NP-MRD: Showing NP-Card for 3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one (NP0253036)

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Record Information

Version

2.0

Created at

2022-09-07 16:47:00 UTC

Updated at

2022-09-07 16:47:00 UTC

NP-MRD ID

NP0253036

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

Description

Daphnodorin K 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. 3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one is found in Daphne acutiloba and Daphne odora. Based on a literature review very few articles have been published on Daphnodorin K.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072218472D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072218472D          

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 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
  2 39  1  0  0  0  0
 32 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0253036

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1CCC2=C(O)C(=C(O)C=C2O1)C1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H22O9/c31-16-5-1-14(2-6-16)22-10-9-19-23(38-22)13-21(35)26(28(19)36)27-29(37)25-20(34)11-18(33)12-24(25)39-30(27)15-3-7-17(32)8-4-15/h1-8,11-13,22,31-36H,9-10H2

> <INCHI_KEY>
FCUWDVBZVROKAY-UHFFFAOYSA-N

> <FORMULA>
C30H22O9

> <MOLECULAR_WEIGHT>
526.497

> <EXACT_MASS>
526.126382288

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
53.7481617260736

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <JCHEM_LOGP>
5.575107057

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.9218276784025425

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.506205685561232

> <JCHEM_PKA_STRONGEST_BASIC>
-4.784916798876727

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
141.9653

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  -2.310   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  O   UNK     0      -5.335  -0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -8.907  -4.326   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -16.004  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -16.004   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0     -17.338   2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0     -14.670   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15                                                       
CONECT   22   14    8                                                       
CONECT   23    3   24   31                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   24                                                       
CONECT   31   23   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37    2   32                                                  
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₂O₉

Average Mass

526.4970 Da

Monoisotopic Mass

526.12638 Da

IUPAC Name

3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1CCC2=C(O)C(=C(O)C=C2O1)C1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C30H22O9/c31-16-5-1-14(2-6-16)22-10-9-19-23(38-22)13-21(35)26(28(19)36)27-29(37)25-20(34)11-18(33)12-24(25)39-30(27)15-3-7-17(32)8-4-15/h1-8,11-13,22,31-36H,9-10H2

InChI Key

FCUWDVBZVROKAY-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
Daphne acutiloba	LOTUS Database	35616633
Daphne odora	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
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyisoflavonoid
Flavone
Hydroxyflavonoid
Isoflavone
Flavan
Chromone
Chromane
Benzopyran
1-benzopyran
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
Oxacycle
Ether
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	5.58	ChemAxon
pKa (Strongest Acidic)	6.51	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	141.97 m³·mol⁻¹	ChemAxon
Polarizability	53.75 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

C00058444

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

101701125

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one (NP0253036)

MOL for NP0253036 (3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D MOL for NP0253036 (3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D SDF for NP0253036 (3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D-SDF for NP0253036 (3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

PDB for NP0253036 (3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D PDB for NP0253036 (3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

SMILES for NP0253036 (3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

INCHI for NP0253036 (3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

Structure for NP0253036 (3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D Structure for NP0253036 (3-[5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-6-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)