Record Information
Version2.0
Creation Date2012-07-30 14:55:23 -0600
Update Date2015-06-03 17:21:12 -0600
Secondary Accession Numbers
  • ECMDB21347
Identification
Name:Octadecanoate (N-C18:0)
DescriptionOctadecanoate (n-c18:0) belongs to the class of Straight Chain Fatty Acids. These are fatty acids with a straight aliphatic chain. (inferred from compound structure)Stearic acid (STAIR-ik or STEER-ik) is the saturated fatty acid with an 18 carbon chain and has the IUPAC name octadecanoic acid. It is a waxy solid, and its chemical formula is CH3(CH2)16CO2H. Its name comes from the Greek word στέαρ stéar, which means tallow. The salts and esters of stearic acid are called stearates. Stearic acid is one of the most common saturated fatty acids found in nature following palmitic acid. (WikiPedia)
Structure
Thumb
Synonyms:
  • Octadecanoate (N-C18:0)
  • Octadecanoic acid (N-C18:0)
  • Stearate
  • Stearic acid
Chemical Formula:C18H35O2
Weight:Average: 283.4693
Monoisotopic: 283.263705364
InChI Key:QIQXTHQIDYTFRH-UHFFFAOYSA-M
InChI:InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)/p-1
CAS number:Not Available
IUPAC Name:octadecanoate
Traditional IUPAC Name:n-octadecanoate
SMILES:CCCCCCCCCCCCCCCCCC([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
  • 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 Solubility5.6e-05 g/LALOGPS
logP8.21ALOGPS
logP7.15ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity97.12 m³·mol⁻¹ChemAxon
Polarizability38.16 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 + Octadecanoate (N-C18:0) > Adenosine monophosphate + Hydrogen ion + Pyrophosphate + Stearoyl-CoA
acyl carrier protein + Adenosine triphosphate + Octadecanoate (N-C18:0) > Adenosine monophosphate + Octadecanoyl-ACP (n-C18:0ACP) + Pyrophosphate
Water + Stearoyl-CoA > Coenzyme A + Hydrogen ion + Octadecanoate (N-C18:0)
1-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Octadecanoate (N-C18:0)
1-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + Water > Glycerophosphoglycerol + Hydrogen ion + Octadecanoate (N-C18:0)
1-Octadecanoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate + Hydrogen ion + Octadecanoate (N-C18:0)
Water + Octadecanoyl-phosphate (n-C18:0) >2 Hydrogen ion + Octadecanoate (N-C18:0) + Phosphate
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + Adenosine triphosphate + Octadecanoate (N-C18:0) > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + Adenosine triphosphate + Octadecanoate (N-C18:0) > Adenosine monophosphate + PG(18:0/18:0) + Pyrophosphate
Water + PA(16:0/16:0) > 1-Octadecanoyl-sn-glycerol 3-phosphate + Hydrogen ion + Octadecanoate (N-C18:0)
Water + PA(16:0/16:0) > 2-octadecanoyl-sn-glycerol 3-phosphate + Octadecanoate (N-C18:0)
Water + PE(14:0/14:0) > 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + Hydrogen ion + Octadecanoate (N-C18:0)
Water + PE(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + Hydrogen ion + Octadecanoate (N-C18:0)
Water + PG(18:0/18:0) > 1-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + Hydrogen ion + Octadecanoate (N-C18:0)
Water + PG(18:0/18:0) > 2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + Hydrogen ion + Octadecanoate (N-C18:0)
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Octadecanoate (N-C18:0)
2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + Water > Glycerophosphoglycerol + Hydrogen ion + Octadecanoate (N-C18:0)
2-octadecanoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate +2 Hydrogen ion + Octadecanoate (N-C18:0)
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, Positivesplash10-00lr-0090000000-867ced01348107216866View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00m0-3390000000-bdd5325683dba05cefcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9400000000-8f0a4c3d07b1c10ef2c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-48b9b6a6fb5660ac2107View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-0090000000-47b9b3271b7323f04871View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-4790000000-8aa77bbde9c547498884View 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 ID25629
HMDB IDNot Available
Pubchem Compound ID3033836
Kegg IDC01530
ChemSpider ID2298422
Wikipedia IDNot Available
BioCyc IDSTEARIC_ACID
EcoCyc IDSTEARIC_ACID

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