NP-MRD: Showing NP-Card for 7-O-methylamentoflavone (NP0054331)

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Record Information

Version

2.0

Created at

2022-04-28 00:43:14 UTC

Updated at

2022-04-28 00:43:14 UTC

NP-MRD ID

NP0054331

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-O-methylamentoflavone

Description

Sequoiaflavone 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''. 7-O-methylamentoflavone is found in Amentotaxus yunnanensis, Araucaria araucana, Cephalotaxus harringtonia, Chamaecyparis formosensis, Cryptomeria konishii, Cunninghamia lanceolata, Cupressus cashmeriana, Cupressus sempervirens, Dioon spp., Elateriospermum tapos , Garcinia xanthochymus , Libocedrus bidwillii, Microbiota decussata, Podocarpus montanus, Retrophyllum rospigliosii, Selaginella tamariscina, Sequoia sempervirens, Taiwania cryptomerioides and Zamia angustifolia . Sequoiaflavone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652310051703322D          

 41 46  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652310051703322D          

 41 46  0  0  0  0            999 V2000
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 26 12  2  0  0  0  0
 26 15  1  0  0  0  0
 27 10  2  0  0  0  0
 28 18  1  0  0  0  0
 28 21  1  0  0  0  0
 29 20  2  0  0  0  0
 29 23  1  0  0  0  0
 29 27  1  0  0  0  0
 30 22  2  0  0  0  0
 30 24  1  0  0  0  0
 31 28  2  0  0  0  0
 31 30  1  0  0  0  0
 32 16  1  0  0  0  0
 33 19  1  0  0  0  0
 34 20  1  0  0  0  0
 35 21  1  0  0  0  0
 36 22  1  0  0  0  0
 37 23  2  0  0  0  0
 38 24  2  0  0  0  0
 39  1  1  0  0  0  0
 39 17  1  0  0  0  0
 40 26  1  0  0  0  0
 40 27  1  0  0  0  0
 41 25  1  0  0  0  0
 41 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054331

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC(=C(O)C=C1)C1=C2OC(=CC(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H20O10/c1-39-17-9-20(34)29-23(37)12-26(40-27(29)10-17)15-4-7-19(33)18(8-15)28-21(35)11-22(36)30-24(38)13-25(41-31(28)30)14-2-5-16(32)6-3-14/h2-13,32-36H,1H3

> <INCHI_KEY>
TYUMAYSMJLPFAN-UHFFFAOYSA-N

> <FORMULA>
C31H20O10

> <MOLECULAR_WEIGHT>
552.491

> <EXACT_MASS>
552.105646844

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
55.911536384620014

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dihydroxy-8-[2-hydroxy-5-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)phenyl]-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
4.75

> <JCHEM_LOGP>
5.233251869333333

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.274738002264882

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.22509528883045

> <JCHEM_PKA_STRONGEST_BASIC>
-4.859704876053629

> <JCHEM_POLAR_SURFACE_AREA>
162.97999999999996

> <JCHEM_REFRACTIVITY>
149.38830000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sequoiaflavone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         0                                  
HETATM    1  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334  -6.930   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   39                                                            
CONECT    2    5   14                                                       
CONECT    3    6   14                                                       
CONECT    4    7   15                                                       
CONECT    5    2   16                                                       
CONECT    6    3   16                                                       
CONECT    7    4   19                                                       
CONECT    8   15   18                                                       
CONECT    9   17   20                                                       
CONECT   10   17   27                                                       
CONECT   11   21   22                                                       
CONECT   12   23   26                                                       
CONECT   13   24   25                                                       
CONECT   14    2    3   25                                                  
CONECT   15    4    8   26                                                  
CONECT   16    5    6   32                                                  
CONECT   17    9   10   39                                                  
CONECT   18    8   19   28                                                  
CONECT   19    7   18   33                                                  
CONECT   20    9   29   34                                                  
CONECT   21   11   28   35                                                  
CONECT   22   11   30   36                                                  
CONECT   23   12   29   37                                                  
CONECT   24   13   30   38                                                  
CONECT   25   13   14   41                                                  
CONECT   26   12   15   40                                                  
CONECT   27   10   29   40                                                  
CONECT   28   18   21   31                                                  
CONECT   29   20   23   27                                                  
CONECT   30   22   24   31                                                  
CONECT   31   28   30   41                                                  
CONECT   32   16                                                            
CONECT   33   19                                                            
CONECT   34   20                                                            
CONECT   35   21                                                            
CONECT   36   22                                                            
CONECT   37   23                                                            
CONECT   38   24                                                            
CONECT   39    1   17                                                       
CONECT   40   26   27                                                       
CONECT   41   25   31                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₂₀O₁₀

Average Mass

552.4910 Da

Monoisotopic Mass

552.10565 Da

IUPAC Name

5,7-dihydroxy-8-[2-hydroxy-5-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)phenyl]-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

sequoiaflavone

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC(=C(O)C=C1)C1=C2OC(=CC(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C31H20O10/c1-39-17-9-20(34)29-23(37)12-26(40-27(29)10-17)15-4-7-19(33)18(8-15)28-21(35)11-22(36)30-24(38)13-25(41-31(28)30)14-2-5-16(32)6-3-14/h2-13,32-36H,1H3

InChI Key

TYUMAYSMJLPFAN-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Amentotaxus yunnanensis	Plant	KNApSAcK
Araucaria araucana	LOTUS Database	35616633
Cephalotaxus harringtonia	Plant	KNApSAcK
Chamaecyparis formosensis	Plant	KNApSAcK
Cryptomeria konishii	Plant	KNApSAcK
Cunninghamia lanceolata	LOTUS Database	35616633
Cupressus cashmeriana	Plant	KNApSAcK
Cupressus sempervirens	LOTUS Database	35616633
Dioon spp.	Plant	KNApSAcK
Elateriospermum tapos	Plant	KNApSAcK
Garcinia xanthochymus	Plant	KNApSAcK
Libocedrus bidwillii	Plant	KNApSAcK
Microbiota decussata	LOTUS Database	35616633
Podocarpus montanus	Plant	KNApSAcK
Retrophyllum rospigliosii	LOTUS Database	35616633
Selaginella tamariscina	LOTUS Database	35616633
Sequoia sempervirens	Plant	KNApSAcK
Taiwania cryptomerioides	Plant	KNApSAcK
Zamia angustifolia	Plant	KNApSAcK

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
Hydroxyflavonoid
Flavone
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Chromone
1-benzopyran
Benzopyran
Phenol ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	4.75	ALOGPS
logP	5.23	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	6.23	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	149.39 m³·mol⁻¹	ChemAxon
Polarizability	55.91 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

HMDB0146325

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

5484010

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 7-O-methylamentoflavone (NP0054331)

MOL for NP0054331 (7-O-methylamentoflavone)

3D MOL for NP0054331 (7-O-methylamentoflavone)

3D SDF for NP0054331 (7-O-methylamentoflavone)

3D-SDF for NP0054331 (7-O-methylamentoflavone)

PDB for NP0054331 (7-O-methylamentoflavone)

3D PDB for NP0054331 (7-O-methylamentoflavone)

SMILES for NP0054331 (7-O-methylamentoflavone)

INCHI for NP0054331 (7-O-methylamentoflavone)

Structure for NP0054331 (7-O-methylamentoflavone)

3D Structure for NP0054331 (7-O-methylamentoflavone)