NP-MRD: Showing NP-Card for (2e,6e,8z)-n-(2-methylpropyl)deca-2,6,8-trienimidic acid (NP0308380)

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Record Information

Version

2.0

Created at

2022-09-11 02:06:56 UTC

Updated at

2022-09-11 02:06:56 UTC

NP-MRD ID

NP0308380

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,6e,8z)-n-(2-methylpropyl)deca-2,6,8-trienimidic acid

Description

Spilanthol, also known as affinin, belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage. (2e,6e,8z)-n-(2-methylpropyl)deca-2,6,8-trienimidic acid is found in Acmella oleracea and Blainvillea acmella. (2e,6e,8z)-n-(2-methylpropyl)deca-2,6,8-trienimidic acid was first documented in 2021 (PMID: 35361327). Based on a literature review a small amount of articles have been published on Spilanthol (PMID: 36044910) (PMID: 35994943) (PMID: 35228190).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 38  0  0  0  0  0  0  0  0999 V2000
    6.3995   -0.1146    1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6890   -0.5601   -0.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7120   -0.6008   -1.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3775   -0.2030   -0.8334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3399   -0.2149   -1.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9645    0.2015   -1.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0759   -1.0025   -1.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3254   -0.7336   -0.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9481   -1.4115   -0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3245   -1.1485    0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8832   -1.9292    1.3421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9703   -0.2174   -0.2343 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3151    0.1677    0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4258    1.4377    0.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7663    1.3319    2.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9204    1.7231    1.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3176   -0.0172    1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8881    0.8914    0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7408   -0.8317    1.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7170   -0.8482   -0.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8930   -0.9215   -2.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1878    0.1194    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5204   -0.5369   -2.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6252    1.0782   -1.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0073    0.4723   -0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -1.8224   -0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1517   -1.3370   -2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8556    0.0640   -1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3591   -2.2117    0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8030   -2.3483    1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7992    0.4070   -0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8646   -0.6646    0.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9914    2.3007    0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2450    2.0774    2.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8960    0.3463    2.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7046    1.6324    2.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0143    2.6726    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3976    0.8680    1.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3074    1.8839   -0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
M  END


  Mrv1652309112204062D          

 16 15  0  0  0  0            999 V2000
    6.1875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  4  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0308380

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C/C=C/CC\C=C\C(O)=NCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H23NO/c1-4-5-6-7-8-9-10-11-14(16)15-12-13(2)3/h4-7,10-11,13H,8-9,12H2,1-3H3,(H,15,16)/b5-4-,7-6+,11-10+

> <INCHI_KEY>
BXOCHUWSGYYSFW-NIYQBQGDSA-N

> <FORMULA>
C14H23NO

> <MOLECULAR_WEIGHT>
221.344

> <EXACT_MASS>
221.177964365

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.928620420700828

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,6E,8Z)-N-(2-methylpropyl)deca-2,6,8-trienimidic acid

> <JCHEM_LOGP>
3.7353424188032767

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.516127282636929

> <JCHEM_PKA_STRONGEST_BASIC>
7.4503253760634145

> <JCHEM_POLAR_SURFACE_AREA>
32.59

> <JCHEM_REFRACTIVITY>
73.78890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E,6E,8Z)-N-(2-methylpropyl)deca-2,6,8-trienimidic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      11.550   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.780   5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+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   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
Affinin	MeSH
(2E,6Z,8E)-N-Isobutyl-2,6,8-decatrienamid	MeSH
N-Isobutyl-2E-decenamide	MeSH

