NP-MRD: Showing NP-Card for Nordihydrocapsaicin (NP0048484)

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Record Information

Version

2.0

Created at

2022-03-17 20:57:11 UTC

Updated at

2022-03-17 20:57:12 UTC

NP-MRD ID

NP0048484

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nordihydrocapsaicin

Description

Nordihydrocapsaicin belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Pure nordihydrocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. Nordihydrocapsaicin is an extremely weak basic (essentially neutral) compound (based on its pKa). Like capsaicin, it is an irritant. Outside of the human body, Nordihydrocapsaicin 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). Nordihydrocapsaicin has also been detected, but not quantified in, herbs and spices and italian sweet red peppers. This could make nordihydrocapsaicin a potential biomarker for the consumption of these foods. Nordihydrocapsaicin accounts for about 7% of the total capsaicinoids mixture and has about half the pungency of capsaicin. Nordihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Nordihydrocapsaicin is found in Capsicum pubescens. On the Scoville scale it has 9,100,000 SHU (Scoville heat units), significantly higher than pepper spray.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241216392D          

 21 21  0  0  0  0            999 V2000
   -3.9295    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9295   -0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2161   -1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5039   -0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5039    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2161    0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2161    1.4427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6429    0.6179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7891   -1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0742   -0.6179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9295    1.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608   -1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608   -1.8551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687   -1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7836   -0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4984   -1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2133   -0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9281   -1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6429   -0.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9281   -1.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1  8  1  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
  4  9  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7 11  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  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
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048484

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H27NO3/c1-13(2)7-5-4-6-8-17(20)18-12-14-9-10-15(19)16(11-14)21-3/h9-11,13,19H,4-8,12H2,1-3H3,(H,18,20)

> <INCHI_KEY>
VQEONGKQWIFHMN-UHFFFAOYSA-N

> <FORMULA>
C17H27NO3

> <MOLECULAR_WEIGHT>
293.4012

> <EXACT_MASS>
293.199093735

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.35478058183505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(4-hydroxy-3-methoxyphenyl)methyl]-7-methyloctanamide

> <ALOGPS_LOGP>
3.85

> <JCHEM_LOGP>
3.667022536

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.951998651026233

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.92869169291128

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5190928434197922

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
84.59979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nordihydrocapsaicin

> <JCHEM_VEBER_RULE>
0

$$$$

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  C   UNK     0      -7.335   0.386   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.335  -1.153   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.003  -1.923   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.674  -1.153   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.674   0.386   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.003   1.153   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.003   2.693   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -8.667   1.153   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.340  -1.923   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -2.005  -1.153   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -7.335   3.463   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.673  -1.923   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.661  -1.153   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.673  -3.463   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.995  -1.923   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.329  -1.153   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.664  -1.923   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.998  -1.153   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.332  -1.923   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.667  -1.153   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.332  -3.463   0.000  0.00  0.00           C+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6   11                                                       
CONECT    8    1                                                            
CONECT    9    4   10                                                       
CONECT   10    9   12                                                       
CONECT   11    7                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
N-((4-H Ydroxy-3-methoxyphenyl)methyl)-7-methyl-octanamide	Kegg
7-Methyl nordihydrocapsaicin	HMDB
N-((4-Hydroxy-3-methoxyphenyl)methyl)-7-methyl-octanamide	HMDB
N-[(4-Hydroxy-3-methoxyphenyl)methyl]-7-methyloctanamide, 9ci	HMDB
Nordihydrocapsacin	HMDB

Chemical Formula

C₁₇H₂₇NO₃

Average Mass

293.4012 Da

Monoisotopic Mass

293.19909 Da

IUPAC Name

N-[(4-hydroxy-3-methoxyphenyl)methyl]-7-methyloctanamide

Traditional Name

nordihydrocapsaicin

CAS Registry Number

28789-35-7

SMILES

COC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O

InChI Identifier

InChI=1S/C17H27NO3/c1-13(2)7-5-4-6-8-17(20)18-12-14-9-10-15(19)16(11-14)21-3/h9-11,13,19H,4-8,12H2,1-3H3,(H,18,20)

InChI Key

VQEONGKQWIFHMN-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
Capsicum pubescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty acyl
Fatty amide
N-acyl-amine
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

an alkaloid (CPD-9182 )

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	3.85	ALOGPS
logP	3.67	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	-0.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	84.6 m³·mol⁻¹	ChemAxon
Polarizability	34.35 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon