NP-MRD: Showing NP-Card for Oxyresveratrol (cis-) (NP0340016)

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Record Information

Version

2.0

Created at

2024-09-12 01:01:10 UTC

Updated at

2024-09-12 01:01:10 UTC

NP-MRD ID

NP0340016

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oxyresveratrol (cis-)

Description

4-[(Z)-2-(3,5-dihydroxyphenyl)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. 4-[(Z)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

cis-oxyresveratrol
  Mrv1652304022019492D          

 20 21  0  0  0  0            999 V2000
   13.5162   -4.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1037   -3.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2787   -4.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5162   -5.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8663   -5.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1037   -6.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8663   -4.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8663   -2.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6288   -3.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1037   -4.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2787   -3.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2787   -6.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0413   -4.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0413   -2.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8663   -7.1231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6288   -4.9795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6288   -2.1219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3411   -4.2650    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5162   -2.8364    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2249   -5.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  1  2  2  0  0  0  0
  1 10  1  0  0  0  0
  2 19  1  0  0  0  0
  2 11  1  0  0  0  0
  3  5  1  0  0  0  0
  3 10  2  0  0  0  0
  4  6  2  0  0  0  0
  4 10  1  0  0  0  0
  5 12  2  0  0  0  0
  6 12  1  0  0  0  0
  7 11  2  0  0  0  0
  7 13  1  0  0  0  0
  8 11  1  0  0  0  0
  8 14  2  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  1  0  0  0  0
  4 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0340016

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(/[H])C1=CC=C(O)C=C1O)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-UPHRSURJSA-N

> <FORMULA>
C14H12O4

> <MOLECULAR_WEIGHT>
244.246

> <EXACT_MASS>
244.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
24.461581762626743

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(Z)-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>
9.417617068517844

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.848038163928706

> <JCHEM_PKA_STRONGEST_BASIC>
-5.644739694148101

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
69.43640000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: cis-oxyresveratrol                                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0      25.230  -7.961   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.460  -6.629   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.920  -9.295   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.230 -10.629   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.150 -10.629   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.460 -11.963   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.150  -7.961   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.150  -5.295   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.840  -6.629   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.460  -9.295   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.920  -6.629   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.920 -11.963   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.610  -7.961   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.610  -5.295   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      22.150 -13.296   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      19.840  -9.295   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      19.840  -3.961   0.000  0.00  0.00           O+0
HETATM   18  H   UNK     0      26.770  -7.961   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0      25.230  -5.295   0.000  0.00  0.00           H+0
HETATM   20  O   UNK     0      26.553 -10.317   0.000  0.00  0.00           O+0
CONECT    1   18    2   10                                                  
CONECT    2    1   19   11                                                  
CONECT    3    5   10                                                       
CONECT    4    6   10   20                                                  
CONECT    5    3   12                                                       
CONECT    6    4   12                                                       
CONECT    7   11   13                                                       
CONECT    8   11   14                                                       
CONECT    9   13   14                                                       
CONECT   10    1    3    4                                                  
CONECT   11    2    7    8                                                  
CONECT   12    5    6   15                                                  
CONECT   13    7    9   16                                                  
CONECT   14    8    9   17                                                  
CONECT   15   12                                                            
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18    1                                                            
CONECT   19    2                                                            
CONECT   20    4                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₂O₄

Average Mass

244.2460 Da

Monoisotopic Mass

244.07356 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]\C(=C(/[H])C1=CC=C(O)C=C1O)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-UPHRSURJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

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
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

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	2.06	ALOGPS
logP	3.1	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.85	ChemAxon
pKa (Strongest Basic)	-5.6	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	24.46 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

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

92272165

PDB ID

EZH

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Oxyresveratrol (cis-) (NP0340016)

MOL for NP0340016 (Oxyresveratrol (cis-))

3D MOL for NP0340016 (Oxyresveratrol (cis-))

3D SDF for NP0340016 (Oxyresveratrol (cis-))

3D-SDF for NP0340016 (Oxyresveratrol (cis-))

PDB for NP0340016 (Oxyresveratrol (cis-))

3D PDB for NP0340016 (Oxyresveratrol (cis-))

SMILES for NP0340016 (Oxyresveratrol (cis-))

INCHI for NP0340016 (Oxyresveratrol (cis-))

Structure for NP0340016 (Oxyresveratrol (cis-))

3D Structure for NP0340016 (Oxyresveratrol (cis-))