NP-MRD: Showing NP-Card for chamaeflavone A (NP0043371)

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Record Information

Version

2.0

Created at

2021-06-21 00:47:49 UTC

Updated at

2021-06-30 00:19:00 UTC

NP-MRD ID

NP0043371

Secondary Accession Numbers

None

Natural Product Identification

Common Name

chamaeflavone A

Provided By

JEOL Database JEOL Logo

Description

Chamaeflavone a 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''. Thus, chamaeflavone a is considered to be a flavonoid. chamaeflavone A is found in Stellera chamaejasme. chamaeflavone A was first documented in 2013 (Asada, Y., et al.). Based on a literature review very few articles have been published on Chamaeflavone a.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102473D          

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     RDKit          3D

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M  END


  Mrv1652306212102473D          

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M  END
> <DATABASE_ID>
NP0043371

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])[C@]1([H])OC2=C([H])C(O[H])=C([H])C(O[H])=C2C(=O)[C@@]1([H])[C@]1([H])C(=O)C2=C(O[C@@]1([H])C1=C([H])C([H])=C(OC([H])([H])[H])C([H])=C1[H])C([H])=C(OC([H])([H])[H])C([H])=C2O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C32H26O10/c1-39-19-9-5-16(6-10-19)32-28(30(38)26-22(36)13-20(40-2)14-24(26)42-32)27-29(37)25-21(35)11-18(34)12-23(25)41-31(27)15-3-7-17(33)8-4-15/h3-14,27-28,31-36H,1-2H3/t27-,28-,31+,32+/m1/s1

> <INCHI_KEY>
BFPJOJFVZXWMSM-CKROWEISSA-N

> <FORMULA>
C32H26O10

> <MOLECULAR_WEIGHT>
570.55

> <EXACT_MASS>
570.152597037

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
58.643506340000904

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-3-[(2R,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
4.86

> <JCHEM_LOGP>
5.695113536666668

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.612951649249114

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.780250517326459

> <JCHEM_PKA_STRONGEST_BASIC>
-4.540619861979187

> <JCHEM_POLAR_SURFACE_AREA>
151.98

> <JCHEM_REFRACTIVITY>
149.68899999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.86e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-3-[(2R,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.728   3.253   5.237  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.016   3.116   3.851  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.479   2.034   3.211  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.841   1.911   1.869  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.364   0.851   1.093  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.506  -0.106   1.652  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.959  -1.232   0.792  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.282  -2.458   1.478  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.860  -3.574   0.806  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.561  -4.755   1.064  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.197  -5.939   0.419  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.803  -7.155   0.573  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.909  -7.219   1.465  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.122  -5.931  -0.475  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.411  -4.757  -0.715  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.641  -4.840  -1.587  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.775  -3.574  -0.069  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.013  -2.324  -0.249  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.962  -2.314  -0.998  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.435  -1.126   0.583  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.033   0.218  -0.040  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.369   0.347  -1.498  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.339  -0.233  -1.984  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.404   1.284  -2.334  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.059   1.538  -3.667  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.981   0.913  -4.302  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.773   2.471  -4.415  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.828   3.155  -3.818  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.550   4.084  -4.506  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.181   2.912  -2.493  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.478   1.961  -1.756  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.877   1.770  -0.461  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.555   0.456   0.038  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.077   0.400   1.464  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.920  -0.651   1.861  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.375  -0.734   3.177  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.997   0.233   4.100  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.468   0.113   5.374  0.00  0.00           O+0
HETATM   39  C   UNK     0       2.167   1.285   3.731  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.708   1.367   2.414  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.147   0.023   3.003  0.00  0.00           C+0
HETATM   42  C   UNK     0      -2.630   1.084   3.776  0.00  0.00           C+0
HETATM   43  H   UNK     0      -2.656   3.402   5.403  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.101   2.394   5.805  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.248   4.144   5.600  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.506   2.647   1.422  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.665   0.786   0.049  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.507  -1.249  -0.159  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.389  -4.717   1.764  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.727  -6.575   1.125  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.606  -6.968   2.487  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.276  -8.250   1.470  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.831  -6.849  -0.981  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.054  -3.952  -1.656  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.049  -1.268   1.558  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.464   1.052   0.471  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.400   0.292  -3.665  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.490   2.654  -5.447  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.204   4.143  -5.413  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.009   3.454  -2.043  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.118  -0.260  -0.573  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.226  -1.415   1.149  0.00  0.00           H+0
HETATM   63  H   UNK     0       4.027  -1.548   3.480  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.186   0.891   5.883  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.870   2.047   4.444  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.063   2.197   2.131  0.00  0.00           H+0
HETATM   67  H   UNK     0      -1.489  -0.710   3.468  0.00  0.00           H+0
HETATM   68  H   UNK     0      -2.323   1.136   4.816  0.00  0.00           H+0
CONECT    1    2   43   44   45                                             
CONECT    2    1    3                                                       
CONECT    3    4   42    2                                                  
CONECT    4    5    3   46                                                  
CONECT    5    6    4   47                                                  
CONECT    6    7    5   41                                                  
CONECT    7    8    6   20   48                                             
CONECT    8    7    9                                                       
CONECT    9   17   10    8                                                  
CONECT   10    9   11   49                                                  
CONECT   11   14   10   12                                                  
CONECT   12   13   11                                                       
CONECT   13   12   50   51   52                                             
CONECT   14   15   11   53                                                  
CONECT   15   14   17   16                                                  
CONECT   16   15   54                                                       
CONECT   17    9   15   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   21   55   18    7                                             
CONECT   21   20   22   33   56                                             
CONECT   22   24   21   23                                                  
CONECT   23   22                                                            
CONECT   24   25   31   22                                                  
CONECT   25   27   24   26                                                  
CONECT   26   25   57                                                       
CONECT   27   28   25   58                                                  
CONECT   28   27   30   29                                                  
CONECT   29   28   59                                                       
CONECT   30   31   28   60                                                  
CONECT   31   30   24   32                                                  
CONECT   32   31   33                                                       
CONECT   33   21   32   34   61                                             
CONECT   34   33   35   40                                                  
CONECT   35   34   36   62                                                  
CONECT   36   35   37   63                                                  
CONECT   37   36   39   38                                                  
CONECT   38   37   64                                                       
CONECT   39   37   40   65                                                  
CONECT   40   39   34   66                                                  
CONECT   41   42    6   67                                                  
CONECT   42    3   41   68                                                  
CONECT   43    1                                                            
CONECT   44    1                                                            
CONECT   45    1                                                            
CONECT   46    4                                                            
CONECT   47    5                                                            
CONECT   48    7                                                            
CONECT   49   10                                                            
CONECT   50   13                                                            
CONECT   51   13                                                            
CONECT   52   13                                                            
CONECT   53   14                                                            
CONECT   54   16                                                            
CONECT   55   20                                                            
CONECT   56   21                                                            
CONECT   57   26                                                            
CONECT   58   27                                                            
CONECT   59   29                                                            
CONECT   60   30                                                            
CONECT   61   33                                                            
CONECT   62   35                                                            
CONECT   63   36                                                            
CONECT   64   38                                                            
CONECT   65   39                                                            
CONECT   66   40                                                            
CONECT   67   41                                                            
CONECT   68   42                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  146    0
END

