ECMDB: Lauroyl-CoA (ECMDB03571) (M2MDB000516)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (6)XML

Proteins (600)

Record Information

Version

2.0

Creation Date

2012-05-31 13:59:55 -0600

Update Date

2015-06-03 15:54:30 -0600

Secondary Accession Numbers

ECMDB03571

Identification

Name:

Lauroyl-CoA

Description

Lauroyl-CoA is a substrate for Long chain fatty acyl-CoA synthetase. This enzyme is a member of the ligase family that activates the breakdown of complex fatty acids. Long chain fatty acyl-CoA synthetase plays a crucial role in intermediary metabolism by catalyzing the formation of fatty acyl-CoA by a two-step process proceeding through an adenylated intermediate. It is an enzyme present in all organisms from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

Dodecanoyl-CoA
Dodecanoyl-CoA (N-C12:0CoA)
Dodecanoyl-Coenzyme A
Lauroyl coenzyme A

Chemical Formula:

C₃₃H₅₈N₇O₁₇P₃S

Weight:

Average: 949.837
Monoisotopic: 949.282273691

InChI Key:

YMCXGHLSVALICC-GMHMEAMDSA-N

InChI:

InChI=1S/C33H58N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-24(42)61-17-16-35-23(41)14-15-36-31(45)28(44)33(2,3)19-54-60(51,52)57-59(49,50)53-18-22-27(56-58(46,47)48)26(43)32(55-22)40-21-39-25-29(34)37-20-38-30(25)40/h20-22,26-28,32,43-44H,4-19H2,1-3H3,(H,35,41)(H,36,45)(H,49,50)(H,51,52)(H2,34,37,38)(H2,46,47,48)/t22-,26-,27-,28+,32-/m1/s1

CAS number:

6244-92-4

IUPAC Name:

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(dodecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

Traditional IUPAC Name:

lauroyl-coa

SMILES:

CCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12

Chemical Taxonomy

Description

belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Monocyclic benzene moiety
Morpholine
Oxazinane
Piperidine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Primary alcohol
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Amine
Organic oxide
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:16794 )
epoxide (CHEBI:16794 )
propanoate ester (CHEBI:16794 )
tropane alkaloid (CHEBI:16794 )

Physical Properties

State:

Solid

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	2.59 g/L	ALOGPS
logP	1.35	ALOGPS
logP	-1.2	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	30	ChemAxon
Refractivity	218.24 m³·mol⁻¹	ChemAxon
Polarizability	91.94 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	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 + Dodecanoate (N-C12:0) + Hydrogen ion > Adenosine monophosphate + Lauroyl-CoA + Hydrogen ion + Pyrophosphate
Acetyl-CoA + Lauroyl-CoA <> 3-Oxotetradecanoyl-CoA + Coenzyme A
Lauroyl-CoA + FAD <> (2E)-Dodecenoyl-CoA + FADH2
Lauroyl-CoA + Water > Coenzyme A + Dodecanoate (N-C12:0) + Hydrogen ion
3-Oxodecanoyl-CoA + Coenzyme A > Acetyl-CoA + Lauroyl-CoA
Lauroyl-CoA + electron-transfer flavoprotein > (2E)-Tetradecenoyl-CoA + Reduced electron-transfer flavoprotein
Lauroyl-CoA + Acetyl-CoA > 3-Oxotetradecanoyl-CoA + Coenzyme A
Dodecanoic acid + Coenzyme A + Adenosine triphosphate > Adenosine monophosphate + Lauroyl-CoA

SMPDB Pathways:

Fatty acid metabolism	PW000796
fatty acid oxidation (Decanoate)	PW001018
fatty acid oxidation (laurate)	PW001020

KEGG Pathways:

Fatty acid metabolism ec00071

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1911101102-687968f22ae76ca547b2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0931300000-f614ebfa62da3b2be8e6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1910102000-031217cf76abed1b705f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-3922021304-259fa0e4c2115b5176b6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2901100001-efdce198394adecd9a34	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-7e1a4d11b2e1da20a826	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000009-4ced9e4884f4bd265410	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0019-0901100447-ee848f28173670048ea9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0001900000-d82983ad037a63e5050a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000000009-c75a8c2363c43150b22a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0032-4200302409-7fff9c03c40bd4272f8a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057r-5203701928-d7bda2a7e4eb819728f6	View in MoNA
MS	Mass Spectrum (Electron Ionization)	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

References

References:

Hunt MC, Ruiter J, Mooyer P, van Roermond CW, Ofman R, Ijlst L, Wanders RJ: Identification of fatty acid oxidation disorder patients with lowered acyl-CoA thioesterase activity in human skin fibroblasts. Eur J Clin Invest. 2005 Jan;35(1):38-46. Pubmed: 15638818
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

Synthesis Reference:

Eaton, Simon; Turnbull, Douglass M.; Bartlett, Kim. Redox control of b-oxidation in rat liver mitochondria. European Journal of Biochemistry (1994), 220(3), 671-81.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	15521
HMDB ID	HMDB03571
Pubchem Compound ID	165436
Kegg ID	C01832
ChemSpider ID	145018
Wikipedia ID	Not Available
BioCyc ID	LAUROYLCOA-CPD
EcoCyc ID	LAUROYLCOA-CPD
Ligand Expo	DCC

Enzymes

Protein Details

1. 3-ketoacyl-CoA thiolase

General function:: Involved in acetyl-CoA C-acyltransferase activity
Specific function:: Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:: fadA
Uniprot ID:: P21151
Molecular weight:: 40876

Reactions

Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.

Protein Details

2. 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

3. 3-ketoacyl-CoA thiolase_

General function:: Involved in transferase activity
Specific function:: Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long- chain fatty acids
Gene Name:: fadI
Uniprot ID:: P76503
Molecular weight:: 46530

Reactions

Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.

Protein Details

4. Acyl-coenzyme A dehydrogenase

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Catalyzes the dehydrogenation of acyl-CoA
Gene Name:: fadE
Uniprot ID:: Q47146
Molecular weight:: 89224

Reactions

An acyl-CoA + FAD = a dehydrogenated acyl-CoA + FADH(2).

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

Lauroyl-CoA (ECMDB03571) (M2MDB000516)

Structure for #<Compound:0x80e04504>

Enzymes

Reactions

Reactions

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