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Record Information

Version

2.0

Creation Date

2012-08-09 09:25:06 -0600

Update Date

2015-06-03 17:21:37 -0600

Secondary Accession Numbers

ECMDB21484

Identification

Name:

2-Monopalmitin

Description

2-monopalmitin is a member of the chemical class known as Monoacylglycerols. These are glycerides consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. (inferred from compound structure). It is a monoacylglycerol with an acyl chain length of 16 carbons. 2-monoacylglycerols (2-MG) are produced in eukaryotes by lipoprotein lipase (LPL) hydrolysos of triacylgycerols.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

1,2,3-Propanetriol 2-hexandecanoyl ester
2-Hexadecanoyl glycerol
2-Hydroxy-1-(hydroxymethyl)ethyl palmitate
2-Hydroxy-1-(hydroxymethyl)ethyl palmitic acid
2-Mono-Palmitin
2-Monopalmitoyl-sn-glycerol
Glycerol 2-hexadecanoate
Glycerol 2-hexadecanoic acid
Glycerol b-palmitate
Glycerol b-palmitic acid
Glycerol beta-palmitate
Glycerol beta-palmitic acid
Glycerol β-palmitate
Glycerol β-palmitic acid
Glycerol, 2-palmitate
Glycerol, 2-palmitic acid
Palmitate b-monoglyceride
Palmitate beta-monoglyceride
Palmitate β-monoglyceride
Palmitic acid b-monoglyceride
Palmitic acid beta-monoglyceride
Palmitic acid β-monoglyceride

Chemical Formula:

C₁₉H₃₈O₄

Weight:

Average: 330.5026
Monoisotopic: 330.277009704

InChI Key:

BBNYCLAREVXOSG-UHFFFAOYSA-N

InChI:

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

CAS number:

23470-00-0

IUPAC Name:

1,3-dihydroxypropan-2-yl hexadecanoate

Traditional IUPAC Name:

1,3-dihydroxypropan-2-yl hexadecanoate

SMILES:

[H]C(CO)(CO)OC(=O)CCCCCCCCCCCCCCC

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 2-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 2-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Monoradylglycerols

Direct Parent

2-monoacylglycerols

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-monoglyceride (CHEBI:75455 )
Monoacylglycerols (LMGL01010025 )
a monoacylglycerol (CPD66-43 )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.0045 g/L	ALOGPS
logP	5.77	ALOGPS
logP	5.08	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	14.28	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	42.12 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:

Membrane

Reactions:

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fba-1920000000-134607514f54b5fa383a	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fba-1920000000-134607514f54b5fa383a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0fy9-8690000000-42e670eb7d2b93c2cf13	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive	splash10-0abd-9201000000-13c26a3dfbe9c2c0ee82	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-001i-0009000000-3fbc80e8b1a6c4769b57	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-03di-0009000000-ab66c5fcbc1ccb42abd0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-0a4i-2590000000-fbd516b957b730aa1e61	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-014i-9000000000-fb41d95361a6747c1394	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-03di-3009000000-1461fc327f550f36fd64	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-08fr-9105000000-5ff0ac490f9e9eb2fd3a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, positive	splash10-0ab9-9101000000-543e82e44e10c0bafe1b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 16V, positive	splash10-0a4i-9000000000-42345c34104efaffa9e5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 18V, positive	splash10-0a4i-9000000000-10f9ae2324888d282fe8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 20V, positive	splash10-0a4i-9000000000-168d6d9e105e242d5381	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 24V, positive	splash10-0a4i-9000000000-788ea5a75eccdebbb706	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 30V, positive	splash10-0a4i-9000000000-f5d8bcb715bb7c4eec96	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 36V, positive	splash10-0a4i-9000000000-bebf6a01d91a3cefd039	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 44V, positive	splash10-0a4i-9000000000-158d88e5fdd09f1bfc44	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 53V, positive	splash10-0a4i-9000000000-e48e57dbfb8d67f5c722	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-0a4i-3890000000-dc3e6fa9504ad7732b36	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-014i-9000000000-fb41d95361a6747c1394	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-0kps-4910000000-366e65362ec66509aff9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-0f79-2910000000-96991d9805c0c30dbaf4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-004i-9000000000-2b3b5490150f8c42c1ef	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0a4m-9201000000-1493642eda69722aa926	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0009000000-88db68411e5bedb3a55c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001k-0009000000-3ea7f1cea75ce9907e95	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00f2-0049000000-f01e41d62e6fdf3b791b	View in MoNA

References

References:

van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	75455
HMDB ID	HMDB0011533
Pubchem Compound ID	1321
Kegg ID	Not Available
ChemSpider ID	110006
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

2-Monopalmitin (M2MDB001879)

Structure for #<Compound:0xa85e9054>