NP-MRD: Showing NP-Card for 5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol (NP0235634)

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Record Information

Version

2.0

Created at

2022-09-06 18:20:05 UTC

Updated at

2022-09-06 18:20:05 UTC

NP-MRD ID

NP0235634

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol

Description

4-[3-(3,5-Dihydroxyphenyl)-6-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,2-diol belongs to the class of organic compounds known as stilbenolignans. These are non-conventional lignans that derived from stilbene. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to one ring of the stilbene moiety. 5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol is found in Caragana rosea and Maackia amurensis. 4-[3-(3,5-Dihydroxyphenyl)-6-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161502212D          

 36 40  0  0  0  0            999 V2000
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004161502212D          

 36 40  0  0  0  0            999 V2000
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0235634

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(C=CC2=CC=C3OC(C(OC3=C2)C2=CC(O)=CC(O)=C2)C2=CC=C(O)C(O)=C2)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H22O8/c29-19-7-16(8-20(30)13-19)2-1-15-3-6-25-26(9-15)36-28(18-10-21(31)14-22(32)11-18)27(35-25)17-4-5-23(33)24(34)12-17/h1-14,27-34H

> <INCHI_KEY>
NKUZVJOKTLLGKC-UHFFFAOYSA-N

> <FORMULA>
C28H22O8

> <MOLECULAR_WEIGHT>
486.476

> <EXACT_MASS>
486.131467668

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
50.9770612577838

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
5.573307821333332

> <ALOGPS_LOGS>
-4.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.137746234586663

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.66910543528215

> <JCHEM_PKA_STRONGEST_BASIC>
-4.66159761063428

> <JCHEM_POLAR_SURFACE_AREA>
139.84

> <JCHEM_REFRACTIVITY>
132.9212

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.12e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -6.930   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  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   36                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   28                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   10                                                       
CONECT   20   16   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20                                                       
CONECT   28   15   29   35                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   28                                                       
CONECT   36    7    2                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₂O₈

Average Mass

486.4760 Da

Monoisotopic Mass

486.13147 Da

IUPAC Name

5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol

Traditional Name

5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol

CAS Registry Number

Not Available

SMILES

OC1=CC(C=CC2=CC=C3OC(C(OC3=C2)C2=CC(O)=CC(O)=C2)C2=CC=C(O)C(O)=C2)=CC(O)=C1

InChI Identifier

InChI=1S/C28H22O8/c29-19-7-16(8-20(30)13-19)2-1-15-3-6-25-26(9-15)36-28(18-10-21(31)14-22(32)11-18)27(35-25)17-4-5-23(33)24(34)12-17/h1-14,27-34H

InChI Key

NKUZVJOKTLLGKC-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

Species Name	Source	Reference
Caragana rosea	LOTUS Database	35616633
Maackia amurensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenolignans. These are non-conventional lignans that derived from stilbene. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to one ring of the stilbene moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Stilbenolignans

Sub Class

Not Available

Direct Parent

Stilbenolignans

Alternative Parents

Substituents

Stilbenolignan skeleton
2-phenylbenzo-1,4-dioxane
Phenylbenzodioxane
Stilbene
Benzo-1,4-dioxane
Benzodioxane
Catechol
Resorcinol
Styrene
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Para-dioxin
Monocyclic benzene moiety
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
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	4.21	ALOGPS
logP	5.57	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	8.67	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	139.84 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	132.92 m³·mol⁻¹	ChemAxon
Polarizability	50.98 Å³	ChemAxon
Number of Rings	5	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

73816195

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol (NP0235634)

MOL for NP0235634 (5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol)

3D MOL for NP0235634 (5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol)

3D SDF for NP0235634 (5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol)

3D-SDF for NP0235634 (5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol)

PDB for NP0235634 (5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol)

3D PDB for NP0235634 (5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol)

SMILES for NP0235634 (5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol)

INCHI for NP0235634 (5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol)

Structure for NP0235634 (5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol)

3D Structure for NP0235634 (5-[3-(3,4-dihydroxyphenyl)-7-[2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,3-diol)