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Caprylic acid (M2MDB000140)

Record Information
Version2.0
Creation Date2012-05-31 10:26:52 -0600
Update Date2015-10-02 02:25:50 -0600
Secondary Accession Numbers
  • ECMDB00482
Identification
Name:Caprylic acid
DescriptionCaprylic acid belongs to the class of Straight Chain Fatty Acids. These are fatty acids with a straight aliphatic chain. (inferred from compound structure). Caprylic acid is the common name for the eight-carbon saturated fatty acid known by the systematic name octanoic acid. (WikiPedia). Caprylic acid is an intermediate in lipoate biosynthesis and incorporation II in E. coli. It is a substrate for lipoate-protein ligase A which catalyzes the chemical reaction a [lipoyl-carrier protein]-L-lysine + caprylic acid + ATP -> a [lipoyl-carrier protein] N6-octanoyl-L-lysine + AMP + diphosphate + H+. It is also a substrate for acyl-ACP synthetase in the reaction caprylic acid + a holo-[acyl-carrier protein] + ATP → an octanoyl-[acp] + AMP + diphosphate (EcoCyc compound: CPD-195).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 1-Heptanecarboxylate
  • 1-Heptanecarboxylic acid
  • C-8 Acid
  • Caprylate
  • Caprylic acid
  • Capryloate
  • Capryloic acid
  • Emery 657
  • Kortacid 0899
  • Lunac 8-95
  • Lunac 8-98
  • N-Caprylate
  • N-Caprylic acid
  • N-Octanoate
  • N-Octanoic acid
  • N-Octate
  • N-Octic acid
  • N-Octoate
  • N-Octoic acid
  • N-Octylate
  • N-Octylic acid
  • Neo-Fat 8
  • Neo-Fat 8S
  • Octanoate
  • Octanoate (N-C8:0)
  • Octanoic acid
  • Octanoic acid (N-C8:0)
  • Octoate
  • Octoic acid
  • Octylate
  • Octylic acid
  • Prifac 2901
Chemical Formula:C8H16O2
Weight:Average: 144.2114
Monoisotopic: 144.115029756
InChI Key:WWZKQHOCKIZLMA-UHFFFAOYSA-N
InChI:InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
CAS number:124-07-2
IUPAC Name:octanoic acid
Traditional IUPAC Name:caprylic acid
SMILES:CCCCCCCC(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-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
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Liquid
Charge:-1
Melting point:16.5 °C
Experimental Properties:
PropertyValueSource
Water Solubility:0.789 mg/ml [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:2.57PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.91 g/LALOGPS
logP2.92ALOGPS
logP2.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)5.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity40.28 m³·mol⁻¹ChemAxon
Polarizability17.4 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Coenzyme A + Hydrogen ion + Caprylic acid > Adenosine monophosphate + Hydrogen ion + Octanoyl-CoA + Pyrophosphate
acyl carrier protein + Adenosine triphosphate + Caprylic acid > Adenosine monophosphate + Octanoyl-ACP (n-C8:0ACP) + Pyrophosphate
Water + Octanoyl-ACP (n-C8:0ACP) > acyl carrier protein + Hydrogen ion + Caprylic acid
Water + Octanoyl-CoA > Coenzyme A + Hydrogen ion + Caprylic acid
Adenosine triphosphate + Hydrogen ion + Caprylic acid > Adenosine monophosphate + octanoate (protein bound) + Pyrophosphate
Caprylic acid + Adenosine triphosphate + a [lipoyl-carrier protein]-L-lysine > Hydrogen ion + Pyrophosphate + Adenosine monophosphate + Protein N6-(octanoyl)lysine
Caprylic acid + Adenosine triphosphate + Coenzyme A > Adenosine monophosphate + Octanoyl-CoA + Octanoyl-CoA
Caprylic acid + a holo-[acyl-carrier protein] + Adenosine triphosphate > Octanoyl-[acyl-carrier protein] + Adenosine monophosphate + Pyrophosphate
SMPDB Pathways:
Fatty acid biosynthesisPW000900 ThumbThumb?image type=greyscaleThumb?image type=simple
Lipoic acid metabolismPW000770 ThumbThumb?image type=greyscaleThumb?image type=simple
fatty acid oxidation (octanoate)PW001022 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • lipoate biosynthesis and incorporation II PWY0-1275
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-0910000000-e609d5de69ede6fbcde0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0gb9-1920000000-1dc6ed976e003f99e23dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03kc-9000000000-74cfce03769b41313952View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uyi-0931100000-7668e36e436054042b5cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0910000000-e609d5de69ede6fbcde0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gb9-1920000000-1dc6ed976e003f99e23dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0910000000-9ecb4ccb46e89710f76aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0596-9100000000-8854c56056d8d3405087View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-062l-9100000000-67da39159980b9078fabView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0006-0900000000-bb237630bedcee6145d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-2900000000-98284f50a271878c8481View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-5900000000-209fbbacd4996b9a770dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03kc-9000000000-74cfce03769b41313952View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-e2c4dff10393086340f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-1900000000-bbde8564b4e5543a636aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-Q-Exactive Plus , Negativesplash10-0006-0900000000-d219a0c6559a4783fd81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-e2c4dff10393086340f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-1900000000-bbde8564b4e5543a636aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0006-0900000000-ca22ecd0b25fa371fc73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0gvp-9100000000-58c00a2024ba0bae4ff4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-9300000000-2505e6738cf5d5877654View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-1ab4cdf8f74c93312743View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-2900000000-ac7c80e50c93b8cc3af7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9400000000-d2694b5f89d8eaeb2ab1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-f2b24072c91d8b0e4078View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-ad62d44e72f4dd1760abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-7900000000-9c869b84815f21dffc7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-b8a648d443695914e479View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6u-9100000000-f5c38fdad70b324e75acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-bee103956686b4840d1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-e7cbd036c8e80018c825View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-8f2b048da6331570976cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-cd31ca01a5fa6be86acbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-682c215be5abe1fe87edView in MoNA
MSMass Spectrum (Electron Ionization)splash10-03kc-9000000000-8c7db9a9d75b2cc1bd1cView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Dieterle F, Muller-Hagedorn S, Liebich HM, Gauglitz G: Urinary nucleosides as potential tumor markers evaluated by learning vector quantization. Artif Intell Med. 2003 Jul;28(3):265-79. Pubmed: 12927336
  • Giannakou SA, Dallas PP, Rekkas DM, Choulis NH: In vitro evaluation of nimodipine permeation through human epidermis using response surface methodology. Int J Pharm. 2002 Jul 8;241(1):27-34. Pubmed: 12086718
  • Habeeb AF, Francis RD: Preparation of human immunoglobulin by caprylic acid precipitation. Prep Biochem. 1984;14(1):1-17. Pubmed: 6718324
  • Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Nair MK, Joy J, Venkitanarayanan KS: Inactivation of Enterobacter sakazakii in reconstituted infant formula by monocaprylin. J Food Prot. 2004 Dec;67(12):2815-9. Pubmed: 15633694
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • 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:Caprylic acid. Jpn. Kokai Tokkyo Koho (1983), 4 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID28837
HMDB IDHMDB00482
Pubchem Compound ID379
Kegg IDC06423
ChemSpider ID370
WikipediaCaprylic acid
BioCyc IDCPD-195
EcoCyc IDCPD-195
Ligand ExpoOCA

