NP-MRD: Showing NP-Card for 5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol (NP0050008)

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Record Information

Version

2.0

Created at

2022-03-17 21:21:44 UTC

Updated at

2022-03-17 21:21:44 UTC

NP-MRD ID

NP0050008

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-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. 5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol is found in Aiphanes horrida, Caragana tibetica, Gnetum africanum, Gnetum gnemon, Gnetum hainanense, Gnetum klossii, Gnetum macrostachyum, Gnetum montanum, Gnetum parvifolium, Gnetum pendulum, Iris domestica, Picea abies, Picea jezoensis, Picea koraiensis, Picea rubens, Pinus koraiensis, Rheum rhaponticum, Schizocarphus nervosus and Smilax corbularia. 5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272007292D          

 19 20  0  0  0  0            999 V2000
 9997.3207 9999.2493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.1823 9999.2493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8967 9998.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.329510001.3161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.474810001.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.758310000.4902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7511 9996.7725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7509 9999.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0365 9998.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0365 9998.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7509 9997.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.4653 9998.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.4653 9998.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.042010000.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.327510000.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.613110000.0753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6130 9999.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.3274 9998.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.0420 9999.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  4  5  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
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
  3 17  1  0  0  0  0
 15  4  1  0  0  0  0
 14  6  1  0  0  0  0
  1  9  1  0  0  0  0
 13  2  1  0  0  0  0
 11  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050008

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(\C=C\C2=CC(O)=CC(O)=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O4/c1-19-15-8-10(4-5-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2+

> <INCHI_KEY>
ANNNBEZJTNCXHY-NSCUHMNNSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.273

> <EXACT_MASS>
258.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.477170816306103

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
3.244719620666666

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.43752984451203

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.594213648115653

> <JCHEM_PKA_STRONGEST_BASIC>
-4.893862070232189

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
73.9187

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8661.6658665.265   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8667.0078665.265   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8668.3408664.498   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8671.0158669.123   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8669.4208670.041   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8673.6828667.582   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8664.3358660.642   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8664.3358665.266   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.0028664.496   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.0028662.956   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.3358662.186   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.6698662.956   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.6698664.496   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8672.3458666.807   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8671.0118667.577   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8669.6788666.807   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8669.6788665.268   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8671.0118664.498   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8672.3458665.268   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    3   13                                                       
CONECT    3    2   17                                                       
CONECT    4    5   15                                                       
CONECT    5    4                                                            
CONECT    6   14                                                            
CONECT    7   11                                                            
CONECT    8    9   13                                                       
CONECT    9    8   10    1                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12    7                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8    2                                                  
CONECT   14   15   19    6                                                  
CONECT   15   14   16    4                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18    3                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
Isorhapontigenin	MeSH, HMDB
3'-Methoxy-resveratrol	MeSH, HMDB
5-[(1E)-2-(4-Hydroxy-3-methoxyphenyl)ethenyl]-1,3-benzenediol	PhytoBank
3'-Methoxyresveratrol	PhytoBank
3’-Methoxyresveratrol	PhytoBank
Isorhapotigenin	PhytoBank
Isorhapotogenin	PhytoBank

Chemical Formula

C₁₅H₁₄O₄

Average Mass

258.2730 Da

Monoisotopic Mass

258.08921 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(\C=C\C2=CC(O)=CC(O)=C2)=C1

InChI Identifier

InChI=1S/C15H14O4/c1-19-15-8-10(4-5-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2+

InChI Key

ANNNBEZJTNCXHY-NSCUHMNNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aiphanes horrida	LOTUS Database	35616633
Caragana tibetica	LOTUS Database	35616633
Gnetum africanum	LOTUS Database	35616633
Gnetum gnemon	LOTUS Database	35616633
Gnetum hainanense	LOTUS Database	35616633
Gnetum klossii	LOTUS Database	35616633
Gnetum macrostachyum	LOTUS Database	35616633
Gnetum montanum	LOTUS Database	35616633
Gnetum parvifolium	LOTUS Database	35616633
Gnetum pendulum	LOTUS Database	35616633
Iris domestica	LOTUS Database	35616633
Picea abies	LOTUS Database	35616633
Picea jezoensis	LOTUS Database	35616633
Picea koraiensis	LOTUS Database	35616633
Picea rubens	LOTUS Database	35616633
Pinus koraiensis	LOTUS Database	35616633
Rheum rhabarbarum	FooDB	PHYTOHUB
Rheum rhaponticum	LOTUS Database	35616633
Schizocarphus nervosus	LOTUS Database	35616633
Smilax corbularia	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
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	2.64	ALOGPS
logP	3.24	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.59	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.92 m³·mol⁻¹	ChemAxon
Polarizability	27.48 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

HMDB0128522

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB087377

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol (NP0050008)

MOL for NP0050008 (5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol)

3D MOL for NP0050008 (5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol)

3D SDF for NP0050008 (5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol)

3D-SDF for NP0050008 (5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol)

PDB for NP0050008 (5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol)

3D PDB for NP0050008 (5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol)

SMILES for NP0050008 (5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol)

INCHI for NP0050008 (5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol)

Structure for NP0050008 (5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol)

3D Structure for NP0050008 (5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol)