lauroyl-CoA (YMDB00530)

Identification

YMDB ID

YMDB00530

Name

lauroyl-CoA

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Lauroyl-CoA, also known as dodecanoyl-CoA or C12:0-CoA, 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. Thus, lauroyl-CoA is considered to be a fatty ester lipid molecule. Lauroyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Lauroyl-CoA exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

C12:0-CoA
coenzyme A, S-dodecanoate
Dodecanoyl-CoA
Dodecanoyl-Coenzyme A
lauroyl coenzyme a
Lauroyl-CoA
Lauroyl-coenzyme A
coenzyme A, S-Dodecanoic acid

CAS number

6244-92-4

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

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

Chemical Formula

C₃₃H₅₈N₇O₁₇P₃S

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

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

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

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

lipid particle
endoplasmic reticulum
peroxisome
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Fatty acid elongation in mitochondria	PW002467
Fatty acid metabolism	PW002460

KEGG Pathways

Fatty acid elongation in mitochondria	ec00062
Fatty acid metabolism	ec00071

SMPDB Reactions

lauroyl-CoA + Acetyl-CoA → 3-oxotetradecanoyl-CoA + Coenzyme A

lauroyl-CoA + electron-transfer flavoprotein → (2E)-Tetradecenoyl-CoA + Reduced electron-transfer flavoprotein

(2E)-Dodecenoyl-CoA + NADPH → lauroyl-CoA + NADP

KEGG Reactions

3-oxotetradecanoyl-CoA + Coenzyme A → Acetyl-CoA + lauroyl-CoA

lauroyl-CoA + oxygen → (2E)-Dodecenoyl-CoA + Hydrogen peroxide

lauric acid + Adenosine triphosphate + Coenzyme A ↔ Adenosine monophosphate + Pyrophosphate + lauroyl-CoA

decanoyl-CoA + malonyl-CoA + hydron + NADPH → Carbon dioxide + NADP + water + lauroyl-CoA + Coenzyme A

malonyl-CoA + lauroyl-CoA + hydron + NADPH → Carbon dioxide + NADP + water + Tetradecanoyl-CoA + Coenzyme A

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1911101102-687968f22ae76ca547b2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0931300000-f614ebfa62da3b2be8e6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1910102000-031217cf76abed1b705f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-3922021304-259fa0e4c2115b5176b6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2901100001-efdce198394adecd9a34	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-7e1a4d11b2e1da20a826	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000009-4ced9e4884f4bd265410	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0019-0901100447-ee848f28173670048ea9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0001900000-d82983ad037a63e5050a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000000009-c75a8c2363c43150b22a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0032-4200302409-7fff9c03c40bd4272f8a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057r-5203701928-d7bda2a7e4eb819728f6	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Jones, J. M., Nau, K., Geraghty, M. T., Erdmann, R., Gould, S. J. (1999). "Identification of peroxisomal acyl-CoA thioesterases in yeast and humans." J Biol Chem 274:9216-9223.10092594

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.

External Links:

Resource	Link
CHEBI ID	15521
HMDB ID	HMDB03571
Pubchem Compound ID	165436
Kegg ID	C01832
ChemSpider ID	24785169
FOODB ID	FDB023198
Wikipedia ID	Not Available
BioCyc ID	LAUROYLCOA-CPD

Enzymes

Protein Details

1. Acyl-coenzyme A oxidase

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Acyl-CoA + O(2) = trans-2,3-dehydroacyl-CoA + H(2)O(2)
Gene Name:: POX1
Uniprot ID:: P13711
Molecular weight:: 84041.39844

Reactions

Acyl-CoA + O(2) → trans-2,3-dehydroacyl-CoA + H(2)O(2).

Protein Details

2. Long-chain-fatty-acid--CoA ligase 2

General function:: Involved in catalytic activity
Specific function:: Esterification, concomitant with transport, of endogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. Preferentially acts on C9:0-C13:0 fatty acids although C7:0-C17:0 fatty acids are tolerated
Gene Name:: FAA2
Uniprot ID:: P39518
Molecular weight:: 83437.10156

Reactions

ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.

Protein Details

3. 3-ketoacyl-CoA thiolase, peroxisomal

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA
Gene Name:: POT1
Uniprot ID:: P27796
Molecular weight:: 44729.89844

Reactions

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

Protein Details

4. Fatty acid synthase subunit beta

General function:: Involved in transferase activity
Specific function:: Fatty acid synthetase catalyzes the formation of long- chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. The beta subunit contains domains for:[acyl-carrier-protein] acetyltransferase and malonyltransferase, S-acyl fatty acid synthase thioesterase, enoyl-[acyl-carrier-protein] reductase, and 3-hydroxypalmitoyl-[acyl-carrier-protein] dehydratase
Gene Name:: FAS1
Uniprot ID:: P07149
Molecular weight:: 228689.0

Reactions

Acetyl-CoA + n malonyl-CoA + 2n NADH + 2n NADPH → long-chain-acyl-CoA + n CoA + n CO(2) + 2n NAD(+) + 2n NADP(+).
Acetyl-CoA + [acyl-carrier-protein] → CoA + acetyl-[acyl-carrier-protein].
Malonyl-CoA + [acyl-carrier-protein] → CoA + malonyl-[acyl-carrier-protein].
(3R)-3-hydroxypalmitoyl-[acyl-carrier-protein] → hexadec-2-enoyl-[acyl-carrier-protein] + H(2)O.
Acyl-[acyl-carrier-protein] + NAD(+) → trans-2,3-dehydroacyl-[acyl-carrier-protein] + NADH.
Oleoyl-[acyl-carrier-protein] + H(2)O → [acyl-carrier-protein] + oleate.

Protein Details

5. Peroxisomal acyl-coenzyme A thioester hydrolase 1

General function:: Involved in acyl-CoA thioesterase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH
Gene Name:: TES1
Uniprot ID:: P41903
Molecular weight:: 40259.39844

Reactions

Palmitoyl-CoA + H(2)O → CoA + palmitate.

Structure for #<Compound:0xb06b23c0>

Enzymes

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