NP-MRD: Showing NP-Card for 3-8'-Biapigenin (NP0054280)

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Record Information

Version

2.0

Created at

2022-04-28 00:41:32 UTC

Updated at

2022-04-28 00:41:32 UTC

NP-MRD ID

NP0054280

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-8'-Biapigenin

Description

4',4''',5,5'',7,7''-Hexahydroxy-3,8''-biflavone, also known as 1,3-benzodioxole-5-propanol, alpha-methyl-, 5-acetate or 13ii8-biapigenin, 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''. 4',4''',5,5'',7,7''-Hexahydroxy-3,8''-biflavone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4',4''',5,5'',7,7''-Hexahydroxy-3,8''-biflavone has been detected, but not quantified in, cereals and cereal products. 3-8'-Biapigenin is found in Fagopyrum esculentum , Garcinia dulcis , Garcinia kola , Garcinia livingstonii, Garcinia xanthochymus , Hypericum aucheri, Hypericum maculatum , Hypericum perforatum , Hypericum scabrum and Hypericum thasium. This could make 4',4''',5,5'',7,7''-hexahydroxy-3,8''-biflavone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02011302032D          

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M  END

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M  END


  Mrv0541 02011302032D          

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 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 32 30  2  0  0  0  0
 30 33  1  0  0  0  0
 31 32  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 31 35  2  0  0  0  0
 21 36  1  0  0  0  0
 23 37  1  0  0  0  0
 27 38  2  0  0  0  0
 35 39  1  0  0  0  0
  9 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054280

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(=C(O)C=C2O)C1=C(OC2=C(C(O)=CC(O)=C2)C1=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H18O10/c31-15-5-1-13(2-6-15)22-12-21(37)24-19(35)11-20(36)26(30(24)39-22)27-28(38)25-18(34)9-17(33)10-23(25)40-29(27)14-3-7-16(32)8-4-14/h1-12,31-36H

> <INCHI_KEY>
IQAMTZLKUHMPPE-UHFFFAOYSA-N

> <FORMULA>
C30H18O10

> <MOLECULAR_WEIGHT>
538.4579

> <EXACT_MASS>
538.089996796

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
52.22300806886526

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
4.43

> <JCHEM_LOGP>
5.108220246666666

> <ALOGPS_LOGS>
-4.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.644506350194981

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.769415324678545

> <JCHEM_PKA_STRONGEST_BASIC>
-5.18053217247406

> <JCHEM_POLAR_SURFACE_AREA>
173.98

> <JCHEM_REFRACTIVITY>
144.22190000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-FEB-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-FEB-13         0                                  
HETATM    1  C   UNK     0      -6.545   0.605   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.879  -0.165   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.879  -1.705   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.545  -2.475   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.211  -1.705   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.211  -0.165   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.878   0.605   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.878  -2.475   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.544  -1.705   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.544  -0.165   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.210   0.605   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.123   2.915   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.210   2.145   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.123  -0.165   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.457   0.605   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.457   2.145   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -9.212   0.605   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -6.545  -4.015   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.878  -4.015   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.791   2.915   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.103  -5.825   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.103  -7.365   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.769  -8.135   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.564  -7.365   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.564  -5.825   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.898  -5.055   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.898  -8.135   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.232  -7.365   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.232  -5.825   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.565  -5.055   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.899  -2.744   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.565  -3.514   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.899  -5.825   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.233  -5.055   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.233  -3.514   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -3.437  -5.055   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -0.769  -9.675   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       1.898  -9.675   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       8.567  -2.745   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.769  -5.055   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   19                                                  
CONECT    9    8   10   40                                                  
CONECT   10    9    7   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16                                                       
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12   20                                                  
CONECT   17    2                                                            
CONECT   18    4                                                            
CONECT   19    8                                                            
CONECT   20   16                                                            
CONECT   21   40   22   36                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   37                                                  
CONECT   24   23   25   27                                                  
CONECT   25   40   26   24                                                  
CONECT   26   25   29                                                       
CONECT   27   24   28   38                                                  
CONECT   28   27   29                                                       
CONECT   29   28   26   30                                                  
CONECT   30   29   32   33                                                  
CONECT   31   32   35                                                       
CONECT   32   30   31                                                       
CONECT   33   30   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   31   39                                                  
CONECT   36   21                                                            
CONECT   37   23                                                            
CONECT   38   27                                                            
CONECT   39   35                                                            
CONECT   40   21   25    9                                                  
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
13Ii8-biapigenin	HMDB
38'-Biapigenin	HMDB
1,3-Benzodioxole-5-propanol, alpha-methyl-, 5-acetate	HMDB
1,3-Benzodioxole-5-propanol, alpha-methyl-, acetate	HMDB
3,8''-Biapigenin	HMDB
3-(1,3-Benzodioxol-5-yl)-1-methylpropyl acetate	HMDB
5,5',7,7'-Tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[3,8'-bi-4H-1-benzopyran]-4,4'-dione, 9ci	HMDB
alpha-Methyl-1,3-benzodioxole-5-propanol, acetate	HMDB

Chemical Formula

C₃₀H₁₈O₁₀

Average Mass

538.4579 Da

Monoisotopic Mass

538.09000 Da

IUPAC Name

8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(=C(O)C=C2O)C1=C(OC2=C(C(O)=CC(O)=C2)C1=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C30H18O10/c31-15-5-1-13(2-6-15)22-12-21(37)24-19(35)11-20(36)26(30(24)39-22)27-28(38)25-18(34)9-17(33)10-23(25)40-29(27)14-3-7-16(32)8-4-14/h1-12,31-36H

InChI Key

IQAMTZLKUHMPPE-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
Fagopyrum esculentum	Plant	KNApSAcK
Garcinia dulcis	Plant	KNApSAcK
Garcinia kola	Plant	KNApSAcK
Garcinia livingstonii	Plant	KNApSAcK
Garcinia xanthochymus	Plant	KNApSAcK
Hypericum aucheri	Plant	KNApSAcK
Hypericum maculatum	Plant	KNApSAcK
Hypericum perforatum	Plant	KNApSAcK
Hypericum scabrum	LOTUS Database	35616633
Hypericum thasium	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
Pyranoisoflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyisoflavonoid
Flavone
Hydroxyflavonoid
Isoflavone
Isoflavonoid skeleton
Isoflavonoid
Chromone
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen 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	4.43	ALOGPS
logP	5.11	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	5.77	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	144.22 m³·mol⁻¹	ChemAxon
Polarizability	52.22 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

HMDB0038856

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018295

KNApSAcK ID

C00006431

Chemspider ID

8590290

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10414856

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3-8'-Biapigenin (NP0054280)

MOL for NP0054280 (3-8'-Biapigenin)

3D MOL for NP0054280 (3-8'-Biapigenin)

3D SDF for NP0054280 (3-8'-Biapigenin)

3D-SDF for NP0054280 (3-8'-Biapigenin)

PDB for NP0054280 (3-8'-Biapigenin)

3D PDB for NP0054280 (3-8'-Biapigenin)

SMILES for NP0054280 (3-8'-Biapigenin)

INCHI for NP0054280 (3-8'-Biapigenin)

Structure for NP0054280 (3-8'-Biapigenin)

3D Structure for NP0054280 (3-8'-Biapigenin)