NP-MRD: Showing NP-Card for 5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-[3,6'-bichromene]-4,4'-dione (NP0203705)

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Record Information

Version

2.0

Created at

2022-09-04 23:13:43 UTC

Updated at

2022-09-04 23:13:43 UTC

NP-MRD ID

NP0203705

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-[3,6'-bichromene]-4,4'-dione

Description

5,5',7,7'-Tetrahydroxy-2'-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-4H,4'H-[3,6'-bichromene]-4,4'-dione belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton. 5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-[3,6'-bichromene]-4,4'-dione is found in Selaginella delicatula. 5,5',7,7'-Tetrahydroxy-2'-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-4H,4'H-[3,6'-bichromene]-4,4'-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201501522D          

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M  END

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  Mrv1533004201501522D          

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 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 26 32  1  0  0  0  0
 32 33  2  0  0  0  0
 22 33  1  0  0  0  0
 33 34  1  0  0  0  0
 28 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 35 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0203705

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=C(C(=O)C2=C(O)C=C(O)C=C2O1)C1=C(O)C=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H20O10/c1-39-18-8-4-15(5-9-18)31-28(30(38)25-19(34)10-17(33)11-23(25)41-31)27-21(36)13-24-26(29(27)37)20(35)12-22(40-24)14-2-6-16(32)7-3-14/h2-13,32-34,36-37H,1H3

> <INCHI_KEY>
CWDHFSUXDBJDID-UHFFFAOYSA-N

> <FORMULA>
C31H20O10

> <MOLECULAR_WEIGHT>
552.491

> <EXACT_MASS>
552.105646844

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
55.84994455956312

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-6-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
4.66

> <JCHEM_LOGP>
5.254114302666666

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.511830912377257

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.701222321648416

> <JCHEM_PKA_STRONGEST_BASIC>
-4.725931721449145

> <JCHEM_POLAR_SURFACE_AREA>
162.98

> <JCHEM_REFRACTIVITY>
148.70419999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.96e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-6-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -5.390   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       0.000  -3.080   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  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.573  -4.326   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+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   21                                                  
CONECT   10    9   11   22                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   13   21                                                  
CONECT   21   20    9                                                       
CONECT   22   10   23   33                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   26   33                                                  
CONECT   33   32   22   34                                                  
CONECT   34   33                                                            
CONECT   35   28   36   41                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   35                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₂₀O₁₀

Average Mass

552.4910 Da

Monoisotopic Mass

552.10565 Da

IUPAC Name

3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-6-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-6-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=C(C(=O)C2=C(O)C=C(O)C=C2O1)C1=C(O)C=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C31H20O10/c1-39-18-8-4-15(5-9-18)31-28(30(38)25-19(34)10-17(33)11-23(25)41-31)27-21(36)13-24-26(29(27)37)20(35)12-22(40-24)14-2-6-16(32)7-3-14/h2-13,32-34,36-37H,1H3

InChI Key

CWDHFSUXDBJDID-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 pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Pyranoisoflavonoids

Direct Parent

Pyranoisoflavonoids

Alternative Parents

Substituents

Pyranoisoflavonoid
4p-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyisoflavonoid
Flavone
Hydroxyflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Ether
Oxacycle
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	4.66	ALOGPS
logP	5.25	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	5.7	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	148.7 m³·mol⁻¹	ChemAxon
Polarizability	55.85 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

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 5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-[3,6'-bichromene]-4,4'-dione (NP0203705)

MOL for NP0203705 (5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-[3,6'-bichromene]-4,4'-dione)

3D MOL for NP0203705 (5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-[3,6'-bichromene]-4,4'-dione)

3D SDF for NP0203705 (5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-[3,6'-bichromene]-4,4'-dione)

3D-SDF for NP0203705 (5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-[3,6'-bichromene]-4,4'-dione)

PDB for NP0203705 (5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-[3,6'-bichromene]-4,4'-dione)

3D PDB for NP0203705 (5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-[3,6'-bichromene]-4,4'-dione)

SMILES for NP0203705 (5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-[3,6'-bichromene]-4,4'-dione)

INCHI for NP0203705 (5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-[3,6'-bichromene]-4,4'-dione)

Structure for NP0203705 (5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-[3,6'-bichromene]-4,4'-dione)

3D Structure for NP0203705 (5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-2-(4-methoxyphenyl)-[3,6'-bichromene]-4,4'-dione)