NP-MRD: Showing NP-Card for 8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one (NP0159842)

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Record Information

Version

2.0

Created at

2022-09-02 17:39:55 UTC

Updated at

2022-09-02 17:39:55 UTC

NP-MRD ID

NP0159842

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one

Description

AC1NSXAL belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. 8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one is found in Afrocarpus gracilior, Araucaria araucana, Taxus cuspidata and Taxus wallichiana. AC1NSXAL is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261500492D          

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  Mrv1533004261500492D          

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    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 35 42  1  0  0  0  0
 42 43  1  0  0  0  0
 31 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159842

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(OC)C(=C2O1)C1=CC(OC)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C33H24O10/c1-39-18-6-4-16(5-7-18)26-13-24(37)32-25(38)15-28(41-3)30(33(32)43-26)21-12-19(40-2)8-9-20(21)27-14-23(36)31-22(35)10-17(34)11-29(31)42-27/h4-15,34-35,38H,1-3H3

> <INCHI_KEY>
IMQNAOBCKHPLGV-UHFFFAOYSA-N

> <FORMULA>
C33H24O10

> <MOLECULAR_WEIGHT>
580.545

> <EXACT_MASS>
580.136946973

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
57.766555172125564

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-[2-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
4.96

> <JCHEM_LOGP>
5.525039981333332

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
7.0266306337814175

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.1222695225071515

> <JCHEM_PKA_STRONGEST_BASIC>
-4.37171265842582

> <JCHEM_POLAR_SURFACE_AREA>
140.98000000000002

> <JCHEM_REFRACTIVITY>
158.3529

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.19e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -9.499  -7.392   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -9.975  -5.927   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -8.944  -4.783   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.420  -3.318   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.390  -2.174   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.883  -2.494   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.407  -3.959   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.438  -5.103   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.853  -1.349   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.329   0.115   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.298   1.260   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.774   2.724   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.792   0.939   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.761   2.084   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.237   3.549   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.255   1.764   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.779   0.299   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.727  -0.021   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.758   1.123   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.810  -0.845   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.316  -0.525   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.346  -1.670   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   21                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   23                                                  
CONECT   21   20   13   22                                                  
CONECT   22   21    9                                                       
CONECT   23   20   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   23   31                                                  
CONECT   31   30   32   43                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   42                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   35   43                                                  
CONECT   43   42   31                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₂₄O₁₀

Average Mass

580.5450 Da

Monoisotopic Mass

580.13695 Da

IUPAC Name

8-[2-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(OC)C(=C2O1)C1=CC(OC)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C33H24O10/c1-39-18-6-4-16(5-7-18)26-13-24(37)32-25(38)15-28(41-3)30(33(32)43-26)21-12-19(40-2)8-9-20(21)27-14-23(36)31-22(35)10-17(34)11-29(31)42-27/h4-15,34-35,38H,1-3H3

InChI Key

IMQNAOBCKHPLGV-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Afrocarpus gracilior	LOTUS Database	35616633
Araucaria araucana	LOTUS Database	35616633
Taxus cuspidata	LOTUS Database	35616633
Taxus wallichiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	4.96	ALOGPS
logP	5.53	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	6.12	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	140.98 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	158.35 m³·mol⁻¹	ChemAxon
Polarizability	57.77 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318788

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one (NP0159842)

MOL for NP0159842 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one)

3D MOL for NP0159842 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one)

3D SDF for NP0159842 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one)

3D-SDF for NP0159842 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one)

PDB for NP0159842 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one)

3D PDB for NP0159842 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one)

SMILES for NP0159842 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one)

INCHI for NP0159842 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one)

Structure for NP0159842 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one)

3D Structure for NP0159842 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-methoxyphenyl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one)