NP-MRD: Showing NP-Card for (2s)-5-hydroxy-8-{2-hydroxy-5-[(2s)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one (NP0160631)

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Record Information

Version

2.0

Created at

2022-09-02 18:37:39 UTC

Updated at

2022-09-02 18:37:39 UTC

NP-MRD ID

NP0160631

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-5-hydroxy-8-{2-hydroxy-5-[(2s)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one

Description

(2S,2''S)-7,7''-Di-O-methyltetrahydroamentoflavone 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''. (2s)-5-hydroxy-8-{2-hydroxy-5-[(2s)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one is found in Erigeron canadensis. Based on a literature review very few articles have been published on (2S,2''S)-7,7''-Di-O-methyltetrahydroamentoflavone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022220372D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309022220372D          

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    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  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
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 29 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 25 37  1  0  0  0  0
 37 38  2  0  0  0  0
 17 39  2  0  0  0  0
 12 39  1  0  0  0  0
 11 40  1  0  0  0  0
 40 41  1  0  0  0  0
  7 41  1  0  0  0  0
 41 42  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0160631

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C[C@H](OC2=C1)C1=CC=C(O)C(=C1)C1=C(OC)C=C(O)C2=C1O[C@@H](CC2=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H26O10/c1-39-18-10-21(35)30-22(36)12-26(41-28(30)11-18)16-5-8-20(34)19(9-16)29-27(40-2)14-24(38)31-23(37)13-25(42-32(29)31)15-3-6-17(33)7-4-15/h3-11,14,25-26,33-35,38H,12-13H2,1-2H3/t25-,26-/m0/s1

> <INCHI_KEY>
VAXDHDRILRWGDK-UIOOFZCWSA-N

> <FORMULA>
C32H26O10

> <MOLECULAR_WEIGHT>
570.55

> <EXACT_MASS>
570.152597037

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
55.837414744891625

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-5-hydroxy-8-{2-hydroxy-5-[(2S)-5-hydroxy-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]phenyl}-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
4.56

> <JCHEM_LOGP>
5.635983758666665

> <ALOGPS_LOGS>
-5.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.718451396826069

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.242873607141018

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5687556434962255

> <JCHEM_POLAR_SURFACE_AREA>
151.98000000000002

> <JCHEM_REFRACTIVITY>
150.62240000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.89e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-5-hydroxy-8-{2-hydroxy-5-[(2S)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.335  10.780   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -8.002   6.160   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.001  -0.770   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  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335   1.540   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  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   41                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12   40                                                  
CONECT   12   11   13   39                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   39                                                  
CONECT   18   17   19   26                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   37                                                  
CONECT   26   25   18   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   36                                                  
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   29                                                       
CONECT   36   28   37                                                       
CONECT   37   36   25   38                                                  
CONECT   38   37                                                            
CONECT   39   17   12                                                       
CONECT   40   11   41                                                       
CONECT   41   40    7   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₂₆O₁₀

Average Mass

570.5500 Da

Monoisotopic Mass

570.15260 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C[C@H](OC2=C1)C1=CC=C(O)C(=C1)C1=C(OC)C=C(O)C2=C1O[C@@H](CC2=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C32H26O10/c1-39-18-10-21(35)30-22(36)12-26(41-28(30)11-18)16-5-8-20(34)19(9-16)29-27(40-2)14-24(38)31-23(37)13-25(42-32(29)31)15-3-6-17(33)7-4-15/h3-11,14,25-26,33-35,38H,12-13H2,1-2H3/t25-,26-/m0/s1

InChI Key

VAXDHDRILRWGDK-UIOOFZCWSA-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
Erigeron canadensis	LOTUS Database	35616633

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
7-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	4.56	ALOGPS
logS	-5.1	ALOGPS

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

8501163

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10325701

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-5-hydroxy-8-{2-hydroxy-5-[(2s)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one (NP0160631)

MOL for NP0160631 ((2s)-5-hydroxy-8-{2-hydroxy-5-[(2s)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0160631 ((2s)-5-hydroxy-8-{2-hydroxy-5-[(2s)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0160631 ((2s)-5-hydroxy-8-{2-hydroxy-5-[(2s)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0160631 ((2s)-5-hydroxy-8-{2-hydroxy-5-[(2s)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0160631 ((2s)-5-hydroxy-8-{2-hydroxy-5-[(2s)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0160631 ((2s)-5-hydroxy-8-{2-hydroxy-5-[(2s)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0160631 ((2s)-5-hydroxy-8-{2-hydroxy-5-[(2s)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0160631 ((2s)-5-hydroxy-8-{2-hydroxy-5-[(2s)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0160631 ((2s)-5-hydroxy-8-{2-hydroxy-5-[(2s)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0160631 ((2s)-5-hydroxy-8-{2-hydroxy-5-[(2s)-5-hydroxy-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-1-benzopyran-4-one)