ECMDB: 1,2-Diacyl-sn-glycerol (didodecanoyl, n-C12:0) (ECMDB21103) (M2MDB001512)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (3)

Record Information

Version

2.0

Creation Date

2012-07-30 14:54:38 -0600

Update Date

2015-06-03 17:20:38 -0600

Secondary Accession Numbers

ECMDB21103

Identification

Name:

1,2-Diacyl-sn-glycerol (didodecanoyl, n-C12:0)

Description

1,2-diacyl-sn-glycerol (didodecanoyl, n-c12:0) belongs to the class of Diacylglycerols. These are glycerides consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. (inferred from compound structure)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(2S)-2-dodecanoyloxy-3-hydroxypropyl dodecanoate
(2S)-2-Dodecanoyloxy-3-hydroxypropyl dodecanoic acid

Chemical Formula:

C₂₇H₅₂O₅

Weight:

Average: 456.6988
Monoisotopic: 456.381474774

InChI Key:

OQQOAWVKVDAJOI-VWLOTQADSA-N

InChI:

InChI=1S/C27H52O5/c1-3-5-7-9-11-13-15-17-19-21-26(29)31-24-25(23-28)32-27(30)22-20-18-16-14-12-10-8-6-4-2/h25,28H,3-24H2,1-2H3/t25-/m0/s1

CAS number:

Not Available

IUPAC Name:

(2S)-1-(dodecanoyloxy)-3-hydroxypropan-2-yl dodecanoate

Traditional IUPAC Name:

(2S)-1-(dodecanoyloxy)-3-hydroxypropan-2-yl dodecanoate

SMILES:

CCCCCCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCCCCCC

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Diradylglycerols

Direct Parent

1,2-diacylglycerols

Alternative Parents

Substituents

1,2-acyl-sn-glycerol
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Carboxylic acid ester
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

Diacylglycerols (LMGL02010323 )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	6.8e-05 g/L	ALOGPS
logP	8.19	ALOGPS
logP	8.45	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	14.58	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	130.89 m³·mol⁻¹	ChemAxon
Polarizability	57.77 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:

Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (didodecanoyl, n-C12:0) + Phosphate
1,2-Diacyl-sn-glycerol (didodecanoyl, n-C12:0) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)
a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA + PE(12:0/10:0) + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA > 1,2-Diacyl-sn-glycerol (didodecanoyl, n-C12:0) + phosphoethanolamine-Kdo2-lipid A + Phosphoethanolamine KDO(2)-lipid (A)

SMPDB Pathways:

Lipopolysaccharide biosynthesis

PW000831

KEGG Pathways:

Lipopolysaccharide biosynthesis ec00540

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-020r-7917630000-1c071b617668e0eedd76	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000900000-d3ce757c7d77e6c1be44	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-0090900000-6ef2c93167204571eefa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-0090900000-6e02300046f9f3d0ba35	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-1490800000-18d42897aa4b538bb98f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-4972200000-8bf0dc177fbb992d3fe9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9520000000-a1bc798bac9b5758447b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000900000-f4d3ed62660285fb1766	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000900000-f4d3ed62660285fb1766	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0090100000-d6418435e21ebeb07527	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000900000-fe4ad345fcc9c1b96ae8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-0080900000-2021c9c67a87211de23e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-0080900000-4a323f60ea8a1e7a9560	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4j-1540900000-e078ec43d41cb3157252	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052b-2970100000-af92add4600e0160c423	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0910000000-75918b523af3cd4255fe	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

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	Not Available
HMDB ID	HMDB0093027
Pubchem Compound ID	151838
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Phosphatidylglycerophosphatase B

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes phosphatidylglycerophosphate, phosphatidic acid, and lysophosphatidic acid; the pattern of activities varies according to subcellular location
Gene Name:: pgpB
Uniprot ID:: P0A924
Molecular weight:: 29021

Reactions

Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate.

Protein Details

2. Diacylglycerol kinase

General function:: Involved in diacylglycerol kinase activity
Specific function:: Recycling of diacylglycerol produced during the turnover of membrane phospholipid
Gene Name:: dgkA
Uniprot ID:: P0ABN1
Molecular weight:: 13245

Reactions

ATP + 1,2-diacylglycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate.

Protein Details

3. Phosphoethanolamine transferase eptB

General function:: Involved in catalytic activity
Specific function:: Catalyzes the addition of a phosphoethanolamine (pEtN) moiety to the outer 3-deoxy-D-manno-octulosonic acid (KDO) residue of a KDO(2)-lipid A. Phosphatidylethanolamines with one unsaturated acyl group functions as pEtN donors and the reaction releases diacylglycerol
Gene Name:: eptB
Uniprot ID:: P37661
Molecular weight:: 63804

1,2-Diacyl-sn-glycerol (didodecanoyl, n-C12:0) (ECMDB21103) (M2MDB001512)

Structure for #<Compound:0xa8b09700>

Enzymes

Reactions

Reactions