NP-MRD: Showing NP-Card for (2e)-3-[(1s,2r,5s,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-pentyl-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl]-1-(pyrrolidin-1-yl)prop-2-en-1-one (NP0278350)

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Record Information

Version

2.0

Created at

2022-09-09 03:20:39 UTC

Updated at

2022-09-09 03:20:40 UTC

NP-MRD ID

NP0278350

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-[(1s,2r,5s,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-pentyl-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl]-1-(pyrrolidin-1-yl)prop-2-en-1-one

Description

Nigramide M belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. (2e)-3-[(1s,2r,5s,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-pentyl-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl]-1-(pyrrolidin-1-yl)prop-2-en-1-one is found in Piper nigrum. Based on a literature review very few articles have been published on Nigramide M.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092205202D          

 37 41  0  0  1  0            999 V2000
    3.3523    6.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0668    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4957    3.1729    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2102    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309092205202D          

 37 41  0  0  1  0            999 V2000
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    1.2089    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    4.4104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559    4.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5108    5.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358    5.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5908    4.8954    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  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 18 28  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 33 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0278350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC[C@H]1[C@H](\C=C\C(=O)N2CCCC2)[C@@H](C=C[C@@H]1C(=O)N1CCCCC1)C1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H42N2O4/c1-2-3-5-10-25-26(14-16-30(34)32-17-8-9-18-32)24(23-11-15-28-29(21-23)37-22-36-28)12-13-27(25)31(35)33-19-6-4-7-20-33/h11-16,21,24-27H,2-10,17-20,22H2,1H3/b16-14+/t24-,25-,26+,27-/m0/s1

> <INCHI_KEY>
VUFKHUAQGORHEN-UXTVBOLNSA-N

> <FORMULA>
C31H42N2O4

> <MOLECULAR_WEIGHT>
506.687

> <EXACT_MASS>
506.31445784

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
58.31038099826186

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-[(1S,2R,5S,6S)-2-(2H-1,3-benzodioxol-5-yl)-6-pentyl-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl]-1-(pyrrolidin-1-yl)prop-2-en-1-one

> <JCHEM_LOGP>
5.028305924333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.7461525288538593

> <JCHEM_POLAR_SURFACE_AREA>
59.080000000000005

> <JCHEM_REFRACTIVITY>
147.74909999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[(1S,2R,5S,6S)-2-(2H-1,3-benzodioxol-5-yl)-6-pentyl-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl]-1-(pyrrolidin-1-yl)prop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       6.258  12.853   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258  11.313   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.591  10.543   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591   9.003   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.259   5.923   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.592   6.693   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.926   5.923   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      11.592   8.233   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      10.259   9.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.259  10.543   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.592  11.313   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.926  10.543   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.926   9.003   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.590   6.693   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.257   5.923   0.000  0.00  0.00           O+0
HETATM   33  N   UNK     0       3.590   8.233   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       2.344   9.138   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.820  10.603   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.360  10.603   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.836   9.138   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    7   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   28                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   18    6   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   37                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   33                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₂N₂O₄

Average Mass

506.6870 Da

Monoisotopic Mass

506.31446 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCCCC[C@H]1[C@H](\C=C\C(=O)N2CCCC2)[C@@H](C=C[C@@H]1C(=O)N1CCCCC1)C1=CC=C2OCOC2=C1

InChI Identifier

InChI=1S/C31H42N2O4/c1-2-3-5-10-25-26(14-16-30(34)32-17-8-9-18-32)24(23-11-15-28-29(21-23)37-22-36-28)12-13-27(25)31(35)33-19-6-4-7-20-33/h11-16,21,24-27H,2-10,17-20,22H2,1H3/b16-14+/t24-,25-,26+,27-/m0/s1

InChI Key

VUFKHUAQGORHEN-UXTVBOLNSA-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 nigrum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
N-acyl-piperidine
N-acylpyrrolidine
Piperidine
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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

C00057592

Chemspider ID

9927214

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11752511

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-3-[(1s,2r,5s,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-pentyl-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl]-1-(pyrrolidin-1-yl)prop-2-en-1-one (NP0278350)

MOL for NP0278350 ((2e)-3-[(1s,2r,5s,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-pentyl-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl]-1-(pyrrolidin-1-yl)prop-2-en-1-one)

3D MOL for NP0278350 ((2e)-3-[(1s,2r,5s,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-pentyl-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl]-1-(pyrrolidin-1-yl)prop-2-en-1-one)

3D SDF for NP0278350 ((2e)-3-[(1s,2r,5s,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-pentyl-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl]-1-(pyrrolidin-1-yl)prop-2-en-1-one)

3D-SDF for NP0278350 ((2e)-3-[(1s,2r,5s,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-pentyl-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl]-1-(pyrrolidin-1-yl)prop-2-en-1-one)

PDB for NP0278350 ((2e)-3-[(1s,2r,5s,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-pentyl-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl]-1-(pyrrolidin-1-yl)prop-2-en-1-one)

3D PDB for NP0278350 ((2e)-3-[(1s,2r,5s,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-pentyl-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl]-1-(pyrrolidin-1-yl)prop-2-en-1-one)

SMILES for NP0278350 ((2e)-3-[(1s,2r,5s,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-pentyl-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl]-1-(pyrrolidin-1-yl)prop-2-en-1-one)

INCHI for NP0278350 ((2e)-3-[(1s,2r,5s,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-pentyl-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl]-1-(pyrrolidin-1-yl)prop-2-en-1-one)

Structure for NP0278350 ((2e)-3-[(1s,2r,5s,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-pentyl-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl]-1-(pyrrolidin-1-yl)prop-2-en-1-one)

3D Structure for NP0278350 ((2e)-3-[(1s,2r,5s,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-pentyl-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl]-1-(pyrrolidin-1-yl)prop-2-en-1-one)