066ce44	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 40V, Negative-QTOF	splash10-0uxu-4960000000-ee3c93ba84300846c333	2015-05-27	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

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 Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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