NP-MRD: Showing NP-Card for 6-Hydroxyluteolin (NP0048556)

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Record Information

Version

2.0

Created at

2022-03-17 20:58:19 UTC

Updated at

2022-03-17 20:58:19 UTC

NP-MRD ID

NP0048556

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Hydroxyluteolin

Description

6-Hydroxyluteolin, also known as 6-OH-luteolin, 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). Thus, 6-hydroxyluteolin is considered to be a flavonoid lipid molecule. 6-Hydroxyluteolin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 6-Hydroxyluteolin is found, on average, in the highest concentration within mexican oregano. 6-Hydroxyluteolin has also been detected, but not quantified in, a few different foods, such as common thymes, green vegetables, and lemon verbena. This could make 6-hydroxyluteolin a potential biomarker for the consumption of these foods. 6-Hydroxyluteolin is found in Aloysia citrodora, Artemisia tridentata, Buddleja globosa, Catalpa bignonioides, Centaurea bracteata, Centaurea bracteata Scop., Crocus sativus , Daphne laureola, Dendroviguiera quinqueradiata, Globularia bisnagarica, Globularia vulgaris, Lepidagathis cristata, Lippia citriodora , Phyla nodiflora, Lippia origanoides, Persicaria hydropiper, Polygonum hydropiper L. , Tabebuia caraiba, Tecoma australis, Thymus moroderi , Valerianella eriocarpa , Veronica hederifolia and Veronica triloba. 6-Hydroxyluteolin was first documented in 1999 (PMID: 10048707). A pentahydroxyflavone that is luteolin with an additional hydroxy group at position 6 (PMID: 12693635) (PMID: 19666078) (PMID: 21236437).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309152D          

 22 24  0  0  0  0            999 V2000
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  1  1  0  0  0  0
  6  3  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  7  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 11  4  2  0  0  0  0
 11  6  1  0  0  0  0
 12  5  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14 10  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16  7  1  0  0  0  0
 17  8  1  0  0  0  0
 18  9  2  0  0  0  0
 19 10  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22 11  1  0  0  0  0
 22 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048556

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C(O)=C1O)C(=O)C=C(O2)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O7/c16-7-2-1-6(3-8(7)17)11-4-9(18)13-12(22-11)5-10(19)14(20)15(13)21/h1-5,16-17,19-21H

> <INCHI_KEY>
VYAKIUWQLHRZGK-UHFFFAOYSA-N

> <FORMULA>
C15H10O7

> <MOLECULAR_WEIGHT>
302.2357

> <EXACT_MASS>
302.042652674

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
28.66922222876231

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5,6,7-trihydroxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.099558490333333

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.637832249485694

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.802642642111855

> <JCHEM_PKA_STRONGEST_BASIC>
-5.367697866974028

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
76.87570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxyluteolin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    7                                                       
CONECT    3    6    8                                                       
CONECT    4    9   11                                                       
CONECT    5   10   12                                                       
CONECT    6    1    3   11                                                  
CONECT    7    2    8   16                                                  
CONECT    8    3    7   17                                                  
CONECT    9    4   13   18                                                  
CONECT   10    5   14   19                                                  
CONECT   11    4    6   22                                                  
CONECT   12    5   13   22                                                  
CONECT   13    9   12   15                                                  
CONECT   14   10   15   20                                                  
CONECT   15   13   14   21                                                  
CONECT   16    7                                                            
CONECT   17    8                                                            
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-5,6,7-trihydroxy-4H-1-benzopyran-4-one	ChEBI
3',4',5,6,7-Pentahydroxyflavone	ChEBI
5,6,7,3',4'-Pentahydroxyflavone	ChEBI
2-(3,4-Dihydroxyphenyl)-5,6,7-trihydroxy-4H-chromen-4-one	HMDB
6-OH-Luteolin	HMDB

Chemical Formula

C₁₅H₁₀O₇

Average Mass

302.2357 Da

Monoisotopic Mass

302.04265 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,6,7-trihydroxy-4H-chromen-4-one

Traditional Name

6-hydroxyluteolin

CAS Registry Number

18003-33-3

SMILES

OC1=CC2=C(C(O)=C1O)C(=O)C=C(O2)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C15H10O7/c16-7-2-1-6(3-8(7)17)11-4-9(18)13-12(22-11)5-10(19)14(20)15(13)21/h1-5,16-17,19-21H

