NP-MRD: Showing NP-Card for methyl myristate (NP0271975)

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Record Information

Version

2.0

Created at

2022-09-08 18:26:35 UTC

Updated at

2022-09-08 18:26:36 UTC

NP-MRD ID

NP0271975

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl myristate

Description

Methyl tetradecanoate, also known as myristate methyl ester or metholeneat 2495, belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group. Methyl tetradecanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Methyl tetradecanoate is a fatty, orris, and petal tasting compound. Outside of the human body, Methyl tetradecanoate has been detected, but not quantified in, evergreen blackberries. This could make methyl tetradecanoate a potential biomarker for the consumption of these foods. methyl myristate is found in Acyrthosiphon pisum, Aleuroglyphus ovatus, Astragalus membranaceus, Bistorta manshuriensis, Brassica rapa, Catharanthus roseus, Cyperus conglomeratus, Daphne odora, Hamamelis virginiana, Iris germanica, Morchella esculenta, Pueraria montana and Smenospongia aurea. methyl myristate was first documented in 2013 (PMID: 23621022). A fatty acid methyl ester resulting from the formal condensation of the carboxy group of tetradecanoic acid (myristic acid) with methanol (PMID: 27556271).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 46  0  0  0  0  0  0  0  0999 V2000
   -6.2294    1.2122    1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3945    0.2810    0.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3726    0.7898   -0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6146   -0.0089   -1.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1558   -0.1446   -1.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5019   -0.6989   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9924   -0.8712   -0.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3964    0.4495   -0.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1077    0.3214   -1.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7383   -0.2188    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2505   -0.3684   -0.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9397    0.9295   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4205    0.6766   -0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9521    0.1132    0.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9675   -1.1185    0.9584 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4458    0.9767    1.7117 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9503    0.4142    2.9060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5509    0.5968    2.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0866    1.5503    1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6121    2.0599    1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4893    0.0453    1.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9955   -0.6843    0.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9759    1.8650   -0.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4407    0.8994   -1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0451   -1.0671   -1.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8214    0.3690   -2.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242    0.9198   -1.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8116   -0.6352   -2.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707   -1.6233    0.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4862    0.0656    0.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8552   -1.5846   -1.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6133   -1.3572    0.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8605    0.8114   -1.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6565    1.1800   -0.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145    1.2953   -1.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2227   -0.4270   -1.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189    0.4603    0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3816   -1.2709    0.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6872   -0.8384    0.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4182   -1.0721   -0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5166    1.4152   -1.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7822    1.6688    0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9367    1.6274   -0.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5784   -0.0583   -1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8973    1.1817    3.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3212   -0.4594    3.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0052    0.1333    2.7038 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  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 17 45  1  0
 17 46  1  0
 17 47  1  0
M  END


  Mrv0541 05061305152D          

 17 16  0  0  0  0            999 V2000
    5.9961    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    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
    8.1395    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
    9.5684    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
   10.9974    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
   12.4263    4.6993    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
   13.8552    4.6993    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
   15.2842    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842    5.5243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  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  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  2  0  0  0  0
 17  2  1  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0271975

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCC(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C15H30O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15(16)17-2/h3-14H2,1-2H3

> <INCHI_KEY>
ZAZKJZBWRNNLDS-UHFFFAOYSA-N

> <FORMULA>
C15H30O2

> <MOLECULAR_WEIGHT>
242.3975

> <EXACT_MASS>
242.224580204

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
32.136854357951705

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl tetradecanoate

> <ALOGPS_LOGP>
6.38

> <JCHEM_LOGP>
5.513339503666666

> <ALOGPS_LOGS>
-5.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0239806136690355

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
72.65069999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.59e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl myristate

