NP-MRD: Showing NP-Card for 2,4-Dodecadienoic acid pyrrolidide (NP0049246)

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Record Information

Version

2.0

Created at

2022-03-17 21:09:25 UTC

Updated at

2022-03-17 21:09:25 UTC

NP-MRD ID

NP0049246

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4-Dodecadienoic acid pyrrolidide

Description

2,4-Dodecadienoic acid pyrrolidide, also known as 1-(2,4-dodecadienoyl)pyrrolidine, belongs to the class of organic compounds known as n-acylpyrrolidines. These are n-Acylated Pyrrolidine derivatives. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. 2,4-Dodecadienoic acid pyrrolidide is a moderately basic compound (based on its pKa). Outside of the human body, 2,4-Dodecadienoic acid pyrrolidide has been detected, but not quantified in, herbs and spices and pepper (spice). 2,4-Dodecadienoic acid pyrrolidide is found in Piper nigrum. This could make 2,4-dodecadienoic acid pyrrolidide a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310412D          

 18 18  0  0  0  0            999 V2000
   -2.1298    8.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4153    8.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7008    8.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0136    8.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7281    8.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4426    8.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570    8.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8715    8.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5860    8.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3004    8.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3371    7.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7496    7.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0149    8.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5301    7.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1975    8.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7294    8.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4439    8.0685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7294    9.3060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0049246

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC\C=C\C=C\C(=O)N1CCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C16H27NO/c1-2-3-4-5-6-7-8-9-10-13-16(18)17-14-11-12-15-17/h8-10,13H,2-7,11-12,14-15H2,1H3/b9-8+,13-10+

> <INCHI_KEY>
UAIYHWLHQSKQLW-PEGOPYGQSA-N

> <FORMULA>
C16H27NO

> <MOLECULAR_WEIGHT>
249.3917

> <EXACT_MASS>
249.209264491

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
32.0253648018102

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E)-1-(pyrrolidin-1-yl)dodeca-2,4-dien-1-one

> <ALOGPS_LOGP>
5.06

> <JCHEM_LOGP>
4.160416935

> <ALOGPS_LOGS>
-5.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.0702156834667393

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
80.0461

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E)-1-(pyrrolidin-1-yl)dodeca-2,4-dien-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      -3.976  15.061   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.642  15.831   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.308  15.061   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.025  15.831   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.359  15.061   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.693  15.831   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.026  15.061   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.360  15.831   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.694  15.061   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.027  15.831   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.696  13.209   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.466  14.543   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.361  15.061   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.190  13.530   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.435  15.688   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.695  15.831   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      12.029  15.061   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      10.695  17.371   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   13                                                       
CONECT   11   12   14                                                       
CONECT   12   11   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   17                                                       
CONECT   16   13   17   18                                                  
CONECT   17   14   15   16                                                  
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
2,4-Dodecadienoate pyrrolidide	Generator
1-(2,4-Dodecadienoyl)pyrrolidine	HMDB
[(2E,4E)-Dodecadienoyl]-pyrrolidine	HMDB

Chemical Formula

C₁₆H₂₇NO

Average Mass

249.3917 Da

Monoisotopic Mass

249.20926 Da

IUPAC Name

(2E,4E)-1-(pyrrolidin-1-yl)dodeca-2,4-dien-1-one

Traditional Name

(2E,4E)-1-(pyrrolidin-1-yl)dodeca-2,4-dien-1-one

CAS Registry Number

117137-69-6

SMILES

CCCCCCC\C=C\C=C\C(=O)N1CCCC1

InChI Identifier

InChI=1S/C16H27NO/c1-2-3-4-5-6-7-8-9-10-13-16(18)17-14-11-12-15-17/h8-10,13H,2-7,11-12,14-15H2,1H3/b9-8+,13-10+

InChI Key

UAIYHWLHQSKQLW-PEGOPYGQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
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 n-acylpyrrolidines. These are n-Acylated Pyrrolidine derivatives. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

N-acylpyrrolidines

Direct Parent

N-acylpyrrolidines

Alternative Parents

Substituents

N-acylpyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acylpyrrolidine (CHEBI:70093 )

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	5.06	ALOGPS
logP	4.16	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	2.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	80.05 m³·mol⁻¹	ChemAxon
Polarizability	32.03 Å³	ChemAxon
Number of Rings	1	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

HMDB0038841

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018276

KNApSAcK ID

C00031479

Chemspider ID

9174623

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10999431

PDB ID

Not Available

ChEBI ID

70093

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2,4-Dodecadienoic acid pyrrolidide (NP0049246)

MOL for NP0049246 (2,4-Dodecadienoic acid pyrrolidide)

3D MOL for NP0049246 (2,4-Dodecadienoic acid pyrrolidide)

3D SDF for NP0049246 (2,4-Dodecadienoic acid pyrrolidide)

3D-SDF for NP0049246 (2,4-Dodecadienoic acid pyrrolidide)

PDB for NP0049246 (2,4-Dodecadienoic acid pyrrolidide)

3D PDB for NP0049246 (2,4-Dodecadienoic acid pyrrolidide)

SMILES for NP0049246 (2,4-Dodecadienoic acid pyrrolidide)

INCHI for NP0049246 (2,4-Dodecadienoic acid pyrrolidide)

Structure for NP0049246 (2,4-Dodecadienoic acid pyrrolidide)

3D Structure for NP0049246 (2,4-Dodecadienoic acid pyrrolidide)