NP-MRD: Showing NP-Card for piperyline (NP0330233)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 15:23:23 UTC

Updated at

2022-09-12 15:23:23 UTC

NP-MRD ID

NP0330233

Secondary Accession Numbers

None

Natural Product Identification

Common Name

piperyline

Description

(E,E)-Trichostachine 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 (E,E)-Trichostachine is a moderately basic compound (based on its pKa). Outside of the human body, (E,E)-Trichostachine has been detected, but not quantified in, herbs and spices and pepper (spice). piperyline is found in Piper amalago, Piper arboreum, Piper guineense, Piper nigrum and Piper trichostachyon. This could make (e,e)-trichostachine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.1545   -2.0395   -0.4193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9702   -0.8099   -0.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423   -0.2581   -0.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5992   -1.0641   -0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7661   -0.5843    0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7686   -1.4314   -0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1702   -1.0995    0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1192   -2.0860   -0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4841   -1.8327    0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8369   -0.5251    0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9089    0.4859    0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5521    0.1996    0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5446    1.7043    0.6056 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9288    1.4257    0.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0887    0.0628    0.4535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0928    0.0553   -0.1682 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0701    1.5107    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4732    1.9574   -0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2804    0.7571    0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4634   -0.3849   -0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5057    0.7865    0.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7354   -2.1399   -0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9701    0.4704    0.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5236   -2.4968   -0.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7946   -3.1076   -0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2104   -2.6272    0.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8502    1.0336    0.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4560    2.0494   -0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2734    1.6347    1.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8650    1.7483    1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2953    1.9929   -0.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7688    2.8876    0.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5262    1.9983   -1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3180    0.7773   -0.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2190    0.7955    1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6293   -1.3293    0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6377   -0.5172   -1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 15  1  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 12  7  1  0
 20 16  1  0
 11 10  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 14 28  1  0
 14 29  1  0
 12 27  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 20 37  1  0
M  END


  Mrv0541 02241212512D          

 20 22  0  0  0  0            999 V2000
    1.3069    3.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0214    3.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7359    3.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4503    3.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648    3.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8793    3.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5937    3.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3082    3.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0227    3.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0227    2.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6358    2.0051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3002    1.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4797    1.3377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3082    2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5937    2.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0214    4.6197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888    5.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339    5.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6089    5.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3540    5.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 14  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 15  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 20  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
M  END
> <DATABASE_ID>
NP0330233

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C(\C=C\C=C\C1=CC=C2OCOC2=C1)N1CCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO3/c18-16(17-9-3-4-10-17)6-2-1-5-13-7-8-14-15(11-13)20-12-19-14/h1-2,5-8,11H,3-4,9-10,12H2/b5-1+,6-2+

> <INCHI_KEY>
GQIJYUMTOUBHSH-IJIVKGSJSA-N

> <FORMULA>
C16H17NO3

> <MOLECULAR_WEIGHT>
271.3111

> <EXACT_MASS>
271.120843415

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.955589395088925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
2.332742385333334

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.06823807404301

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
78.30199999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trichostachine

> <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  O   UNK     0       2.440   6.313   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.773   7.083   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.107   6.313   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.441   7.083   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.774   6.313   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.108   7.083   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.442   6.313   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.775   7.083   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.109   6.313   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.109   4.773   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      14.253   3.743   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      13.627   2.336   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.095   2.497   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.775   4.003   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.442   4.773   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       3.773   8.623   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       5.019   9.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.543  10.993   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.003  10.993   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.527   9.529   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   10   13   15                                                  
CONECT   15   14    7                                                       
CONECT   16    2   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   16   19                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
Trichostachine	Kegg
1-Piperoyl-(e,e)-pyrrolidine	HMDB

Chemical Formula

C₁₆H₁₇NO₃

Average Mass

271.3111 Da

Monoisotopic Mass

271.12084 Da

IUPAC Name

(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one

Traditional Name

trichostachine

CAS Registry Number

Not Available

SMILES

O=C(\C=C\C=C\C1=CC=C2OCOC2=C1)N1CCCC1

InChI Identifier

InChI=1S/C16H17NO3/c18-16(17-9-3-4-10-17)6-2-1-5-13-7-8-14-15(11-13)20-12-19-14/h1-2,5-8,11H,3-4,9-10,12H2/b5-1+,6-2+

InChI Key

GQIJYUMTOUBHSH-IJIVKGSJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Piper amalago	LOTUS Database	35616633
Piper arboreum	LOTUS Database	35616633
Piper guineense	LOTUS Database	35616633
Piper nigrum	LOTUS Database	35616633
Piper trichostachyon	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-acylpyrrolidine
Styrene
Benzenoid
Pyrrolidine
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

benzodioxoles (CHEBI:9691 )

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	3.01	ALOGPS
logP	2.33	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	2.07	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	3	ChemAxon
Refractivity	78.3 m³·mol⁻¹	ChemAxon
Polarizability	29.96 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