ECMDB: Hexanoate (N-C6:0) (ECMDB21229) (M2MDB001637)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (5)Transporters (5)XML

Proteins (10)

Record Information

Version

2.0

Creation Date

2012-07-30 14:55:00 -0600

Update Date

2015-06-03 17:20:56 -0600

Secondary Accession Numbers

ECMDB21229

Identification

Name:

Hexanoate (N-C6:0)

Description

Hexanoate (n-c6:0) belongs to the class of Carboxylic Acid Salts. These are ionic derivatives of carboxylic acid. (inferred from compound structure)Hexanoic acid (caproic acid), is the carboxylic acid derived from hexane with the general formula C5H11COOH. It is a colorless oily liquid with an odor that is fatty, cheesy, waxy, and like that of goats or other barnyard animals. It is a fatty acid found naturally in various animal fats and oils, and is one of the chemicals that give the decomposing fleshy seed coat of the ginkgo its characteristic unpleasant odor. The primary use of hexanoic acid is in the manufacture of its esters for artificial flavors, and in the manufacture of hexyl derivatives such as hexylphenols. The salts and esters of this acid are known as hexanoates or caproates. Two other acids are named after goats: caprylic (C8) and capric (C10). Along with hexanoic acid, these total 15% in goat milk fat. Caproic, caprylic, and capric acids (capric is a crystal- or wax-like substance, whereas the other 2 are mobile liquids) are not only used for the formation of esters but also commonly used neat in: butter, milk, cream, strawberry, bread, beer, nut, and other flavors. (WikiPedia)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

Caproate
Caproic acid
Hexanoate
Hexanoate (N-C6:0)
Hexanoic acid
Hexanoic acid (N-C6:0)

Chemical Formula:

C₆H₁₁O₂

Weight:

Average: 115.1503
Monoisotopic: 115.075904596

InChI Key:

FUZZWVXGSFPDMH-UHFFFAOYSA-M

InChI:

InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)/p-1

CAS number:

Not Available

IUPAC Name:

hexanoic acid

Traditional IUPAC Name:

hexanoic acid

SMILES:

CCCCCC([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:30776 )
straight-chain saturated fatty acid (CHEBI:30776 )
Straight chain fatty acids (C01585 )
Saturated fatty acids (C01585 )
Straight chain fatty acids (LMFA01010006 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	9.72 g/L	ALOGPS
logP	1.88	ALOGPS
logP	1.81	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	5.09	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	4	ChemAxon
Refractivity	31.07 m³·mol⁻¹	ChemAxon
Polarizability	13.27 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 + Hexanoate (N-C6:0) > Adenosine monophosphate + Hydrogen ion + Hexanoyl-CoA + Pyrophosphate
Acetyl-CoA + Hexanoate (N-C6:0) > Acetic acid + Hexanoyl-CoA
Water + Hexanoyl-CoA > Coenzyme A + Hydrogen ion + Hexanoate (N-C6:0)

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00yi-3900000000-8d7942410dfae70c7c9d	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-9000000000-f4bf00b677d90d54ba69	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00yi-3900000000-8d7942410dfae70c7c9d	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-9ee618fa3c0bd9d56748	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9200000000-be939d8c0455d1af93a6	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 (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)	splash10-014i-0900000000-ba8c7078846c268d61a6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-03di-0900000000-151d5971be58b6799d2e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-02t9-1900000000-36096ef7dfebaa193910	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03di-9000000000-f4bf00b677d90d54ba69	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-f5b00c5e9d90d801ab16	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-014i-0900000000-5013166dd3b692762812	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-5900000000-52b3e7f8b01498621772	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-e3af905666760ff49069	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-f5b00c5e9d90d801ab16	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-5013166dd3b692762812	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-5900000000-52b3e7f8b01498621772	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-e3af905666760ff49069	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-01b9-6900000000-763e9a8e0f15e13fae3c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-9000000000-df670aaa002d77689cc7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9700000000-5489131065e0934751a7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fs-9100000000-68f7c2883fb339578ace	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-8e5e925d60baa2f176c2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-e877f22e42e8323f59e3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-9800000000-b5d583466919719819a1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-791ecce51d7cdde8f0f5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05tg-9000000000-b176d73a7b4fabde1ad4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9000000000-08e066ae069da04a8689	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-808b7302aa744c7a1c20	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-21c5ae8d52f2e0f4cd33	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-9000000000-3e67c250e6a67f63a0dd	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-03di-9000000000-fe3fab44832ddab1082e	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
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
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
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
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
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
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

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

Links

External Links:

Resource	Link
CHEBI ID	17120
HMDB ID	HMDB0000535
Pubchem Compound ID	4398339
Kegg ID	C01585
ChemSpider ID	3599616
Wikipedia	Hexanoate
BioCyc ID	HEXANOATE
EcoCyc ID	HEXANOATE

Enzymes

Protein Details

1. 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

2. Acetate CoA-transferase subunit alpha

General function:: Involved in CoA-transferase activity
Specific function:: Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA
Gene Name:: atoD
Uniprot ID:: P76458
Molecular weight:: 23526

Reactions

Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA.

Protein Details

3. Acetate CoA-transferase subunit beta

General function:: Involved in CoA-transferase activity
Specific function:: Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA
Gene Name:: atoA
Uniprot ID:: P76459
Molecular weight:: 22960

Reactions

Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA.

Protein Details

4. 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

5. 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

Transporters

Protein Details

1. Short-chain fatty acids transporter

General function:: Lipid transport and metabolism
Specific function:: Responsible for the intake of short-chain fatty acids
Gene Name:: atoE
Uniprot ID:: P76460
Molecular weight:: 47527

Protein Details

2. 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

3. 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

4. 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

5. 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

Hexanoate (N-C6:0) (ECMDB21229) (M2MDB001637)

Structure for #<Compound:0xa40ef96c>

Enzymes

Reactions

Reactions

Reactions

Reactions

Transporters