NP-MRD: Showing NP-Card for nornordihydrocapsaicin (NP0341926)

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Record Information

Version

2.0

Created at

2024-10-25 12:59:10 UTC

Updated at

2024-10-27 00:06:57 UTC

NP-MRD ID

NP0341926

Natural Product DOI

https://doi.org/10.57994/3416

Secondary Accession Numbers

None

Natural Product Identification

Common Name

nornordihydrocapsaicin

Description

Nornordihydrocapsaicin 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. nornordihydrocapsaicin was first documented in 2018 (PMID: 28873562). Based on a literature review very few articles have been published on nornordihydrocapsaicin.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01222313102D          

 20 20  0  0  0  0            999 V2000
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  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  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  8 16  2  0  0  0  0
  5 17  1  0  0  0  0
 17 18  2  0  0  0  0
  3 19  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0341926

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(CNC(=O)CCCCC(C)C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NO3/c1-12(2)6-4-5-7-16(19)17-11-13-8-9-14(18)15(10-13)20-3/h8-10,12,18H,4-7,11H2,1-3H3,(H,17,19)

> <INCHI_KEY>
WQFXXCXOXXAOII-UHFFFAOYSA-N

> <FORMULA>
C16H25NO3

> <MOLECULAR_WEIGHT>
279.38

> <EXACT_MASS>
279.183443669

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
32.29205679670474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(4-hydroxy-3-methoxyphenyl)methyl]-6-methylheptanamide

> <JCHEM_LOGP>
3.2224538709999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.91578142789488

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.928691581543994

> <JCHEM_PKA_STRONGEST_BASIC>
-1.419854110918113

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
79.9988

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-[(4-hydroxy-3-methoxyphenyl)methyl]-6-methylheptanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JAN-23         0                                  
HETATM    1  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.334   3.850   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.000   6.160   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    8                                                            
CONECT   17    5   18                                                       
CONECT   18   17   19                                                       
CONECT   19    3   18   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₅NO₃

Average Mass

279.3800 Da

Monoisotopic Mass

279.18344 Da

IUPAC Name

N-[(4-hydroxy-3-methoxyphenyl)methyl]-6-methylheptanamide

Traditional Name

N-[(4-hydroxy-3-methoxyphenyl)methyl]-6-methylheptanamide

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(CNC(=O)CCCCC(C)C)=C1

InChI Identifier

InChI=1S/C16H25NO3/c1-12(2)6-4-5-7-16(19)17-11-13-8-9-14(18)15(10-13)20-3/h8-10,12,18H,4-7,11H2,1-3H3,(H,17,19)

InChI Key

WQFXXCXOXXAOII-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3CN, experimental)	joshua.smith@uochb.cas.cz	Institute of Organic Chemistry and Biochemistry	Joshua Smith	2024-10-25	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3CN, experimental)	joshua.smith@uochb.cas.cz	Institute of Organic Chemistry and Biochemistry	Joshua Smith	2024-10-25	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3CN, experimental)	joshua.smith@uochb.cas.cz	Institute of Organic Chemistry and Biochemistry	Joshua Smith	2024-10-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3CN, experimental)	joshua.smith@uochb.cas.cz	Institute of Organic Chemistry and Biochemistry	Joshua Smith	2024-10-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3CN, experimental)	joshua.smith@uochb.cas.cz	Institute of Organic Chemistry and Biochemistry	Joshua Smith	2024-10-25	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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 amide
Fatty acyl
N-acyl-amine
Carboxamide group
Secondary carboxylic acid amide
Ether
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

an alkaloid (CPD-9332 )

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	3.22	ChemAxon
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	-1.4	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	8	ChemAxon
Refractivity	80 m³·mol⁻¹	ChemAxon
Polarizability	32.29 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

25200611

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Stipcovich T, Barbero GF, Ferreiro-Gonzalez M, Palma M, Barroso CG: Fast analysis of capsaicinoids in Naga Jolokia extracts (Capsicum chinense) by high-performance liquid chromatography using fused core columns. Food Chem. 2018 Jan 15;239:217-224. doi: 10.1016/j.foodchem.2017.06.098. Epub 2017 Jun 20. [PubMed:28873562 ]

Showing NP-Card for nornordihydrocapsaicin (NP0341926)

MOL for NP0341926 (nornordihydrocapsaicin)

3D MOL for NP0341926 (nornordihydrocapsaicin)

3D SDF for NP0341926 (nornordihydrocapsaicin)

3D-SDF for NP0341926 (nornordihydrocapsaicin)

PDB for NP0341926 (nornordihydrocapsaicin)

3D PDB for NP0341926 (nornordihydrocapsaicin)

SMILES for NP0341926 (nornordihydrocapsaicin)

INCHI for NP0341926 (nornordihydrocapsaicin)

Structure for NP0341926 (nornordihydrocapsaicin)

3D Structure for NP0341926 (nornordihydrocapsaicin)