lauroyl-CoA (CHEBI:15521)

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CHEBI:15521 - lauroyl-CoA

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ChEBI Name	lauroyl-CoA

ChEBI ID	CHEBI:15521

Definition	A medium-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of lauric (dodecanoic) acid.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:14188, CHEBI:41874, CHEBI:6392, CHEBI:14501, CHEBI:25014

Supplier Information	ChemicalBook:CB5165597, eMolecules:481365, ZINC000100009542

Download	Molfile XML SDF

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The Resolver thinks Mol

DCC - Ideal conformer

Mrv1927 06092109503D

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Time for openFile(DCC - Ideal conformer

Mrv1927 06092109503D

119121 0 0 0 0 999 V2000

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2.8840 4.5380 -0.6240 N 0 0 0 0 0 0 0 0 0 0 0 0

4.2100 4.7780 -0.0490 C 0 0 2 0 0 0 0 0 0 0 0 0

5.1230 3.5900 -0.3600 C 0 0 2 0 0 0 0 0 0 0 0 0

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9.7010 1.9700 0.3450 C 0 0 2 0 0 0 0 0 0 0 0 0

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4.1220 4.8940 1.0320 H 0 0 0 0 0 0 0 0 0 0 0 0

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9.2120 4.0650 0.2270 H 0 0 0 0 0 0 0 0 0 0 0 0

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13.6780 0.6110 2.0330 H 0 0 0 0 0 0 0 0 0 0 0 0

14.1910 1.4020 0.5230 H 0 0 0 0 0 0 0 0 0 0 0 0

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17 19 1 0 0 0 0

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53 55 1 0 0 0 0

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55 56 1 0 0 0 0

55106 1 0 0 0 0

55107 1 0 0 0 0

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60116 1 0 0 0 0

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61118 1 0 0 0 0

61119 1 0 0 0 0

M END): 22 ms

reading 119 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

119 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Formula

C33H58N7O17P3S

Net Charge

Average Mass

949.840

Monoisotopic Mass

949.28228

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

InChIKey

YMCXGHLSVALICC-GMHMEAMDSA-N

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=C1N=CN=C2N

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Brassica napus (NCBI:txid3708)	From MetaboLights See: MetaboLights Study
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Chemical Role(s):	acyl donor Any donor that can transfer acyl groups between molecular entities. (via acyl-CoA )

Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	lauroyl-CoA (CHEBI:15521) has functional parent dodecanoic acid (CHEBI:30805) lauroyl-CoA (CHEBI:15521) has role Escherichia coli metabolite (CHEBI:76971) lauroyl-CoA (CHEBI:15521) has role mouse metabolite (CHEBI:75771) lauroyl-CoA (CHEBI:15521) is a medium-chain fatty acyl-CoA (CHEBI:61907) lauroyl-CoA (CHEBI:15521) is a saturated fatty acyl-CoA (CHEBI:231546) lauroyl-CoA (CHEBI:15521) is conjugate acid of lauroyl-CoA(4−) (CHEBI:57375)

Incoming	(S)-3-hydroxylauroyl-CoA (CHEBI:27668) has functional parent lauroyl-CoA (CHEBI:15521) 3-oxolauroyl-CoA (CHEBI:27868) has functional parent lauroyl-CoA (CHEBI:15521) lauroyl-CoA(4−) (CHEBI:57375) is conjugate base of lauroyl-CoA (CHEBI:15521)

IUPAC Name

3'-phosphoadenosine 5'-(3-{(3R)-4-[(3-{[2-(dodecanoylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-3-hydroxy-2,2-dimethyl-4-oxobutyl} dihydrogen diphosphate)

Synonyms	Sources
C12:0-CoA	ChEBI
coenzyme A, S-dodecanoate	ChemIDplus
Dodecanoyl-CoA	KEGG COMPOUND
dodecanoyl-coenzyme A	ChEBI
Lauroyl coenzyme A	KEGG COMPOUND
Lauroyl-CoA	KEGG COMPOUND
Lauroyl-coenzyme A	ChemIDplus

