NP-MRD: Showing NP-Card for 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol (NP0050007)

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Record Information

Version

2.0

Created at

2022-03-17 21:21:42 UTC

Updated at

2022-03-17 21:21:43 UTC

NP-MRD ID

NP0050007

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol, also known as 2,4,3',5'-tetrahydroxystilbene or puag-haad, 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-[(e)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol is considered to be an aromatic polyketide lipid molecule. 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol is found in Artocarpus chaplasha, Artocarpus dadah , Artocarpus gomezianus , Artocarpus lakoocha , Artocarpus reticulatus, Artocarpus reticulatus Miq, Bagassa guianensis, Chlorophora excelsa, Chlorophora regia , Cudrania javanensis , Erythrina variegata , Fatsia japonica, Gnetum hainanense, Gnetum montanum, Maclura pomifera, Melaleuca leucadendra, Milicia excelsa, Morus alba , Morus bombycis , Morus indica, Morus laevigata, Morus mongolica, Morus rubra , Morus serrata , Schoenocaulon officinale, Sorocea muriculata, Spirotropis longifolia, Toxylon pomifera, Toxylon pomiferum, Veratrum album and Veratrum grandiflorum. 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652308211903082D          

 20 21  0  0  0  0            999 V2000
   -0.7145   -5.3625    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   -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   -6.6000    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
   -0.7145   -7.8375    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
   -0.7145   -6.1875    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   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  2  0  0  0  0
  9  1  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  4  1  0  0  0  0
 11  8  2  0  0  0  0
 12  5  1  0  0  0  0
 12  7  2  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  2  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19  1  1  0  0  0  0
 20  2  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050007

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])C1=C(O)C=C(O)C=C1)C1=CC(O)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O4/c15-11-4-3-10(14(18)8-11)2-1-9-5-12(16)7-13(17)6-9/h1-8,15-18H/b2-1+

> <INCHI_KEY>
PDHAOJSHSJQANO-OWOJBTEDSA-N

> <FORMULA>
C14H12O4

> <MOLECULAR_WEIGHT>
244.246

> <EXACT_MASS>
244.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
25.370234488903556

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
3.0988255646666665

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.0691310770927

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.46626008517966

> <JCHEM_PKA_STRONGEST_BASIC>
-5.747849458670243

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
69.4364

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oxyresveratrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-AUG-19         0                                  
HETATM    1  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0      -2.667  -9.240   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.334 -10.010   0.000  0.00  0.00           H+0
CONECT    1    2    9   19                                                  
CONECT    2    1   10   20                                                  
CONECT    3    4   10                                                       
CONECT    4    3   11                                                       
CONECT    5    9   12                                                       
CONECT    6    9   13                                                       
CONECT    7   12   13                                                       
CONECT    8   11   14                                                       
CONECT    9    1    5    6                                                  
CONECT   10    2    3   14                                                  
CONECT   11    4    8   15                                                  
CONECT   12    5    7   16                                                  
CONECT   13    6    7   17                                                  
CONECT   14    8   10   18                                                  
CONECT   15   11                                                            
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19    1                                                            
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
2,4,3',5'-Tetrahydroxystilbene	MeSH
Puag-haad	MeSH
trans-243'5'-Tetrahydroxystilbene	ChEMBL, HMDB
Oxyresveratrol	MeSH, HMDB

Chemical Formula

C₁₄H₁₂O₄

Average Mass

244.2460 Da

Monoisotopic Mass

244.07356 Da

IUPAC Name

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

Traditional Name

oxyresveratrol

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=C(O)C=C(O)C=C1)C1=CC(O)=CC(O)=C1

InChI Identifier

InChI=1S/C14H12O4/c15-11-4-3-10(14(18)8-11)2-1-9-5-12(16)7-13(17)6-9/h1-8,15-18H/b2-1+

InChI Key

PDHAOJSHSJQANO-OWOJBTEDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artocarpus chama	Plant	KNApSAcK
Artocarpus dadah	Plant	KNApSAcK
Artocarpus gomezianus	Plant	KNApSAcK
Artocarpus heterophyllus	FooDB	PHYTOHUB
Artocarpus lacucha	Plant	KNApSAcK
Artocarpus reticulatus	LOTUS Database	35616633
Artocarpus reticulatus Miq	Plant	KNApSAcK
Bagassa guianensis	LOTUS Database	35616633
Chlorophora excelsa	Plant	KNApSAcK
Chlorophora regia	Plant	KNApSAcK
Cudrania javanensis	Plant	KNApSAcK
Erythrina variegata	Plant	KNApSAcK
Fatsia japonica	LOTUS Database	35616633
Gnetum hainanense	LOTUS Database	35616633
Gnetum montanum	LOTUS Database	35616633
Maclura pomifera	Plant	KNApSAcK
Melaleuca leucadendra	LOTUS Database	35616633
Milicia excelsa	LOTUS Database	35616633
Morus	FooDB	PHYTOHUB
Morus alba	Plant	KNApSAcK
Morus bombycis	Plant	KNApSAcK
Morus indica	Plant	KNApSAcK
Morus laevigata	Plant	KNApSAcK
Morus mongolica	LOTUS Database	35616633
Morus rubra	Plant	KNApSAcK
Morus serrata	Plant	KNApSAcK
Prunus dulcis	FooDB	PHYTOHUB
Schoenocaulon officinale	Plant	KNApSAcK
Sorocea muriculata	LOTUS Database	35616633
Spirotropis longifolia	LOTUS Database	35616633
Toxylon pomifera	-	KNApSAcK
Toxylon pomiferum	-	KNApSAcK
Veratrum album	Plant	KNApSAcK
Veratrum grandiflorum	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
Styrene
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

stilbenoid (CHEBI:7870 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (C10273 )
Stilbenes (C10273 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090011 )

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	2.06	ALOGPS
logP	3.1	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.47	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.44 m³·mol⁻¹	ChemAxon
Polarizability	25.37 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

HMDB0128505

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB087360

KNApSAcK ID

C00002893

Chemspider ID

Not Available

KEGG Compound ID

C10273

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281717

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol (NP0050007)

MOL for NP0050007 (4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol)

3D MOL for NP0050007 (4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol)

3D SDF for NP0050007 (4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol)

3D-SDF for NP0050007 (4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol)

PDB for NP0050007 (4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol)

3D PDB for NP0050007 (4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol)

SMILES for NP0050007 (4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol)

INCHI for NP0050007 (4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol)

Structure for NP0050007 (4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol)

3D Structure for NP0050007 (4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol)