NP-MRD: Showing NP-Card for (2r,3s)-3,5,7-trihydroxy-2-[(2s,3r)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-1-benzopyran-4-one (NP0196047)

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Record Information

Version

2.0

Created at

2022-09-04 14:02:29 UTC

Updated at

2022-09-04 14:02:29 UTC

NP-MRD ID

NP0196047

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s)-3,5,7-trihydroxy-2-[(2s,3r)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-1-benzopyran-4-one

Description

(2R,3S)-3,5,7-trihydroxy-2-[(2S,3R)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-3,4-dihydro-2H-1-benzopyran-4-one belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (2r,3s)-3,5,7-trihydroxy-2-[(2s,3r)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-1-benzopyran-4-one is found in Anastatica hierochuntica. Based on a literature review very few articles have been published on (2R,3S)-3,5,7-trihydroxy-2-[(2S,3R)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-3,4-dihydro-2H-1-benzopyran-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042216022D          

 35 39  0  0  1  0            999 V2000
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   -1.1067   -2.9815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6942   -3.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1308   -3.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -4.4104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8532   -3.7430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042216022D          

 35 39  0  0  1  0            999 V2000
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   -1.1067   -2.9815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0196047

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)[C@H]1OC2=C(O)C=C(C=C2[C@@H]1CO)[C@H]1OC2=CC(O)=CC(O)=C2C(=O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H22O10/c1-33-18-6-10(2-3-15(18)28)23-14(9-26)13-4-11(5-17(30)25(13)35-23)24-22(32)21(31)20-16(29)7-12(27)8-19(20)34-24/h2-8,14,22-24,26-30,32H,9H2,1H3/t14-,22+,23+,24+/m0/s1

> <INCHI_KEY>
BMLIIPOXVWESJG-XFZNKDDRSA-N

> <FORMULA>
C25H22O10

> <MOLECULAR_WEIGHT>
482.441

> <EXACT_MASS>
482.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
47.67012379766669

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-3,5,7-trihydroxy-2-[(2S,3R)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
2.2950213670000004

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.14821086859665

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.75034215963565

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7156325842314954

> <JCHEM_POLAR_SURFACE_AREA>
166.14000000000001

> <JCHEM_REFRACTIVITY>
121.42919999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-3,5,7-trihydroxy-2-[(2S,3R)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.606  -5.565   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.066  -5.565   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.296  -6.899   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.244  -6.899   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.014  -8.233   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.554  -8.233   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.459  -6.987   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.924  -7.463   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.258  -5.153   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.925  -9.773   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.259  -9.003   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.592  -9.773   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.926  -9.003   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.260  -9.773   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      15.593  -9.003   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.260 -11.313   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.926 -12.083   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.926 -13.623   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.592 -11.313   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.259 -12.083   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.259 -13.623   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.925 -11.313   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.591 -12.083   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.258  -9.773   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.924  -9.003   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.459  -9.479   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.983 -10.943   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.477 -11.264   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.244  -9.567   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.296  -9.567   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.066  -8.233   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.606  -8.233   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7   29                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   28                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   27                                                  
CONECT   13   12   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   13   26                                                  
CONECT   26   25                                                            
CONECT   27   12   28                                                       
CONECT   28   27    8   29                                                  
CONECT   29   28    6   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32    5   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    3   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₂O₁₀

Average Mass

482.4410 Da

Monoisotopic Mass

482.12130 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)[C@H]1OC2=C(O)C=C(C=C2[C@@H]1CO)[C@H]1OC2=CC(O)=CC(O)=C2C(=O)[C@H]1O

InChI Identifier

InChI=1S/C25H22O10/c1-33-18-6-10(2-3-15(18)28)23-14(9-26)13-4-11(5-17(30)25(13)35-23)24-22(32)21(31)20-16(29)7-12(27)8-19(20)34-24/h2-8,14,22-24,26-30,32H,9H2,1H3/t14-,22+,23+,24+/m0/s1

InChI Key

BMLIIPOXVWESJG-XFZNKDDRSA-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
Anastatica hierochuntica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Flavonolignan
Furanoflavonoid or dihydroflavonoid
3'-hydroxyflavonoid
3-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Flavanonol
Hydroxyflavonoid
Neolignan skeleton
Flavan
Chromone
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Benzofuran
Coumaran
Aryl ketone
Anisole
Phenoxy compound
Methoxybenzene
Aryl alkyl ketone
Phenol ether
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Secondary alcohol
Ketone
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen 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

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

12442784

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s)-3,5,7-trihydroxy-2-[(2s,3r)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-1-benzopyran-4-one (NP0196047)

MOL for NP0196047 ((2r,3s)-3,5,7-trihydroxy-2-[(2s,3r)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0196047 ((2r,3s)-3,5,7-trihydroxy-2-[(2s,3r)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0196047 ((2r,3s)-3,5,7-trihydroxy-2-[(2s,3r)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0196047 ((2r,3s)-3,5,7-trihydroxy-2-[(2s,3r)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0196047 ((2r,3s)-3,5,7-trihydroxy-2-[(2s,3r)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0196047 ((2r,3s)-3,5,7-trihydroxy-2-[(2s,3r)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0196047 ((2r,3s)-3,5,7-trihydroxy-2-[(2s,3r)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0196047 ((2r,3s)-3,5,7-trihydroxy-2-[(2s,3r)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0196047 ((2r,3s)-3,5,7-trihydroxy-2-[(2s,3r)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0196047 ((2r,3s)-3,5,7-trihydroxy-2-[(2s,3r)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-1-benzopyran-4-one)