NP-MRD: Showing NP-Card for (2e,6z,8e,10z)-n-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid (NP0211256)

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Record Information

Version

2.0

Created at

2022-09-05 09:26:51 UTC

Updated at

2022-09-05 09:26:52 UTC

NP-MRD ID

NP0211256

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,6z,8e,10z)-n-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid

Description

Neoherculin belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group). Neoherculin is a very strong basic compound (based on its pKa). Outside of the human body, Neoherculin has been detected, but not quantified in, herbs and spices. (2e,6z,8e,10z)-n-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid is found in Zanthoxylum clava-herculis. This could make neoherculin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 42  0  0  0  0  0  0  0  0999 V2000
    8.1851    0.1466   -0.4170 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3247   -0.8318   -1.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0144   -0.6838   -1.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4781    0.4272   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1410    0.5996   -0.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6309    1.7056    0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3519    1.9234    0.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3285    1.0735    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4516    0.4668    1.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6006   -0.4039    0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8803   -0.1566    0.7940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9059   -1.0125    0.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5862   -2.1201   -0.5610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1614   -0.7818    0.3783 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2067   -1.6092   -0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3371   -0.6859   -0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8183    0.0589    0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8126    0.2972   -1.6795 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2685   -0.1397   -0.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0290    1.1665   -0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9127    0.1812    0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7476   -1.6624   -1.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3284   -1.3608   -1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1020    1.1339    0.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5422   -0.1361   -0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3691    2.3779    1.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0491    2.7981    1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6869    0.3103   -0.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6960    1.7586   -0.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0516    1.2550    1.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106   -0.1219    1.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3647   -1.2743    0.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1385    0.7053    1.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4368   -2.0480   -1.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8299   -2.2084   -1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6408   -2.3206    0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1473   -1.2848   -1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0862    0.8930    0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8229    0.4793    0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7667   -0.6168    1.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6703    0.7282   -2.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1579   -0.1810   -2.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3254    1.1540   -1.1522 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
M  END


  Mrv0541 05061305372D          

 18 17  0  0  0  0            999 V2000
    7.4250    1.4289    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
    7.0125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    1.4289    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
   -0.4125   -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
    0.8250    0.0000    0.0000 C   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
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  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
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 15  2  1  0  0  0  0
 15  3  1  0  0  0  0
 15 14  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  2  0  0  0  0
 18 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211256

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NO/c1-4-5-6-7-8-9-10-11-12-13-16(18)17-14-15(2)3/h4-9,12-13,15H,10-11,14H2,1-3H3,(H,17,18)/b5-4-,7-6+,9-8-,13-12+

> <INCHI_KEY>
SBXYHCVXUCYYJT-JRNWQWJGSA-N

> <FORMULA>
C16H25NO

> <MOLECULAR_WEIGHT>
247.3758

> <EXACT_MASS>
247.193614427

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
31.349701840287118

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(Z,2E,6Z,8E,10Z)-N-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid

> <ALOGPS_LOGP>
5.52

> <JCHEM_LOGP>
4.8710073923333335

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.690625491834572

> <JCHEM_PKA_STRONGEST_BASIC>
6.023839741937433

> <JCHEM_POLAR_SURFACE_AREA>
32.59

> <JCHEM_REFRACTIVITY>
84.10750000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(Z,2E,6Z,8E,10Z)-N-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid

> <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      13.860   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.090   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.550   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.780   2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.240   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2   15                                                            
CONECT    3   15                                                            
CONECT    4    1    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                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   16                                                       
CONECT   14   15   17                                                       
CONECT   15    2    3   14                                                  
CONECT   16   13   17   18                                                  
CONECT   17   14   16                                                       
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
(e,e,Z,e)-N-(2-Methylpropyl)-2,6,8,10-dodecatetraenamide	HMDB
a-Sanshool	HMDB
alpha-Sanshool	HMDB
Echinacein	HMDB
N-Isobutyl-2,6,8,10-dodecatetraenamide	HMDB
(2E,6Z,8E,10Z)-N-(2-Methylpropyl)dodeca-2,6,8,10-tetraenimidate	Generator

Chemical Formula

C₁₆H₂₅NO

Average Mass

247.3758 Da

Monoisotopic Mass

247.19361 Da

IUPAC Name

(Z,2E,6Z,8E,10Z)-N-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid

Traditional Name

(Z,2E,6Z,8E,10Z)-N-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H25NO/c1-4-5-6-7-8-9-10-11-12-13-16(18)17-14-15(2)3/h4-9,12-13,15H,10-11,14H2,1-3H3,(H,17,18)/b5-4-,7-6+,9-8-,13-12+

InChI Key

SBXYHCVXUCYYJT-JRNWQWJGSA-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
Zanthoxylum clava-herculis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboximidic acids and derivatives

Sub Class

Carboximidic acids

Direct Parent

Carboximidic acids

Alternative Parents

Substituents

Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
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	5.52	ALOGPS
logP	4.87	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	8.69	ChemAxon
pKa (Strongest Basic)	6.02	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	8	ChemAxon
Refractivity	84.11 m³·mol⁻¹	ChemAxon
Polarizability	31.35 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

HMDB0030955

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002933

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751109

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e,6z,8e,10z)-n-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid (NP0211256)

MOL for NP0211256 ((2e,6z,8e,10z)-n-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid)

3D MOL for NP0211256 ((2e,6z,8e,10z)-n-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid)

3D SDF for NP0211256 ((2e,6z,8e,10z)-n-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid)

3D-SDF for NP0211256 ((2e,6z,8e,10z)-n-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid)

PDB for NP0211256 ((2e,6z,8e,10z)-n-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid)

3D PDB for NP0211256 ((2e,6z,8e,10z)-n-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid)

SMILES for NP0211256 ((2e,6z,8e,10z)-n-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid)

INCHI for NP0211256 ((2e,6z,8e,10z)-n-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid)

Structure for NP0211256 ((2e,6z,8e,10z)-n-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid)

3D Structure for NP0211256 ((2e,6z,8e,10z)-n-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid)