NP-MRD: Showing NP-Card for (2e)-3-phenyl-1-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one (NP0214002)

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Record Information

Version

2.0

Created at

2022-09-05 13:10:10 UTC

Updated at

2022-09-05 13:10:10 UTC

NP-MRD ID

NP0214002

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-phenyl-1-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one

Description

Nigerazine 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. Nigerazine B is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on nigerazine B.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
   -4.5639   -1.5522   -0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3277   -1.1081    0.6658 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1451   -1.7448    0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0315   -0.7670   -0.1311 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2616   -1.2013    0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4368   -2.4344    0.5606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875   -0.4264    0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6589   -0.9478    0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8979   -0.1934    0.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0958   -0.8189    0.8137 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2652   -0.1219    0.8011 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3279    1.2056    0.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1605    1.8331    0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9583    1.1243    0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4997    0.4919   -0.5960 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5772    1.4385   -1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2219    1.0702    0.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3767    0.2729    0.8323 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    0.9374    0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3600   -1.4162   -1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4670   -1.0483    0.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6725   -2.6625    0.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4612   -1.6035    1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3443   -2.0893   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7589   -2.6085    0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4488    0.6002   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6959   -1.9976    0.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0468   -1.8740    1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1643   -0.6771    1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2700    1.7275    0.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1602    2.8792   -0.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0652    1.6829   -0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3518    0.2689   -1.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0942    0.9195   -1.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2257    2.0757   -1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1174    2.1938   -0.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5680    0.9857    1.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5166    2.1136    0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2789    2.0203    0.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7154    0.5580   -0.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4018    0.8938    0.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 18  2  1  0
 14  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
 15 33  1  6
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
M  END


  Mrv1652309052215102D          

 19 20  0  0  1  0            999 V2000
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 N   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
    5.0013   -3.7125    0.0000 O   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
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  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
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  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
  4 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0214002

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CN([C@H](C)CN1C)C(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H22N2O/c1-13-12-18(14(2)11-17(13)3)16(19)10-9-15-7-5-4-6-8-15/h4-10,13-14H,11-12H2,1-3H3/b10-9+/t13-,14+/m0/s1

> <INCHI_KEY>
MIGGJPIAMPJCES-XACNLCELSA-N

> <FORMULA>
C16H22N2O

> <MOLECULAR_WEIGHT>
258.365

> <EXACT_MASS>
258.173213336

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.57391829988146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-phenyl-1-[(2R,5S)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one

> <JCHEM_LOGP>
2.4567654059999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.71449175765223

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
79.5632

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-phenyl-1-[(2R,5S)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       6.668  -6.930   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       4.001  -5.390   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15    4   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17    2   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₂N₂O

Average Mass

258.3650 Da

Monoisotopic Mass

258.17321 Da

IUPAC Name

(2E)-3-phenyl-1-[(2R,5S)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one

Traditional Name

(2E)-3-phenyl-1-[(2R,5S)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CN([C@H](C)CN1C)C(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H22N2O/c1-13-12-18(14(2)11-17(13)3)16(19)10-9-15-7-5-4-6-8-15/h4-10,13-14H,11-12H2,1-3H3/b10-9+/t13-,14+/m0/s1

InChI Key

MIGGJPIAMPJCES-XACNLCELSA-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
Styrene
N-methylpiperazine
N-alkylpiperazine
Monocyclic benzene moiety
1,4-diazinane
Piperazine
Benzenoid
Tertiary carboxylic acid amide
Tertiary aliphatic amine
Tertiary amine
Carboxamide group
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxide
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxygen compound
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	2.46	ChemAxon
pKa (Strongest Basic)	7.71	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.56 m³·mol⁻¹	ChemAxon
Polarizability	30.57 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

Not Available

Chemspider ID

57309953

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92475874

PDB ID

Not Available

ChEBI ID

133754

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-3-phenyl-1-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one (NP0214002)

MOL for NP0214002 ((2e)-3-phenyl-1-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one)

3D MOL for NP0214002 ((2e)-3-phenyl-1-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one)

3D SDF for NP0214002 ((2e)-3-phenyl-1-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one)

3D-SDF for NP0214002 ((2e)-3-phenyl-1-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one)

PDB for NP0214002 ((2e)-3-phenyl-1-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one)

3D PDB for NP0214002 ((2e)-3-phenyl-1-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one)

SMILES for NP0214002 ((2e)-3-phenyl-1-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one)

INCHI for NP0214002 ((2e)-3-phenyl-1-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one)

Structure for NP0214002 ((2e)-3-phenyl-1-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one)

3D Structure for NP0214002 ((2e)-3-phenyl-1-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]prop-2-en-1-one)