NP-MRD: Showing NP-Card for 8-methylherbacetin (NP0050630)

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Record Information

Version

2.0

Created at

2022-04-27 21:59:38 UTC

Updated at

2022-04-27 21:59:38 UTC

NP-MRD ID

NP0050630

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-methylherbacetin

Description

3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-8-methoxy-4H-chromen-4-one, also known as herbacetin 8-methyl ether or 3,5,7,4'-tetrahydroxy-8-methoxyflavone, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-methoxy-4H-chromen-4-one is considered to be a flavonoid lipid molecule. 8-methylherbacetin is found in Askidiosperma paniculatum, Camellia japonica, Crataegus monogyna, Crataegus pinnatifida, Crataegus sanguinea, Dorycnium pentaphyllum, Enceliopsis nudicaulis, Eupatorium gracile, Fagonia mollis, Lotus corniculatus , Ozothamnus spp., Randonia africana, Rhodiola crenulata, Rhodiola rosea, Sorbus intermedia, Sedum grisebachii and Sedum sexangulare. 8-methylherbacetin was first documented in 2009 (PMID: 19683245). 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-8-methoxy-4H-chromen-4-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652308221903412D          

 23 25  0  0  0  0            999 V2000
   -1.4289    2.4750    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    1.4289    0.8250    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    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
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  7  1  0  0  0  0
 14 13  2  0  0  0  0
 15 10  2  0  0  0  0
 16 11  2  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 18  9  1  0  0  0  0
 19 10  1  0  0  0  0
 20 12  2  0  0  0  0
 21 13  1  0  0  0  0
 22  1  1  0  0  0  0
 22 15  1  0  0  0  0
 23 14  1  0  0  0  0
 23 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050630

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(O)C2=C1OC(=C(O)C2=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O7/c1-22-15-10(19)6-9(18)11-12(20)13(21)14(23-16(11)15)7-2-4-8(17)5-3-7/h2-6,17-19,21H,1H3

> <INCHI_KEY>
AZFYHRHUTXBGJS-UHFFFAOYSA-N

> <FORMULA>
C16H12O7

> <MOLECULAR_WEIGHT>
316.265

> <EXACT_MASS>
316.058302726

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.339148216790907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
2.30219352

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.173405555526791

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.891816445844215

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9640406880531858

> <JCHEM_POLAR_SURFACE_AREA>
116.45

> <JCHEM_REFRACTIVITY>
81.34450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sexangularetin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-AUG-19         0                                  
HETATM    1  C   UNK     0      -2.667   4.620   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       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2    4    7                                                       
CONECT    3    5    7                                                       
CONECT    4    2    8                                                       
CONECT    5    3    8                                                       
CONECT    6    9   10                                                       
CONECT    7    2    3   14                                                  
CONECT    8    4    5   17                                                  
CONECT    9    6   11   18                                                  
CONECT   10    6   15   19                                                  
CONECT   11    9   12   16                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14   21                                                  
CONECT   14    7   13   23                                                  
CONECT   15   10   16   22                                                  
CONECT   16   11   15   23                                                  
CONECT   17    8                                                            
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22    1   15                                                       
CONECT   23   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
3,5,7,4'-Tetrahydroxy-8-methoxyflavone	ChEBI
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-8-methoxy-chromen-4-one	ChEBI
8-Methoxykaempferol	ChEBI
Herbacetin 8-methyl ether	ChEBI

Chemical Formula

C₁₆H₁₂O₇

Average Mass

316.2650 Da

Monoisotopic Mass

316.05830 Da

IUPAC Name

3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-methoxy-4H-chromen-4-one

Traditional Name

sexangularetin

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(O)C2=C1OC(=C(O)C2=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H12O7/c1-22-15-10(19)6-9(18)11-12(20)13(21)14(23-16(11)15)7-2-4-8(17)5-3-7/h2-6,17-19,21H,1H3

InChI Key

AZFYHRHUTXBGJS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Askidiosperma paniculatum	LOTUS Database	35616633
Camellia japonica	LOTUS Database	35616633
Crataegus monogyna	LOTUS Database	35616633
Crataegus pinnatifida	LOTUS Database	35616633
Crataegus sanguinea	LOTUS Database	35616633
Dorycnium pentaphyllum	Plant	KNApSAcK
Enceliopsis nudicaulis	Plant	KNApSAcK
Eupatorium gracile	Plant	KNApSAcK
Fagonia mollis	LOTUS Database	35616633
Lotus corniculatus	Plant	KNApSAcK
Ozothamnus spp.	Plant	KNApSAcK
Randonia africana	LOTUS Database	35616633
Rhodiola crenulata	Plant	KNApSAcK
Rhodiola rosea	LOTUS Database	35616633
Scandosorbus intermedia	LOTUS Database	35616633
Sedum grisebachii	LOTUS Database	35616633
Sedum sexangulare	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

3-hydroxyflavone
8-methoxyflavonoid-skeleton
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
7-hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Anisole
Pyranone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyran
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Heteroaromatic compound
Ether
Polyol
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavone (CHEBI:9131 )
tetrahydroxyflavone (CHEBI:9131 )
7-hydroxyflavonol (CHEBI:9131 )
flavonols (C10185 )
Flavones and Flavonols (C10185 )
Flavones and Flavonols (LMPK12113150 )

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	1.92	ALOGPS
logP	2.3	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.89	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.34 m³·mol⁻¹	ChemAxon
Polarizability	30.34 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

HMDB0132128

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB089627

KNApSAcK ID

C00001100

Chemspider ID

Not Available

KEGG Compound ID

C10185

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281698

PDB ID

Not Available

ChEBI ID

9131

Good Scents ID

Not Available

References

General References

Truchado P, Ferreres F, Tomas-Barberan FA: Liquid chromatography-tandem mass spectrometry reveals the widespread occurrence of flavonoid glycosides in honey, and their potential as floral origin markers. J Chromatogr A. 2009 Oct 23;1216(43):7241-8. doi: 10.1016/j.chroma.2009.07.057. Epub 2009 Aug 3. [PubMed:19683245 ]

Showing NP-Card for 8-methylherbacetin (NP0050630)

MOL for NP0050630 (8-methylherbacetin)

3D MOL for NP0050630 (8-methylherbacetin)

3D SDF for NP0050630 (8-methylherbacetin)

3D-SDF for NP0050630 (8-methylherbacetin)

PDB for NP0050630 (8-methylherbacetin)

3D PDB for NP0050630 (8-methylherbacetin)

SMILES for NP0050630 (8-methylherbacetin)

INCHI for NP0050630 (8-methylherbacetin)

Structure for NP0050630 (8-methylherbacetin)

3D Structure for NP0050630 (8-methylherbacetin)