NP-MRD: Showing NP-Card for 3,3',4'5-Tetrahydroxystilbene (NP0049960)

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Record Information

Version

2.0

Created at

2022-03-17 21:20:54 UTC

Updated at

2022-03-17 21:20:54 UTC

NP-MRD ID

NP0049960

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,3',4'5-Tetrahydroxystilbene

Description

3,3',4'5-Tetrahydroxystilbene, also known as 3-hydroxyresveratol or piceatanol, 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, 3,3',4'5-tetrahydroxystilbene is considered to be an aromatic polyketide lipid molecule. 3,3',4'5-Tetrahydroxystilbene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3,3',4'5-Tetrahydroxystilbene exists in all living species, ranging from bacteria to humans. Outside of the human body, 3,3',4'5-Tetrahydroxystilbene has been detected, but not quantified in, several different foods, such as black tea, dessert wines, red champagnes, deerberries, and fruit juices. This could make 3,3',4'5-tetrahydroxystilbene a potential biomarker for the consumption of these foods. 3,3',4'5-Tetrahydroxystilbene is found in Abies alba, Abies spectabilis, Aiphanes horrida, Apis cerana, Bolboschoenus fluviatilis, Callistemon rigidus, Caragana tibetica, Centrolobium tomentosum, Chamaecrista flexuosa, Cissus quadrangularis, Cladrastis platycarpa, Cyperus longus, Dioscorea antaly, Eucalyptus sideroxylon, Euphorbia lagascae, Fagopyrum megacarpum, Intsia bijuga, Laburnum alpinum, Maackia amurensis, Medicago sativa, Melaleuca leucadendra, Parthenocissus quinquefolia, Parthenocissus tricuspidata, Pericopsis elata, Picea abies, Picea engelmannii, Picea glauca, Picea glehnii, Picea jezoensis, Picea mariana, Picea obovata, Picea rubens, Picea sitchensis, Pinus koraiensis, Rheum officinale, Rheum rhaponticum, Rheum sublanceolatum, Rheum undulatum, Saccharum officinarum, Schoenoplectus californicus, Schotia brachypetala, Senna garrettiana, Senna lindheimeriana, Senna siamea, Senna skinneri, Smilax bracteata, Smilax corbularia, Spirotropis longifolia, Streptomyces avermitilis, Syagrus romanzoffiana, Vitis amurensis, Vitis vinifera and Vouacapoua macropetala. 3,3',4'5-Tetrahydroxystilbene was first documented in 1989 (PMID: 2590224). A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5 (PMID: 10370868) (PMID: 12038794) (PMID: 16216908) (PMID: 10425214) (PMID: 10641182) (PMID: 11696049).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272007422D          

 18 19  0  0  0  0            999 V2000
 9988.1631 9990.0929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.0247 9990.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.7391 9989.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1720 9992.1597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6007 9991.3338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.5935 9987.6161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.5933 9990.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.8789 9989.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.8789 9988.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.5933 9988.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.3078 9988.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.3078 9989.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8845 9990.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1700 9991.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.4555 9990.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.4554 9990.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1699 9989.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.8845 9990.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  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  7  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 13  1  0  0  0  0
  3 16  1  0  0  0  0
 14  4  1  0  0  0  0
 13  5  1  0  0  0  0
  1  8  1  0  0  0  0
 12  2  1  0  0  0  0
 10  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049960

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(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-OWOJBTEDSA-N

> <FORMULA>
C14H12O4

> <MOLECULAR_WEIGHT>
244.246

> <EXACT_MASS>
244.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
25.458696611337054

> <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-1,2-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>
8.99495200373355