Chemical Formula

C₁₄H₂₃NO

Average Mass

221.3440 Da

Monoisotopic Mass

221.17796 Da

IUPAC Name

(2E,6E,8Z)-N-(2-methylpropyl)deca-2,6,8-trienimidic acid

Traditional Name

(2E,6E,8Z)-N-(2-methylpropyl)deca-2,6,8-trienimidic acid

CAS Registry Number

Not Available

SMILES

C\C=C/C=C/CC\C=C\C(O)=NCC(C)C

InChI Identifier

InChI=1S/C14H23NO/c1-4-5-6-7-8-9-10-11-14(16)15-12-13(2)3/h4-7,10-11,13H,8-9,12H2,1-3H3,(H,15,16)/b5-4-,7-6+,11-10+

InChI Key

BXOCHUWSGYYSFW-NIYQBQGDSA-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
Acmella oleracea	LOTUS Database	35616633
Blainvillea acmella	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

N-acyl amines

Alternative Parents

Substituents

N-acyl-amine
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	3.74	ChemAxon
pKa (Strongest Acidic)	5.52	ChemAxon
pKa (Strongest Basic)	7.45	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.59 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	73.79 m³·mol⁻¹	ChemAxon
Polarizability	27.93 Å³	ChemAxon
Number of Rings	0	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00040347

Chemspider ID

75596558

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Spilanthol

METLIN ID

Not Available

PubChem Compound

15558482

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Grymel M, Mazurkiewicz R, Bajkacz S, Bilik J, Kowalczyk S: Extraction, Purification, Quantification, and Stability of Bioactive Spilanthol from Acmella oleracea. Planta Med. 2022 Aug 31. doi: 10.1055/a-1903-2226. [PubMed:36044910 ]
Bellumori M, Zonfrillo B, Maggini V, Bogani P, Gallo E, Firenzuoli F, Mulinacci N, Innocenti M: Acmella oleracea (L.) R.K. Jansen: Alkylamides and phenolic compounds in aerial parts and roots of in vitro seedlings. J Pharm Biomed Anal. 2022 Oct 25;220:114991. doi: 10.1016/j.jpba.2022.114991. Epub 2022 Aug 9. [PubMed:35994943 ]
Stepniowska A, Cieplinska P, Fac W, Gorska J: Selected Alkaloids Used in the Cosmetics Industry. J Cosmet Sci. 2021 Mar-Apr;72(2):229-245. [PubMed:35361327 ]
Afzal A, Shah NH, Hussain I, Munawar SH, Mumtaz A, Qureshi N: Preparation of Spilanthes acmella based emulgel: Antimicrobial study and evaluation. Pak J Pharm Sci. 2022 Jan;35(1(Supplementary)):287-295. [PubMed:35228190 ]
LOTUS database [Link]

Showing NP-Card for (2e,6e,8z)-n-(2-methylpropyl)deca-2,6,8-trienimidic acid (NP0308380)

MOL for NP0308380 ((2e,6e,8z)-n-(2-methylpropyl)deca-2,6,8-trienimidic acid)

3D MOL for NP0308380 ((2e,6e,8z)-n-(2-methylpropyl)deca-2,6,8-trienimidic acid)

3D SDF for NP0308380 ((2e,6e,8z)-n-(2-methylpropyl)deca-2,6,8-trienimidic acid)

3D-SDF for NP0308380 ((2e,6e,8z)-n-(2-methylpropyl)deca-2,6,8-trienimidic acid)

PDB for NP0308380 ((2e,6e,8z)-n-(2-methylpropyl)deca-2,6,8-trienimidic acid)

3D PDB for NP0308380 ((2e,6e,8z)-n-(2-methylpropyl)deca-2,6,8-trienimidic acid)

SMILES for NP0308380 ((2e,6e,8z)-n-(2-methylpropyl)deca-2,6,8-trienimidic acid)

INCHI for NP0308380 ((2e,6e,8z)-n-(2-methylpropyl)deca-2,6,8-trienimidic acid)

Structure for NP0308380 ((2e,6e,8z)-n-(2-methylpropyl)deca-2,6,8-trienimidic acid)

3D Structure for NP0308380 ((2e,6e,8z)-n-(2-methylpropyl)deca-2,6,8-trienimidic acid)