NP-MRD: Showing NP-Card for (2s,3r)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzopyran-4-one (NP0213404)

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Record Information

Version

2.0

Created at

2022-09-05 12:23:03 UTC

Updated at

2022-09-05 12:23:03 UTC

NP-MRD ID

NP0213404

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzopyran-4-one

Description

(2S,3R)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. (2s,3r)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzopyran-4-one is found in Butea monosperma. Based on a literature review very few articles have been published on (2S,3R)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052214232D          

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M  END

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  Mrv1652309052214232D          

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 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 25 32  1  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 34 40  1  0  0  0  0
  2 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213404

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2C(OC(=CC3=CC(O)=C(O)C=C3[C@@H]3[C@H](OC4=CC(O)=CC=C4C3=O)C3=CC=C(O)C(O)=C3)C2=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H20O10/c31-15-2-4-17-24(10-15)39-26(28(17)37)9-14-8-22(35)23(36)12-19(14)27-29(38)18-5-3-16(32)11-25(18)40-30(27)13-1-6-20(33)21(34)7-13/h1-12,27,30-36H/t27-,30+/m0/s1

> <INCHI_KEY>
VHTMUCCOQREBDS-BHBYDHKZSA-N

> <FORMULA>
C30H20O10

> <MOLECULAR_WEIGHT>
540.48

> <EXACT_MASS>
540.105646844

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
53.56434223859668

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
4.1802308366666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.945067728139889

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.380956885313766

> <JCHEM_PKA_STRONGEST_BASIC>
-4.94464843738435

> <JCHEM_POLAR_SURFACE_AREA>
173.98

> <JCHEM_REFRACTIVITY>
142.8903

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0      -3.349  -8.756   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.873  -7.291   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.778  -6.045   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.318  -6.045   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.088  -4.711   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.318  -3.378   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.088  -2.044   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.318  -0.710   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -7.628  -2.044   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -8.398  -0.710   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -8.398  -3.378   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.628  -4.711   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.398  -6.045   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -7.628  -7.379   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.088  -7.379   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -8.398  -8.712   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.628 -10.046   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.398 -11.380   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -9.938 -11.380   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -10.708 -12.713   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -10.708 -10.046   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.938  -8.712   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -10.708  -7.379   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -9.938  -6.045   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -10.708  -4.711   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.248  -4.711   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -13.018  -3.378   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -12.248  -2.044   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -13.018  -0.710   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -10.708  -2.044   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -9.938  -0.710   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -9.938  -3.378   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.873  -4.799   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.408  -5.275   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.075  -4.505   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.259  -5.275   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.593  -4.505   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.259  -6.815   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.075  -7.585   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.408  -6.815   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   16   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   13   25                                                  
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   25                                                       
CONECT   33    3   34                                                       
CONECT   34   33   35   40                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   34    2                                                  
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₀O₁₀

Average Mass

540.4800 Da

Monoisotopic Mass

540.10565 Da

IUPAC Name

(2S,3R)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S,3R)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C2C(OC(=CC3=CC(O)=C(O)C=C3[C@@H]3[C@H](OC4=CC(O)=CC=C4C3=O)C3=CC=C(O)C(O)=C3)C2=O)=C1

InChI Identifier

InChI=1S/C30H20O10/c31-15-2-4-17-24(10-15)39-26(28(17)37)9-14-8-22(35)23(36)12-19(14)27-29(38)18-5-3-16(32)11-25(18)40-30(27)13-1-6-20(33)21(34)7-13/h1-12,27,30-36H/t27-,30+/m0/s1

InChI Key

VHTMUCCOQREBDS-BHBYDHKZSA-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
Butea monosperma	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflavanone
Hydroxyflavonoid
Flavanone
Aurone
7-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Isoflavonoid
Isoflavonoid skeleton
Isoflavan
Stilbene
Chromone
1-benzopyran
Benzopyran
Chromane
Coumaran
Benzofuran
Aryl alkyl ketone
Aryl ketone
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	4.18	ChemAxon
pKa (Strongest Acidic)	7.38	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.98 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	142.89 m³·mol⁻¹	ChemAxon
Polarizability	53.56 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

162985635

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzopyran-4-one (NP0213404)

MOL for NP0213404 ((2s,3r)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0213404 ((2s,3r)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0213404 ((2s,3r)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0213404 ((2s,3r)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0213404 ((2s,3r)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0213404 ((2s,3r)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0213404 ((2s,3r)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0213404 ((2s,3r)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0213404 ((2s,3r)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0213404 ((2s,3r)-3-{4,5-dihydroxy-2-[(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)methyl]phenyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzopyran-4-one)