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.405793112852761

> <JCHEM_PKA_STRONGEST_BASIC>
-6.178026138943371

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
69.4364

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-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    8644.5718648.173   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8649.9138648.173   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8651.2468647.406   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8653.9218652.031   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8656.5888650.490   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8647.2418643.550   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8647.2418648.174   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8645.9078647.404   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8645.9078645.864   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8647.2418645.094   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8648.5748645.864   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8648.5748647.404   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8655.2518649.716   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8653.9178650.486   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8652.5848649.715   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8652.5838648.176   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8653.9178647.405   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8655.2518648.176   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    3   12                                                       
CONECT    3    2   16                                                       
CONECT    4   14                                                            
CONECT    5   13                                                            
CONECT    6   10                                                            
CONECT    7    8   12                                                       
CONECT    8    7    9    1                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11    6                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7    2                                                  
CONECT   13   14   18    5                                                  
CONECT   14   13   15    4                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17    3                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
3,5,3',4'-Tetrahydroxystilbene	ChEBI
3-Hydroxyresveratol	ChEBI
4-[(e)-2-(3,5-Dihydroxyphenyl)vinyl]benzene-1,2-diol	ChEBI
3,4,3',5'-Tetrahydroxy-trans-stilbene	HMDB
3,3',4',5-Tetrahydroxystilbene	HMDB
3,3',4,5'-Tetrahydroxy stilbene	HMDB
RSVL-1	HMDB
3'-Hydroxyresveratol	HMDB
3,3',4,5'-Tetrahydroxystilbene	HMDB
3,5,3',4'-Tetrahydroxy-trans-stilbene	HMDB
Astringinin	HMDB
Demethyl isorhapontigenin	HMDB
Piceatanol	HMDB
3,5,3',4'-Tetrahydroxy-stilbene	HMDB
Piceatannol	HMDB
3,3',4'5-Tetrahydroxystilbene	ChEBI
(E)-3,3',4,5'-Stilbenetetrol	PhytoBank
(E)-3,3’,4,5’-Stilbenetetrol	PhytoBank
4-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,2-benzenediol	PhytoBank
(E)-Piceatannol	PhytoBank
Astringenin	PhytoBank
trans-3,3',4,5'-Tetrahydroxystilbene	PhytoBank
trans-3,3’,4,5’-Tetrahydroxystilbene	PhytoBank
trans-Piceatannol	PhytoBank

Chemical Formula

C₁₄H₁₂O₄

Average Mass

244.2460 Da

Monoisotopic Mass

244.07356 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

10083-24-6

SMILES

OC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(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-OWOJBTEDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abies alba	LOTUS Database	35616633
Abies spectabilis	LOTUS Database	35616633
Aiphanes horrida	LOTUS Database	35616633
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Apis cerana	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bolboschoenus fluviatilis	LOTUS Database	35616633
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Callistemon rigidus	LOTUS Database	35616633
Capra aegagrus hircus	FooDB	FooDB
Caragana tibetica	LOTUS Database	35616633
Centrolobium tomentosum	LOTUS Database	35616633
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chamaecrista flexuosa	LOTUS Database	35616633
Cissus quadrangularis	LOTUS Database	35616633
Cladrastis platycarpa	LOTUS Database	35616633
Coffea arabica L.	FooDB	PHYTOHUB
Coffea canephora	FooDB	PHYTOHUB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Cyperus longus	LOTUS Database	35616633
Dioscorea antaly	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Eucalyptus sideroxylon	LOTUS Database	35616633
Euphorbia lagascae	LOTUS Database	35616633
Fagopyrum megacarpum	LOTUS Database	35616633
Gallus gallus	FooDB	FooDB
Intsia bijuga	LOTUS Database	35616633
Laburnum alpinum	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Maackia amurensis	LOTUS Database	35616633
Medicago sativa	LOTUS Database	35616633
Melaleuca leucadendra	LOTUS Database	35616633
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Parthenocissus quinquefolia	LOTUS Database	35616633
Parthenocissus tricuspidata	LOTUS Database	35616633
Pericopsis elata	LOTUS Database	35616633
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Picea abies	LOTUS Database	35616633
Picea engelmannii	LOTUS Database	35616633
Picea glauca	LOTUS Database	35616633
Picea glehnii	LOTUS Database	35616633
Picea jezoensis	LOTUS Database	35616633
Picea mariana	LOTUS Database	35616633
Picea obovata	LOTUS Database	35616633
Picea rubens	LOTUS Database	35616633
Picea sitchensis	LOTUS Database	35616633
Pinus koraiensis	LOTUS Database	35616633
Prunus dulcis	FooDB	PHYTOHUB
Rheum officinale	LOTUS Database	35616633
Rheum rhabarbarum	FooDB	PHYTOHUB
Rheum rhaponticum	LOTUS Database	35616633
Rheum sublanceolatum	LOTUS Database	35616633
Rheum undulatum	LOTUS Database	35616633
Saccharum officinarum	LOTUS Database	35616633
Schoenoplectus californicus	LOTUS Database	35616633
Schotia brachypetala	LOTUS Database	35616633
Senna garrettiana	LOTUS Database	35616633
Senna lindheimeriana	LOTUS Database	35616633
Senna siamea	LOTUS Database	35616633
Senna skinneri	LOTUS Database	35616633
Smilax bracteata	LOTUS Database	35616633
Smilax corbularia	LOTUS Database	35616633
Spirotropis longifolia	LOTUS Database	35616633
Streptomyces avermitilis	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Syagrus romanzoffiana	LOTUS Database	35616633
Vaccinium stamineum	FooDB	PHYTOHUB
Vitis amurensis	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Vouacapoua macropetala	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
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

stilbenol (CHEBI:28814 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (C05901 )
Stilbenes (C05901 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090006 )

