NP-MRD: Showing NP-Card for Capsiamide (NP0049757)

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Record Information

Version

2.0

Created at

2022-03-17 21:17:39 UTC

Updated at

2022-03-17 21:17:39 UTC

NP-MRD ID

NP0049757

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Capsiamide

Description

Capsiamide, also known as cap-a, belongs to the class of organic compounds known as acetamides. These are organic compounds with the general formula RNHC(=O)CH3, where R= organyl group. Capsiamide is a very strong basic compound (based on its pKa). Outside of the human body, Capsiamide is found, on average, in the highest concentration within a few different foods, such as yellow bell peppers, red bell peppers, and pepper (c. Annuum) and in a lower concentration in orange bell peppers, green bell peppers, and pepper (c. Frutescens). Capsiamide has also been detected, but not quantified in, a few different foods, such as fruits, herbs and spices, and italian sweet red peppers. This could make capsiamide a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061312162D          

 19 18  0  0  0  0            999 V2000
   16.7131   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2816   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1408   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105   -4.6993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961   -3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16 14  1  0  0  0  0
 17  3  1  0  0  0  0
 18 15  1  0  0  0  0
 18 17  2  0  0  0  0
 19 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049757

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H35NO/c1-16(2)14-12-10-8-6-4-5-7-9-11-13-15-18-17(3)19/h16H,4-15H2,1-3H3,(H,18,19)

> <INCHI_KEY>
AMLDBWWQKYLAHJ-UHFFFAOYSA-N

> <FORMULA>
C17H35NO

> <MOLECULAR_WEIGHT>
269.4659

> <EXACT_MASS>
269.271864747

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.88804576270398

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(Z)-N-(13-methyltetradecyl)ethenimidic acid

> <ALOGPS_LOGP>
7.26

> <JCHEM_LOGP>
6.069596625666668

> <ALOGPS_LOGS>
-6.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.326848821353392

> <JCHEM_PKA_STRONGEST_BASIC>
5.696144073084228

> <JCHEM_POLAR_SURFACE_AREA>
32.59

> <JCHEM_REFRACTIVITY>
84.31649999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.69e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(Z)-N-(13-methyltetradecyl)ethenimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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      31.198  -8.772   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.864  -6.462   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.859  -8.772   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.862  -8.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.528  -8.772   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.196  -8.772   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.195  -8.002   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.529  -8.002   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.861  -8.772   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.863  -8.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.527  -8.002   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.197  -8.002   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.194  -8.772   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.531  -8.772   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.860  -8.002   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.864  -8.002   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.193  -8.002   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      12.526  -8.772   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      11.193  -6.462   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   18                                                       
CONECT   16    1    2   14                                                  
CONECT   17    3   18   19                                                  
CONECT   18   15   17                                                       
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol

Synonyms

Value	Source
N-(13-Methyltetradecyl)acetamide	Kegg
CAP-a	Kegg
Capsi-amide	HMDB
N-(13-METHYLTETRADECYL)-acetamide	HMDB

Chemical Formula

C₁₇H₃₅NO

Average Mass

269.4659 Da

Monoisotopic Mass

269.27186 Da

IUPAC Name

(Z)-N-(13-methyltetradecyl)ethenimidic acid

Traditional Name

(Z)-N-(13-methyltetradecyl)ethenimidic acid

CAS Registry Number

64317-66-4

SMILES

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

InChI Identifier

InChI=1S/C17H35NO/c1-16(2)14-12-10-8-6-4-5-7-9-11-13-15-18-17(3)19/h16H,4-15H2,1-3H3,(H,18,19)

InChI Key

AMLDBWWQKYLAHJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Capsicum annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Capsicum annuum var. annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acetamides. These are organic compounds with the general formula RNHC(=O)CH3, where R= organyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Acetamides

Alternative Parents

Substituents

Acetamide
Secondary carboxylic acid amide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxamide (CHEBI:81149 )

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	7.26	ALOGPS
logP	6.07	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	8.33	ChemAxon
pKa (Strongest Basic)	5.7	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	13	ChemAxon
Refractivity	84.32 m³·mol⁻¹	ChemAxon
Polarizability	36.89 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0040940

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020783

KNApSAcK ID

Not Available

Chemspider ID

43094

KEGG Compound ID

C17515

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

47346

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Capsiamide (NP0049757)

MOL for NP0049757 (Capsiamide)

3D MOL for NP0049757 (Capsiamide)

3D SDF for NP0049757 (Capsiamide)

3D-SDF for NP0049757 (Capsiamide)

PDB for NP0049757 (Capsiamide)

3D PDB for NP0049757 (Capsiamide)

SMILES for NP0049757 (Capsiamide)

INCHI for NP0049757 (Capsiamide)

Structure for NP0049757 (Capsiamide)

3D Structure for NP0049757 (Capsiamide)