NP-MRD: Showing NP-Card for (2e)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl benzoate (NP0237207)

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Record Information

Version

1.0

Created at

2022-09-06 20:17:02 UTC

Updated at

2022-09-06 20:17:03 UTC

NP-MRD ID

NP0237207

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl benzoate

Description

3,4-Dimethoxycinnamyl benzoate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. (2e)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl benzoate is found in Baccharis genistelloides. It was first documented in 1992 (PMID: 27759204). Based on a literature review a significant number of articles have been published on 3,4-dimethoxycinnamyl benzoate (PMID: 36088123) (PMID: 36088122) (PMID: 36088121) (PMID: 36088120).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -6.0916   -0.6093   -2.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3955    0.0158   -1.3263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1356   -0.4734   -0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5673   -1.5414   -1.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300   -1.9985   -1.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6554   -1.3741   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -1.8358    0.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4095   -1.3390    1.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7608   -1.8784    1.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7749   -0.9343    1.2929 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0205   -0.3443    0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3199   -0.6688   -0.8965 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0854    0.6407   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8681    1.0082    1.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8787    1.9402    0.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1444    2.5469   -0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3726    2.1980   -1.3877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3606    1.2541   -1.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2133   -0.3155    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4735    0.1550    0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0296    1.2253    0.7208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144    1.8335    1.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1211   -0.2330   -2.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5463   -0.4533   -3.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1074   -1.7170   -2.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055   -2.0184   -2.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8395   -2.8380   -1.8089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1243   -2.6900   -0.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0454   -0.5108    1.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0182   -2.7567    0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6993   -2.2095    2.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6501    0.5246    1.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4908    2.2273    1.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9395    3.2817   -0.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5957    2.6814   -2.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7945    1.0258   -2.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7286    0.2056    1.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071    1.0744    2.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4120    2.3167    1.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464    2.5844    2.2949 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20  3  1  0
 18 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 22 38  1  0
 22 39  1  0
 22 40  1  0
M  END


  Mrv1652309062222172D          

 22 23  0  0  0  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  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
 13 18  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0237207

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(\C=C\COC(=O)C2=CC=CC=C2)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O4/c1-20-16-11-10-14(13-17(16)21-2)7-6-12-22-18(19)15-8-4-3-5-9-15/h3-11,13H,12H2,1-2H3/b7-6+

> <INCHI_KEY>
LFZYARKXYLJCFN-VOTSOKGWSA-N

> <FORMULA>
C18H18O4

> <MOLECULAR_WEIGHT>
298.338

> <EXACT_MASS>
298.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.76073297885691

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl benzoate

> <JCHEM_LOGP>
3.995769039333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.589917037965124

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
85.94090000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335 -16.940   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000 -18.480   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000 -16.940   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    6   20                                                       
CONECT   20   19    3   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
3,4-Dimethoxycinnamyl benzoic acid	Generator

Chemical Formula

C₁₈H₁₈O₄

Average Mass

298.3380 Da

Monoisotopic Mass

298.12051 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC=C(\C=C\COC(=O)C2=CC=CC=C2)C=C1OC

InChI Identifier

InChI=1S/C18H18O4/c1-20-16-11-10-14(13-17(16)21-2)7-6-12-22-18(19)15-8-4-3-5-9-15/h3-11,13H,12H2,1-2H3/b7-6+

InChI Key

LFZYARKXYLJCFN-VOTSOKGWSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Baccharis genistelloides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Dimethoxybenzene
O-dimethoxybenzene
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Styrene
Methoxybenzene
Alkyl aryl ether
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
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

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

4946704

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6442637

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xu X, Rothrock MJ Jr, Reeves J, Kumar GD, Mishra A: Using E. coli population to predict foodborne pathogens in pastured poultry farms. Food Microbiol. 2022 Dec;108:104092. doi: 10.1016/j.fm.2022.104092. Epub 2022 Jul 14. [PubMed:36088123 ]
Lanzl MI, Zwietering MH, Abee T, den Besten HMW: Combining enrichment with multiplex real-time PCR leads to faster detection and identification of Campylobacter spp. in food compared to ISO 10272-1:2017. Food Microbiol. 2022 Dec;108:104117. doi: 10.1016/j.fm.2022.104117. Epub 2022 Aug 19. [PubMed:36088122 ]
Cacciatore FA, Maders C, Alexandre B, Barreto Pinilla CM, Brandelli A, da Silva Malheiros P: Carvacrol encapsulation into nanoparticles produced from chia and flaxseed mucilage: Characterization, stability and antimicrobial activity against Salmonella and Listeria monocytogenes. Food Microbiol. 2022 Dec;108:104116. doi: 10.1016/j.fm.2022.104116. Epub 2022 Aug 18. [PubMed:36088121 ]
Liu X, Li Y, Micallef SA: Developmentally related and drought-induced shifts in the kale metabolome limited Salmonella enterica association, providing novel insights to enhance food safety. Food Microbiol. 2022 Dec;108:104113. doi: 10.1016/j.fm.2022.104113. Epub 2022 Aug 18. [PubMed:36088120 ]
Jakubas WJ, Shah PS, Mason JR, Norman DM: Avian Repellency of Coniferyl and Cinnamyl Derivatives. Ecol Appl. 1992 May;2(2):147-156. doi: 10.2307/1941771. [PubMed:27759204 ]
LOTUS database [Link]

Showing NP-Card for (2e)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl benzoate (NP0237207)

MOL for NP0237207 ((2e)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl benzoate)

3D MOL for NP0237207 ((2e)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl benzoate)

3D SDF for NP0237207 ((2e)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl benzoate)

3D-SDF for NP0237207 ((2e)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl benzoate)

PDB for NP0237207 ((2e)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl benzoate)

3D PDB for NP0237207 ((2e)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl benzoate)

SMILES for NP0237207 ((2e)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl benzoate)

INCHI for NP0237207 ((2e)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl benzoate)

Structure for NP0237207 ((2e)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl benzoate)

3D Structure for NP0237207 ((2e)-3-(3,4-dimethoxyphenyl)prop-2-en-1-yl benzoate)