NP-MRD: Showing NP-Card for 5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-7-methoxychromen-4-one (NP0179779)

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Record Information

Version

2.0

Created at

2022-09-03 18:01:00 UTC

Updated at

2022-09-03 18:01:00 UTC

NP-MRD ID

NP0179779

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-7-methoxychromen-4-one

Description

5-Hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl]oxy}phenyl)-7-methoxy-4H-chromen-4-one 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. 5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-7-methoxychromen-4-one is found in Selaginella delicatula. 5-Hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl]oxy}phenyl)-7-methoxy-4H-chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261500502D          

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M  END

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  Mrv1533004261500502D          

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    4.2868   -2.4750    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
  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  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 20 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 27 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 34 40  1  0  0  0  0
 18 41  1  0  0  0  0
 41 42  2  0  0  0  0
 15 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0179779

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(OC2=C(O)C3=C(OC(CC3=O)C3=CC=C(O)C=C3)C=C2OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H24O10/c1-38-20-11-21(34)29-22(35)13-24(41-26(29)12-20)17-5-9-19(10-6-17)40-32-28(39-2)15-27-30(31(32)37)23(36)14-25(42-27)16-3-7-18(33)8-4-16/h3-13,15,25,33-34,37H,14H2,1-2H3

> <INCHI_KEY>
GRDGMXLERDFPHE-UHFFFAOYSA-N

> <FORMULA>
C32H24O10

> <MOLECULAR_WEIGHT>
568.534

> <EXACT_MASS>
568.136946973

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
58.76562998595405

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl]oxy}phenyl)-7-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
4.88

> <JCHEM_LOGP>
5.664191984666666

> <ALOGPS_LOGS>
-5.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.903454418792241

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.218381890468504

> <JCHEM_PKA_STRONGEST_BASIC>
-3.708779714435298

> <JCHEM_POLAR_SURFACE_AREA>
140.98000000000002

> <JCHEM_REFRACTIVITY>
151.37019999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-7-methoxychromen-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      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  11.550   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  11.550   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -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  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13    3                                                       
CONECT   15   11   16   42                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   41                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   31                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   23   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   20   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   27   35   40                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   34                                                       
CONECT   41   18   42                                                       
CONECT   42   41   15                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₂₄O₁₀

Average Mass

568.5340 Da

Monoisotopic Mass

568.13695 Da

IUPAC Name

5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl]oxy}phenyl)-7-methoxy-4H-chromen-4-one

Traditional Name

5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-7-methoxychromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(OC2=C(O)C3=C(OC(CC3=O)C3=CC=C(O)C=C3)C=C2OC)C=C1

InChI Identifier

InChI=1S/C32H24O10/c1-38-20-11-21(34)29-22(35)13-24(41-26(29)12-20)17-5-9-19(10-6-17)40-32-28(39-2)15-27-30(31(32)37)23(36)14-25(42-27)16-3-7-18(33)8-4-16/h3-13,15,25,33-34,37H,14H2,1-2H3

InChI Key

GRDGMXLERDFPHE-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
Selaginella delicatula	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

7-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Flavone
Hydroxyflavonoid
Flavan
Chromone
Diaryl ether
Chromane
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Aryl alkyl ketone
Phenol ether
Aryl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Benzenoid
Pyran
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen 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	4.88	ALOGPS
logP	5.66	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	7.22	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	140.98 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	151.37 m³·mol⁻¹	ChemAxon
Polarizability	58.77 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	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-7-methoxychromen-4-one (NP0179779)

MOL for NP0179779 (5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-7-methoxychromen-4-one)

3D MOL for NP0179779 (5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-7-methoxychromen-4-one)

3D SDF for NP0179779 (5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-7-methoxychromen-4-one)

3D-SDF for NP0179779 (5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-7-methoxychromen-4-one)

PDB for NP0179779 (5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-7-methoxychromen-4-one)

3D PDB for NP0179779 (5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-7-methoxychromen-4-one)

SMILES for NP0179779 (5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-7-methoxychromen-4-one)

INCHI for NP0179779 (5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-7-methoxychromen-4-one)

Structure for NP0179779 (5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-7-methoxychromen-4-one)

3D Structure for NP0179779 (5-hydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-7-methoxychromen-4-one)