NP-MRD: Showing NP-Card for Piperettine (NP0047951)

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Record Information

Version

2.0

Created at

2022-03-17 20:48:36 UTC

Updated at

2022-03-17 20:48:36 UTC

NP-MRD ID

NP0047951

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Piperettine

Description

Piperettine 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. Piperettine is a moderately basic compound (based on its pKa). Outside of the human body, Piperettine is found, on average, in the highest concentration within pepper (spice). Piperettine has also been detected, but not quantified in, herbs and spices. Piperettine is found in Piper guineense and Piper nigrum. This could make piperettine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307462D          

 23 25  0  0  0  0            999 V2000
    6.1368   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
 11 10  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 16  8  1  0  0  0  0
 16 10  1  0  0  0  0
 16 14  2  0  0  0  0
 17 11  1  0  0  0  0
 18 14  1  0  0  0  0
 18 17  2  0  0  0  0
 19  9  1  0  0  0  0
 20 12  1  0  0  0  0
 20 13  1  0  0  0  0
 20 19  1  0  0  0  0
 21 19  2  0  0  0  0
 22 15  1  0  0  0  0
 22 17  1  0  0  0  0
 23 15  1  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047951

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C(\C=C\C=C\C=C\C1=CC2=C(OCO2)C=C1)N1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO3/c21-19(20-12-6-3-7-13-20)9-5-2-1-4-8-16-10-11-17-18(14-16)23-15-22-17/h1-2,4-5,8-11,14H,3,6-7,12-13,15H2/b2-1+,8-4+,9-5+

> <INCHI_KEY>
DLKOUKNODPCIHZ-UMYWTXKFSA-N

> <FORMULA>
C19H21NO3

> <MOLECULAR_WEIGHT>
311.3749

> <EXACT_MASS>
311.152143543

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.043483489414854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E)-7-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)hepta-2,4,6-trien-1-one

> <ALOGPS_LOGP>
4.03

> <JCHEM_LOGP>
3.3045267236666667

> <ALOGPS_LOGS>
-4.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.3685199525885285

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
93.2216

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E)-7-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)hepta-2,4,6-trien-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      11.455  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.123 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.122   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.789  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.456  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.789  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.789  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.456  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.789  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.123  -5.390   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      14.123  -6.930   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      15.456  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    5                                                       
CONECT    3    6    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    3   12                                                       
CONECT    7    3   13                                                       
CONECT    8    4   16                                                       
CONECT    9    5   19                                                       
CONECT   10   11   16                                                       
CONECT   11   10   17                                                       
CONECT   12    6   20                                                       
CONECT   13    7   20                                                       
CONECT   14   16   18                                                       
CONECT   15   22   23                                                       
CONECT   16    8   10   14                                                  
CONECT   17   11   18   22                                                  
CONECT   18   14   17   23                                                  
CONECT   19    9   20   21                                                  
CONECT   20   12   13   19                                                  
CONECT   21   19                                                            
CONECT   22   15   17                                                       
CONECT   23   15   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
1-[7-(1,3-Benzodioxol-5-yl)-1-oxo-2,4,6-heptatrienyl]piperidine, 9ci	HMDB
1-[7-(3,4-Methylenedioxyphenyl)heptatrienoyl]piperidine	HMDB

Chemical Formula

C₁₉H₂₁NO₃

Average Mass

311.3749 Da

Monoisotopic Mass

311.15214 Da

IUPAC Name

(2E,4E,6E)-7-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)hepta-2,4,6-trien-1-one

Traditional Name

(2E,4E,6E)-7-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)hepta-2,4,6-trien-1-one

CAS Registry Number

583-34-6

SMILES

O=C(\C=C\C=C\C=C\C1=CC2=C(OCO2)C=C1)N1CCCCC1

InChI Identifier

InChI=1S/C19H21NO3/c21-19(20-12-6-3-7-13-20)9-5-2-1-4-8-16-10-11-17-18(14-16)23-15-22-17/h1-2,4-5,8-11,14H,3,6-7,12-13,15H2/b2-1+,8-4+,9-5+

InChI Key

DLKOUKNODPCIHZ-UMYWTXKFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Piper guineense	LOTUS Database	35616633
Piper nigrum	LOTUS Database	35616633
Piper nigrum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Styrene
Piperidine
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
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	4.03	ALOGPS
logP	3.3	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	2.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.22 m³·mol⁻¹	ChemAxon
Polarizability	36.04 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034371

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012745

KNApSAcK ID

Not Available

Chemspider ID

8420440

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10244953

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Piperettine (NP0047951)

MOL for NP0047951 (Piperettine)

3D MOL for NP0047951 (Piperettine)

3D SDF for NP0047951 (Piperettine)

3D-SDF for NP0047951 (Piperettine)

PDB for NP0047951 (Piperettine)

3D PDB for NP0047951 (Piperettine)

SMILES for NP0047951 (Piperettine)

INCHI for NP0047951 (Piperettine)

Structure for NP0047951 (Piperettine)

3D Structure for NP0047951 (Piperettine)