NP-MRD: Showing NP-Card for (2e)-n-[2-(4-methoxyphenyl)ethyl]-n-methyl-3-phenylprop-2-enamide (NP0244865)

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Record Information

Version

2.0

Created at

2022-09-07 05:45:18 UTC

Updated at

2022-09-07 05:45:18 UTC

NP-MRD ID

NP0244865

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-n-[2-(4-methoxyphenyl)ethyl]-n-methyl-3-phenylprop-2-enamide

Description

(E)-Herclavine belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid (E)-Herclavine is a moderately basic compound (based on its pKa). Outside of the human body, (E)-Herclavine has been detected, but not quantified in, herbs and spices. This could make (e)-herclavine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
    7.7599    1.5634    0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1999    0.2766    0.1378 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8256    0.1582   -0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9854    1.2592    0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6210    1.1591   -0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0856   -0.0951   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6349   -0.3076   -0.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9929   -0.5470    0.8352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4484   -0.7462    0.5375 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8241   -2.0919    0.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2465    0.3777    0.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6583    1.5233    0.7941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6638    0.5624    0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5636   -0.3460    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9735   -0.0168   -0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5157    1.2285   -0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8634    1.4900   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7130    0.4472   -0.6731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1836   -0.8245   -0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8523   -1.0718   -0.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9155   -1.1965   -0.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2828   -1.1085   -0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2250    2.0350    1.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5765    2.1731   -0.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8543    1.4701    0.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4534    2.2230    0.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9783    2.0289   -0.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1257    0.5863   -0.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4409   -1.2261   -1.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4118   -1.4299    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1456    0.3339    1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5759   -2.4106    1.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0678   -2.7946    0.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2729   -2.2569   -0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0819    1.5990    0.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2513   -1.3780   -0.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9041    2.0783    0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2665    2.4890   -0.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7711    0.6601   -0.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8769   -1.6214   -0.9735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4719   -2.0843   -0.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4706   -2.1857   -0.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9252   -1.9828   -0.2653 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  1  0
  8  9  1  0
  9 10  1  0
  9 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
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21 22  2  0
 22  3  1  0
 20 15  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
  7 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 13 35  1  0
 14 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
M  END


  Mrv0541 05061305062D          

 22 23  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   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
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   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
    2.8579    2.4750    0.0000 C   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
   -3.5724    1.2375    0.0000 C   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
    0.0000    2.4750    0.0000 N   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
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13 10  2  0  0  0  0
 15 14  1  0  0  0  0
 16  6  2  0  0  0  0
 16  7  1  0  0  0  0
 16 10  1  0  0  0  0
 17  8  2  0  0  0  0
 17  9  1  0  0  0  0
 17 14  1  0  0  0  0
 18 11  2  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20  1  1  0  0  0  0
 20 15  1  0  0  0  0
 20 19  1  0  0  0  0
 21 19  2  0  0  0  0
 22  2  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244865

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO2/c1-20(15-14-17-8-11-18(22-2)12-9-17)19(21)13-10-16-6-4-3-5-7-16/h3-13H,14-15H2,1-2H3/b13-10+

> <INCHI_KEY>
VANLAWLPWTVXIB-JLHYYAGUSA-N

> <FORMULA>
C19H21NO2

> <MOLECULAR_WEIGHT>
295.3755

> <EXACT_MASS>
295.157228921

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.67056535714122

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-N-[2-(4-methoxyphenyl)ethyl]-N-methyl-3-phenylprop-2-enamide

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
3.631958834333333

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
1.4489278743561558

> <JCHEM_POLAR_SURFACE_AREA>
29.540000000000003

> <JCHEM_REFRACTIVITY>
90.50629999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-[2-(4-methoxyphenyl)ethyl]-N-methyl-3-phenylprop-2-enamide

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       0.000   4.620   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   22                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   16                                                       
CONECT    7    5   16                                                       
CONECT    8   11   17                                                       
CONECT    9   12   17                                                       
CONECT   10   13   16                                                       
CONECT   11    8   18                                                       
CONECT   12    9   18                                                       
CONECT   13   10   19                                                       
CONECT   14   15   17                                                       
CONECT   15   14   20                                                       
CONECT   16    6    7   10                                                  
CONECT   17    8    9   14                                                  
CONECT   18   11   12   22                                                  
CONECT   19   13   20   21                                                  
CONECT   20    1   15   19                                                  
CONECT   21   19                                                            
CONECT   22    2   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₁NO₂

Average Mass

295.3755 Da

Monoisotopic Mass

295.15723 Da

IUPAC Name

(2E)-N-[2-(4-methoxyphenyl)ethyl]-N-methyl-3-phenylprop-2-enamide

Traditional Name

(2E)-N-[2-(4-methoxyphenyl)ethyl]-N-methyl-3-phenylprop-2-enamide

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CCN(C)C(=O)\C=C\C2=CC=CC=C2)C=C1

InChI Identifier

InChI=1S/C19H21NO2/c1-20(15-14-17-8-11-18(22-2)12-9-17)19(21)13-10-16-6-4-3-5-7-16/h3-13H,14-15H2,1-2H3/b13-10+

InChI Key

VANLAWLPWTVXIB-JLHYYAGUSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Not Available

Direct Parent

Cinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid or derivatives
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Styrene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Ether
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Carbonyl group
Organopnictogen 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	3.99	ALOGPS
logP	3.63	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	1.45	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	90.51 m³·mol⁻¹	ChemAxon
Polarizability	33.67 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

HMDB0030242

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002065

KNApSAcK ID

Not Available

Chemspider ID

4511953

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5356194

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-n-[2-(4-methoxyphenyl)ethyl]-n-methyl-3-phenylprop-2-enamide (NP0244865)

MOL for NP0244865 ((2e)-n-[2-(4-methoxyphenyl)ethyl]-n-methyl-3-phenylprop-2-enamide)

3D MOL for NP0244865 ((2e)-n-[2-(4-methoxyphenyl)ethyl]-n-methyl-3-phenylprop-2-enamide)

3D SDF for NP0244865 ((2e)-n-[2-(4-methoxyphenyl)ethyl]-n-methyl-3-phenylprop-2-enamide)

3D-SDF for NP0244865 ((2e)-n-[2-(4-methoxyphenyl)ethyl]-n-methyl-3-phenylprop-2-enamide)

PDB for NP0244865 ((2e)-n-[2-(4-methoxyphenyl)ethyl]-n-methyl-3-phenylprop-2-enamide)

3D PDB for NP0244865 ((2e)-n-[2-(4-methoxyphenyl)ethyl]-n-methyl-3-phenylprop-2-enamide)

SMILES for NP0244865 ((2e)-n-[2-(4-methoxyphenyl)ethyl]-n-methyl-3-phenylprop-2-enamide)

INCHI for NP0244865 ((2e)-n-[2-(4-methoxyphenyl)ethyl]-n-methyl-3-phenylprop-2-enamide)

Structure for NP0244865 ((2e)-n-[2-(4-methoxyphenyl)ethyl]-n-methyl-3-phenylprop-2-enamide)

3D Structure for NP0244865 ((2e)-n-[2-(4-methoxyphenyl)ethyl]-n-methyl-3-phenylprop-2-enamide)