Bovine Metabolome Database: Showing metabocard for Lauroyl-CoA (BMDB0003571)

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Bovine Metabolome Database.

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:05:22 UTC

Update Date

2020-05-21 16:29:09 UTC

BMDB ID

BMDB0003571

Secondary Accession Numbers

BMDB03571

Metabolite Identification

Common Name

Lauroyl-CoA

Description

Lauroyl-CoA, also known as dodecanoyl-CoA or C12:0-CoA, belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain. 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. Lauroyl-CoA and L-carnitine can be biosynthesized from dodecanoic acid and coenzyme A; which is mediated by the enzyme carnitine O-palmitoyltransferase 2, mitochondrial. In cattle, lauroyl-CoA is involved in the metabolic pathway called the Beta oxidation OF very long chain fatty acids pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
C12:0-CoA	ChEBI
coenzyme A, S-Dodecanoate	ChEBI
Dodecanoyl-CoA	ChEBI
Dodecanoyl-coenzyme A	ChEBI
Lauroyl coenzyme A	ChEBI
Lauroyl-coenzyme A	ChEBI
coenzyme A, S-Dodecanoic acid	Generator

Chemical Formula

C₃₃H₅₈N₇O₁₇P₃S

Average Molecular Weight

949.837

Monoisotopic Molecular Weight

949.282273691

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 Name

lauroyl-coa

CAS Registry Number

6244-92-4

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

InChI Identifier

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

InChI Key

YMCXGHLSVALICC-GMHMEAMDSA-N

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 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane
Peroxisome

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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 (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane
Peroxisome

Biospecimen Locations

Fibroblasts

Pathways

Name	SMPDB/Pathwhiz	KEGG
Fatty Acid Metabolism		Not Available
Fatty Acid Elongation in Mitochondria		Not Available
Beta Oxidation of Very Long Chain Fatty Acids		Not Available
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids		Not Available
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0003571

DrugBank ID

DB03264

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023198

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

6959

PubChem Compound

165436

PDB ID

Not Available

ChEBI ID

15521

References

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

General References

Not Available

Enzymes

Enzyme Details

1. Peroxisomal carnitine O-octanoyltransferase

General function:: Involved in carnitine O-octanoyltransferase activity
Specific function:: Beta-oxidation of fatty acids. The highest activity concerns the C6 to C10 chain length substrate.
Gene Name:: CROT
Uniprot ID:: O19094
Molecular weight:: 70263.0

Reactions

Lauroyl-CoA → Coenzyme A + Dodecanoic acid	details

Enzyme Details

2. Carnitine O-palmitoyltransferase 2, mitochondrial

General function:: Involved in carnitine O-palmitoyltransferase activity
Specific function:: Not Available
Gene Name:: CPT2
Uniprot ID:: Q2KJB7
Molecular weight:: 74483.0

Reactions

Dodecanoic acid + Coenzyme A → Lauroyl-CoA + L-Carnitine	details

Enzyme Details

3. Acyl-coenzyme A synthetase ACSM1, mitochondrial

General function:: Lipid transport and metabolism
Specific function:: Catalyzes the activation of fatty acids by CoA to produce an acyl-CoA, the first step in fatty acid metabolism (PubMed:11382754, PubMed:10561077). Capable of activating medium-chain fatty acids (e.g. butyric (C4) to decanoic (C10) acids), and certain carboxylate-containing xenobiotics, e.g. benzoate (PubMed:10561077, PubMed:11382754). Also catalyzes the activation of lipoate to lipoyl-nucleoside monophosphate (PubMed:11382754). Activates lipoate with GTP at a 1000-fold higher rate than with ATP and activates both (R)- and (S)-lipoate to the respective lipoyl-GMP, with a preference for (R)-lipoate (PubMed:11382754).
Gene Name:: ACSM1
Uniprot ID:: Q9BEA2
Molecular weight:: 64923.0

Reactions

Dodecanoic acid + Adenosine triphosphate + Coenzyme A → Lauroyl-CoA + Adenosine monophosphate + Pyrophosphate	details

Enzyme Details

4. Diacylglycerol O-acyltransferase 1

General function:: Not Available
Specific function:: Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders. In liver, plays a role in esterifying exogenous fatty acids to glycerol.
Gene Name:: DGAT1
Uniprot ID:: Q8MK44
Molecular weight:: 55602.0

