NP-MRD: Showing NP-Card for Scutellarein (NP0045947)

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Record Information

Version

2.0

Created at

2022-03-17 19:45:50 UTC

Updated at

2022-03-17 19:45:51 UTC

NP-MRD ID

NP0045947

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Scutellarein

Description

5,6,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one, also known as 6-hydroxyapigenin or isocarthamidin, 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, 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one is considered to be a flavonoid lipid molecule. 5,6,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one has been detected, but not quantified in, winter savories. This could make 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one a potential biomarker for the consumption of these foods. Scutellarein is found in Achillea alpina, Ageratum conyzoides, Artemisia anomala, Artemisia douglasiana, Asphodeline globifera, Baptisia calycosa, Carthamus tinctorius, Caryopteris tangutica, Centaurea clementei, Centaurea jacea, Citrus sinensis, Clerodendron fragrans, Clerodendron phlomoides, Clerodendron serratum , Clerodendrum indicum, Clerodendrum phlomidis , Dicoma capensis, Digitalis grandiflora, Dittrichia graveolens, Duranta erecta, Duranta plumieri , Duranta repens, Erigeron breviscapus, Garcinia andamanica, Lippia origanoides, Lycopus asper, Millingtonia hortensis , Origanum majorana , Oroxylum indicum , Persicaria hydropiper, Polygonum viscosum, Plantago major, Polygonum hydropiper L. , Pulicaria dysenterica , Salvia officinalis , Scoparia dulcis , Scutellaria alpina, Scutellaria baicalensis, Scutellaria barbata , Scutellaria galericulata, Scutellaria immaculata, Scutellaria indica, Scutellaria lateriflora, Scutellaria rivularis , Scutellaria scandens, Scutellaria spp., Scutettaria baicalensis, Striga passargei and Volkameria inermis. Scutellarein was first documented in 2000 (PMID: 10724177). Flavone substituted with hydroxy groups at C-4', -5, -6 and -7.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309161706592D          

 21 23  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
   -1.4289   -0.0000    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
   -2.1434   -0.4125    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
    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
    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
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  7  1  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  5  2  0  0  0  0
 11  7  1  0  0  0  0
 12  6  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  8  1  0  0  0  0
 17  9  2  0  0  0  0
 18 10  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 11  1  0  0  0  0
 21 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045947

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C(O)=C2O

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

> <INCHI_KEY>
JVXZRQGOGOXCEC-UHFFFAOYSA-N

> <FORMULA>
C15H10O6

> <MOLECULAR_WEIGHT>
286.2363

> <EXACT_MASS>
286.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.72989978433684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
2.4031238119999996

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.198481855903111

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.750400042530137

> <JCHEM_PKA_STRONGEST_BASIC>
-5.3665190169673105

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
74.89480000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
scutellarein

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-SEP-17         0                                  
HETATM    1  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   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      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335  -0.000   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       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    3    7                                                       
CONECT    2    4    7                                                       
CONECT    3    1    8                                                       
CONECT    4    2    8                                                       
CONECT    5    9   11                                                       
CONECT    6   10   12                                                       
CONECT    7    1    2   11                                                  
CONECT    8    3    4   16                                                  
CONECT    9    5   13   17                                                  
CONECT   10    6   14   18                                                  
CONECT   11    5    7   21                                                  
CONECT   12    6   13   21                                                  
CONECT   13    9   12   15                                                  
CONECT   14   10   15   19                                                  
CONECT   15   13   14   20                                                  
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
4',5,6,7-Tetrahydroxyflavanone	ChEBI
5,6,7,4'-Tetrahydroxyflavone	ChEBI
5,6,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
6-Hydroxyapigenin	ChEBI
Isocarthamidin	ChEBI
4',5,6,7-Tetrahydroxy-flavanone	MeSH
6-Hydroxy-apigenin	MeSH

