ECMDB: Caprylic acid (ECMDB00482) (M2MDB000140)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (7)Transporters (4)XML

Proteins (15)

Record Information

Version

2.0

Creation Date

2012-05-31 10:26:52 -0600

Update Date

2015-10-02 02:25:50 -0600

Secondary Accession Numbers

ECMDB00482

Identification

Name:

Caprylic acid

Description

Caprylic 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

MOL SDF PDB SMILES InChI

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-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 Framework

Aliphatic acyclic compounds

External Descriptors

medium-chain fatty acid (CHEBI:28837 )
straight-chain saturated fatty acid (CHEBI:28837 )
Straight chain fatty acids (C06423 )
Saturated fatty acids (C06423 )
Straight chain fatty acids (LMFA01010008 )

Physical Properties

State:

Liquid

Charge:

-1

Melting point:

16.5 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	0.789 mg/ml [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP:	2.57	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.91 g/L	ALOGPS
logP	2.92	ALOGPS
logP	2.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	5.19	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	40.28 m³·mol⁻¹	ChemAxon
Polarizability	17.4 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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 biosynthesis	PW000900
Lipoic acid metabolism	PW000770
fatty acid oxidation (octanoate)	PW001022

KEGG Pathways:

Fatty acid biosynthesis ec00061
Lipoic acid metabolism ec00785

EcoCyc Pathways:

lipoate biosynthesis and incorporation II PWY0-1275

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0159-0910000000-e609d5de69ede6fbcde0	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0gb9-1920000000-1dc6ed976e003f99e23d	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03kc-9000000000-74cfce03769b41313952	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0uyi-0931100000-7668e36e436054042b5c	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0910000000-e609d5de69ede6fbcde0	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0gb9-1920000000-1dc6ed976e003f99e23d	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0910000000-9ecb4ccb46e89710f76a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0596-9100000000-8854c56056d8d3405087	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-062l-9100000000-67da39159980b9078fab	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 (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0006-0900000000-bb237630bedcee6145d1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-2900000000-98284f50a271878c8481	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-5900000000-209fbbacd4996b9a770d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03kc-9000000000-74cfce03769b41313952	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-e2c4dff10393086340f7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-1900000000-bbde8564b4e5543a636a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-Q-Exactive Plus , Negative	splash10-0006-0900000000-d219a0c6559a4783fd81	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0900000000-e2c4dff10393086340f7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-1900000000-bbde8564b4e5543a636a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0006-0900000000-ca22ecd0b25fa371fc73	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0gvp-9100000000-58c00a2024ba0bae4ff4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9300000000-2505e6738cf5d5877654	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-1ab4cdf8f74c93312743	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-2900000000-ac7c80e50c93b8cc3af7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9400000000-d2694b5f89d8eaeb2ab1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-f2b24072c91d8b0e4078	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1900000000-ad62d44e72f4dd1760ab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-7900000000-9c869b84815f21dffc7c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-b8a648d443695914e479	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6u-9100000000-f5c38fdad70b324e75ac	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-bee103956686b4840d1e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-e7cbd036c8e80018c825	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-8f2b048da6331570976c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-cd31ca01a5fa6be86acb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-682c215be5abe1fe87ed	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-03kc-9000000000-8c7db9a9d75b2cc1bd1c	View in MoNA
1D NMR	1H 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
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View 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)

Links

External Links:

Resource	Link
CHEBI ID	28837
HMDB ID	HMDB00482
Pubchem Compound ID	379
Kegg ID	C06423
ChemSpider ID	370
Wikipedia	Caprylic acid
BioCyc ID	CPD-195
EcoCyc ID	CPD-195
Ligand Expo	OCA

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

Caprylic acid (ECMDB00482) (M2MDB000140)

Structure for #<Compound:0xa82f0f3c>

Enzymes

Reactions

Reactions

Reactions

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Reactions

Transporters