NP-MRD: Showing NP-Card for Lauric acid, methyl ester (NP0074460)

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Record Information

Version

2.0

Created at

2022-04-28 19:42:53 UTC

Updated at

2022-04-28 19:42:54 UTC

NP-MRD ID

NP0074460

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lauric acid, methyl ester

Description

Methyl dodecanoate, also known as methyl laurinate or laate methyl ester, 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 dodecanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Methyl dodecanoate is a coconut, creamy, and fat tasting compound. Outside of the human body, Methyl dodecanoate has been detected, but not quantified in, several different foods, such as fats and oils, milk and milk products, pomes, alcoholic beverages, and fruits. This could make methyl dodecanoate a potential biomarker for the consumption of these foods. Methyl dodecanoate is a potentially toxic compound. Lauric acid, methyl ester is found in Acyrthosiphon pisum, Astragalus membranaceus, Brassica juncea, Capsicum frutescens , Citrus iyo, Houttuynia cordata, Mandragora autumnalis , Pinus sibirica, Pueraria montana and Vitis labrusca . Lauric acid, methyl ester was first documented in 2015 (PMID: 25964351). Found in concord grape (Vitis labrusca), melon, pineapple, heated blackberry, red chilli (Capsicum frutescens) and other fruitsand is also present in cheeses, hop oil, white wine, spirits and other foodstuffs.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 40  0  0  0  0  0  0  0  0999 V2000
   -5.2379    1.9879    0.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2728    1.1832   -0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9388    0.6102   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3552   -0.3055    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0122   -0.8015   -0.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4319   -1.7151    0.5564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1084   -2.3033    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9564   -1.2470   -0.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2487   -1.9373   -0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3949   -1.0078   -0.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6884   -0.1866    0.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8453    0.7469    0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0060    0.2677    0.3573 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7012    2.0886    0.0371 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8067    2.9577   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3011    2.1030    1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9102    3.0514    0.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6868    1.5502    1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5877    1.8729   -1.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0634    0.4228   -0.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2324    1.3978   -1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1284    0.0121   -1.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0580   -1.1261    0.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1603    0.3124    0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3528    0.1124   -0.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1261   -1.2169   -1.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1498   -2.5449    0.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3887   -1.1617    1.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2359   -2.9211    1.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979   -2.9497   -0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6391   -0.6684   -0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0769   -0.6103    0.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1133   -2.6685   -1.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5632   -2.5656    0.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2610   -1.6382   -0.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2093   -0.3569   -1.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7828    0.3966    0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9307   -0.8351    1.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4019    2.6843   -1.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3748    3.9683   -0.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4646    3.0410    0.6954 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  2  0
 12 14  1  0
 14 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
M  END

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       8.883   6.668   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.221   7.438   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.216   7.438   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.884   7.438   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.217   6.668   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.551   7.438   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.885   6.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.218   7.438   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.552   6.668   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.886   7.438   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.219   6.668   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.553   7.438   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      23.553   8.978   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      24.887   6.668   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   15                                                            
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   15                                                  
CONECT   14   13                                                            
CONECT   15    2   13                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
Lauric acid methyl ester	ChEBI
Methyl dodecylate	ChEBI
Methyl laurinate	ChEBI
Methyl N-dodecanoate	ChEBI
Laate methyl ester	Generator
Laic acid methyl ester	Generator
Methyl dodecylic acid	Generator
Methyl laurinic acid	Generator
Methyl N-dodecanoic acid	Generator
Methyl dodecanoic acid	Generator
Dodecanoic acid, methyl ester	HMDB
FEMA 2715	HMDB
Lauric acid, methyl ester	HMDB
Metholene 2296	HMDB
METHYL dodecanoATE, 99.8%	HMDB
Methyl laurate	HMDB
Stepan C40	HMDB
Uniphat a40	HMDB
Uniphat a40 in 511	HMDB
Lauric acid methyl ester, C14-labeled	MeSH

Chemical Formula

C₁₃H₂₆O₂

Average Mass

214.3443 Da

Monoisotopic Mass

214.19328 Da

IUPAC Name

methyl dodecanoate

Traditional Name

methyl laurate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC(=O)OC

InChI Identifier

InChI=1S/C13H26O2/c1-3-4-5-6-7-8-9-10-11-12-13(14)15-2/h3-12H2,1-2H3

InChI Key

UQDUPQYQJKYHQI-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Astragalus membranaceus	LOTUS Database	35616633
Brassica juncea	LOTUS Database	35616633
Capsicum frutescens L.	Plant	KNApSAcK
Citrus iyo	LOTUS Database	35616633
Houttuynia cordata	LOTUS Database	35616633
Mandragora autumnalis	Plant	KNApSAcK
Pinus sibirica	Plant	KNApSAcK
Pueraria montana	LOTUS Database	35616633
Vitis labrusca	Plant	KNApSAcK

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

laurate ester (CHEBI:87494 )
fatty acid methyl ester (CHEBI:87494 )
Wax monoesters (LMFA07010463 )

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	5.51	ALOGPS
logP	4.62	ChemAxon
logS	-5.2	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	11	ChemAxon
Refractivity	63.45 m³·mol⁻¹	ChemAxon
Polarizability	27.88 Å³	ChemAxon
Number of Rings	0	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

HMDB0031018

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003011

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

8139

PDB ID

Not Available

ChEBI ID

87494

Good Scents ID

Not Available

References

General References

Dweck HK, Ebrahim SA, Thoma M, Mohamed AA, Keesey IW, Trona F, Lavista-Llanos S, Svatos A, Sachse S, Knaden M, Hansson BS: Pheromones mediating copulation and attraction in Drosophila. Proc Natl Acad Sci U S A. 2015 May 26;112(21):E2829-35. doi: 10.1073/pnas.1504527112. Epub 2015 May 11. [PubMed:25964351 ]

Showing NP-Card for Lauric acid, methyl ester (NP0074460)

MOL for NP0074460 (Lauric acid, methyl ester)

3D MOL for NP0074460 (Lauric acid, methyl ester)

3D SDF for NP0074460 (Lauric acid, methyl ester)

3D-SDF for NP0074460 (Lauric acid, methyl ester)

PDB for NP0074460 (Lauric acid, methyl ester)

3D PDB for NP0074460 (Lauric acid, methyl ester)

SMILES for NP0074460 (Lauric acid, methyl ester)

INCHI for NP0074460 (Lauric acid, methyl ester)

Structure for NP0074460 (Lauric acid, methyl ester)

3D Structure for NP0074460 (Lauric acid, methyl ester)