NP-MRD: Showing NP-Card for Trans-3,3′,5,5′-tetrahydroxy-4′-methoxystilbene (NP0331441)

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Record Information

Version

1.0

Created at

2023-01-14 16:04:50 UTC

Updated at

2024-05-11 13:24:27 UTC

NP-MRD ID

NP0331441

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Trans-3,3′,5,5′-tetrahydroxy-4′-methoxystilbene

Description

CHEMBL470459 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. Based on a literature review very few articles have been published on CHEMBL470459.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    5.9602    0.1925   -0.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2187    0.0124    0.6880 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8201    0.1115    0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0440   -0.9873    0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126   -2.1983    0.1446 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6591   -0.9327    0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0539    0.2866    0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3972    0.4416    0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2574   -0.5070   -0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6886   -0.3231   -0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4725   -1.4259   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8359   -1.3008   -0.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6108   -2.4291   -0.8091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4757   -0.1020   -0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7023    1.0118   -0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3049    2.2591    0.0605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145    0.8692    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8201    1.4187    0.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1854    1.3235    0.7239 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511    2.4538    1.0014 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5715    1.0610   -1.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0358    0.3888   -0.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8897   -0.7198   -1.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1601   -3.0144   -0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0902   -1.8368   -0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8325    1.4346    0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8421   -1.5069   -0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0133   -2.4200   -0.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9471   -2.9517    0.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5355    0.0430   -0.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4083    2.8207   -0.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7887    1.7842    0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000    2.3550    0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9550    2.3879    1.0879 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  7 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
 17 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 20 34  1  0
M  END


  Mrv1652304282208052D          

 20 21  0  0  0  0            999 V2000
    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
    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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   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  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 18  1  0  0  0  0
  3 19  1  0  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331441

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c1-20-15-13(18)6-10(7-14(15)19)3-2-9-4-11(16)8-12(17)5-9/h2-8,16-19H,1H3/b3-2+

> <INCHI_KEY>
BKJYMZRGLINXRP-NSCUHMNNSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.272

> <EXACT_MASS>
274.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.510729209628472

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-methoxybenzene-1,3-diol

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
2.941154299

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.222433114070478

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.536882706234838

> <JCHEM_PKA_STRONGEST_BASIC>
-4.953538211807846

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
75.8996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-methoxybenzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -5.390   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       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13                                                            
CONECT   16   12   17                                                       
CONECT   17   16                                                            
CONECT   18   11                                                            
CONECT   19    3                                                            
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
trans-3,3',5,5'-Tetrahydroxy-4'-methoxystilbene	MeSH

Chemical Formula

C₁₅H₁₄O₅

Average Mass

274.2720 Da

Monoisotopic Mass

274.08412 Da

IUPAC Name

5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-methoxybenzene-1,3-diol

Traditional Name

5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-methoxybenzene-1,3-diol

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(\C=C\C2=CC(O)=CC(O)=C2)C=C1O

InChI Identifier

InChI=1S/C15H14O5/c1-20-15-13(18)6-10(7-14(15)19)3-2-9-4-11(16)8-12(17)5-9/h2-8,16-19H,1H3/b3-2+

InChI Key

BKJYMZRGLINXRP-NSCUHMNNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 126 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500.2, CD₃OD, simulated)	lpecio@iung.pulawy.pl	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
schidigera		Not Available

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
Anisole
Phenoxy compound
Phenol ether
Resorcinol
Styrene
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
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	2.21	ALOGPS
logP	2.94	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.54	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.9 m³·mol⁻¹	ChemAxon
Polarizability	28.51 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

C00015561

Chemspider ID

10298688

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13499470

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pecio L, Alilou M, Kozachok S, Orhan IE, Eren G, Senol Deniz FS, Stuppner H, Oleszek W: Absolute configuration of spiro-flavostilbenoids from Yucca schidigera Roezl ex Ortgies: First indication of (2R)-naringenin as the key building block. Phytochemistry. 2023 Mar;207:113584. doi: 10.1016/j.phytochem.2022.113584. Epub 2023 Jan 2. [PubMed:36603655 ]

Showing NP-Card for Trans-3,3′,5,5′-tetrahydroxy-4′-methoxystilbene (NP0331441)

MOL for NP0331441 (Trans-3,3′,5,5′-tetrahydroxy-4′-methoxystilbene)

3D MOL for NP0331441 (Trans-3,3′,5,5′-tetrahydroxy-4′-methoxystilbene)

3D SDF for NP0331441 (Trans-3,3′,5,5′-tetrahydroxy-4′-methoxystilbene)

3D-SDF for NP0331441 (Trans-3,3′,5,5′-tetrahydroxy-4′-methoxystilbene)

PDB for NP0331441 (Trans-3,3′,5,5′-tetrahydroxy-4′-methoxystilbene)

3D PDB for NP0331441 (Trans-3,3′,5,5′-tetrahydroxy-4′-methoxystilbene)

SMILES for NP0331441 (Trans-3,3′,5,5′-tetrahydroxy-4′-methoxystilbene)

INCHI for NP0331441 (Trans-3,3′,5,5′-tetrahydroxy-4′-methoxystilbene)

Structure for NP0331441 (Trans-3,3′,5,5′-tetrahydroxy-4′-methoxystilbene)

3D Structure for NP0331441 (Trans-3,3′,5,5′-tetrahydroxy-4′-methoxystilbene)