MG(16:0/0:0/0:0) (YMDB13381)

Identification

YMDB ID

YMDB13381

Name

MG(16:0/0:0/0:0)

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

1-monohexadecanoylglycerol, also known as (R)-1-monopalmitin or sn-glycerol 3-palmitate, belongs to the class of organic compounds known as 1-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 1-position. 1-monohexadecanoylglycerol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

(2R)-2,3-Dihydroxypropyl palmitate
(R)-1-Monopalmitin
(R)-2,3-Dihydroxypropyl N-hexadecanoate
3-Hexadecanoyl-sn-glycerol
sn-Glycerol 3-palmitate
(2R)-2,3-Dihydroxypropyl palmitic acid
(R)-2,3-Dihydroxypropyl N-hexadecanoic acid
sn-Glycerol 3-palmitic acid
Palmitoyl glycerol
Palmitoyl glycerol, (+,-)-isomer
Palmitoyl glycerol, hexadecanoic-1-(14)C-labeled CPD, (R)-isomer
rac-1(3)-Palmitoyl glycerol
1-Monohexadecanoyl-rac-glycerol
1-Monopalmitin
1-Glyceryl hexadecanoate
1-Monohexadecanoylglycerol

CAS number

Not Available

Weight

Average: 330.5026
Monoisotopic: 330.277009704

InChI Key

QHZLMUACJMDIAE-GOSISDBHSA-N

InChI

InChI=1S/C19H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)23-17-18(21)16-20/h18,20-21H,2-17H2,1H3/t18-/m1/s1

IUPAC Name

(2R)-2,3-dihydroxypropyl hexadecanoate

Traditional IUPAC Name

(2R)-2,3-dihydroxypropyl hexadecanoate

Chemical Formula

C₁₉H₃₈O₄

SMILES

CCCCCCCCCCCCCCCC(=O)OC[C@H](O)CO

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 1-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Monoradylglycerols

Direct Parent

1-monoacylglycerols

Alternative Parents

Substituents

1-acyl-sn-glycerol
Fatty acid ester
Fatty acyl
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-acyl-sn-glycerol (CHEBI:64757 )
1-monopalmitoylglycerol (CHEBI:64757 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.0047 g/L	ALOGPS
logP	5.73	ALOGPS
logP	5.08	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	94.11 m³·mol⁻¹	ChemAxon
Polarizability	42.39 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum

Organoleptic Properties

Not Available

SMPDB Pathways

Triacylglycerol metabolism	PW002695
Triacylglycerol metabolism TG(10:0/10:0/25:1(15Z))	PW007682
Triacylglycerol metabolism TG(10:0/10:0/26:1(5Z))	PW007711
Triacylglycerol metabolism TG(10:0/15:1(9Z)/15:1(9Z))	PW007606
Triacylglycerol metabolism TG(10:0/15:1(9Z)/20:1(13Z))	PW007692

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9351000000-f2f6a9e7c360a0c0a5b4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-003r-6149000000-46e003ac9032083459dc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9231000000-984ad8a5384b8670209d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056u-9420000000-2b1d5a640ca0c7b0f0d0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a70-2094000000-2727de3f777ddd17bb39	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-4090000000-3e968d1b6b44f5a6c1e4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9060000000-9cc1ac16deaed570ab82	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	64757
HMDB ID	Not Available
Pubchem Compound ID	11359451
Kegg ID	Not Available
ChemSpider ID	Not Available
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xa470f018>