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Showing NP-Card for Dihydroretrofractamide B (NP0047444)

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Record Information
Version2.0
Created at2022-03-17 20:40:19 UTC
Updated at2022-03-17 20:40:19 UTC
NP-MRD IDNP0047444
Secondary Accession NumbersNone
Natural Product Identification
Common NameDihydroretrofractamide B
DescriptionDihydroretrofractamide B, also known as 10,11-dihydropipercide, 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. Dihydroretrofractamide B is a moderately basic compound (based on its pKa). Outside of the human body, Dihydroretrofractamide B has been detected, but not quantified in, herbs and spices and pepper (spice). This could make dihydroretrofractamide b a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047444 (Dihydroretrofractamide B)


  Mrv0541 02241209412D          

 26 27  0  0  0  0            999 V2000
   -5.4397    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4397   -0.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7258   -1.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0133   -0.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0133    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7258    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2250    0.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7119   -0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2250   -1.0796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2981    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5829    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2750    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9902    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7054    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4206    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1359    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8511    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663    0.0027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8511    1.2351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2815    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9967    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7119    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9967   -0.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4387    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1539    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8677    0.4139    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  1  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 NP0047444 (Dihydroretrofractamide B)

Download
3D SDF for NP0047444 (Dihydroretrofractamide B)

  Mrv0541 02241209412D          

 26 27  0  0  0  0            999 V2000
   -5.4397    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4397   -0.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7258   -1.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0133   -0.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0133    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7258    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2250    0.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7119   -0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2250   -1.0796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2981    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5829    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2750    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9902    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7054    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4206    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1359    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8511    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663    0.0027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8511    1.2351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2815    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9967    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7119    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9967   -0.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4387    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1539    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8677    0.4139    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  1  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>
NP0047444

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CNC(=O)\C=C\C=C\CCCCCCC1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H31NO3/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/h6,8,10,12-15,18H,3-5,7,9,11,16-17H2,1-2H3,(H,23,24)/b8-6+,12-10+

> <INCHI_KEY>
DMIKQRDDTCGOLE-VTKKNFPDSA-N

> <FORMULA>
C22H31NO3

> <MOLECULAR_WEIGHT>
357.4864

> <EXACT_MASS>
357.230393863

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
43.251967025296906

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.94

> <JCHEM_LOGP>
5.532284019000001

> <ALOGPS_LOGS>
-6.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.349871708903887

> <JCHEM_PKA_STRONGEST_BASIC>
2.245618589980612

> <JCHEM_POLAR_SURFACE_AREA>
47.56

> <JCHEM_REFRACTIVITY>
107.21449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.52e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0047444 (Dihydroretrofractamide B)
Download
PDB for NP0047444 (Dihydroretrofractamide B)
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     -10.154   0.005   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.154  -1.535   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.821  -2.306   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.491  -1.535   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.491   0.005   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.821   0.773   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -11.620   0.483   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -12.529  -0.765   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0     -11.620  -2.015   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.156   0.773   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.821   0.005   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.513   0.005   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.848   0.773   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.183   0.005   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.518   0.773   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   0.773   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   0.773   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      12.529   0.773   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.194  -1.535   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.819   0.773   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.154   0.005   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.486   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 NP0047444 (Dihydroretrofractamide B)
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SMILES for NP0047444 (Dihydroretrofractamide B)
CC(C)CNC(=O)\C=C\C=C\CCCCCCC1=CC2=C(OCO2)C=C1
Download
INCHI for NP0047444 (Dihydroretrofractamide B)
InChI=1S/C22H31NO3/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/h6,8,10,12-15,18H,3-5,7,9,11,16-17H2,1-2H3,(H,23,24)/b8-6+,12-10+
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View in JSmol
Synonyms
ValueSource
10,11-DihydropipercideHMDB
(2E,4E)-11-(2H-1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,4-dienimidateGenerator
Chemical FormulaC22H31NO3
Average Mass357.4864 Da
Monoisotopic Mass357.23039 Da
IUPAC Name(2E,4E)-11-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,4-dienamide
Traditional Name(2E,4E)-11-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,4-dienamide
CAS Registry Number75022-26-3
SMILES
CC(C)CNC(=O)\C=C\C=C\CCCCCCC1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C22H31NO3/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/h6,8,10,12-15,18H,3-5,7,9,11,16-17H2,1-2H3,(H,23,24)/b8-6+,12-10+
InChI KeyDMIKQRDDTCGOLE-VTKKNFPDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Piper nigrum L.FooDB
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
    • 

  • N-acyl-amine
    • 

  • Benzenoid
    • 

  • Carboxamide group
    • 

  • Secondary carboxylic acid amide
    • 

  • Acetal
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • 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
logP5.94ALOGPS
logP5.53ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)16.35ChemAxon
pKa (Strongest Basic)2.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.56 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity107.21 m³·mol⁻¹ChemAxon
Polarizability43.25 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032718  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010679  
KNApSAcK IDNot Available
Chemspider ID9068941  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10893678  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available