NP-MRD: Showing NP-Card for (4s,5s,11r,12s)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-triene-7,12-diol (NP0254897)

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Record Information

Version

2.0

Created at

2022-09-07 19:12:30 UTC

Updated at

2022-09-07 19:12:30 UTC

NP-MRD ID

NP0254897

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,5s,11r,12s)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-triene-7,12-diol

Description

(4S,5S,11R,12S)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0²,⁶]Trideca-1(9),2(6),7-triene-7,12-diol belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (4s,5s,11r,12s)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-triene-7,12-diol is found in Gnetum africanum. Based on a literature review very few articles have been published on (4S,5S,11R,12S)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0²,⁶]Trideca-1(9),2(6),7-triene-7,12-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072221122D          

 38 43  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309072221122D          

 38 43  0  0  1  0            999 V2000
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 22 23  2  0  0  0  0
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 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 20 27  1  0  0  0  0
 19 28  1  0  0  0  0
 12 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  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 29 36  1  0  0  0  0
  5 37  1  0  0  0  0
 37 38  2  0  0  0  0
  2 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0254897

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CC2=C3O[C@@H]([C@H](C3=C(O)C=C2O[C@@H]1C1=CC=C(O)C=C1)C1=CC(O)=CC(O)=C1)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H24O9/c30-16-4-1-13(2-5-16)27-23(36)11-19-24(37-27)12-22(35)26-25(15-7-17(31)10-18(32)8-15)28(38-29(19)26)14-3-6-20(33)21(34)9-14/h1-10,12,23,25,27-28,30-36H,11H2/t23-,25-,27+,28+/m0/s1

> <INCHI_KEY>
NZDIYRLCAMWPPU-FRRISVFZSA-N

> <FORMULA>
C29H24O9

> <MOLECULAR_WEIGHT>
516.502

> <EXACT_MASS>
516.142032353

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
53.1815913583676

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,5S,11R,12S)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0^{2,6}]trideca-1,6,8-triene-7,12-diol

> <JCHEM_LOGP>
4.3532105990000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.219157670970944

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.761428153637459

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2868459520296724

> <JCHEM_POLAR_SURFACE_AREA>
160.07

> <JCHEM_REFRACTIVITY>
136.5837

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5S,11R,12S)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0^{2,6}]trideca-1,6,8-triene-7,12-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0      -5.029  -1.300   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.490  -1.348   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.678  -0.039   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.139  -0.087   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.411  -1.444   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.128  -1.492   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.939  -0.183   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.479  -0.231   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.290   1.078   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.829   1.030   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.640   2.339   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.557  -0.327   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.746  -1.636   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.207  -1.588   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.395  -2.897   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.856  -2.849   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.045  -4.158   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.740  -2.812   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.166  -2.230   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.475  -3.041   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.832  -2.313   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.141  -3.125   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.093  -4.664   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.402  -5.475   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.736  -5.392   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.688  -6.931   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.427  -4.581   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.053  -0.694   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.229   0.300   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.956   1.816   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.132   2.810   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.859   4.325   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      11.581   2.288   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.854   0.773   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      13.303   0.251   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.678  -0.221   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.222  -2.753   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.762  -2.705   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   37                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   28                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    6   17                                                  
CONECT   17   16                                                            
CONECT   18   13   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20                                                       
CONECT   28   19   12   29                                                  
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29                                                       
CONECT   37    5   38                                                       
CONECT   38   37    2                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₂₄O₉

Average Mass

516.5020 Da

Monoisotopic Mass

516.14203 Da

IUPAC Name

(4S,5S,11R,12S)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0^{2,6}]trideca-1,6,8-triene-7,12-diol

Traditional Name

(4S,5S,11R,12S)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0^{2,6}]trideca-1,6,8-triene-7,12-diol

CAS Registry Number

Not Available

SMILES

O[C@H]1CC2=C3O[C@@H]([C@H](C3=C(O)C=C2O[C@@H]1C1=CC=C(O)C=C1)C1=CC(O)=CC(O)=C1)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C29H24O9/c30-16-4-1-13(2-5-16)27-23(36)11-19-24(37-27)12-22(35)26-25(15-7-17(31)10-18(32)8-15)28(38-29(19)26)14-3-6-20(33)21(34)9-14/h1-10,12,23,25,27-28,30-36H,11H2/t23-,25-,27+,28+/m0/s1

InChI Key

NZDIYRLCAMWPPU-FRRISVFZSA-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
Gnetum africanum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Furanoflavonoid or dihydroflavonoid
Linear 1,7-diphenylheptane skeleton
3-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Neolignan skeleton
Flavan
1-phenylcoumaran
Stilbene
Chromane
Benzopyran
1-benzopyran
Coumaran
Resorcinol
Catechol
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
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	4.35	ChemAxon
pKa (Strongest Acidic)	8.76	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	160.07 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	136.58 m³·mol⁻¹	ChemAxon
Polarizability	53.18 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

163088499

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s,5s,11r,12s)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-triene-7,12-diol (NP0254897)

MOL for NP0254897 ((4s,5s,11r,12s)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-triene-7,12-diol)

3D MOL for NP0254897 ((4s,5s,11r,12s)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-triene-7,12-diol)

3D SDF for NP0254897 ((4s,5s,11r,12s)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-triene-7,12-diol)

3D-SDF for NP0254897 ((4s,5s,11r,12s)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-triene-7,12-diol)

PDB for NP0254897 ((4s,5s,11r,12s)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-triene-7,12-diol)

3D PDB for NP0254897 ((4s,5s,11r,12s)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-triene-7,12-diol)

SMILES for NP0254897 ((4s,5s,11r,12s)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-triene-7,12-diol)

INCHI for NP0254897 ((4s,5s,11r,12s)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-triene-7,12-diol)

Structure for NP0254897 ((4s,5s,11r,12s)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-triene-7,12-diol)

3D Structure for NP0254897 ((4s,5s,11r,12s)-4-(3,4-dihydroxyphenyl)-5-(3,5-dihydroxyphenyl)-11-(4-hydroxyphenyl)-3,10-dioxatricyclo[7.4.0.0²,⁶]trideca-1,6,8-triene-7,12-diol)