NP-MRD: Showing NP-Card for (2r,3r)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-7-one (NP0192963)

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Record Information

Version

2.0

Created at

2022-09-04 10:17:04 UTC

Updated at

2022-09-04 10:17:04 UTC

NP-MRD ID

NP0192963

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-7-one

Description

5-MethoxyanthocercinA belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. (2r,3r)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-7-one is found in Dipteryx odorata. Based on a literature review very few articles have been published on 5-MethoxyanthocercinA.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042212172D          

 39 43  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309042212172D          

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 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  2  0  0  0  0
 22 32  1  0  0  0  0
 21 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 11 36  1  0  0  0  0
  6 37  1  0  0  0  0
 37 38  2  0  0  0  0
  3 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0192963

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1O)C1=COC2=C3O[C@H](CO)[C@H](OC3=C(OC)C=C2C1=O)C1=CC(OC)=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H26O11/c1-33-18-6-5-13(7-17(18)30)16-12-37-26-15(23(16)31)10-21(36-4)27-28(26)38-22(11-29)25(39-27)14-8-19(34-2)24(32)20(9-14)35-3/h5-10,12,22,25,29-30,32H,11H2,1-4H3/t22-,25-/m1/s1

> <INCHI_KEY>
PDFRGLKIUUWXHS-RCZVLFRGSA-N

> <FORMULA>
C28H26O11

> <MOLECULAR_WEIGHT>
538.505

> <EXACT_MASS>
538.147511657

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
55.595695238694205

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2H,3H,7H-[1,4]dioxino[2,3-h]chromen-7-one

> <JCHEM_LOGP>
2.7667904193333324

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.557206548662842

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.950182113271918

> <JCHEM_PKA_STRONGEST_BASIC>
-2.990496525797737

> <JCHEM_POLAR_SURFACE_AREA>
142.37000000000003

> <JCHEM_REFRACTIVITY>
136.75750000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2H,3H-[1,4]dioxino[2,3-h]chromen-7-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      -7.136  -5.184   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.366  -3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.826  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.056  -2.516   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.516  -2.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.746  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.104  -5.184   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -1.183   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.184   0.151   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.414   1.485   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.874  -1.183   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.206  -1.183   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.724  -2.516   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.034  -3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.804  -2.516   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.344  -2.516   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.114  -1.183   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.344   0.151   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.114  -3.850   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.654  -3.850   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.344  -5.184   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.114  -6.517   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.344  -7.851   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.804  -5.184   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.494  -6.517   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.724  -7.851   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       5.184  -5.184   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.516  -5.184   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.056  -5.184   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -4.826  -6.517   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   38                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   37                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   36                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   10   18                                                  
CONECT   18   17    7   19                                                  
CONECT   19   18                                                            
CONECT   20   12   21                                                       
CONECT   21   20   22   33                                                  
CONECT   22   21   23   32                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   22                                                       
CONECT   33   21   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   11                                                       
CONECT   37    6   38                                                       
CONECT   38   37    3   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
5-Methoxyxanthocercin a	MeSH

Chemical Formula

C₂₈H₂₆O₁₁

Average Mass

538.5050 Da

Monoisotopic Mass

538.14751 Da

IUPAC Name

(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2H,3H,7H-[1,4]dioxino[2,3-h]chromen-7-one

Traditional Name

(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2H,3H-[1,4]dioxino[2,3-h]chromen-7-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1O)C1=COC2=C3O[C@H](CO)[C@H](OC3=C(OC)C=C2C1=O)C1=CC(OC)=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C28H26O11/c1-33-18-6-5-13(7-17(18)30)16-12-37-26-15(23(16)31)10-21(36-4)27-28(26)38-22(11-29)25(39-27)14-8-19(34-2)24(32)20(9-14)35-3/h5-10,12,22,25,29-30,32H,11H2,1-4H3/t22-,25-/m1/s1

InChI Key

PDFRGLKIUUWXHS-RCZVLFRGSA-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
Dipteryx odorata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-hydroxy,4'-methoxyisoflavonoids

Alternative Parents

Substituents

4p-o-methylisoflavone
3'-hydroxy,4'-methoxyisoflavonoid
Hydroxyisoflavonoid
Isoflavone
2-phenylbenzo-1,4-dioxane
Phenylbenzodioxane
Chromone
Benzo-1,4-dioxane
Benzodioxane
Benzopyran
Methoxyphenol
M-dimethoxybenzene
Dimethoxybenzene
1-benzopyran
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Pyranone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Pyran
Monocyclic benzene moiety
Para-dioxin
Heteroaromatic compound
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
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	2.77	ChemAxon
pKa (Strongest Acidic)	8.95	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	142.37 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	136.76 m³·mol⁻¹	ChemAxon
Polarizability	55.6 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

9061292

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10886024

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-7-one (NP0192963)

MOL for NP0192963 ((2r,3r)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-7-one)

3D MOL for NP0192963 ((2r,3r)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-7-one)

3D SDF for NP0192963 ((2r,3r)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-7-one)

3D-SDF for NP0192963 ((2r,3r)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-7-one)

PDB for NP0192963 ((2r,3r)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-7-one)

3D PDB for NP0192963 ((2r,3r)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-7-one)

SMILES for NP0192963 ((2r,3r)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-7-one)

INCHI for NP0192963 ((2r,3r)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-7-one)

Structure for NP0192963 ((2r,3r)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-7-one)

3D Structure for NP0192963 ((2r,3r)-3-(4-hydroxy-3,5-dimethoxyphenyl)-8-(3-hydroxy-4-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-7-one)