Manual Xrefs	Databases
145018	ChemSpider
C01832	KEGG COMPOUND
c0567	UM-BBD
DB03264	DrugBank
DCC	PDBeChem
FDB023198	FooDB
HMDB0003571	HMDB
LMFA07050340	LIPID MAPS
View more database links

Registry Numbers	Types	Sources
6244-92-4	CAS Registry Number	KEGG COMPOUND
6244-92-4	CAS Registry Number	ChemIDplus
8033507	Reaxys Registry Number	Reaxys

Citations

Yang C, Zhao K, Chen X, Jiang L, Li P, Huang P (2021)
Pellino1 deficiency reprograms cardiomyocytes energy metabolism in lipopolysaccharide-induced myocardial dysfunction.
Amino acids 53, 713-737 [PubMed:33885999]
[show Abstract]

Almeida MGMD, Arêdes DS, Majerowicz D, Færgeman NJ, Knudsen J, Gondim KC (2020)
Expression of acyl-CoA-binding protein 5 from Rhodnius prolixus and its inhibition by RNA interference.
PloS one 15, e0227685 [PubMed:31935250]
[show Abstract]

Wang K, Sybers D, Maklad HR, Lemmens L, Lewyllie C, Zhou X, Schult F, Bräsen C, Siebers B, Valegård K, Lindås AC, Peeters E (2019)
A TetR-family transcription factor regulates fatty acid metabolism in the archaeal model organism Sulfolobus acidocaldarius.
Nature communications 10, 1542 [PubMed:30948713]
[show Abstract]

Goblirsch BR, Jensen MR, Mohamed FA, Wackett LP, Wilmot CM (2016)
Substrate Trapping in Crystals of the Thiolase OleA Identifies Three Channels That Enable Long Chain Olefin Biosynthesis.
The Journal of biological chemistry 291, 26698-26706 [PubMed:27815501]
[show Abstract]

Fujihashi M, Nakatani T, Hirooka K, Matsuoka H, Fujita Y, Miki K (2014)
Structural characterization of a ligand-bound form of Bacillus subtilis FadR involved in the regulation of fatty acid degradation.
Proteins 82, 1301-1310 [PubMed:24356978]
[show Abstract]

Bond-Watts BB, Weeks AM, Chang MC (2012)
Biochemical and structural characterization of the trans-enoyl-CoA reductase from Treponema denticola.
Biochemistry 51, 6827-6837 [PubMed:22906002]
[show Abstract]

Agari Y, Agari K, Sakamoto K, Kuramitsu S, Shinkai A (2011)
TetR-family transcriptional repressor Thermus thermophilus FadR controls fatty acid degradation.
Microbiology (Reading, England) 157, 1589-1601 [PubMed:21349973]
[show Abstract]

Oba Y, Sato M, Ojika M, Inouye S (2005)
Enzymatic and genetic characterization of firefly luciferase and Drosophila CG6178 as a fatty acyl-CoA synthetase.
Bioscience, biotechnology, and biochemistry 69, 819-828 [PubMed:15849423]
[show Abstract]

Musayev F, Sachdeva S, Scarsdale JN, Reynolds KA, Wright HT (2005)
Crystal structure of a substrate complex of Mycobacterium tuberculosis beta-ketoacyl-acyl carrier protein synthase III (FabH) with lauroyl-coenzyme A.
Journal of molecular biology 346, 1313-1321 [PubMed:15713483]
[show Abstract]

Badger J, Sauder JM, Adams JM, Antonysamy S, Bain K, Bergseid MG, Buchanan SG, Buchanan MD, Batiyenko Y, Christopher JA, Emtage S, Eroshkina A, Feil I, Furlong EB, Gajiwala KS, Gao X, He D, Hendle J, Huber A, Hoda K, Kearins P, Kissinger C, Laubert B, Lewis HA, Lin J, Loomis K, Lorimer D, Louie G, Maletic M, Marsh CD, Miller I, Molinari J, Muller-Dieckmann HJ, Newman JM, Noland BW, Pagarigan B, Park F, Peat TS, Post KW, Radojicic S, Ramos A, Romero R, Rutter ME, Sanderson WE, Schwinn KD, Tresser J, Winhoven J, Wright TA, Wu L, Xu J, Harris TJ (2005)
Structural analysis of a set of proteins resulting from a bacterial genomics project.
Proteins 60, 787-796 [PubMed:16021622]
[show Abstract]

