NP-MRD: Showing NP-Card for (+)-2-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-[8,8'-bi-4H-1-benzopyran]-4,4'-dione (NP0060866)

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Record Information

Version

2.0

Created at

2022-04-28 05:50:39 UTC

Updated at

2022-04-28 05:50:39 UTC

NP-MRD ID

NP0060866

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-2-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-[8,8'-bi-4H-1-benzopyran]-4,4'-dione

Description

2-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-4H,4'H-[8,8'-bichromene]-4,4'-dione belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. (+)-2-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-[8,8'-bi-4H-1-benzopyran]-4,4'-dione is found in Glossostemon bruguieri. 2-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-4H,4'H-[8,8'-bichromene]-4,4'-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251503102D          

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M  END

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  Mrv1533004251503102D          

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 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 21 33  1  0  0  0  0
 27 33  2  0  0  0  0
 31 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  1  0  0  0  0
 39 41  2  0  0  0  0
 34 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060866

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C(=C2O1)C1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H18O11/c31-14-4-1-12(2-5-14)23-10-21(38)25-17(34)8-19(36)27(29(25)40-23)28-20(37)9-18(35)26-22(39)11-24(41-30(26)28)13-3-6-15(32)16(33)7-13/h1-11,31-37H

> <INCHI_KEY>
CTQMEXNJZGRPKL-UHFFFAOYSA-N

> <FORMULA>
C30H18O11

> <MOLECULAR_WEIGHT>
554.463

> <EXACT_MASS>
554.0849114

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
53.0365218622008

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
4.23

> <JCHEM_LOGP>
4.7837924916666665

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.605264815740437

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.818357134638635

> <JCHEM_PKA_STRONGEST_BASIC>
-6.3786433249132

> <JCHEM_POLAR_SURFACE_AREA>
194.20999999999998

> <JCHEM_REFRACTIVITY>
146.88689999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.001  -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  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+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   33                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   33                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32   21   27                                                  
CONECT   34   31   35   41                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   34                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₁₈O₁₁

Average Mass

554.4630 Da

Monoisotopic Mass

554.08491 Da

IUPAC Name

8-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

8-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-8-yl]-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=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C30H18O11/c31-14-4-1-12(2-5-14)23-10-21(38)25-17(34)8-19(36)27(29(25)40-23)28-20(37)9-18(35)26-22(39)11-24(41-30(26)28)13-3-6-15(32)16(33)7-13/h1-11,31-37H

InChI Key

CTQMEXNJZGRPKL-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Glossostemon bruguieri	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

Bi- and polyflavonoid skeleton
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Biphenol
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
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	4.23	ALOGPS
logP	4.78	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	5.82	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	194.21 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	146.89 m³·mol⁻¹	ChemAxon
Polarizability	53.04 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

Not Available

Showing NP-Card for (+)-2-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-[8,8'-bi-4H-1-benzopyran]-4,4'-dione (NP0060866)

MOL for NP0060866 ((+)-2-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-[8,8'-bi-4H-1-benzopyran]-4,4'-dione)

3D MOL for NP0060866 ((+)-2-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-[8,8'-bi-4H-1-benzopyran]-4,4'-dione)

3D SDF for NP0060866 ((+)-2-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-[8,8'-bi-4H-1-benzopyran]-4,4'-dione)

3D-SDF for NP0060866 ((+)-2-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-[8,8'-bi-4H-1-benzopyran]-4,4'-dione)

PDB for NP0060866 ((+)-2-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-[8,8'-bi-4H-1-benzopyran]-4,4'-dione)

3D PDB for NP0060866 ((+)-2-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-[8,8'-bi-4H-1-benzopyran]-4,4'-dione)

SMILES for NP0060866 ((+)-2-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-[8,8'-bi-4H-1-benzopyran]-4,4'-dione)

INCHI for NP0060866 ((+)-2-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-[8,8'-bi-4H-1-benzopyran]-4,4'-dione)

Structure for NP0060866 ((+)-2-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-[8,8'-bi-4H-1-benzopyran]-4,4'-dione)

3D Structure for NP0060866 ((+)-2-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2'-(4-hydroxyphenyl)-[8,8'-bi-4H-1-benzopyran]-4,4'-dione)