Chemical Formula

C₁₅H₁₀O₆

Average Mass

286.2363 Da

Monoisotopic Mass

286.04774 Da

IUPAC Name

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

Traditional Name

scutellarein

CAS Registry Number

529-53-3

SMILES

OC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C(O)=C2O

InChI Identifier

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

InChI Key

JVXZRQGOGOXCEC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achillea alpina	LOTUS Database	35616633
Ageratum conyzoides	LOTUS Database	35616633
Artemisia anomala	LOTUS Database	35616633
Artemisia douglasiana	LOTUS Database	35616633
Asphodeline globifera	Plant	KNApSAcK
Baptisia calycosa	Plant	KNApSAcK
Carthamus tinctorius	LOTUS Database	35616633
Caryopteris tangutica	LOTUS Database	35616633
Centaurea clementei	LOTUS Database	35616633
Centaurea jacea	Plant	KNApSAcK
Citrus sinensis	LOTUS Database	35616633
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Clerodendron fragrans	Plant	KNApSAcK
Clerodendron phlomoides	Plant	KNApSAcK
Clerodendron serratum	Plant	KNApSAcK
Clerodendrum indicum	LOTUS Database	35616633
Clerodendrum phlomidis	Plant	KNApSAcK
Dicoma capensis	LOTUS Database	35616633
Digitalis grandiflora	LOTUS Database	35616633
Dittrichia graveolens	LOTUS Database	35616633
Duranta erecta	LOTUS Database	35616633
Duranta plumieri	Plant	KNApSAcK
Duranta repens	Plant	KNApSAcK
Erigeron breviscapus	LOTUS Database	35616633
Garcinia andamanica	Plant	KNApSAcK
Lippia origanoides	LOTUS Database	35616633
Lycopus asper	LOTUS Database	35616633
Millingtonia hortensis	Plant	KNApSAcK
Origanum majorana	Plant	KNApSAcK
Oroxylum indicum	Plant	KNApSAcK
Persicaria hydropiper	LOTUS Database	35616633
Persicaria viscosa	Plant	KNApSAcK
Plantago major	LOTUS Database	35616633
Polygonum hydropiper L.	Plant	KNApSAcK
Pulicaria dysenterica	Plant	KNApSAcK
Salvia officinalis	Plant	KNApSAcK
Satureja montana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Scoparia dulcis	Plant	KNApSAcK
Scutellaria alpina	LOTUS Database	35616633
Scutellaria baicalensis	LOTUS Database	35616633
Scutellaria barbata	Plant	KNApSAcK
Scutellaria galericulata	LOTUS Database	35616633
Scutellaria immaculata	LOTUS Database	35616633
Scutellaria indica	Plant	KNApSAcK
Scutellaria lateriflora	LOTUS Database	35616633
Scutellaria rivularis	Plant	KNApSAcK
Scutellaria scandens	Plant	KNApSAcK
Scutellaria spp.	Plant	KNApSAcK
Scutettaria baicalensis	-	KNApSAcK
Striga passargei	LOTUS Database	35616633
Volkameria inermis	LOTUS Database	35616633

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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydroxyflavone (CHEBI:9062 )
flavones (C10184 )
flavanones (C10184 )
Flavones and Flavonols (LMPK12111160 )
a flavone (CPD-12726 )

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	2.74	ALOGPS
logP	2.4	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.75	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

External Links

HMDB ID

HMDB0128587

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Scutellarein

METLIN ID

Not Available

PubChem Compound

5281697

PDB ID

Not Available

ChEBI ID

9062

Good Scents ID

Not Available

References

General References

Nagashima S, Hirotani M, Yoshikawa T: Purification and characterization of UDP-glucuronate: baicalein 7-O-glucuronosyltransferase from Scutellaria baicalensis Georgi. cell suspension cultures. Phytochemistry. 2000 Mar;53(5):533-8. doi: 10.1016/s0031-9422(99)00593-2. [PubMed:10724177 ]

Showing NP-Card for Scutellarein (NP0045947)

MOL for NP0045947 (Scutellarein)

3D MOL for NP0045947 (Scutellarein)

3D SDF for NP0045947 (Scutellarein)

3D-SDF for NP0045947 (Scutellarein)

PDB for NP0045947 (Scutellarein)

3D PDB for NP0045947 (Scutellarein)

SMILES for NP0045947 (Scutellarein)

INCHI for NP0045947 (Scutellarein)

Structure for NP0045947 (Scutellarein)

3D Structure for NP0045947 (Scutellarein)