NP-MRD: Showing NP-Card for (1s,2s,5r,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-[(1e)-hept-1-en-1-yl]-n-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid (NP0248991)

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Record Information

Version

2.0

Created at

2022-09-07 11:25:50 UTC

Updated at

2022-09-07 11:25:50 UTC

NP-MRD ID

NP0248991

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,5r,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-[(1e)-hept-1-en-1-yl]-n-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid

Description

(3R)-3beta-(Piperidinocarbonyl)-4beta-(1-heptenyl)-5alpha-(isobutylcarbamoyl)-6beta-(1,3-benzodioxole-5-yl)-1-cyclohexene 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. (1s,2s,5r,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-[(1e)-hept-1-en-1-yl]-n-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid is found in Piper nigrum. Based on a literature review very few articles have been published on (3R)-3beta-(Piperidinocarbonyl)-4beta-(1-heptenyl)-5alpha-(isobutylcarbamoyl)-6beta-(1,3-benzodioxole-5-yl)-1-cyclohexene.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072213252D          

 37 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072213252D          

 37 40  0  0  1  0            999 V2000
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    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    6.2102    4.4104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    4.8229    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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  4  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 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
 32 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0248991

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C31H44N2O4/c1-4-5-6-7-9-12-25-26(31(35)33-17-10-8-11-18-33)15-14-24(29(25)30(34)32-20-22(2)3)23-13-16-27-28(19-23)37-21-36-27/h9,12-16,19,22,24-26,29H,4-8,10-11,17-18,20-21H2,1-3H3,(H,32,34)/b12-9+/t24-,25-,26-,29-/m1/s1

> <INCHI_KEY>
IQEDQEFKHVXVLW-LDOJEKBXSA-N

> <FORMULA>
C31H44N2O4

> <MOLECULAR_WEIGHT>
508.703

> <EXACT_MASS>
508.330107905

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
58.7245611879311

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5R,6S)-2-(2H-1,3-benzodioxol-5-yl)-6-[(1E)-hept-1-en-1-yl]-N-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid

> <JCHEM_LOGP>
5.4516614726902555

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8962012924759684

> <JCHEM_PKA_STRONGEST_BASIC>
6.270935913005302

> <JCHEM_POLAR_SURFACE_AREA>
71.36

> <JCHEM_REFRACTIVITY>
149.6265

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,6S)-2-(2H-1,3-benzodioxol-5-yl)-6-[(1E)-hept-1-en-1-yl]-N-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      19.594   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.261   4.383   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.927   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.593   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.260   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.926   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.592   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.591   1.303   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      10.259   1.303   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      10.259  -0.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.592  -1.007   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.926  -0.237   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.592  -2.547   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.259   5.923   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.592   6.693   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.926   5.923   0.000  0.00  0.00           O+0
HETATM   32  N   UNK     0      11.592   8.233   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      10.259   9.003   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.259  10.543   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.592  11.313   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.926  10.543   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.926   9.003   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                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    9   18   27                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   18                                                       
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   17   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    8   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
(3R)-3b-(Piperidinocarbonyl)-4b-(1-heptenyl)-5a-(isobutylcarbamoyl)-6b-(1,3-benzodioxole-5-yl)-1-cyclohexene	Generator
(3R)-3Β-(piperidinocarbonyl)-4β-(1-heptenyl)-5α-(isobutylcarbamoyl)-6β-(1,3-benzodioxole-5-yl)-1-cyclohexene	Generator

Chemical Formula

C₃₁H₄₄N₂O₄

Average Mass

508.7030 Da

Monoisotopic Mass

508.33011 Da

IUPAC Name

(1S,2S,5R,6S)-2-(2H-1,3-benzodioxol-5-yl)-6-[(1E)-hept-1-en-1-yl]-N-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid

Traditional Name

(1S,2S,5R,6S)-2-(2H-1,3-benzodioxol-5-yl)-6-[(1E)-hept-1-en-1-yl]-N-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C31H44N2O4/c1-4-5-6-7-9-12-25-26(31(35)33-17-10-8-11-18-33)15-14-24(29(25)30(34)32-20-22(2)3)23-13-16-27-28(19-23)37-21-36-27/h9,12-16,19,22,24-26,29H,4-8,10-11,17-18,20-21H2,1-3H3,(H,32,34)/b12-9+/t24-,25-,26-,29-/m1/s1

InChI Key

IQEDQEFKHVXVLW-LDOJEKBXSA-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
Piperidine
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Secondary carboxylic acid amide
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic oxide
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
logP	5.45	ChemAxon
pKa (Strongest Acidic)	3.9	ChemAxon
pKa (Strongest Basic)	6.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.36 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	149.63 m³·mol⁻¹	ChemAxon
Polarizability	58.72 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00057593

Chemspider ID

9447169

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11272161

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,5r,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-[(1e)-hept-1-en-1-yl]-n-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid (NP0248991)

MOL for NP0248991 ((1s,2s,5r,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-[(1e)-hept-1-en-1-yl]-n-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid)

3D MOL for NP0248991 ((1s,2s,5r,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-[(1e)-hept-1-en-1-yl]-n-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid)

3D SDF for NP0248991 ((1s,2s,5r,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-[(1e)-hept-1-en-1-yl]-n-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid)

3D-SDF for NP0248991 ((1s,2s,5r,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-[(1e)-hept-1-en-1-yl]-n-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid)

PDB for NP0248991 ((1s,2s,5r,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-[(1e)-hept-1-en-1-yl]-n-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid)

3D PDB for NP0248991 ((1s,2s,5r,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-[(1e)-hept-1-en-1-yl]-n-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid)

SMILES for NP0248991 ((1s,2s,5r,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-[(1e)-hept-1-en-1-yl]-n-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid)

INCHI for NP0248991 ((1s,2s,5r,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-[(1e)-hept-1-en-1-yl]-n-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid)

Structure for NP0248991 ((1s,2s,5r,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-[(1e)-hept-1-en-1-yl]-n-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid)

3D Structure for NP0248991 ((1s,2s,5r,6s)-2-(2h-1,3-benzodioxol-5-yl)-6-[(1e)-hept-1-en-1-yl]-n-(2-methylpropyl)-5-(piperidine-1-carbonyl)cyclohex-3-ene-1-carboximidic acid)