Nakagawa T, Imanaka T, Morita M, Ishiguro K, Yurimoto H, Yamashita A, Kato N, Sakai Y (2000)
Peroxisomal membrane protein Pmp47 is essential in the metabolism of middle-chain fatty acid in yeast peroxisomes and Is associated with peroxisome proliferation.
The Journal of biological chemistry 275, 3455-3461 [PubMed:10652339]
[show Abstract]
Pmp47 of the methylotrophic yeast Candida boidinii belongs to a mitochondrial family of solute transporters and is localized in peroxisomal membranes. Its human homolog, Pmp34, is also known. In this study, we characterized the role of Pmp47 in fatty acid metabolism and peroxisome proliferation using the PMP47-deleted strain of C. boidinii (strain pmp47Delta). The wild-type strain grew well on a middle-chain fatty acid, laureate, as the single carbon source, and mild peroxisome proliferation was observed during its growth. The pmp47Delta strain could not grow on laureate but could grow on long-chain fatty acids including palmitate, myristate, and oleate. The levels of laureate oxidation activity in intact cells and in semi-permeabilized cells of strain pmp47Delta were lower than the respective level in the wild-type strain, although the level of laureate oxidation activity in the cell lysate and the level of lauroyl-CoA oxidation in semi-permeabilized cells of strain pmp47Delta were indistinguishable from the respective level in the wild-type strain. When lauroyl-CoA was provided in the cytosol of strain pmp47Delta through expression of Saccharomyces cerevisiae Faa2p (lauroyl-CoA synthetase) in which its peroxisome targeting signal was deleted, the growth of strain pmp47Delta on laureate was recovered to the level of growth of the wild-type strain. Laureate is converted to its CoA form in peroxisomes by the action of lauroyl-CoA synthetase. These results suggested that Pmp47 is involved in the transport of a small molecule (possibly ATP) required in the conversion of laureate to its CoA form in peroxisomes and that the absence of Pmp47 causes impairment of laureate metabolism, which results in the inability of pmp47Delta cells to grow on laureate. In addition, Pmp47 may be involved in peroxisome proliferation, because the pmp47Delta strain contained a reduced number of peroxisomes, as judged from the fluorescence analysis of cells expressing green fluorescent protein tagged with the peroxisome targeting signal 1 (GFP-AKL).

Tamvakopoulos CS, Willi S, Anderson VE, Hale DE (1995)
Long-chain acyl-CoA profiles in cultured fibroblasts from patients with defects in fatty acid oxidation.
Biochemical and molecular medicine 55, 15-21 [PubMed:7551821]
[show Abstract]

Cao YZ, Huang AH (1987)
Acyl coenzyme a preference of diacylglycerol acyltransferase from the maturing seeds of cuphea, maize, rapeseed, and canola.
Plant physiology 84, 762-765 [PubMed:16665518]
[show Abstract]

Poosch MS, Yamazaki RK (1986)
Determination of peroxisomal fatty acyl-CoA oxidase activity using a lauroyl-CoA-based fluorometric assay.
Biochimica et biophysica acta 884, 585-593 [PubMed:3778940]
[show Abstract]

Lazarow PB (1978)
Rat liver peroxisomes catalyze the beta oxidation of fatty acids.
The Journal of biological chemistry 253, 1522-1528 [PubMed:627552]
[show Abstract]

Kienle MG, Cighetti G, Santaniello E, Fiecchi A (1976)
beta-Oxidative cleavage of octanoyl- and dodecanoyl-CoA in rat liver cytoplasm.
Lipids 11, 235-240 [PubMed:1263766]
[show Abstract]

Last Modified

07 June 2024

CHEBI:15521 - lauroyl-CoA

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