NP-MRD: Showing NP-Card for 2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1h-indene-4,6-diol (NP0156569)

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Record Information

Version

2.0

Created at

2022-09-02 13:47:41 UTC

Updated at

2022-09-02 13:47:41 UTC

NP-MRD ID

NP0156569

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1h-indene-4,6-diol

Description

2-(3,5-Dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1H-indene-4,6-diol belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. 2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1h-indene-4,6-diol is found in Salacia lehmbachii. Based on a literature review very few articles have been published on 2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1H-indene-4,6-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022215472D          

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M  END

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M  END


  Mrv1652309022215472D          

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    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -2.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    0.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
  5 13  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 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
 30 31  1  0  0  0  0
 29 32  2  0  0  0  0
 24 32  1  0  0  0  0
 23 33  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 34 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0156569

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(C1C(C(C2=C(O)C=C(O)C=C12)C1=CC=C(O)C(OC)=C1)C1=CC(O)=CC(O)=C1)C1=CC=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H32O9/c1-4-41-32(17-6-8-24(37)27(12-17)40-3)31-22-14-21(35)15-25(38)30(22)28(16-5-7-23(36)26(11-16)39-2)29(31)18-9-19(33)13-20(34)10-18/h5-15,28-29,31-38H,4H2,1-3H3

> <INCHI_KEY>
FBOBYSYFSCKMJM-UHFFFAOYSA-N

> <FORMULA>
C32H32O9

> <MOLECULAR_WEIGHT>
560.599

> <EXACT_MASS>
560.20463261

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
58.5032764912649

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1H-indene-4,6-diol

> <ALOGPS_LOGP>
4.42

> <JCHEM_LOGP>
5.398311888999999

> <ALOGPS_LOGS>
-5.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.432064686250602

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.958166221654375

> <JCHEM_PKA_STRONGEST_BASIC>
-4.101844262268563

> <JCHEM_POLAR_SURFACE_AREA>
149.07

> <JCHEM_REFRACTIVITY>
153.22109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.04e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1H-indene-4,6-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.839   3.513   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.333   3.192   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.143   1.728   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.680   2.552   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.187   2.232   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.217   3.376   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.741   4.841   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.772   5.985   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.235   5.161   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.759   6.626   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.253   6.946   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.204   4.017   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.204  -6.622   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.698  -6.943   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.222  -8.407   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.839  -6.118   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.315  -7.583   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.630  -2.637   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -3.400  -3.970   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -3.400  -1.303   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -3.400   1.365   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10    5                                                       
CONECT   14    4   15   33                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22   24   33                                                  
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   24                                                       
CONECT   33   23   14   34                                                  
CONECT   34   33   35   41                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   34                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₂O₉

Average Mass

560.5990 Da

Monoisotopic Mass

560.20463 Da

IUPAC Name

2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1H-indene-4,6-diol

Traditional Name

2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1H-indene-4,6-diol

CAS Registry Number

Not Available

SMILES

CCOC(C1C(C(C2=C(O)C=C(O)C=C12)C1=CC=C(O)C(OC)=C1)C1=CC(O)=CC(O)=C1)C1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C32H32O9/c1-4-41-32(17-6-8-24(37)27(12-17)40-3)31-22-14-21(35)15-25(38)30(22)28(16-5-7-23(36)26(11-16)39-2)29(31)18-9-19(33)13-20(34)10-18/h5-15,28-29,31-38H,4H2,1-3H3

InChI Key

FBOBYSYFSCKMJM-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
Salacia lehmbachii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Methoxyphenol
Benzylether
Indane
Anisole
Phenoxy compound
Phenol ether
Resorcinol
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Ether
Dialkyl ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	4.42	ALOGPS
logP	5.4	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	8.96	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	149.07 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	153.22 m³·mol⁻¹	ChemAxon
Polarizability	58.5 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	Yes	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

138112352

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1h-indene-4,6-diol (NP0156569)

MOL for NP0156569 (2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

3D MOL for NP0156569 (2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

3D SDF for NP0156569 (2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

3D-SDF for NP0156569 (2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

PDB for NP0156569 (2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

3D PDB for NP0156569 (2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

SMILES for NP0156569 (2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

INCHI for NP0156569 (2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

Structure for NP0156569 (2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)

3D Structure for NP0156569 (2-(3,5-dihydroxyphenyl)-1-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1h-indene-4,6-diol)