NP-MRD: Showing NP-Card for 3,5-Dimethoxystilbene (NP0061157)

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Record Information

Version

2.0

Created at

2022-04-28 06:03:08 UTC

Updated at

2022-04-28 06:03:08 UTC

NP-MRD ID

NP0061157

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5-Dimethoxystilbene

Description

3,5-Dimethoxystilbene 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. 3,5-Dimethoxystilbene is found in Alnus pendula, Larix gmelinii, Lonchocarpus chiricanus, Nephrotheca ilicifolia, Pinus albicaulis, Pinus brutia, Pinus parviflora and Pinus sibirica. 3,5-Dimethoxystilbene was first documented in 2012 (PMID: 23134335). Based on a literature review a small amount of articles have been published on 3,5-Dimethoxystilbene (PMID: 35157035) (PMID: 33424593) (PMID: 27450661) (PMID: 22293408).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    4.0294    3.4741    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7332    2.9649    0.1389 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4189    1.6197    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0771    1.2215    0.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6947   -0.0901   -0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6959   -0.5129   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6657    0.3545    0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563   -0.0426    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5195   -1.3330    0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8882   -1.6375    0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8388   -0.6573    0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3924    0.6393    0.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0498    0.9324    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6616   -1.0905   -0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9795   -0.7053   -0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9348   -1.7103   -0.3834 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6076   -3.0680   -0.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3524    0.6172   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8065    2.7655    0.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0479    4.3560    0.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570    3.8471   -0.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    2.0303    0.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9491   -1.5556   -0.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4699    1.4263    0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006   -2.1407   -0.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1984   -2.6747    0.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8946   -0.8802    0.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1496    1.4048    0.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7455    1.9667    0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507   -2.1271   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0582   -3.2954   -1.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5388   -3.6631   -0.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9113   -3.3001    0.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3837    0.8644   -0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  5 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18  3  1  0
 13  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
M  END


  Mrv1652304282208032D          

 18 19  0  0  0  0            999 V2000
    0.7145   -2.8875    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   -4.1250    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   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  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 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0061157

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O2/c1-17-15-10-14(11-16(12-15)18-2)9-8-13-6-4-3-5-7-13/h3-12H,1-2H3/b9-8+

> <INCHI_KEY>
BIYGTLDPTJMNET-CMDGGOBGSA-N

> <FORMULA>
C16H16O2

> <MOLECULAR_WEIGHT>
240.302

> <EXACT_MASS>
240.115029755

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.611186994148326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-dimethoxy-5-[(E)-2-phenylethenyl]benzene

> <ALOGPS_LOGP>
4.47

> <JCHEM_LOGP>
3.99774432

> <ALOGPS_LOGS>
-5.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.537862421334559

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
74.43920000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3-dimethoxy-5-[(E)-2-phenylethenyl]benzene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   11   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₂

Average Mass

240.3020 Da

Monoisotopic Mass

240.11503 Da

IUPAC Name

1,3-dimethoxy-5-[(E)-2-phenylethenyl]benzene

Traditional Name

1,3-dimethoxy-5-[(E)-2-phenylethenyl]benzene

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H16O2/c1-17-15-10-14(11-16(12-15)18-2)9-8-13-6-4-3-5-7-13/h3-12H,1-2H3/b9-8+

InChI Key

BIYGTLDPTJMNET-CMDGGOBGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alnus pendula	Plant	KNApSAcK
Larix gmelini	LOTUS Database	35616633
Lonchocarpus chiricanus	Plant	KNApSAcK
Nephrotheca ilicifolia	LOTUS Database	35616633
Pinus albicaulis	LOTUS Database	35616633
Pinus brutia	LOTUS Database	35616633
Pinus parviflora	LOTUS Database	35616633
Pinus sibirica	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
Dimethoxybenzene
M-dimethoxybenzene
Anisole
Phenol ether
Phenoxy compound
Styrene
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
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	4.47	ALOGPS
logP	4	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.44 m³·mol⁻¹	ChemAxon
Polarizability	27.61 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00015400

Chemspider ID

4475843

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316874

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fujita T, Lin J, Kimishima A, Arai M, Takikawa H, Ogura Y: Synthesis and biological evaluation of cajaninstilbene acid and amorfrutins A-D as cytotoxic agents against human pancreatic carcinoma PANC-1 cells. Biosci Biotechnol Biochem. 2022 Apr 21;86(5):590-595. doi: 10.1093/bbb/zbac025. [PubMed:35157035 ]
Torres F, Robledo SM, Quinones W, Escobar G, Archbold R, Correa E, Gil JF, Arbelaez N, Murillo J, Echeverri F: Exploring Antiparasitic Molecule Sources from Timber by-Product Industries-Leishmanicidal and Trypanocidal Compounds from Clathrotropis brunnea Amshoff. Front Pharmacol. 2020 Dec 24;11:584668. doi: 10.3389/fphar.2020.584668. eCollection 2020. [PubMed:33424593 ]
Weng JQ, Ali A, Estep A, Becnel J, Meyer SL, Wedge DE, Jacob M, Rimando AM: Synthesis and Biological Evaluation of 3,5-Dimethoxystilbene Analogs. Chem Biodivers. 2016 Sep;13(9):1165-1177. doi: 10.1002/cbdv.201500516. Epub 2016 Sep 8. [PubMed:27450661 ]
Trinh Thi Thanh V, Doan Thi Mai H, Pham VC, Litaudon M, Dumontet V, Gueritte F, Nguyen VH, Chau VM: Acetylcholinesterase inhibitors from the leaves of Macaranga kurzii. J Nat Prod. 2012 Nov 26;75(11):2012-5. doi: 10.1021/np300660y. Epub 2012 Nov 7. [PubMed:23134335 ]
Roslie H, Chan KM, Rajab NF, Velu SS, Kadir SA, Bunyamin I, Weber JF, Thomas NF, Majeed AB, Myatt G, Inayat-Hussain SH: 3,5-dibenzyloxy-4'-hydroxystilbene induces early caspase-9 activation during apoptosis in human K562 chronic myelogenous leukemia cells. J Toxicol Sci. 2012 Feb;37(1):13-21. doi: 10.2131/jts.37.13. [PubMed:22293408 ]

Showing NP-Card for 3,5-Dimethoxystilbene (NP0061157)

MOL for NP0061157 (3,5-Dimethoxystilbene)

3D MOL for NP0061157 (3,5-Dimethoxystilbene)

3D SDF for NP0061157 (3,5-Dimethoxystilbene)

3D-SDF for NP0061157 (3,5-Dimethoxystilbene)

PDB for NP0061157 (3,5-Dimethoxystilbene)

3D PDB for NP0061157 (3,5-Dimethoxystilbene)

SMILES for NP0061157 (3,5-Dimethoxystilbene)

INCHI for NP0061157 (3,5-Dimethoxystilbene)

Structure for NP0061157 (3,5-Dimethoxystilbene)

3D Structure for NP0061157 (3,5-Dimethoxystilbene)