> <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      11.193   8.002   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      31.198   8.772   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.526   8.772   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.860   8.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.194   8.772   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.527   8.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.861   8.772   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.195   8.002   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.528   8.772   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.862   8.002   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.196   8.772   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.529   8.002   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.863   8.772   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.197   8.002   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.531   8.772   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      28.531  10.312   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      29.864   8.002   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   17                                                            
CONECT    3    1    4                                                       
CONECT    4    3    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   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17    2   15                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Value	Source
Metholeneat 2495	ChEBI
Methyl myristate	ChEBI
Methyl N-tetradecanoate	ChEBI
Myristic acid methyl ester	ChEBI
Myristic acid, methyl ester	ChEBI
Tetradecanoic acid, methyl ester	ChEBI
Uniphat a50	ChEBI
Methyl myristic acid	Generator
Methyl N-tetradecanoic acid	Generator
Myristate methyl ester	Generator
Myristate, methyl ester	Generator
Tetradecanoate, methyl ester	Generator
Methyl tetradecanoic acid	Generator
Methyl myristylate	HMDB
Myristic acid, methyl ester (8ci)	HMDB
C14-MES	MeSH
Tetradecanoic acid methyl ester	MeSH
Tetradecanoic acid methyl ester sodium salt	MeSH

Chemical Formula

C₁₅H₃₀O₂

Average Mass

242.3975 Da

Monoisotopic Mass

242.22458 Da

IUPAC Name

methyl tetradecanoate

Traditional Name

methyl myristate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC(=O)OC

InChI Identifier

InChI=1S/C15H30O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15(16)17-2/h3-14H2,1-2H3

InChI Key

ZAZKJZBWRNNLDS-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

Species Name	Source	Reference
Acyrthosiphon pisum	LOTUS Database	35616633
Aleuroglyphus ovatus	LOTUS Database	35616633
Astragalus membranaceus	LOTUS Database	35616633
Bistorta manshuriensis	LOTUS Database	35616633
Brassica rapa	LOTUS Database	35616633
Catharanthus roseus	LOTUS Database	35616633
Cyperus conglomeratus	LOTUS Database	35616633
Daphne odora	LOTUS Database	35616633
Hamamelis virginiana	LOTUS Database	35616633
Iris germanica	LOTUS Database	35616633
Morchella esculenta	LOTUS Database	35616633
Pueraria montana	LOTUS Database	35616633
Smenospongia aurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid methyl esters

Alternative Parents

Substituents

Fatty acid methyl ester
Methyl ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Wax monoesters (LMFA07010467 )

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	6.38	ALOGPS
logP	5.51	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	72.65 m³·mol⁻¹	ChemAxon
Polarizability	32.14 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030469

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002338

KNApSAcK ID

C00051572

Chemspider ID

29024

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

31284

PDB ID

Not Available

ChEBI ID

89199

Good Scents ID

Not Available

References

General References

Manosroi A, Chaikul P, Abe M, Manosroi W, Manosroi J: Melanogenesis of methyl myristate loaded niosomes in B16F10 melanoma cells. J Biomed Nanotechnol. 2013 Apr;9(4):626-38. doi: 10.1166/jbn.2013.1565. [PubMed:23621022 ]
Manosroi J, Chankhampan C, Chaikul P, Manosroi W, Manosroi A: Transfollicular enhancement of methyl myristate loaded in cationic niosomes incorporated in hair lotion. J Microencapsul. 2016 Sep;33(6):585-594. doi: 10.1080/02652048.2016.1228705. Epub 2016 Sep 6. [PubMed:27556271 ]
LOTUS database [Link]

Showing NP-Card for methyl myristate (NP0271975)

MOL for NP0271975 (methyl myristate)

3D MOL for NP0271975 (methyl myristate)

3D SDF for NP0271975 (methyl myristate)

3D-SDF for NP0271975 (methyl myristate)

PDB for NP0271975 (methyl myristate)

3D PDB for NP0271975 (methyl myristate)

SMILES for NP0271975 (methyl myristate)

INCHI for NP0271975 (methyl myristate)

Structure for NP0271975 (methyl myristate)

3D Structure for NP0271975 (methyl myristate)