NP-MRD: Showing NP-Card for n-[(4-hydroxy-3-methoxyphenyl)methyl]octanimidic acid (NP0317552)

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Record Information

Version

2.0

Created at

2022-09-11 17:30:33 UTC

Updated at

2022-09-11 17:30:34 UTC

NP-MRD ID

NP0317552

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(4-hydroxy-3-methoxyphenyl)methyl]octanimidic acid

Description

N-[(4-Hydroxy-3-methoxyphenyl)methyl]octanamide, also known as N-vanillyl octanamide, 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. N-[(4-Hydroxy-3-methoxyphenyl)methyl]octanamide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, N-[(4-Hydroxy-3-methoxyphenyl)methyl]octanamide has been detected, but not quantified in, several different foods, such as red bell peppers, herbs and spices, yellow bell peppers, orange bell peppers, and italian sweet red peppers. This could make N-[(4-hydroxy-3-methoxyphenyl)methyl]octanamide a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 45  0  0  0  0  0  0  0  0999 V2000
   -7.6128   -0.0510    0.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5932   -1.1441    0.7122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1766   -0.6555    0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7804    0.0698   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3437    0.5204   -0.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3650   -0.6158   -0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9878    0.0099   -0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0599   -1.0564    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1915   -2.1974   -0.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2623   -0.4873    0.6536 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480    0.0237    1.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229    0.2611    0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2619    0.4131   -1.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3147    0.6677   -1.9720 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5793    0.7635   -1.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6549    1.0196   -2.3264 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8879    0.6090   -0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1822    0.7221    0.3210 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5478    0.6100    1.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7952    0.3591    0.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1362    0.9276    0.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2120   -0.2418   -0.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2946   -0.0534    1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7234   -1.8674   -0.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7602   -1.6400    1.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4818   -1.4913    0.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9964    0.0445    1.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3931    1.0143   -0.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9252   -0.4992   -1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0400    1.0787   -1.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1993    1.2284    0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5830   -1.2554    0.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4740   -1.2709   -1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7398    0.4934   -1.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9824    0.6676    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8044   -1.7314    0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173   -0.4324    2.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415    1.1226    1.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2549    0.3488   -1.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0757    0.7736   -3.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6135    0.8464   -2.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2770    1.5601    2.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9675   -0.2106    2.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6406    0.5216    1.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9828    0.2245    1.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 14 40  1  0
 16 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
M  END


  Mrv0541 02241218452D          

 20 20  0  0  0  0            999 V2000
   -3.9288    0.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9288   -0.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2155   -1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034   -0.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034    0.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2155    0.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2155    1.4424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6420    0.6178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7888   -1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0740   -0.6178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9288    1.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3607   -1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -0.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3607   -1.8548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0686   -1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7832   -0.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4980   -1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2127   -0.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9274   -1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6420   -0.6178    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
M  END
> <DATABASE_ID>
NP0317552

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NO3/c1-3-4-5-6-7-8-16(19)17-12-13-9-10-14(18)15(11-13)20-2/h9-11,18H,3-8,12H2,1-2H3,(H,17,19)

> <INCHI_KEY>
JYZDUDMWJFJCON-UHFFFAOYSA-N

> <FORMULA>
C16H25NO3

> <MOLECULAR_WEIGHT>
279.3746

> <EXACT_MASS>
279.183443671

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.55124680560847

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
3.380003439666666

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.91578144682293

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.928691581558333

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5190927901182271

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
80.0512

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.08e-02 g/l

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

> <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      -7.334   0.386   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.334  -1.153   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.002  -1.923   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.673  -1.153   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.673   0.386   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.002   1.153   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.002   2.692   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -8.665   1.153   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.339  -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      -7.334   3.462   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  -3.462   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       4.663  -1.923   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.997  -1.153   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.331  -1.923   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.665  -1.153   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                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
N-((4-Hydroxy-3-methoxyphenyl)methyl)-octanamide	HMDB
N-((4-Hydroxy-3-methoxyphenyl)methyl)octanamide	HMDB
N-Vanillyl octanamide	HMDB
N-Vanillyl-octanamide	HMDB
N-[(4-Hydroxy-3-methoxyphenyl)methyl]octanamide, 9ci	HMDB
N-[(4-Hydroxy-3-methoxyphenyl)methyl]octanimidate	Generator

Chemical Formula

C₁₆H₂₅NO₃

Average Mass

279.3746 Da

Monoisotopic Mass

279.18344 Da

IUPAC Name

N-[(4-hydroxy-3-methoxyphenyl)methyl]octanamide

Traditional Name

N-[(4-hydroxy-3-methoxyphenyl)methyl]octanamide

CAS Registry Number

Not Available

SMILES

CCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C16H25NO3/c1-3-4-5-6-7-8-16(19)17-12-13-9-10-14(18)15(11-13)20-2/h9-11,18H,3-8,12H2,1-2H3,(H,17,19)

InChI Key

JYZDUDMWJFJCON-UHFFFAOYSA-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

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 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-9180 )

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	3.47	ALOGPS
logP	3.38	ChemAxon
logS	-3.7	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	80.05 m³·mol⁻¹	ChemAxon
Polarizability	32.55 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

HMDB0036326

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015197

KNApSAcK ID

Not Available

Chemspider ID

4475485

KEGG Compound ID

Not Available

BioCyc ID

CPD-9180

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316427

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[(4-hydroxy-3-methoxyphenyl)methyl]octanimidic acid (NP0317552)

MOL for NP0317552 (n-[(4-hydroxy-3-methoxyphenyl)methyl]octanimidic acid)

3D MOL for NP0317552 (n-[(4-hydroxy-3-methoxyphenyl)methyl]octanimidic acid)

3D SDF for NP0317552 (n-[(4-hydroxy-3-methoxyphenyl)methyl]octanimidic acid)

3D-SDF for NP0317552 (n-[(4-hydroxy-3-methoxyphenyl)methyl]octanimidic acid)

PDB for NP0317552 (n-[(4-hydroxy-3-methoxyphenyl)methyl]octanimidic acid)

3D PDB for NP0317552 (n-[(4-hydroxy-3-methoxyphenyl)methyl]octanimidic acid)

SMILES for NP0317552 (n-[(4-hydroxy-3-methoxyphenyl)methyl]octanimidic acid)

INCHI for NP0317552 (n-[(4-hydroxy-3-methoxyphenyl)methyl]octanimidic acid)

Structure for NP0317552 (n-[(4-hydroxy-3-methoxyphenyl)methyl]octanimidic acid)

3D Structure for NP0317552 (n-[(4-hydroxy-3-methoxyphenyl)methyl]octanimidic acid)