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Showing NP-Card for Pipercide (NP0047647)

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Record Information
Version2.0
Created at2022-03-17 20:43:38 UTC
Updated at2022-03-17 20:43:38 UTC
NP-MRD IDNP0047647
Secondary Accession NumbersNone
Natural Product Identification
Common NamePipercide
DescriptionPipercide, also known as retrofractamide b, 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. Pipercide is a moderately basic compound (based on its pKa). Outside of the human body, Pipercide has been detected, but not quantified in, herbs and spices and pepper (spice). Pipercide is found in Piper longum, Piper mullesua, Piper nigrum and Piper chaba . This could make pipercide a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047647 (Pipercide)


  Mrv0541 02241216002D          

 26 27  0  0  0  0            999 V2000
   -5.4400    0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4400   -0.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7261   -1.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0136   -0.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0136    0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7261    0.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2254    0.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7123   -0.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2254   -1.0797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2984    0.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5832    0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2751   -0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9903    0.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7055   -0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4208    0.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1360   -0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8513    0.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5665   -0.0027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8513    1.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2817    0.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9970   -0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7123    0.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9970   -0.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4388    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1541    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680    0.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  2  0  0  0  0
 11 26  1  0  0  0  0
 12 13  1  0  0  0  0
 12 24  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
Download

3D MOL for NP0047647 (Pipercide)

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3D SDF for NP0047647 (Pipercide)

  Mrv0541 02241216002D          

 26 27  0  0  0  0            999 V2000
   -5.4400    0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4400   -0.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7261   -1.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0136   -0.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0136    0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7261    0.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2254    0.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7123   -0.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2254   -1.0797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2984    0.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5832    0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2751   -0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9903    0.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7055   -0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4208    0.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1360   -0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8513    0.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5665   -0.0027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8513    1.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2817    0.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9970   -0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7123    0.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9970   -0.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4388    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1541    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680    0.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  2  0  0  0  0
 11 26  1  0  0  0  0
 12 13  1  0  0  0  0
 12 24  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047647

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CNC(=O)\C=C\C=C\CCCC\C=C\C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H29NO3/c1-18(2)16-23-22(24)12-10-8-6-4-3-5-7-9-11-19-13-14-20-21(15-19)26-17-25-20/h6,8-15,18H,3-5,7,16-17H2,1-2H3,(H,23,24)/b8-6+,11-9+,12-10+

> <INCHI_KEY>
RPOYGOULCHMVBB-ADDDGJNWSA-N

> <FORMULA>
C22H29NO3

> <MOLECULAR_WEIGHT>
355.4706

> <EXACT_MASS>
355.214743799

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
42.79931518995807

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,10E)-11-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,4,10-trienamide

> <ALOGPS_LOGP>
5.55

> <JCHEM_LOGP>
5.253062362333334

> <ALOGPS_LOGS>
-5.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.401622113923118

> <JCHEM_PKA_STRONGEST_BASIC>
2.245618588062122

> <JCHEM_POLAR_SURFACE_AREA>
47.56

> <JCHEM_REFRACTIVITY>
108.33109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.34e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,10E)-11-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,4,10-trienamide

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047647 (Pipercide)
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PDB for NP0047647 (Pipercide)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0     -10.155   0.005   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.155  -1.535   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.822  -2.306   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.492  -1.535   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.492   0.005   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.822   0.773   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -11.621   0.483   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -12.530  -0.765   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0     -11.621  -2.015   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.157   0.773   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.822   0.005   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.514  -0.005   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.849   0.762   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.184  -0.005   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.519   0.762   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.854  -0.005   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.189   0.762   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       8.524  -0.005   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       7.189   2.306   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.859   0.762   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.194  -0.005   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.530   0.762   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.194  -1.546   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.819   0.768   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.154   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.487   0.773   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    1    5                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    2    8                                                       
CONECT   10    5   11                                                       
CONECT   11   10   26                                                       
CONECT   12   13   24                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   20                                                       
CONECT   19   17                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   12   25                                                       
CONECT   25   24   26                                                       
CONECT   26   11   25                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

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3D PDB for NP0047647 (Pipercide)
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SMILES for NP0047647 (Pipercide)
CC(C)CNC(=O)\C=C\C=C\CCCC\C=C\C1=CC2=C(OCO2)C=C1
Download
INCHI for NP0047647 (Pipercide)
InChI=1S/C22H29NO3/c1-18(2)16-23-22(24)12-10-8-6-4-3-5-7-9-11-19-13-14-20-21(15-19)26-17-25-20/h6,8-15,18H,3-5,7,16-17H2,1-2H3,(H,23,24)/b8-6+,11-9+,12-10+
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View in JSmol
Synonyms
ValueSource
Retrofractamide bHMDB
(2E,4E,10E)-11-(2H-1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,4,10-trienimidateGenerator
Chemical FormulaC22H29NO3
Average Mass355.4706 Da
Monoisotopic Mass355.21474 Da
IUPAC Name(2E,4E,10E)-11-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,4,10-trienamide
Traditional Name(2E,4E,10E)-11-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,4,10-trienamide
CAS Registry Number54794-74-0
SMILES
CC(C)CNC(=O)\C=C\C=C\CCCC\C=C\C1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C22H29NO3/c1-18(2)16-23-22(24)12-10-8-6-4-3-5-7-9-11-19-13-14-20-21(15-19)26-17-25-20/h6,8-15,18H,3-5,7,16-17H2,1-2H3,(H,23,24)/b8-6+,11-9+,12-10+
InChI KeyRPOYGOULCHMVBB-ADDDGJNWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Piper longumLOTUS Database
Piper mullesuaLOTUS Database
Piper nigrumLOTUS Database
Piper nigrum L.FooDB
Piper retrofractumPlant
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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzodioxoles  
Sub ClassNot Available
Direct ParentBenzodioxoles  
Alternative Parents
Substituents
  • Benzodioxole
    • 

  • Styrene
    • 

  • N-acyl-amine
    • 

  • Benzenoid
    • 

  • Carboxamide group
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxylic acid derivative
    • 

  • Acetal
    • 

  • Oxacycle
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP5.55ALOGPS
logP5.25ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)16.4ChemAxon
pKa (Strongest Basic)2.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.56 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity108.33 m³·mol⁻¹ChemAxon
Polarizability42.8 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033449  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011487  
KNApSAcK IDC00034631  
Chemspider ID4522504  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5372162  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available