P. aeruginosa Metabolome Database: 1-Octadec-11-enoyl-sn-glycerol 3-phosphate (PAMDB001539)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB001539

Identification

Name:

1-Octadec-11-enoyl-sn-glycerol 3-phosphate

Description:

1-octadec-11-enoyl-sn-glycerol 3-phosphate belongs to the class of Lysophosphatidic Acids. These are glycerophosphates where the glycerol is esterified with one saturated fatty acid. (inferred from compound structure)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

1-Octadec-11-enoyl-sn-glycerol 3-phosphoric acid

Chemical Formula:

C₂₁H₃₉O₇P

Average Molecular Weight:

434.5039

Monoisotopic Molecular Weight:

434.243340114

InChI Key:

LWSYATLSXCUNTB-BQYQJAHWSA-L

InChI:

InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h7-8,20,22H,2-6,9-19H2,1H3,(H2,24,25,26)/p-2/b8-7+

CAS number:

Not Available

IUPAC Name:

2-hydroxy-3-(phosphonatooxy)propyl (11E)-octadec-11-enoate

Traditional IUPAC Name:

2-hydroxy-3-(phosphonatooxy)propyl (11E)-octadec-11-enoate

SMILES:

[H]\C(CCCCCC)=C(\[H])CCCCCCCCCC(=O)OCC(O)COP([O-])([O-])=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1-acylglycerol-3-phosphates

Alternative Parents

Substituents

1-acylglycerol-3-phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.00228 mg/mL	ALOGPS
logP	5.56	ALOGPS
logP	5.49	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	118.95 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	113.06 m³·mol^-1	ChemAxon
Polarizability	49.61 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:

Glycerol 3-phosphate + cis-octadec-11-enoyl-[acyl-carrier protein] (n-C18:1) > 1-Octadec-11-enoyl-sn-glycerol 3-phosphate + acyl carrier protein
1-Octadec-11-enoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate + Hydrogen ion + Octadecenoate (N-C18:1)
1-Octadec-11-enoyl-sn-glycerol 3-phosphate + cis-octadec-11-enoyl-[acyl-carrier protein] (n-C18:1) > acyl carrier protein + PA(16:0/16:0)
Glycerol 3-phosphate + Octadecanoyl-phosphate (n-C18:1) > 1-Octadec-11-enoyl-sn-glycerol 3-phosphate + Hydrogen ion + Phosphate
Water + PA(16:0/16:0) > 1-Octadec-11-enoyl-sn-glycerol 3-phosphate + Hydrogen ion + Octadecenoate (N-C18:1)

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000900000-dd4e69952db3bbb3e9a6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004r-2012900000-9735a5482305db332688	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9020000000-70ccf3decdd16e71a274	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000900000-df006bc51f2d7f78cc76	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2240900000-f7c02bd8125db94ad80f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9030000000-c95fb9fae408973b3fc7	View in MoNA

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	Not Available
Pubchem Compound ID	Not Available
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	CPD0-2220
EcoCyc ID	CPD0-2220

Enzymes

Protein Details

• Glycerol-3-phosphate acyltransferase

General function:: Involved in transferase activity, transferring acyl groups
Specific function:: Catalyzes the transfer of an acyl group from acyl-ACP to glycerol-3-phosphate (G3P) to form lysophosphatidic acid (LPA). This enzyme can utilize either acyl-CoA or acyl-ACP as the fatty acyl donor
Gene Name:: plsB
Locus Tag:: PA3673
Molecular weight:: 94.8 kDa

Reactions

Acyl-CoA + sn-glycerol 3-phosphate = CoA + 1-acyl-sn-glycerol 3-phosphate.

Protein Details

• Acyl-CoA thioesterase I

General function:: Involved in hydrolase activity
Specific function:: Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin
Gene Name:: tesA
Locus Tag:: PA2856
Molecular weight:: 21 kDa

Reactions

2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.

Protein Details

• Acyl carrier protein

General function:: Involved in fatty acid biosynthetic process
Specific function:: Carrier of the growing fatty acid chain in fatty acid biosynthesis
Gene Name:: acpP
Locus Tag:: PA2966
Molecular weight:: 8.7 kDa

1-Octadec-11-enoyl-sn-glycerol 3-phosphate (PAMDB001539)

Structure for 1-Octadec-11-enoyl-sn-glycerol 3-phosphate (PAMDB001539)

Enzymes

Reactions

Reactions