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)	8.41	ChemAxon
pKa (Strongest Basic)	-6.2	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	25.46 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

HMDB0004215

DrugBank ID

DB08399

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Piceatannol

METLIN ID

Not Available

PubChem Compound

667639

PDB ID

PIT

ChEBI ID

28814

Good Scents ID

Not Available

References

General References

Palmieri L, Mameli M, Ronca G: Effect of resveratrol and some other natural compounds on tyrosine kinase activity and on cytolysis. Drugs Exp Clin Res. 1999;25(2-3):79-85. [PubMed:10370868 ]
Minuz P, Gaino S, Zuliani V, Tommasoli RM, Benati D, Ortolani R, Zancanaro C, Berton G, Santonastaso CL: Functional role of p38 mitogen activated protein kinase in platelet activation induced by a thromboxane A2 analogue and by 8-iso-prostaglandin F2alpha. Thromb Haemost. 2002 May;87(5):888-98. [PubMed:12038794 ]
Geahlen RL, McLaughlin JL: Piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene) is a naturally occurring protein-tyrosine kinase inhibitor. Biochem Biophys Res Commun. 1989 Nov 30;165(1):241-5. doi: 10.1016/0006-291x(89)91060-7. [PubMed:2590224 ]
Maggiolini M, Recchia AG, Bonofiglio D, Catalano S, Vivacqua A, Carpino A, Rago V, Rossi R, Ando S: The red wine phenolics piceatannol and myricetin act as agonists for estrogen receptor alpha in human breast cancer cells. J Mol Endocrinol. 2005 Oct;35(2):269-81. doi: 10.1677/jme.1.01783. [PubMed:16216908 ]
Zheng J, Ramirez VD: Piceatannol, a stilbene phytochemical, inhibits mitochondrial F0F1-ATPase activity by targeting the F1 complex. Biochem Biophys Res Commun. 1999 Aug 2;261(2):499-503. doi: 10.1006/bbrc.1999.1063. [PubMed:10425214 ]
Mishra NC, Sharma M, Sharma A: Inhibitory effect of piceatannol, a protein tyrosine kinase inhibitor, on asexual maturation of Plasmodium falciparum. Indian J Exp Biol. 1999 Apr;37(4):418-20. [PubMed:10641182 ]
Miura K, Lavens-Phillips S, MacGlashan DW Jr: Piceatannol is an effective inhibitor of IgE-mediated secretion from human basophils but is neither selective for this receptor nor acts on syk kinase at concentrations where mediator release inhibition occurs. Clin Exp Allergy. 2001 Nov;31(11):1732-9. doi: 10.1046/j.1365-2222.2001.01236.x. [PubMed:11696049 ]
Seow CJ, Chue SC, Wong WS: Piceatannol, a Syk-selective tyrosine kinase inhibitor, attenuated antigen challenge of guinea pig airways in vitro. Eur J Pharmacol. 2002 May 17;443(1-3):189-96. doi: 10.1016/s0014-2999(02)01534-0. [PubMed:12044809 ]
Bavaresco L: Role of viticultural factors on stilbene concentrations of grapes and wine. Drugs Exp Clin Res. 2003;29(5-6):181-7. [PubMed:15134373 ]

Showing NP-Card for 3,3',4'5-Tetrahydroxystilbene (NP0049960)

MOL for NP0049960 (3,3',4'5-Tetrahydroxystilbene)

3D MOL for NP0049960 (3,3',4'5-Tetrahydroxystilbene)

3D SDF for NP0049960 (3,3',4'5-Tetrahydroxystilbene)

3D-SDF for NP0049960 (3,3',4'5-Tetrahydroxystilbene)

PDB for NP0049960 (3,3',4'5-Tetrahydroxystilbene)

3D PDB for NP0049960 (3,3',4'5-Tetrahydroxystilbene)

SMILES for NP0049960 (3,3',4'5-Tetrahydroxystilbene)

INCHI for NP0049960 (3,3',4'5-Tetrahydroxystilbene)

Structure for NP0049960 (3,3',4'5-Tetrahydroxystilbene)

3D Structure for NP0049960 (3,3',4'5-Tetrahydroxystilbene)