RDKit          3D

68 73  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₂₆O₁₀

Average Mass

570.5500 Da

Monoisotopic Mass

570.15260 Da

IUPAC Name

(2R,3S)-3-[(2R,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2R,3S)-3-[(2R,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])[C@]1([H])OC2=C([H])C(O[H])=C([H])C(O[H])=C2C(=O)[C@@]1([H])[C@]1([H])C(=O)C2=C(O[C@@]1([H])C1=C([H])C([H])=C(OC([H])([H])[H])C([H])=C1[H])C([H])=C(OC([H])([H])[H])C([H])=C2O[H]

InChI Identifier

InChI=1S/C32H26O10/c1-39-19-9-5-16(6-10-19)32-28(30(38)26-22(36)13-20(40-2)14-24(26)42-32)27-29(37)25-21(35)11-18(34)12-23(25)41-31(27)15-3-7-17(33)8-4-15/h3-14,27-28,31-36H,1-2H3/t27-,28-,31+,32+/m1/s1

InChI Key

BFPJOJFVZXWMSM-CKROWEISSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stellera chamaejasme	JEOL database	Asada, Y., et al, J. Nat. Prod. 76, 852 (2013)

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
4p-methoxyflavonoid-skeleton
Flavanone
Hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Flavan
Chromone
Benzopyran
Chromane
1-benzopyran
Aryl alkyl ketone
Methoxybenzene
Aryl ketone
Phenoxy compound
Anisole
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
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
logP	4.86	ALOGPS
logP	5.7	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	151.98 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	149.69 m³·mol⁻¹	ChemAxon
Polarizability	58.64 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

30809239

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71712662

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Asada, Y., et al. (2013). Asada, Y., et al, J. Nat. Prod. 76, 852 (2013). J. Nat. Prod..

Showing NP-Card for chamaeflavone A (NP0043371)

MOL for NP0043371 (chamaeflavone A)

3D MOL for NP0043371 (chamaeflavone A)

3D SDF for NP0043371 (chamaeflavone A)

3D-SDF for NP0043371 (chamaeflavone A)

PDB for NP0043371 (chamaeflavone A)

3D PDB for NP0043371 (chamaeflavone A)

SMILES for NP0043371 (chamaeflavone A)

INCHI for NP0043371 (chamaeflavone A)

Structure for NP0043371 (chamaeflavone A)

3D Structure for NP0043371 (chamaeflavone A)