NP-MRD: Showing NP-Card for (2z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one (NP0254862)

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Record Information

Version

1.0

Created at

2022-09-07 19:09:02 UTC

Updated at

2022-09-07 19:09:03 UTC

NP-MRD ID

NP0254862

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one

Description

(E)-1-Cinnamoylpyrrolidine 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)-1-Cinnamoylpyrrolidine is a moderately basic compound (based on its pKa). Outside of the human body, (E)-1-Cinnamoylpyrrolidine has been detected, but not quantified in, beverages. (2z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one is found in Piper sarmentosum. This could make (e)-1-cinnamoylpyrrolidine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    0.1860    0.7963    0.7721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4993    0.2115   -0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0422   -0.6862   -1.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -0.9703   -1.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844   -0.5002   -0.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6754    0.7171   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8587    1.0190    0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8169    0.0523    0.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5655   -1.1980    0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4038   -1.4713   -0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9130    0.4811    0.0380 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5547    1.3785    1.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7669    0.5962    1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0534   -0.3564    0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9793   -0.0430   -0.7611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8294   -1.1995   -1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3523   -1.7308   -2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0151    1.5765   -0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0323    2.0099    0.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7352    0.2582    1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3415   -1.9682    0.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2401   -2.4530   -0.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8920    1.6572    1.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9085    2.2642    0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6626    1.2626    1.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6195    0.0130    2.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0691   -0.2368   -0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9277   -1.4109    0.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7433   -0.8972   -1.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3417    0.8282   -1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 10  5  1  0
 15 11  1  0
  3 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
  9 21  1  0
 10 22  1  0
 12 23  1  0
 12 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
M  END


  Mrv0541 05061310412D          

 15 16  0  0  0  0            999 V2000
    2.8579    8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    8.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    3.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    3.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615    4.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964    4.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.7036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.9411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  9  8  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0254862

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C(\C=C/C1=CC=CC=C1)N1CCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C13H15NO/c15-13(14-10-4-5-11-14)9-8-12-6-2-1-3-7-12/h1-3,6-9H,4-5,10-11H2/b9-8-

> <INCHI_KEY>
JSIGICUAXLIURX-HJWRWDBZSA-N

> <FORMULA>
C13H15NO

> <MOLECULAR_WEIGHT>
201.2643

> <EXACT_MASS>
201.115364107

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
22.633019456069626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
2.182293244333333

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
1.6378623793012814

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
62.2165

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one

> <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       5.335  14.940   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  15.710   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  13.400   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.897   6.410   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.437   6.410   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  14.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  12.630   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  12.630   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  11.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.421   7.875   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.913   7.875   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  13.400   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  10.320   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.667   8.780   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       4.001  11.090   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    5   10                                                       
CONECT    5    4   11                                                       
CONECT    6    2   12                                                       
CONECT    7    3   12                                                       
CONECT    8    9   12                                                       
CONECT    9    8   13                                                       
CONECT   10    4   14                                                       
CONECT   11    5   14                                                       
CONECT   12    6    7    8                                                  
CONECT   13    9   14   15                                                  
CONECT   14   10   11   13                                                  
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₅NO

Average Mass

201.2643 Da

Monoisotopic Mass

201.11536 Da

IUPAC Name

(2Z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one

Traditional Name

(2Z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

O=C(\C=C/C1=CC=CC=C1)N1CCCC1

InChI Identifier

InChI=1S/C13H15NO/c15-13(14-10-4-5-11-14)9-8-12-6-2-1-3-7-12/h1-3,6-9H,4-5,10-11H2/b9-8-

InChI Key

JSIGICUAXLIURX-HJWRWDBZSA-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
Piper sarmentosum	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
N-acylpyrrolidine
Styrene
Monocyclic benzene moiety
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.23	ALOGPS
logP	2.18	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	1.64	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	2	ChemAxon
Refractivity	62.22 m³·mol⁻¹	ChemAxon
Polarizability	22.63 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

HMDB0038835

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018270

KNApSAcK ID

Not Available

Chemspider ID

1549879

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2056198

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one (NP0254862)

MOL for NP0254862 ((2z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one)

3D MOL for NP0254862 ((2z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one)

3D SDF for NP0254862 ((2z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one)

3D-SDF for NP0254862 ((2z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one)

PDB for NP0254862 ((2z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one)

3D PDB for NP0254862 ((2z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one)

SMILES for NP0254862 ((2z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one)

INCHI for NP0254862 ((2z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one)

Structure for NP0254862 ((2z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one)

3D Structure for NP0254862 ((2z)-3-phenyl-1-(pyrrolidin-1-yl)prop-2-en-1-one)