NP-MRD: Showing NP-Card for 4,4'-Dihydroxy-3,5-dimethoxybibenzyl (NP0051652)

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Record Information

Version

2.0

Created at

2022-04-27 22:56:23 UTC

Updated at

2022-04-27 22:56:23 UTC

NP-MRD ID

NP0051652

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,4'-Dihydroxy-3,5-dimethoxybibenzyl

Description

4,4'-Dihydroxy-3,5-dimethoxydihydrostilbene 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. Thus, 4,4'-dihydroxy-3,5-dimethoxydihydrostilbene is considered to be an aromatic polyketide lipid molecule. A stilbenoid that is ethane in which one of the hydrogens is replaced by a 4-hydroxyphenyl group and one of the hydrogens of the remaining methyl group is replaced by a 4-hydroxy-3,5-dimethoxyphenyl group. 4,4'-Dihydroxy-3,5-dimethoxybibenzyl is found in Combretum psidioides and Dendrobium candidum . 4,4'-Dihydroxy-3,5-dimethoxydihydrostilbene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -2.1194    3.7135   -1.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563    2.6546   -1.8047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6082    1.4297   -1.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2734    1.2216   -1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8567   -0.0138   -0.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5727   -0.1742   -0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8824    0.1551    1.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3368   -0.0387    1.4074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2637    0.9666    1.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6161    0.7188    1.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0794   -0.5141    1.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4145   -0.7829    2.0735 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1428   -1.5224    2.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8083   -1.2724    1.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7923   -1.0190   -0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1236   -0.8507   -0.7668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0039   -1.9059   -0.6221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6737   -3.1779   -0.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5280    0.3876   -1.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8499    0.6438   -1.5516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2565    3.4112   -2.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7771    3.9897   -0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5766    4.6027   -2.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5938    2.0661   -1.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1938    0.4791   -0.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8382   -1.2408   -0.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6625    1.2331    1.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3477   -0.4562    1.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9244    1.9413    0.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3466    1.4940    1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8709   -0.6669    2.9563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4731   -2.5198    2.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1089   -2.0949    1.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3971   -1.9795   -0.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8257   -3.3314    0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6722   -3.5324   -0.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3914   -3.8975   -0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5071   -0.1173   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  5 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 19  3  1  0
 14  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 20 38  1  0
M  END


  Mrv0541 04121516372D          

 20 21  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    2.1434   -2.8875    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
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   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
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    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 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
  5 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051652

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CCC2=CC=C(O)C=C2)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O4/c1-19-14-9-12(10-15(20-2)16(14)18)4-3-11-5-7-13(17)8-6-11/h5-10,17-18H,3-4H2,1-2H3

> <INCHI_KEY>
DLRAWGGINAZULN-UHFFFAOYSA-N

> <FORMULA>
C16H18O4

> <MOLECULAR_WEIGHT>
274.316

> <EXACT_MASS>
274.12050906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.884381272238556

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[2-(4-hydroxyphenyl)ethyl]-2,6-dimethoxyphenol

> <ALOGPS_LOGP>
3.06

> <JCHEM_LOGP>
3.5871353333333325

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.385330237402261

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.58867226642154

> <JCHEM_PKA_STRONGEST_BASIC>
-4.601883335936916

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
77.28439999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[2-(4-hydroxyphenyl)ethyl]-2,6-dimethoxyphenol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   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  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8                                                       
CONECT   15    5   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16    3   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
4,4'-Dihydroxy-3,5-dimethoxybibenzyl	ChEBI

Chemical Formula

C₁₆H₁₈O₄

Average Mass

274.3160 Da

Monoisotopic Mass

274.12051 Da

IUPAC Name

4-[2-(4-hydroxyphenyl)ethyl]-2,6-dimethoxyphenol

Traditional Name

4-[2-(4-hydroxyphenyl)ethyl]-2,6-dimethoxyphenol

CAS Registry Number

Not Available

SMILES

COC1=CC(CCC2=CC=C(O)C=C2)=CC(OC)=C1O

InChI Identifier

InChI=1S/C16H18O4/c1-19-14-9-12(10-15(20-2)16(14)18)4-3-11-5-7-13(17)8-6-11/h5-10,17-18H,3-4H2,1-2H3

InChI Key

DLRAWGGINAZULN-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
Combretum psidioides	LOTUS Database	35616633
Dendrobium candidum	Plant	KNApSAcK

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
Dimethoxybenzene
M-dimethoxybenzene
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:28571 )
stilbenoid (CHEBI:28571 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (C10256 )
Bibenzyls (C10256 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090036 )

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	3.06	ALOGPS
logP	3.59	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.59	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.28 m³·mol⁻¹	ChemAxon
Polarizability	29.88 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00002880

Chemspider ID

Not Available

KEGG Compound ID

C10256

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442701

PDB ID

Not Available

ChEBI ID

28571

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4,4'-Dihydroxy-3,5-dimethoxybibenzyl (NP0051652)

MOL for NP0051652 (4,4'-Dihydroxy-3,5-dimethoxybibenzyl)

3D MOL for NP0051652 (4,4'-Dihydroxy-3,5-dimethoxybibenzyl)

3D SDF for NP0051652 (4,4'-Dihydroxy-3,5-dimethoxybibenzyl)

3D-SDF for NP0051652 (4,4'-Dihydroxy-3,5-dimethoxybibenzyl)

PDB for NP0051652 (4,4'-Dihydroxy-3,5-dimethoxybibenzyl)

3D PDB for NP0051652 (4,4'-Dihydroxy-3,5-dimethoxybibenzyl)

SMILES for NP0051652 (4,4'-Dihydroxy-3,5-dimethoxybibenzyl)

INCHI for NP0051652 (4,4'-Dihydroxy-3,5-dimethoxybibenzyl)

Structure for NP0051652 (4,4'-Dihydroxy-3,5-dimethoxybibenzyl)

3D Structure for NP0051652 (4,4'-Dihydroxy-3,5-dimethoxybibenzyl)