NP-MRD: Showing NP-Card for 3-[2-(3-{4-[2-(2,3-dihydroxyphenyl)ethyl]phenoxy}-4-hydroxyphenyl)ethyl]benzene-1,2-diol (NP0321153)

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Record Information

Version

2.0

Created at

2022-09-11 23:13:07 UTC

Updated at

2022-09-11 23:13:07 UTC

NP-MRD ID

NP0321153

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[2-(3-{4-[2-(2,3-dihydroxyphenyl)ethyl]phenoxy}-4-hydroxyphenyl)ethyl]benzene-1,2-diol

Description

CHEMBL1795528 belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. 3-[2-(3-{4-[2-(2,3-dihydroxyphenyl)ethyl]phenoxy}-4-hydroxyphenyl)ethyl]benzene-1,2-diol is found in Pellia epiphylla. CHEMBL1795528 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231519492D          

 34 37  0  0  0  0            999 V2000
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -11.1375    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


  Mrv1533004231519492D          

 34 37  0  0  0  0            999 V2000
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0321153

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC(CCC2=CC=C(OC3=CC(CCC4=CC=CC(O)=C4O)=CC=C3O)C=C2)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H26O6/c29-23-16-11-19(8-13-21-4-2-6-25(31)28(21)33)17-26(23)34-22-14-9-18(10-15-22)7-12-20-3-1-5-24(30)27(20)32/h1-6,9-11,14-17,29-33H,7-8,12-13H2

> <INCHI_KEY>
YKQVXJRNXCNWPK-UHFFFAOYSA-N

> <FORMULA>
C28H26O6

> <MOLECULAR_WEIGHT>
458.51

> <EXACT_MASS>
458.172938557

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
48.968772530575485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[2-(4-{5-[2-(2,3-dihydroxyphenyl)ethyl]-2-hydroxyphenoxy}phenyl)ethyl]benzene-1,2-diol

> <ALOGPS_LOGP>
4.71

> <JCHEM_LOGP>
7.028431774666666

> <ALOGPS_LOGS>
-5.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.325558737301543

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.6276143376739

> <JCHEM_PKA_STRONGEST_BASIC>
-3.724370171984296

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
130.87970000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.26e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[2-(4-{5-[2-(2,3-dihydroxyphenyl)ethyl]-2-hydroxyphenoxy}phenyl)ethyl]benzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667 -18.480   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334 -19.250   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000 -18.480   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334 -19.250   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334 -20.790   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667 -21.560   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.668 -23.870   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -8.002 -23.100   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.336 -23.870   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -10.669 -23.100   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -12.003 -23.870   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -12.003 -25.410   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -13.337 -26.180   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -13.337 -27.720   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -14.670 -28.490   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -16.004 -27.720   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -16.004 -26.180   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -17.338 -25.410   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0     -14.670 -25.410   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0     -14.670 -23.870   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0     -10.669 -21.560   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -9.336 -20.790   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -8.002 -21.560   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.668 -20.790   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.001 -20.790   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000 -16.940   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.334 -16.170   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   31                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   19   26                                                  
CONECT   26   25                                                            
CONECT   27   16   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   14   30                                                  
CONECT   30   29                                                            
CONECT   31   12   32                                                       
CONECT   32   31    9                                                       
CONECT   33    6    2   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₆O₆

Average Mass

458.5100 Da

Monoisotopic Mass

458.17294 Da

IUPAC Name

3-[2-(4-{5-[2-(2,3-dihydroxyphenyl)ethyl]-2-hydroxyphenoxy}phenyl)ethyl]benzene-1,2-diol

Traditional Name

3-[2-(4-{5-[2-(2,3-dihydroxyphenyl)ethyl]-2-hydroxyphenoxy}phenyl)ethyl]benzene-1,2-diol

CAS Registry Number

Not Available

SMILES

OC1=CC=CC(CCC2=CC=C(OC3=CC(CCC4=CC=CC(O)=C4O)=CC=C3O)C=C2)=C1O

InChI Identifier

InChI=1S/C28H26O6/c29-23-16-11-19(8-13-21-4-2-6-25(31)28(21)33)17-26(23)34-22-14-9-18(10-15-22)7-12-20-3-1-5-24(30)27(20)32/h1-6,9-11,14-17,29-33H,7-8,12-13H2

InChI Key

YKQVXJRNXCNWPK-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
Pellia epiphylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Oxyneolignan skeleton
Stilbene
Diphenylether
Diaryl ether
Phenoxy compound
Catechol
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	4.71	ALOGPS
logP	7.03	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	8.63	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.88 m³·mol⁻¹	ChemAxon
Polarizability	48.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

10253626

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[2-(3-{4-[2-(2,3-dihydroxyphenyl)ethyl]phenoxy}-4-hydroxyphenyl)ethyl]benzene-1,2-diol (NP0321153)

MOL for NP0321153 (3-[2-(3-{4-[2-(2,3-dihydroxyphenyl)ethyl]phenoxy}-4-hydroxyphenyl)ethyl]benzene-1,2-diol)

3D MOL for NP0321153 (3-[2-(3-{4-[2-(2,3-dihydroxyphenyl)ethyl]phenoxy}-4-hydroxyphenyl)ethyl]benzene-1,2-diol)

3D SDF for NP0321153 (3-[2-(3-{4-[2-(2,3-dihydroxyphenyl)ethyl]phenoxy}-4-hydroxyphenyl)ethyl]benzene-1,2-diol)

3D-SDF for NP0321153 (3-[2-(3-{4-[2-(2,3-dihydroxyphenyl)ethyl]phenoxy}-4-hydroxyphenyl)ethyl]benzene-1,2-diol)

PDB for NP0321153 (3-[2-(3-{4-[2-(2,3-dihydroxyphenyl)ethyl]phenoxy}-4-hydroxyphenyl)ethyl]benzene-1,2-diol)

3D PDB for NP0321153 (3-[2-(3-{4-[2-(2,3-dihydroxyphenyl)ethyl]phenoxy}-4-hydroxyphenyl)ethyl]benzene-1,2-diol)

SMILES for NP0321153 (3-[2-(3-{4-[2-(2,3-dihydroxyphenyl)ethyl]phenoxy}-4-hydroxyphenyl)ethyl]benzene-1,2-diol)

INCHI for NP0321153 (3-[2-(3-{4-[2-(2,3-dihydroxyphenyl)ethyl]phenoxy}-4-hydroxyphenyl)ethyl]benzene-1,2-diol)

Structure for NP0321153 (3-[2-(3-{4-[2-(2,3-dihydroxyphenyl)ethyl]phenoxy}-4-hydroxyphenyl)ethyl]benzene-1,2-diol)

3D Structure for NP0321153 (3-[2-(3-{4-[2-(2,3-dihydroxyphenyl)ethyl]phenoxy}-4-hydroxyphenyl)ethyl]benzene-1,2-diol)