NP-MRD: Showing NP-Card for (2e)-n-methyl-3-phenyl-n-[(1e)-2-phenylethenyl]prop-2-enamide (NP0147283)

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Record Information

Version

2.0

Created at

2022-09-02 02:51:18 UTC

Updated at

2022-09-02 02:51:18 UTC

NP-MRD ID

NP0147283

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-n-methyl-3-phenyl-n-[(1e)-2-phenylethenyl]prop-2-enamide

Description

Lansiumamide B 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. Lansiumamide B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Lansiumamide B has been detected, but not quantified in, fruits. (2e)-n-methyl-3-phenyl-n-[(1e)-2-phenylethenyl]prop-2-enamide is found in Clausena lansium. This could make lansiumamide b a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.0018    1.4341   -0.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4312    0.2367   -0.1657 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8492   -0.0577    0.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8262    0.6931   -0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2381    0.3804   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6915   -0.7532    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0616   -1.0102    0.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9538   -0.0683    0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5387    1.0911   -0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2028    1.2934   -0.5768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4615   -0.7319    0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1335   -1.7847    0.8640 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8803   -0.8643    0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7627   -0.0204   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2159   -0.2935   -0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0717    0.6807   -0.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4294    0.5076   -0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9408   -0.6428    0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1161   -1.5965    0.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7316   -1.4125    0.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6275    2.0108   -0.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5689    1.2363   -1.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8227    2.1414   -1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1143   -1.0058    0.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5828    1.6347   -0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9979   -1.4859    0.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3718   -1.9123    1.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0072   -0.2327    0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2353    1.8465   -0.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8576    2.2055   -1.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2908   -1.8129    0.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4395    0.8887   -0.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6528    1.5624   -1.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0563    1.2860   -0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0198   -0.7807    0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5246   -2.4747    0.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1278   -2.1886    0.9311 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  2  0
  2 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
 10  5  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
M  END


  Mrv0541 05061310322D          

 20 21  0  0  0  0            999 V2000
    9.2881    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 13 12  2  0  0  0  0
 15 14  2  0  0  0  0
 16  8  2  0  0  0  0
 16  9  1  0  0  0  0
 16 12  1  0  0  0  0
 17 10  2  0  0  0  0
 17 11  1  0  0  0  0
 17 14  1  0  0  0  0
 18 13  1  0  0  0  0
 19  1  1  0  0  0  0
 19 15  1  0  0  0  0
 19 18  1  0  0  0  0
 20 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0147283

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(\C=C\C1=CC=CC=C1)C(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO/c1-19(15-14-17-10-6-3-7-11-17)18(20)13-12-16-8-4-2-5-9-16/h2-15H,1H3/b13-12+,15-14+

> <INCHI_KEY>
VJGRWRRIAJQNFU-SQIWNDBBSA-N

> <FORMULA>
C18H17NO

> <MOLECULAR_WEIGHT>
263.3337

> <EXACT_MASS>
263.131014171

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
30.291459914675716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-N-methyl-3-phenyl-N-[(E)-2-phenylethenyl]prop-2-enamide

> <ALOGPS_LOGP>
3.83

> <JCHEM_LOGP>
3.8843091450000005

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7688101669739393

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
84.13619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.33e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-methyl-3-phenyl-N-[(E)-2-phenylethenyl]prop-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      17.338   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.338  16.170   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.671   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.004  15.400   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.672  15.400   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.671   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.004  13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.672  13.860   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.671   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.338  11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.004  10.780   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.338  13.090   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.671   8.470   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      16.004   9.240   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      13.337   9.240   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    4    5                                                       
CONECT    3    6    7                                                       
CONECT    4    2    8                                                       
CONECT    5    2    9                                                       
CONECT    6    3   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4   16                                                       
CONECT    9    5   16                                                       
CONECT   10    6   17                                                       
CONECT   11    7   17                                                       
CONECT   12   13   16                                                       
CONECT   13   12   18                                                       
CONECT   14   15   17                                                       
CONECT   15   14   19                                                       
CONECT   16    8    9   12                                                  
CONECT   17   10   11   14                                                  
CONECT   18   13   19   20                                                  
CONECT   19    1   15   18                                                  
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
N-Methyl-N-cis-styrylcinnamamide	HMDB
N-Methyl-N-styrylcinnamamide	MeSH
Lansiumamide b	MeSH

Chemical Formula

C₁₈H₁₇NO

Average Mass

263.3337 Da

Monoisotopic Mass

263.13101 Da

IUPAC Name

(2E)-N-methyl-3-phenyl-N-[(E)-2-phenylethenyl]prop-2-enamide

Traditional Name

(2E)-N-methyl-3-phenyl-N-[(E)-2-phenylethenyl]prop-2-enamide

CAS Registry Number

Not Available

SMILES

CN(\C=C\C1=CC=CC=C1)C(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H17NO/c1-19(15-14-17-10-6-3-7-11-17)18(20)13-12-16-8-4-2-5-9-16/h2-15H,1H3/b13-12+,15-14+

InChI Key

VJGRWRRIAJQNFU-SQIWNDBBSA-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
Clausena lansium	LOTUS Database	35616633

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
Styrene
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen 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	3.83	ALOGPS
logP	3.88	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	84.14 m³·mol⁻¹	ChemAxon
Polarizability	30.29 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

HMDB0038573

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017963

KNApSAcK ID

Not Available

Chemspider ID

9417532

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11242495

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-methyl-3-phenyl-n-[(1e)-2-phenylethenyl]prop-2-enamide (NP0147283)

MOL for NP0147283 ((2e)-n-methyl-3-phenyl-n-[(1e)-2-phenylethenyl]prop-2-enamide)

3D MOL for NP0147283 ((2e)-n-methyl-3-phenyl-n-[(1e)-2-phenylethenyl]prop-2-enamide)

3D SDF for NP0147283 ((2e)-n-methyl-3-phenyl-n-[(1e)-2-phenylethenyl]prop-2-enamide)

3D-SDF for NP0147283 ((2e)-n-methyl-3-phenyl-n-[(1e)-2-phenylethenyl]prop-2-enamide)

PDB for NP0147283 ((2e)-n-methyl-3-phenyl-n-[(1e)-2-phenylethenyl]prop-2-enamide)

3D PDB for NP0147283 ((2e)-n-methyl-3-phenyl-n-[(1e)-2-phenylethenyl]prop-2-enamide)

SMILES for NP0147283 ((2e)-n-methyl-3-phenyl-n-[(1e)-2-phenylethenyl]prop-2-enamide)

INCHI for NP0147283 ((2e)-n-methyl-3-phenyl-n-[(1e)-2-phenylethenyl]prop-2-enamide)

Structure for NP0147283 ((2e)-n-methyl-3-phenyl-n-[(1e)-2-phenylethenyl]prop-2-enamide)

3D Structure for NP0147283 ((2e)-n-methyl-3-phenyl-n-[(1e)-2-phenylethenyl]prop-2-enamide)