NP-MRD: Showing NP-Card for taiwanhomoflavone-b (NP0236965)

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Record Information

Version

2.0

Created at

2022-09-06 19:59:32 UTC

Updated at

2022-09-06 19:59:32 UTC

NP-MRD ID

NP0236965

Secondary Accession Numbers

None

Natural Product Identification

Common Name

taiwanhomoflavone-b

Description

Taiwanhomoflavone-B belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Taiwanhomoflavone-B is an extremely weak basic (essentially neutral) compound (based on its pKa). taiwanhomoflavone-b was first documented in 2002 (PMID: 12499600). A biflavonoid isolated from Cephalotaxus wilsoniana and has been shown to exhibit antineoplastic activity.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241518132D          

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  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  5 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 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
 20 21  2  0  0  0  0
 16 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
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 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
 29 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 26 34  1  0  0  0  0
 34 35  1  0  0  0  0
 22 35  1  0  0  0  0
  7 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 36 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0236965

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(=O)CC(O2)C2=CC=C(O)C=C2)C(O)=C1OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C(C)=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C32H24O10/c1-15-20(34)11-25-28(30(15)37)21(35)12-24(41-25)17-5-9-19(10-6-17)40-32-27(39-2)14-26-29(31(32)38)22(36)13-23(42-26)16-3-7-18(33)8-4-16/h3-12,14,23,33-34,37-38H,13H2,1-2H3

> <INCHI_KEY>
QNXAIIZZUIKOEY-UHFFFAOYSA-N

> <FORMULA>
C32H24O10

> <MOLECULAR_WEIGHT>
568.534

> <EXACT_MASS>
568.136946973

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
58.912927412946146

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl]oxy}phenyl)-6-methyl-4H-chromen-4-one

> <ALOGPS_LOGP>
5.06

> <JCHEM_LOGP>
6.031719318

> <ALOGPS_LOGS>
-5.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.743575584492371

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.891976947481703

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7405975230581556

> <JCHEM_POLAR_SURFACE_AREA>
151.98

> <JCHEM_REFRACTIVITY>
151.92909999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-6-methylchromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -5.390   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  -0.000   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  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0     -10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0     -14.670   2.310   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   36                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    3   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19   23   35                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   34                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   26   35                                                  
CONECT   35   34   22                                                       
CONECT   36    7   37   42                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   36                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₂₄O₁₀

Average Mass

568.5340 Da

Monoisotopic Mass

568.13695 Da

IUPAC Name

5,7-dihydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-6-yl]oxy}phenyl)-6-methyl-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-2-(4-{[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-6-yl]oxy}phenyl)-6-methylchromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(=O)CC(O2)C2=CC=C(O)C=C2)C(O)=C1OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C(C)=C(O)C=C2O1

InChI Identifier

InChI=1S/C32H24O10/c1-15-20(34)11-25-28(30(15)37)21(35)12-24(41-25)17-5-9-19(10-6-17)40-32-27(39-2)14-26-29(31(32)38)22(36)13-23(42-26)16-3-7-18(33)8-4-16/h3-12,14,23,33-34,37-38H,13H2,1-2H3

InChI Key

QNXAIIZZUIKOEY-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

7-methoxyflavonoid-skeleton
Flavanone
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Flavan
Diaryl ether
Chromone
Benzopyran
Chromane
1-benzopyran
Phenol ether
Phenoxy compound
Anisole
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

biflavonoid (CHEBI:66183 )
hydroxyflavone (CHEBI:66183 )
methoxyflavone (CHEBI:66183 )

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	5.06	ALOGPS
logP	6.03	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	6.89	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	151.98 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	151.93 m³·mol⁻¹	ChemAxon
Polarizability	58.91 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

Not Available

PDB ID

Not Available

ChEBI ID

66183

Good Scents ID

Not Available

References

General References

Kuo YH, Hwang SY, Yang Kuo LM, Lee YL, Li SY, Shen YC: A novel cytotoxic C-methylated biflavone, taiwanhomoflavone-B from the twigs of Cephalotaxus wilsoniana. Chem Pharm Bull (Tokyo). 2002 Dec;50(12):1607-8. doi: 10.1248/cpb.50.1607. [PubMed:12499600 ]
LOTUS database [Link]

Showing NP-Card for taiwanhomoflavone-b (NP0236965)

MOL for NP0236965 (taiwanhomoflavone-b)

3D MOL for NP0236965 (taiwanhomoflavone-b)

3D SDF for NP0236965 (taiwanhomoflavone-b)

3D-SDF for NP0236965 (taiwanhomoflavone-b)

PDB for NP0236965 (taiwanhomoflavone-b)

3D PDB for NP0236965 (taiwanhomoflavone-b)

SMILES for NP0236965 (taiwanhomoflavone-b)

INCHI for NP0236965 (taiwanhomoflavone-b)

Structure for NP0236965 (taiwanhomoflavone-b)

3D Structure for NP0236965 (taiwanhomoflavone-b)