Reactions

DG(19:0/21:0/0:0) + Lauroyl-CoA → TG(19:0/21:0/12:0) + Coenzyme A	details
DG(20:0/14:0/0:0) + Lauroyl-CoA → TG(20:0/14:0/12:0) + Coenzyme A	details
DG(19:0/22:0/0:0) + Lauroyl-CoA → TG(19:0/22:0/12:0) + Coenzyme A	details
DG(20:0/15:0/0:0) + Lauroyl-CoA → TG(20:0/15:0/12:0) + Coenzyme A	details
DG(20:0/12:0/0:0) + Lauroyl-CoA → TG(20:0/12:0/12:0) + Coenzyme A	details
DG(20:0/20:0/0:0) + Lauroyl-CoA → TG(20:0/20:0/12:0) + Coenzyme A	details
DG(21:0/8:0/0:0) + Lauroyl-CoA → TG(21:0/8:0/12:0) + Coenzyme A	details
DG(21:0/12:0/0:0) + Lauroyl-CoA → TG(21:0/12:0/12:0) + Coenzyme A	details
DG(21:0/10:0/0:0) + Lauroyl-CoA → TG(21:0/10:0/12:0) + Coenzyme A	details
DG(21:0/17:0/0:0) + Lauroyl-CoA → TG(21:0/17:0/12:0) + Coenzyme A	details
DG(22:0/17:0/0:0) + Lauroyl-CoA → TG(22:0/17:0/12:0) + Coenzyme A	details
DG(22:0/12:0/0:0) + Lauroyl-CoA → TG(22:0/12:0/12:0) + Coenzyme A	details
DG(22:0/16:0/0:0) + Lauroyl-CoA → TG(22:0/16:0/12:0) + Coenzyme A	details
DG(22:0/10:0/0:0) + Lauroyl-CoA → TG(22:0/10:0/12:0) + Coenzyme A	details
DG(22:0/22:0/0:0) + Lauroyl-CoA → TG(22:0/22:0/12:0) + Coenzyme A	details
DG(8:0/19:0/0:0) + Lauroyl-CoA → TG(8:0/19:0/12:0) + Coenzyme A	details
DG(8:0/13:0/0:0) + Lauroyl-CoA → TG(8:0/13:0/12:0) + Coenzyme A	details
DG(10:0/17:0/0:0) + Lauroyl-CoA → TG(10:0/17:0/12:0) + Coenzyme A	details
DG(10:0/12:0/0:0) + Lauroyl-CoA → TG(10:0/12:0/12:0) + Coenzyme A	details
DG(8:0/14:0/0:0) + Lauroyl-CoA → TG(8:0/14:0/12:0) + Coenzyme A	details
DG(10:0/16:0/0:0) + Lauroyl-CoA → TG(10:0/16:0/12:0) + Coenzyme A	details
DG(8:0/15:0/0:0) + Lauroyl-CoA → TG(8:0/15:0/12:0) + Coenzyme A	details
DG(10:0/18:0/0:0) + Lauroyl-CoA → TG(10:0/18:0/12:0) + Coenzyme A	details
DG(8:0/12:0/0:0) + Lauroyl-CoA → TG(8:0/12:0/12:0) + Coenzyme A	details
DG(10:0/19:0/0:0) + Lauroyl-CoA → TG(10:0/19:0/12:0) + Coenzyme A	details
DG(8:0/17:0/0:0) + Lauroyl-CoA → TG(8:0/17:0/12:0) + Coenzyme A	details
DG(19:0/a-21:0/0:0) + Lauroyl-CoA → TG(19:0/a-21:0/12:0) + Coenzyme A	details
DG(19:0/a-25:0/0:0) + Lauroyl-CoA → TG(19:0/a-25:0/12:0) + Coenzyme A	details
DG(19:0/i-21:0/0:0) + Lauroyl-CoA → TG(19:0/i-21:0/12:0) + Coenzyme A	details
DG(19:0/i-22:0/0:0) + Lauroyl-CoA → TG(19:0/i-22:0/12:0) + Coenzyme A	details
DG(19:0/i-24:0/0:0) + Lauroyl-CoA → TG(19:0/i-24:0/12:0) + Coenzyme A	details
DG(20:0/a-21:0/0:0) + Lauroyl-CoA → TG(20:0/a-21:0/12:0)[rac] + Coenzyme A	details
DG(a-21:0/12:0/0:0) + Lauroyl-CoA → TG(a-21:0/12:0/12:0)[rac] + Coenzyme A	details
DG(a-21:0/a-21:0/0:0) + Lauroyl-CoA → TG(a-21:0/a-21:0/12:0)[rac] + Coenzyme A	details
DG(a-25:0/12:0/0:0) + Lauroyl-CoA → TG(a-25:0/12:0/12:0)[rac] + Coenzyme A	details
DG(a-25:0/a-25:0/0:0) + Lauroyl-CoA → TG(a-25:0/a-25:0/12:0)[rac] + Coenzyme A	details
DG(i-19:0/i-21:0/0:0) + Lauroyl-CoA → TG(i-19:0/i-21:0/12:0) + Coenzyme A	details
DG(i-19:0/i-22:0/0:0) + Lauroyl-CoA → TG(i-19:0/i-22:0/12:0) + Coenzyme A	details
DG(i-19:0/i-24:0/0:0) + Lauroyl-CoA → TG(i-19:0/i-24:0/12:0) + Coenzyme A	details
DG(i-20:0/12:0/0:0) + Lauroyl-CoA → TG(i-20:0/12:0/12:0) + Coenzyme A	details
DG(i-20:0/i-20:0/0:0) + Lauroyl-CoA → TG(i-20:0/i-20:0/12:0) + Coenzyme A	details
DG(i-21:0/12:0/0:0) + Lauroyl-CoA → TG(i-21:0/12:0/12:0) + Coenzyme A	details
DG(i-21:0/i-21:0/0:0) + Lauroyl-CoA → TG(i-21:0/i-21:0/12:0) + Coenzyme A	details
DG(i-22:0/12:0/0:0) + Lauroyl-CoA → TG(i-22:0/12:0/12:0) + Coenzyme A	details
DG(i-22:0/i-22:0/0:0) + Lauroyl-CoA → TG(i-22:0/i-22:0/12:0) + Coenzyme A	details
DG(i-24:0/12:0/0:0) + Lauroyl-CoA → TG(i-24:0/12:0/12:0) + Coenzyme A	details
DG(i-24:0/i-24:0/0:0) + Lauroyl-CoA → TG(i-24:0/i-24:0/12:0) + Coenzyme A	details

Showing metabocard for Lauroyl-CoA (BMDB0003571)

Structure for BMDB0003571 (Lauroyl-CoA)

Enzymes

Reactions

Reactions

Reactions

Reactions