stearic acid (YMDB00682)

Identification

YMDB ID

YMDB00682

Name

stearic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Stearic acid, also known as stearate or 18:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Based on a literature review a significant number of articles have been published on Stearic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1-Heptadecanecarboxylate
1-Heptadecanecarboxylic acid
18:0
2-Oxooctadecanoic acid
2-Oxostearate
acide octadecanoique
acide stearique
Barolub FTA
C18:0
Cetylacetic acid
ELA
Heptadecanecarboxylic acid
Isooctadecanoic acid
Isostearic acid
Macrogol ester
n-Octadecanoate
n-Octadecanoic acid
N-octadecanoic acidd
n-Octadecylic acid
Octadecanoate
octadecanoic acid
octadecanoic acid, ion(1-)
Octadecansaeure
Octadecoic acid
Oktadekansaeure
OLA
Pearl stearic
Promulsin
Proviscol wax
stearate
STEARIC ACID
stearic acid, ion(1-)
Stearinsaeure
Stearite
Stearophanate
Stearophanic acid
Steric acid
Vanicol
VCA
CH3-[CH2]16-COOH
Octadecoate
Magnesium stearate
Zinc stearate
Aluminum tristearate
Ammonium stearate
Calcium stearate
Aluminum monostearate
Sodium stearate
Stearex beads
Stearic acid cherry
FA(18:0)

CAS number

57-11-4

Weight

Average: 284.4772
Monoisotopic: 284.271530396

InChI Key

QIQXTHQIDYTFRH-UHFFFAOYSA-N

InChI

InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)

IUPAC Name

octadecanoic acid

Traditional IUPAC Name

stearic acid

Chemical Formula

C₁₈H₃₆O₂

SMILES

CCCCCCCCCCCCCCCCCC(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

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

long-chain fatty acid (CHEBI:28842 )
saturated fatty acid (CHEBI:28842 )
straight-chain saturated fatty acid (CHEBI:28842 )
Straight chain fatty acids (C01530 )
Saturated fatty acids (C01530 )
Straight chain fatty acids (LMFA01010018 )

Physical Properties

State

Solid

Charge

Melting point

68.8 °C

Experimental Properties

Property	Value	Reference
Water Solubility	0.000597 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	8.23 [SANGSTER (1993)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	6.6e-05 g/L	ALOGPS
logP	8.02	ALOGPS
logP	7.15	ChemAxon
logS	-6.6	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	16	ChemAxon
Refractivity	86.29 m³·mol⁻¹	ChemAxon
Polarizability	38.64 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

Cytoplasm
Extracellular
Peroxisome

Organoleptic Properties

Flavour/Odour	Source
Fatty	FDB002941
Mild	FDB002941
Odorless	FDB002941

SMPDB Pathways

Biosynthesis of unsaturated fatty acids	PW002403
Biosynthesis of unsaturated fatty acids (docosanoyl)	PW002408
Biosynthesis of unsaturated fatty acids (icosanoyl)	PW002434
Biosynthesis of unsaturated fatty acids (tetracosanoyl-CoA)	PW002404
Fatty acid biosynthesis	PW002458

KEGG Pathways

Biosynthesis of unsaturated fatty acids	ec01040
Fatty acid biosynthesis	ec00061

SMPDB Reactions

stearoyl-CoA + water → hydron + Coenzyme A + stearic acid

KEGG Reactions

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

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

stearic acid + Adenosine triphosphate + Coenzyme A ↔ Adenosine monophosphate + Pyrophosphate + stearoyl-CoA

