Record Information
Version2.0
Creation Date2012-07-30 14:55:23 -0600
Update Date2015-06-03 17:21:12 -0600
Secondary Accession Numbers
  • ECMDB21348
Identification
Name:Octadecenoate (N-C18:1)
DescriptionOctadecenoate is the salt or easter of octadecenoic acid (oleic acid).
Structure
Thumb
Synonyms:
  • Octadecenoic acid (N-C18:1)
Chemical Formula:C18H33O2
Weight:Average: 281.4534
Monoisotopic: 281.2480553
InChI Key:ZQPPMHVWECSIRJ-MDZDMXLPSA-M
InChI:InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/p-1/b10-9+
CAS number:Not Available
IUPAC Name:(9E)-octadec-9-enoate
Traditional IUPAC Name:elaidate
SMILES:[H]\C(CCCCCCCC)=C(\[H])CCCCCCCC([O-])=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.1e-05 g/LALOGPS
logP7.71ALOGPS
logP6.78ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity98.24 m³·mol⁻¹ChemAxon
Polarizability37.16 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Adenosine triphosphate + Coenzyme A + Hydrogen ion + Octadecenoate (N-C18:1) > Adenosine monophosphate + Hydrogen ion + Octadecenoyl-CoA (N-C18:1CoA) + Pyrophosphate
acyl carrier protein + Adenosine triphosphate + Octadecenoate (N-C18:1) > Adenosine monophosphate + cis-octadec-11-enoyl-[acyl-carrier protein] (n-C18:1) + Pyrophosphate
Water + Octadecenoyl-CoA (N-C18:1CoA) > Coenzyme A + Hydrogen ion + Octadecenoate (N-C18:1)
1-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Octadecenoate (N-C18:1)
1-Acyl-sn-glycero-3-phosphoglycerol (N-C18:1) + Water > Glycerophosphoglycerol + Hydrogen ion + Octadecenoate (N-C18:1)
1-Octadec-11-enoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate + Hydrogen ion + Octadecenoate (N-C18:1)
Water + Octadecanoyl-phosphate (n-C18:1) >2 Hydrogen ion + Octadecenoate (N-C18:1) + Phosphate
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + Adenosine triphosphate + Octadecenoate (N-C18:1) > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:1) + Adenosine triphosphate + Octadecenoate (N-C18:1) > Adenosine monophosphate + PG(18:1(11Z)/18:1(11Z)) + Pyrophosphate
Water + PA(16:0/16:0) > 1-Octadec-11-enoyl-sn-glycerol 3-phosphate + Hydrogen ion + Octadecenoate (N-C18:1)
Water + PA(16:0/16:0) > 2-octadec-11-enoyl-sn-glycerol 3-phosphate + Octadecenoate (N-C18:1)
Water + PE(14:0/14:0) > 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + Hydrogen ion + Octadecenoate (N-C18:1)
Water + PE(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + Hydrogen ion + Octadecenoate (N-C18:1)
Water + PG(18:1(11Z)/18:1(11Z)) > 1-Acyl-sn-glycero-3-phosphoglycerol (N-C18:1) + Hydrogen ion + Octadecenoate (N-C18:1)
Water + PG(18:1(11Z)/18:1(11Z)) > 2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:1) + Hydrogen ion + Octadecenoate (N-C18:1)
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Octadecenoate (N-C18:1)
2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:1) + Water > Glycerophosphoglycerol + Hydrogen ion + Octadecenoate (N-C18:1)
2-octadec-11-enoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate +2 Hydrogen ion + Octadecenoate (N-C18:1)
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-71e618da168ffaa9204dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-4190000000-be1f46ab866e8b6f4824View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9210000000-8077b899f8e0e5270203View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-4a7b76ecd62c26e9a13eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-0090000000-4413d771cbd2cb37d92bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-6490000000-bfe007b561c200afd767View in MoNA
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
External Links:
ResourceLink
CHEBI ID30825
HMDB IDNot Available
Pubchem Compound ID5461071
Kegg IDNot Available
ChemSpider ID4574429
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Lipid transport and metabolism
Specific function:
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:
pldB
Uniprot ID:
P07000
Molecular weight:
38978
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in phospholipase activity
Specific function:
Has broad substrate specificity including hydrolysis of phosphatidylcholine with phospholipase A2 (EC 3.1.1.4) and phospholipase A1 (EC 3.1.1.32) activities. Strong expression leads to outer membrane breakdown and cell death; is dormant in normal growing cells. Required for efficient secretion of bacteriocins
Gene Name:
pldA
Uniprot ID:
P0A921
Molecular weight:
33163
Reactions
Phosphatidylcholine + H(2)O = 2-acylglycerophosphocholine + a carboxylate.
Phosphatidylcholine + H(2)O = 1-acylglycerophosphocholine + a carboxylate.
General function:
Involved in acylphosphatase activity
Specific function:
An acylphosphate + H(2)O = a carboxylate + phosphate
Gene Name:
yccX
Uniprot ID:
P0AB65
Molecular weight:
10300
Reactions
An acylphosphate + H(2)O = a carboxylate + phosphate.
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin
Gene Name:
tesA
Uniprot ID:
P0ADA1
Molecular weight:
23622
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Plays a role in lysophospholipid acylation. Transfers fatty acids to the 1-position via an enzyme-bound acyl-ACP intermediate in the presence of ATP and magnesium. Its physiological function is to regenerate phosphatidylethanolamine from 2-acyl-glycero-3-phosphoethanolamine (2-acyl-GPE) formed by transacylation reactions or degradation by phospholipase A1
Gene Name:
aas
Uniprot ID:
P31119
Molecular weight:
80699
Reactions
Acyl-[acyl-carrier-protein] + O-(2-acyl-sn-glycero-3-phospho)ethanolamine = [acyl-carrier-protein] + O-(1-beta-acyl-2-acyl-sn-glycero-3-phospho)ethanolamine.
ATP + an acid + [acyl-carrier-protein] = AMP + diphosphate + acyl-[acyl-carrier-protein].
General function:
Involved in catalytic activity
Specific function:
Catalyzes the esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids
Gene Name:
fadD
Uniprot ID:
P69451
Molecular weight:
62332
Reactions
ATP + a long-chain fatty acid + CoA = AMP + diphosphate + an acyl-CoA.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the esterification, concomitant with transport, of exogenous fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. It has a low activity on medium or long chain fatty acids and is maximally active on C6 and C8 substrates
Gene Name:
fadK
Uniprot ID:
P38135
Molecular weight:
60773
Reactions
ATP + a short-chain carboxylic acid + CoA = AMP + diphosphate + an acyl-CoA.
General function:
Involved in acyl-CoA hydrolase activity
Specific function:
Can hydrolyze a broad range of acyl-CoA thioesters. Its physiological function is not known
Gene Name:
tesB
Uniprot ID:
P0AGG2
Molecular weight:
31966
General function:
Involved in fatty acid biosynthetic process
Specific function:
Carrier of the growing fatty acid chain in fatty acid biosynthesis
Gene Name:
acpP
Uniprot ID:
P0A6A8
Molecular weight:
8640

Transporters

General function:
Lipid transport and metabolism
Specific function:
Involved in translocation of long-chain fatty acids across the outer membrane. It is a receptor for the bacteriophage T2. FadL may form a specific channel
Gene Name:
fadL
Uniprot ID:
P10384
Molecular weight:
48541