NP-MRD: Showing NP-Card for Piperanine (NP0047777)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 20:45:47 UTC

Updated at

2022-03-17 20:45:47 UTC

NP-MRD ID

NP0047777

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Piperanine

Description

Piperanine, also known as delata-Alpha or dalpha, 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. Piperanine is a moderately basic compound (based on its pKa). Outside of the human body, Piperanine has been detected, but not quantified in, herbs and spices and pepper (spice). Piperanine is found in Piper capense, Piper guineense, Piper longum, Piper nigrum, Piper swartzianum and Piper tuberculatum. This could make piperanine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241208082D          

 21 23  0  0  0  0            999 V2000
   -2.9358   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7211    0.2558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2080   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7211   -1.0824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2220   -1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5094   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5094    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2220    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7942    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0790    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3514    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0666    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7818    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0666    1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7818   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4956   -1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2080   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2080    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4956    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  1  0  0  0  0
 15 21  1  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
M  END
> <DATABASE_ID>
NP0047777

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C(\C=C\CCC1=CC2=C(OCO2)C=C1)N1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h3,7-9,12H,1-2,4-6,10-11,13H2/b7-3+

> <INCHI_KEY>
QHWOFMXDKFORMO-XVNBXDOJSA-N

> <FORMULA>
C17H21NO3

> <MOLECULAR_WEIGHT>
287.3535

> <EXACT_MASS>
287.152143543

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.72132058897919

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)pent-2-en-1-one

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
3.0565327070000006

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.4709512561866833

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
81.7864

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)pent-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

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      -5.480  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.480   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.946   0.477   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -7.855  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -6.946  -2.020   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.148  -2.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.818  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.818   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.148   0.768   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.483   0.768   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.147   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.188   0.768   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.523   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.858   0.768   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       5.193   0.000   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       3.858   2.311   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.193  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.525  -2.311   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.855  -1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.855   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.525   0.768   0.000  0.00  0.00           C+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    1    4                                                       
CONECT    6    1    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    2    8                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   17   21                                                  
CONECT   16   14                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   15   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
Delata-Alpha	HMDB
Beta-Dihydropiperine	HMDB
Dalpha	HMDB
Delata-a	HMDB
Delata-α	HMDB
b-Dihydropiperine	HMDB
Β-dihydropiperine	HMDB
1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2-pentenyl]piperidine	HMDB
5-(3,4-Methylenedioxyphenyl)-2-pentenoic acid piperidide	HMDB
b-Hydropiperylpiperidine	HMDB
Da,b-dihydropiperine	HMDB

Chemical Formula

C₁₇H₂₁NO₃

Average Mass

287.3535 Da

Monoisotopic Mass

287.15214 Da

IUPAC Name

(2E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)pent-2-en-1-one

Traditional Name

(2E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)pent-2-en-1-one

CAS Registry Number

23512-46-1

SMILES

O=C(\C=C\CCC1=CC2=C(OCO2)C=C1)N1CCCCC1

InChI Identifier

InChI=1S/C17H21NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h3,7-9,12H,1-2,4-6,10-11,13H2/b7-3+

InChI Key

QHWOFMXDKFORMO-XVNBXDOJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Piper capense	LOTUS Database	35616633
Piper guineense	LOTUS Database	35616633
Piper longum	LOTUS Database	35616633
Piper nigrum	LOTUS Database	35616633
Piper nigrum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Piper swartzianum	LOTUS Database	35616633
Piper tuberculatum	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
Azacycle
Carboxylic acid derivative
Acetal
Oxacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
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	3.48	ALOGPS
logP	3.06	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	2.47	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	81.79 m³·mol⁻¹	ChemAxon
Polarizability	32.72 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

HMDB0033874

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012066

KNApSAcK ID

Not Available

Chemspider ID

4478657

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320618

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Piperanine (NP0047777)

MOL for NP0047777 (Piperanine)

3D MOL for NP0047777 (Piperanine)

3D SDF for NP0047777 (Piperanine)

3D-SDF for NP0047777 (Piperanine)

PDB for NP0047777 (Piperanine)

3D PDB for NP0047777 (Piperanine)

SMILES for NP0047777 (Piperanine)

INCHI for NP0047777 (Piperanine)

Structure for NP0047777 (Piperanine)

3D Structure for NP0047777 (Piperanine)