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Showing NP-Card for Pipericine (NP0047311)

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Record Information
Version2.0
Created at2022-03-17 20:38:04 UTC
Updated at2022-03-17 20:38:04 UTC
NP-MRD IDNP0047311
Secondary Accession NumbersNone
Natural Product Identification
Common NamePipericine
DescriptionPipericine belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage. Thus, pipericine is considered to be a fatty amide lipid molecule. Pipericine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Pipericine has been detected, but not quantified in, herbs and spices and pepper (spice). Pipericine is found in Piper nigrum. This could make pipericine a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047311 (Pipericine)


  Mrv0541 03191306562D          

 24 23  0  0  0  0            999 V2000
   -6.3250    5.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6105    6.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8961    5.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1816    6.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4671    5.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7526    6.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0382    5.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3237    6.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6092    5.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1052    6.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8197    5.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5342    6.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2487    5.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0395    6.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7539    5.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2487    5.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9632    4.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9632    3.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6777    3.3786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6777    2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3922    2.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2488    3.3786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3923    1.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1067    2.5537    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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  1 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 22  2  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
M  END
Download

3D MOL for NP0047311 (Pipericine)

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3D SDF for NP0047311 (Pipericine)

  Mrv0541 03191306562D          

 24 23  0  0  0  0            999 V2000
   -6.3250    5.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6105    6.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8961    5.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1816    6.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4671    5.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7526    6.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0382    5.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3237    6.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6092    5.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1052    6.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8197    5.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5342    6.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2487    5.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0395    6.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7539    5.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2487    5.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9632    4.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9632    3.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6777    3.3786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6777    2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3922    2.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2488    3.3786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3923    1.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1067    2.5537    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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  1 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 22  2  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047311

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCC\C=C/C=C/C(=O)NCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H41NO/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)23-20-21(2)3/h16-19,21H,4-15,20H2,1-3H3,(H,23,24)/b17-16-,19-18+

> <INCHI_KEY>
QQCGKIZHTJLRNN-JUJVUSMPSA-N

> <FORMULA>
C22H41NO

> <MOLECULAR_WEIGHT>
335.567

> <EXACT_MASS>
335.318814939

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
44.55761310565311

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4Z)-N-(2-methylpropyl)octadeca-2,4-dienamide

> <ALOGPS_LOGP>
8.11

> <JCHEM_LOGP>
7.442658568666668

> <ALOGPS_LOGS>
-6.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.34987170890389

> <JCHEM_PKA_STRONGEST_BASIC>
2.245618544755534

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
108.95859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.97e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4Z)-N-(2-methylpropyl)octadeca-2,4-dienamide

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047311 (Pipericine)
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PDB for NP0047311 (Pipericine)
HEADER    PROTEIN                                 19-MAR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-13         0                                  
HETATM    1  C   UNK     0     -11.807  10.927   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.473  11.697   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.139  10.927   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.806  11.697   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.472  10.927   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.138  11.697   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.805  10.927   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.471  11.697   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.137  10.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.196  11.697   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.530  10.927   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.864  11.697   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.198  10.927   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -13.140  11.697   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -14.474  10.927   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.198   9.387   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.531   8.617   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.531   7.077   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       6.865   6.307   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       6.865   4.767   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.199   3.997   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.198   6.307   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.199   2.457   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.533   4.767   0.000  0.00  0.00           C+0
CONECT    1    2   14                                                       
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                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   16                                                       
CONECT   14    1   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   23   24                                                  
CONECT   22   18                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

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3D PDB for NP0047311 (Pipericine)
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SMILES for NP0047311 (Pipericine)
CCCCCCCCCCCCC\C=C/C=C/C(=O)NCC(C)C
Download
INCHI for NP0047311 (Pipericine)
InChI=1S/C22H41NO/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)23-20-21(2)3/h16-19,21H,4-15,20H2,1-3H3,(H,23,24)/b17-16-,19-18+
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View in JSmol
SynonymsNot Available
Chemical FormulaC22H41NO
Average Mass335.5670 Da
Monoisotopic Mass335.31881 Da
IUPAC Name(2E,4Z)-N-(2-methylpropyl)octadeca-2,4-dienamide
Traditional Name(2E,4Z)-N-(2-methylpropyl)octadeca-2,4-dienamide
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCC\C=C/C=C/C(=O)NCC(C)C
InChI Identifier
InChI=1S/C22H41NO/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)23-20-21(2)3/h16-19,21H,4-15,20H2,1-3H3,(H,23,24)/b17-16-,19-18+
InChI KeyQQCGKIZHTJLRNN-JUJVUSMPSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Piper nigrumLOTUS Database
Piper nigrum L.FooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty amides  
Direct ParentN-acyl amines  
Alternative Parents
Substituents
  • N-acyl-amine
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxamide group
    • 

  • Carboxylic acid derivative
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.11ALOGPS
logP7.44ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)16.35ChemAxon
pKa (Strongest Basic)2.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity108.96 m³·mol⁻¹ChemAxon
Polarizability44.56 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031678  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008338  
KNApSAcK IDNot Available
Chemspider ID8149826  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9974234  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References