Enzymes

Protein Details
1. Acyl carrier protein phosphodiesterase
General function:
Involved in [acyl-carrier-protein] phosphodiesterase activity
Specific function:
Converts holo-ACP to apo-ACP by hydrolytic cleavage of the phosphopantetheine prosthetic group from ACP
Gene Name:
acpH
Uniprot ID:
P21515
Molecular weight:
22961
Reactions
Holo-[acyl-carrier-protein] + H(2)O = 4'-phosphopantetheine + apo-[acyl-carrier-protein].
Protein Details
2. Bifunctional protein aas
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].
Protein Details
3. Lipoate-protein ligase A
General function:
Involved in catalytic activity
Specific function:
Catalyzes both the ATP-dependent activation of exogenously supplied lipoate to lipoyl-AMP and the transfer of the activated lipoyl onto the lipoyl domains of lipoate-dependent enzymes. Is also able to catalyze very poorly the transfer of lipoyl and octanoyl moiety from their acyl carrier protein
Gene Name:
lplA
Uniprot ID:
P32099
Molecular weight:
37926
Reactions
ATP + lipoate = diphosphate + lipoyl-AMP.
Lipoyl-AMP + protein = protein N(6)-(lipoyl)lysine + AMP.
Protein Details
4. Long-chain-fatty-acid--CoA ligase
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.
Protein Details
5. Short-chain-fatty-acid--CoA ligase
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.
Protein Details
6. Acyl-CoA thioesterase 2
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
Protein Details
7. 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
Uniprot ID:
P0A6A8
Molecular weight:
8640

Transporters

Protein Details
1. Outer membrane protein N
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
Protein Details
2. Outer membrane pore protein E
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
Protein Details
3. Outer membrane protein F
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
Protein Details
4. Outer membrane protein C
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368