stearoyl-CoA + water → stearic 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) (1 TMS)	splash10-0159-1900000000-9cc966384906cd35537d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0159-0900000000-b87a9955374d11966ba6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-0100-9700000000-979da356343fa0697993	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0159-2901000000-16194c704b7abd193647	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-06yo-9110000000-6f345827577cdc861aca	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-075c-9220000000-207b53a511763954eb66	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-1900000000-9cc966384906cd35537d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0900000000-b87a9955374d11966ba6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0100-9700000000-979da356343fa0697993	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0159-2901000000-16194c704b7abd193647	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1900000000-d34fc01a79cc27a32080	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9540000000-c6c002443ac3a40dabdb	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-009l-9551000000-b9a196da32e6273fad4f	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-001i-0090000000-1368043827a20e28c172	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-001i-0090000000-5c3fa1d38cf3d0a38d74	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 , Negative	splash10-004r-0791000000-10ab351997f48e512657	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 30V, Negative	splash10-001i-0090000000-55efcdc9c7bfd521ef5a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-001i-0090000000-9441e6362046ae198384	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-001i-0090000000-f629b105972a0728beb6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-001i-0090000000-fbf3f8e91badb0ec251d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-001i-0090000000-55efcdc9c7bfd521ef5a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-00lr-0090000000-a702a9f469dbb513856a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-001i-0090000000-9441e6362046ae198384	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-001i-0090000000-fbf3f8e91badb0ec251d	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0090000000-34a309d09cb2def46a19	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-4690000000-f68e827f7ebccd80d5bf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-8920000000-2e865f09d760af582c07	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0090000000-34a309d09cb2def46a19	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-4690000000-f68e827f7ebccd80d5bf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-8920000000-2e865f09d760af582c07	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-b3ce35f839a30b41c718	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00m0-1090000000-bbb339a3dbe1b9ba0d54	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9240000000-1b84b49819fa37fce1ae	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-b3ce35f839a30b41c718	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00m0-1090000000-bbb339a3dbe1b9ba0d54	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9240000000-1b84b49819fa37fce1ae	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0c03-9200000000-5dd52f837d56d80fa968	JSpectraViewer \| MoNA
1D NMR	1H 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
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
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
Le Guedard, M., Bessoule, J. J., Boyer, V., Ayciriex, S., Velours, G., Kulik, W., Ejsing, C. S., Shevchenko, A., Coulon, D., Lessire, R., Testet, E. (2009). "PSI1 is responsible for the stearic acid enrichment that is characteristic of phosphatidylinositol in yeast." FEBS J 276:6412-6424.19796168
Petschnigg, J., Wolinski, H., Kolb, D., Zellnig, G., Kurat, C. F., Natter, K., Kohlwein, S. D. (2009). "Good fat, essential cellular requirements for triacylglycerol synthesis to maintain membrane homeostasis in yeast." J Biol Chem 284:30981-30993.19608739
Sakuradani, E., Murata, S., Kanamaru, H., Shimizu, S. (2008). "Functional analysis of a fatty acid elongase from arachidonic acid-producing Mortierella alpina 1S-4." Appl Microbiol Biotechnol 81:497-503.18795285
You, K. M., Rosenfield, C. L., Knipple, D. C. (2003). "Ethanol tolerance in the yeast Saccharomyces cerevisiae is dependent on cellular oleic acid content." Appl Environ Microbiol 69:1499-1503.12620835
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
Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	28842
HMDB ID	HMDB00827
Pubchem Compound ID	5281
Kegg ID	C01530
ChemSpider ID	5091
FOODB ID	FDB002941
Wikipedia	Stearic_acid
BioCyc ID	STEARIC_ACID

Enzymes

Protein Details

1. Long-chain-fatty-acid--CoA ligase 4

General function:: Involved in catalytic activity
Specific function:: Esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. Contributes, with FAA1, to the activation of imported myristate
Gene Name:: FAA4
Uniprot ID:: P47912
Molecular weight:: 77266.5

Reactions

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

Protein Details

2. 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

3. Long-chain-fatty-acid--CoA ligase 1

General function:: Involved in catalytic activity
Specific function:: Esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. It may supplement intracellular myristoyl-CoA pools from exogenous myristate. Preferentially acts on C12:0-C16:0 fatty acids with myristic and pentadecanic acid (C15:0) having the highest activities
Gene Name:: FAA1
Uniprot ID:: P30624
Molecular weight:: 77865.79688

Reactions

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

Protein Details

4. Long-chain-fatty-acid--CoA ligase 3

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. This enzyme acts preferentially on C16 and C18 fatty acids with a cis-double bond at C-9-C-10
Gene Name:: FAA3
Uniprot ID:: P39002
Molecular weight:: 77946.0

Reactions

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

Protein Details

5. 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

6. 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. Peroxisomal long-chain fatty acid import protein 2

General function:: Involved in transport
Specific function:: Involved in the import of activated long-chain fatty acids from the cytosol to the peroxisomal matrix
Gene Name:: PXA1
Uniprot ID:: P41909
Molecular weight:: 100024.0

Structure for #<Compound:0xa4e0ab74>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Transporters