lignoceric acid (YMDB00684)

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Identification

YMDB ID

YMDB00684

Name

lignoceric acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Tetracosanoic acid, also known as N-tetracosanoate or lignoceric acid, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Based on a literature review a significant number of articles have been published on Tetracosanoic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Lignocerat
Lignocerate
Lignoceric acid
Lignozerinsaeure
n-Tetracosanoate
n-Tetracosanoic acid
tetracosanate
tetracosanic acid
Tetracosanoat
Tetracosanoate
tetracosanoic acid
Tetracosansaeure
tetracosoate
tetracosoic acid
tetraeicosanoate
tetraeicosanoic acid
tetraicosanoic acid
CH3-[CH2]22-COOH
Tetraicosanoate
Lignoceric acid, silver (1+) salt
Lignoceric acid, sodium salt
Lignoceric acid, potassium salt
Tetracosanoic acid, potassium salt (1:1)
Potassium tetracosanoate
FA(24:0)

CAS number

557-59-5

Weight

Average: 368.6367
Monoisotopic: 368.36543078

InChI Key

QZZGJDVWLFXDLK-UHFFFAOYSA-N

InChI

InChI=1S/C24H48O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h2-23H2,1H3,(H,25,26)

IUPAC Name

tetracosanoic acid

Traditional IUPAC Name

lignoceric acid

Chemical Formula

C₂₄H₄₈O₂

SMILES

CCCCCCCCCCCCCCCCCCCCCCCC(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-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

very long-chain fatty acid (CHEBI:28866 )
straight-chain saturated fatty acid (CHEBI:28866 )
Straight chain fatty acids (C08320 )
Saturated fatty acids (C08320 )
Straight chain fatty acids (LMFA01010024 )

Physical Properties

State

Solid

Charge

Melting point

84.2 °C

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	2.3e-05 g/L	ALOGPS
logP	9.56	ALOGPS
logP	9.81	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	4.95	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	22	ChemAxon
Refractivity	113.89 m³·mol⁻¹	ChemAxon
Polarizability	51.57 Å³	ChemAxon
Number of Rings	0	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

Cell Envelope
Cytoplasm
Endoplasmic Reticulum
Extracellular
Lipid Particle
Mitochondrion
Peroxisome

Organoleptic Properties

Not Available

SMPDB Pathways

Biosynthesis of unsaturated fatty acids

PW002403

KEGG Pathways

Biosynthesis of unsaturated fatty acids

ec01040

SMPDB Reactions

Not Available

KEGG Reactions

stearic acid + NADPH + hydron + malonyl-CoA → Coenzyme A + lignoceric acid + NADP + Carbon dioxide + water

lignoceric acid + malonyl-CoA + hydron + NADPH → cerotic acid + Carbon dioxide + NADP + water + Coenzyme A

Adenosine triphosphate + lignoceric acid + Coenzyme A ↔ Adenosine monophosphate + Pyrophosphate + Tetracosanoyl-CoA

water + Tetracosanoyl-CoA → lignoceric acid + hydron + Coenzyme A

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0159-1900000000-3507c183bf018486d18f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0159-2900000000-9dedfb3583ae4e553948	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-07bf-9000000000-2ae141518702212751a7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-1900000000-3507c183bf018486d18f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0159-2900000000-9dedfb3583ae4e553948	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-1900000000-2826f8c66ba3647dda0f	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7690000000-51ad38c3eba8f98c3565	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00g0-9550000000-6d38b4af18d7872e12a9	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-016r-0509000000-b590f3868a4aa3c86803	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-0903000000-a6d1b482b61c2d36ee1d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-0900000000-4ef3dd8c92115a6d4e0c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-07bf-9000000000-2ae141518702212751a7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0a4i-0900000000-3c3e69329be8a7148076	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004r-0791000000-10ab351997f48e512657	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004r-0791000000-10ab351997f48e512657	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004r-0791000000-10ab351997f48e512657	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0009000000-5c9df57aa4e8e48bd80f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0009000000-a22a23dbfe780a163a38	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0009000000-7907c6ab3ef19e9cdf86	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0009000000-847587fdc96a653e9651	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0009000000-5c9df57aa4e8e48bd80f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0009000000-a22a23dbfe780a163a38	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0009000000-847587fdc96a653e9651	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0900000000-3c3e69329be8a7148076	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0009000000-847587fdc96a653e9651	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-014i-0009000000-7bccb707d42bca681a58	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-a22a23dbfe780a163a38	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-48bd2e6f8cbaa8fda6bd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kmi-2339000000-6881995e14be93cee803	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-6982000000-bcce0a5d41ac456500c7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-249bc2a1e0da9132abb1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ba-0009000000-bb2e8d3e4fc1a5f88c77	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9113000000-18bb969031b0d8959a2f	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0avl-9200000000-6a6f857b59886189b246	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D 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
Matias, A. C., Pedroso, N., Teodoro, N., Marinho, H. S., Antunes, F., Nogueira, J. M., Herrero, E., Cyrne, L. (2007). "Down-regulation of fatty acid synthase increases the resistance of Saccharomyces cerevisiae cells to H2O2." Free Radic Biol Med 43:1458-1465.17936191
Hatch, G. M., Smith, A. J., Xu, F. Y., Hall, A. M., Bernlohr, D. A. (2002). "FATP1 channels exogenous FA into 1,2,3-triacyl-sn-glycerol and down-regulates sphingomyelin and cholesterol metabolism in growing 293 cells." J Lipid Res 43:1380-1389.12235169
Kohlwein, S. D., Eder, S., Oh, C. S., Martin, C. E., Gable, K., Bacikova, D., Dunn, T. (2001). "Tsc13p is required for fatty acid elongation and localizes to a novel structure at the nuclear-vacuolar interface in Saccharomyces cerevisiae." Mol Cell Biol 21:109-125.11113186
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:

Not Available

External Links:

Resource	Link
CHEBI ID	28866
HMDB ID	HMDB02003
Pubchem Compound ID	11197
Kegg ID	C08320
ChemSpider ID	10724
FOODB ID	FDB004651
Wikipedia	Lignoceric_acid
BioCyc ID	TETRACOSANOATE

Enzymes

Protein Details

1. Elongation of fatty acids protein 2

General function:: Involved in fatty acid elongase activity
Specific function:: Involved in synthesis of 1,3-beta-glucan. Could be a subunit of 1,3-beta-glucan synthase. Could be also a component of the membrane bound fatty acid elongation systems that produce the 26-carbon very long chain fatty acids that are precursors for ceramide and sphingolipids. Appears to be involved in the elongation of fatty acids up to 24 carbons. Appears to have the highest affinity for substrates with chain length less than 22 carbons
Gene Name:: FEN1
Uniprot ID:: P25358
Molecular weight:: 40001.80078

Reactions

Acyl-CoA + malonyl-CoA → 3-oxoacyl-CoA + CoA + CO(2).

Protein Details

2. 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.

Transporters

Protein Details

1. Very long-chain fatty acid transport protein

General function:: Involved in catalytic activity
Specific function:: May be involved in long-chain fatty acids uptake, and thus may play a pivotal role in regulating their accessibility prior to metabolic utilization. May play an important role in uptake of these hydrophobic compounds under conditions where fatty acid synthesis is compromised
Gene Name:: FAT1
Uniprot ID:: P38225
Molecular weight:: 77140.29688

Reactions

Structure for #<Compound:0xb07b6c08>

Enzymes

Reactions

Reactions

Transporters

Reactions