NP-MRD: Showing NP-Card for 8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one (NP0177396)

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Record Information

Version

2.0

Created at

2022-09-03 15:13:47 UTC

Updated at

2022-09-03 15:13:47 UTC

NP-MRD ID

NP0177396

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

2',8'-Biapigenin 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). 8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one is found in Selaginella tamariscina. 2',8'-Biapigenin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171519302D          

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M  END

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  Mrv1533004171519302D          

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 39 40  1  0  0  0  0
 28 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0177396

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C(=C2O1)C1=CC(O)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C30H18O10/c31-14-3-1-13(2-4-14)24-11-23(38)29-21(36)10-20(35)27(30(29)40-24)18-7-15(32)5-6-17(18)25-12-22(37)28-19(34)8-16(33)9-26(28)39-25/h1-12,31-36H

> <INCHI_KEY>
IDXPHFRRYHNPFG-UHFFFAOYSA-N

> <FORMULA>
C30H18O10

> <MOLECULAR_WEIGHT>
538.464

> <EXACT_MASS>
538.08999678

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
51.66829286768539

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.47

> <JCHEM_LOGP>
5.087357813333332

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.338472818212435

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.714769210819254

> <JCHEM_PKA_STRONGEST_BASIC>
-6.3948559936005624

> <JCHEM_POLAR_SURFACE_AREA>
173.98

> <JCHEM_REFRACTIVITY>
144.90599999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.30e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0     -10.669  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002  -3.080   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      -5.335   1.540   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  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.532   0.161   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   19                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   21                                                  
CONECT   19   18   12   20                                                  
CONECT   20   19    8                                                       
CONECT   21   18   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   21   28                                                  
CONECT   28   27   29   40                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   39                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   32   40                                                  
CONECT   40   39   28                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
2'8'-Biapigenin	ChEMBL

Chemical Formula

C₃₀H₁₈O₁₀

Average Mass

538.4640 Da

Monoisotopic Mass

538.09000 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C(=C2O1)C1=CC(O)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C30H18O10/c31-14-3-1-13(2-4-14)24-11-23(38)29-21(36)10-20(35)27(30(29)40-24)18-7-15(32)5-6-17(18)25-12-22(37)28-19(34)8-16(33)9-26(28)39-25/h1-12,31-36H

InChI Key

IDXPHFRRYHNPFG-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 tamariscina	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
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Biphenol
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
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	4.47	ALOGPS
logP	5.09	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	5.71	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	144.91 m³·mol⁻¹	ChemAxon
Polarizability	51.67 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

11958336

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-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one (NP0177396)

MOL for NP0177396 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D MOL for NP0177396 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D SDF for NP0177396 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D-SDF for NP0177396 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

PDB for NP0177396 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D PDB for NP0177396 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

SMILES for NP0177396 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

INCHI for NP0177396 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

Structure for NP0177396 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D Structure for NP0177396 (8-[2-(5,7-dihydroxy-4-oxochromen-2-yl)-5-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)