InChI Key

VYAKIUWQLHRZGK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aloysia citrodora	LOTUS Database	35616633
Aloysia triphylla	FooDB	KNAPSACK
Artemisia tridentata	LOTUS Database	35616633
Buddleja globosa	LOTUS Database	35616633
Catalpa bignonioides	Plant	KNApSAcK
Centaurea bracteata	LOTUS Database	35616633
Centaurea bracteata Scop.	Plant	KNApSAcK
Crocus sativus	Plant	KNApSAcK
Daphne laureola	LOTUS Database	35616633
Dendroviguiera quinqueradiata	LOTUS Database	35616633
Globularia bisnagarica	LOTUS Database	35616633
Globularia vulgaris	Plant	KNApSAcK
Lepidagathis cristata	LOTUS Database	35616633
Lippia citriodora	Plant	KNApSAcK
Lippia nodiflora	LOTUS Database	35616633
Lippia origanoides	LOTUS Database	35616633
Persicaria hydropiper	LOTUS Database	35616633
Polygonum hydropiper L.	Plant	KNApSAcK
Tabebuia caraiba	Plant	KNApSAcK
Tecoma australis	Plant	KNApSAcK
Thymus moroderi	Plant	KNApSAcK
Thymus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Valerianella eriocarpa	Plant	KNApSAcK
Veronica hederifolia	Plant	KNApSAcK
Veronica triloba	Plant	KNApSAcK

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pentahydroxyflavone (CHEBI:2197 )
flavones (C10072 )
Flavones and Flavonols (C10072 )
Flavones and Flavonols (LMPK12111229 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.36	ALOGPS
logP	2.1	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.8	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.88 m³·mol⁻¹	ChemAxon
Polarizability	28.67 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

External Links

HMDB ID

HMDB0036632

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281642

PDB ID

Not Available

ChEBI ID

2197

Good Scents ID

Not Available

References

General References

Yokozawa T, Dong E, Kawai Y, Gemba M, Shimizu M: Protective effects of some flavonoids on the renal cellular membrane. Exp Toxicol Pathol. 1999 Jan;51(1):9-14. doi: 10.1016/S0940-2993(99)80050-5. [PubMed:10048707 ]
Greenham J, Harborne JB, Williams CA: Identification of lipophilic flavones and flavonols by comparative HPLC, TLC and UV spectral analysis. Phytochem Anal. 2003 Mar-Apr;14(2):100-18. doi: 10.1002/pca.693. [PubMed:12693635 ]
Androutsopoulos VP, Ruparelia K, Arroo RR, Tsatsakis AM, Spandidos DA: CYP1-mediated antiproliferative activity of dietary flavonoids in MDA-MB-468 breast cancer cells. Toxicology. 2009 Oct 29;264(3):162-70. doi: 10.1016/j.tox.2009.07.023. Epub 2009 Aug 8. [PubMed:19666078 ]
de Beer D, Joubert E, Malherbe CJ, Jacobus Brand D: Use of countercurrent chromatography during isolation of 6-hydroxyluteolin-7-O-beta-glucoside, a major antioxidant of Athrixia phylicoides. J Chromatogr A. 2011 Sep 9;1218(36):6179-86. doi: 10.1016/j.chroma.2010.12.096. Epub 2010 Dec 29. [PubMed:21236437 ]

Showing NP-Card for 6-Hydroxyluteolin (NP0048556)

MOL for NP0048556 (6-Hydroxyluteolin)

3D MOL for NP0048556 (6-Hydroxyluteolin)

3D SDF for NP0048556 (6-Hydroxyluteolin)

3D-SDF for NP0048556 (6-Hydroxyluteolin)

PDB for NP0048556 (6-Hydroxyluteolin)

3D PDB for NP0048556 (6-Hydroxyluteolin)

SMILES for NP0048556 (6-Hydroxyluteolin)

INCHI for NP0048556 (6-Hydroxyluteolin)

Structure for NP0048556 (6-Hydroxyluteolin)

3D Structure for NP0048556 (6-Hydroxyluteolin)