NP-MRD: Showing NP-Card for Piceatannol (NP0047833)

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Record Information

Version

2.0

Created at

2022-03-17 20:46:43 UTC

Updated at

2022-03-17 20:46:43 UTC

NP-MRD ID

NP0047833

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Piceatannol

Description

Piceatannol is found in Abies spectabilis, Aiphanes horrida, Vouacapoua americana , Callistemon rigidus, Caragana tibetica, Caragana tibetica KOM., Cassia dentata, Cassia garrettiana, Cassia marginata, Centrolobium robustum, Centrolobium tomentosum, Cissus quadrangularis , Cyperus longus, Dioscorea antaly, Eskemukerjea megacarpum HARA, Eucalyptus sideroxylon, Fagopyrum megacarpum, Intsia bijuga , Laburnum alpinum, Laburnum anagyroides , Maackia amurensis , Melaleuca leucadendra, Morus spp., Parthenocissus quinquefolia, Parthenocissus tricuspidata, Pericopsis angolensis , Pericopsis elata , Picea abies , Picea engelmannii, Picea glauca , Picea glehnii, Picea jezoensis, Picea mariana , Picea obovata, Picea ojanensis, Picea rubens, Picea sitchensis , Pinus spp. , Rheum rhabarbarum, Rheum rhaponticum , Rheum spp., Rheum undulatum, Saccharum officinarum , Schotia brachypetala , Scirpus fluviatilis, Scirpus maritimus , Senna garrettiana, Senna lindheimeriana, Smilax bracteata, Smilax corbularia, Spirotropis longifolia, Syagrus romanzoffiana, Vitis amurensis, Vitis vinifera and Vouacapoua macropetala.

Structure

MOL SDF PDB SMILES InChI

cis-piceatannol
  Mrv1572001071617342D          

 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
   13.3899   -7.1174    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
  6 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047833

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
CDRPUGZCRXZLFL-UPHRSURJSA-N

> <FORMULA>
C14H12O4

> <MOLECULAR_WEIGHT>
244.246

> <EXACT_MASS>
244.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
24.30150905058958

> <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-1,2-diol

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
3.0988255646666665

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.49495200373355

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.905793112852761

> <JCHEM_PKA_STRONGEST_BASIC>
-5.678026138943371

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
69.43640000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.70e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: cis-piceatannol                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         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      24.994 -13.286   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                                                       
CONECT    5    3   12                                                       
CONECT    6    4   12   20                                                  
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    6                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
(Z)-3,5,3',4'-Tetrahydroxystilbene	ChEBI

Chemical Formula

C₁₄H₁₂O₄

Average Mass

244.2460 Da

Monoisotopic Mass

244.07356 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

4339-71-3

SMILES

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

InChI Identifier

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

InChI Key

CDRPUGZCRXZLFL-UPHRSURJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abies spectabilis	LOTUS Database	35616633
Aiphanes horrida	LOTUS Database	35616633
Andira aubletii	Plant	KNApSAcK
Callistemon rigidus	LOTUS Database	35616633
Caragana tibetica	LOTUS Database	35616633
Caragana tibetica KOM.	Plant	KNApSAcK
Cassia dentata	Plant	KNApSAcK
Cassia garrettiana	Plant	KNApSAcK
Cassia marginata	Plant	KNApSAcK
Centrolobium robustum	Plant	KNApSAcK
Centrolobium tomentosum	LOTUS Database	35616633
Cissus quadrangularis	Plant	KNApSAcK
Cyperus longus	LOTUS Database	35616633
Dioscorea antaly	LOTUS Database	35616633
Eskemukerjea megacarpum HARA	Plant	KNApSAcK
Eucalyptus sideroxylon	LOTUS Database	35616633
Fagopyrum megacarpum	LOTUS Database	35616633
Intsia bijuga	Plant	KNApSAcK
Laburnum alpinum	Plant	KNApSAcK
Laburnum anagyroides	Plant	KNApSAcK
Maackia amurensis	Plant	KNApSAcK
Melaleuca leucadendra	LOTUS Database	35616633
Morus spp.	Plant	KNApSAcK
Parthenocissus quinquefolia	LOTUS Database	35616633
Parthenocissus tricuspidata	LOTUS Database	35616633
Pericopsis angolensis	Plant	KNApSAcK
Pericopsis elata	Plant	KNApSAcK
Picea abies	Plant	KNApSAcK
Picea engelmannii	Plant	KNApSAcK
Picea glauca	Plant	KNApSAcK
Picea glehnii	Plant	KNApSAcK
Picea jezoensis	Plant	KNApSAcK
Picea mariana	Plant	KNApSAcK
Picea obovata	Plant	KNApSAcK
Picea ojanensis	Plant	KNApSAcK
Picea rubens	Plant	KNApSAcK
Picea sitchensis	Plant	KNApSAcK
Pinus spp.	Plant	KNApSAcK
Rheum rhabarbarum	LOTUS Database	35616633
Rheum rhaponticum	Plant	KNApSAcK
Rheum spp.	Plant	KNApSAcK
Rheum undulatum	LOTUS Database	35616633
Saccharum officinarum	Plant	KNApSAcK
Schotia brachypetala	Plant	KNApSAcK
Scirpus fluviatilis	Plant	KNApSAcK
Scirpus maritimus	Plant	KNApSAcK
Senna garrettiana	LOTUS Database	35616633
Senna lindheimeriana	LOTUS Database	35616633
Smilax bracteata	LOTUS Database	35616633
Smilax corbularia	LOTUS Database	35616633
Spirotropis longifolia	LOTUS Database	35616633
Syagrus romanzoffiana	LOTUS Database	35616633
Vitis amurensis	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Vitis vinifera L.	FooDB	PHENOL EXPLORER
Vouacapoua macropetala	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
Catechol
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

polyphenol (CHEBI:76156 )
stilbenol (CHEBI:76156 )

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	2.12	ALOGPS
logP	3.1	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.91	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	24.3 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

FDB012295

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Piceatannol

METLIN ID

Not Available

PubChem Compound

6603962

PDB ID

Not Available

ChEBI ID

76156

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Piceatannol (NP0047833)

MOL for NP0047833 (Piceatannol)

3D MOL for NP0047833 (Piceatannol)

3D SDF for NP0047833 (Piceatannol)

3D-SDF for NP0047833 (Piceatannol)

PDB for NP0047833 (Piceatannol)

3D PDB for NP0047833 (Piceatannol)

SMILES for NP0047833 (Piceatannol)

INCHI for NP0047833 (Piceatannol)

Structure for NP0047833 (Piceatannol)

3D Structure for NP0047833 (Piceatannol)