Bovine Metabolome Database: Showing metabocard for Stearic acid (BMDB0000827)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:37:12 UTC

Update Date

2020-06-04 22:58:00 UTC

BMDB ID

BMDB0000827

Secondary Accession Numbers

BMDB00827

Metabolite Identification

Common Name

Stearic acid

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. Stearic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Stearic acid exists in all living species, ranging from bacteria to humans. Stearic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
18:0	ChEBI
Acide octadecanoique	ChEBI
Acide stearique	ChEBI
C18:0	ChEBI
CH3-[CH2]16-COOH	ChEBI
N-Octadecanoic acid	ChEBI
Octadecansaeure	ChEBI
Octadecoic acid	ChEBI
Oktadekansaeure	ChEBI
Stearinsaeure	ChEBI
Stearate	Kegg
N-Octadecanoate	Generator
Octadecoate	Generator
Octadecanoic acid	HMDB
Octadecanoate	HMDB
1-Heptadecanecarboxylate	HMDB
1-Heptadecanecarboxylic acid	HMDB
Stearex beads	HMDB
Stearic acid cherry	HMDB
Stearophanate	HMDB
Stearophanic acid	HMDB
Calcium stearate	HMDB
Aluminum tristearate	HMDB
Ammonium stearate	HMDB
Zinc stearate	HMDB
Magnesium stearate	HMDB
Sodium stearate	HMDB
Aluminum monostearate	HMDB
FA(18:0)	HMDB

Chemical Formula

C₁₈H₃₆O₂

Average Molecular Weight

284.4772

Monoisotopic Molecular Weight

284.271530396

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

57-11-4

SMILES

Not Available

InChI Identifier

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)

InChI Key

QIQXTHQIDYTFRH-UHFFFAOYSA-N

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 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Adiposome
Cell membrane
Cytoplasm
Membrane
Myelin sheath

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	68.8 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.000597 mg/mL	Not Available
LogP	8.23	SANGSTER (1993)

Predicted Properties

Not Available

Spectra

Spectrum Type	Description	Splash Key

Biological Properties

Cellular Locations

Adiposome
Cell membrane
Cytoplasm
Membrane
Myelin sheath

Biospecimen Locations

Adipose Tissue
Blood
Brain
Epidermis
Erythrocyte
Fibroblasts
Intestine
Liver
Mammary Gland
Milk
Muscle
Neuron
Oocyte
Placenta
Platelet
Prostate Tissue
Ruminal Fluid
Urine

Pathways

Name	SMPDB/Pathwhiz	KEGG
Plasmalogen Synthesis		Not Available
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Detected and Quantified	32663.0746 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected and Quantified	27546.67 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected and Quantified	798686.15 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected and Quantified	821695.38 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected and Quantified	299512.0171 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected and Quantified	273535.1 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25093808	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25093808	details
Adipose Tissue	Detected and Quantified	295489.41 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 24188642	details
Adipose Tissue	Detected and Quantified	322697.21 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 24188642	details
Adipose Tissue	Detected and Quantified	298498.44 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 24188642	details
Adipose Tissue	Detected and Quantified	330184.63 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 24188642	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25093808	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25093808	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22274861	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22274861	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22274861	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22274861	details
Blood	Detected and Quantified	0.021 +/- 0.011 uM	Not Specified	Not Specified	Normal	PMID: 25875852	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Laura Evans, Stua...	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 20647382	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Erythrocyte	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Milk	Detected and Quantified	6.53 +/- 0.12 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	6046.18 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	11.5 +/- 0.2 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	4569.79 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	1054.566 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	1968.523 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	1054.566 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	12338.423 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	12197.81 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	10897.18 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	13 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	17 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	35.90 +/- 5.72 uM	Not Specified	Not Specified	Normal	Bashar Amer, Caro...	details
Milk	Detected and Quantified	30.18 +/- 1.56 uM	Not Specified	Not Specified	Normal	Bashar Amer, Caro...	details
Milk	Detected and Quantified	12.36 +/- 1.17 uM	Not Specified	Not Specified	Normal	Bashar Amer, Caro...	details
Milk	Detected and Quantified	0.78 +/- 0.26 uM	Not Specified	Not Specified	Normal	Bashar Amer, Caro...	details
Milk	Detected and Quantified	24.33 +/- 0.08 uM	Not Specified	Not Specified	Normal	Bashar Amer, Caro...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 1779072	details
Milk	Detected and Quantified	19685.247 +/- 8436.534 uM	Not Specified	Not Specified	Normal	PMID: 16899705	details
Milk	Detected and Quantified	49.319 +/- 0.34 uM	Not Specified	Not Specified	Normal	Catrienus De Jong...	details
Milk	Detected and Quantified	130 +/- 22.8 uM	Not Specified	Not Specified	Normal	PMID: 11754544	details
Milk	Detected and Quantified	78.2 +/- 9.0 uM	Not Specified	Not Specified	Normal	PMID: 11754544	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 11913692	details
Milk	Detected and Quantified	12936.0194 +/- 3901.897 uM	Not Specified	Not Specified	Normal	M. Ferrand et al....	details
Milk	Detected and Quantified	11846.300 +/- 3655.832 uM	Not Specified	Not Specified	Normal	M. Ferrand et al....	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Lawrence K. Cream...	details
Milk	Detected and Quantified	10194.139 uM	Not Specified	Not Specified	Normal	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	84716.807 uM	Not Specified	Not Specified	Normal	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	99480.732 uM	Not Specified	Not Specified	Normal	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	121626.619 uM	Not Specified	Not Specified	Normal	M.J. Abarghuei, Y...	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23871026	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Oocyte	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 10793638	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	185.6 +/- 27.1 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	186.0 +/- 27.0 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25599412	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Sub/clinical ketosis	PMID: 24070026	details

External Links

HMDB ID

HMDB0000827

DrugBank ID

DB03193

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

28842

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. [PubMed:16899705 ]
Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93. [PubMed:5409465 ]
Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. [PubMed:19038946 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.
M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri (2014). M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021. Livestock Science.
Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

Enzyme Details

1. Dihydroxyacetone phosphate acyltransferase

General function:: Lipid transport and metabolism
Specific function:: Not Available
Gene Name:: GNPAT
Uniprot ID:: A4IF87
Molecular weight:: 77664.0

Reactions

DHAP(18:0) + Octadecanol → DHAP(18:0e) + Stearic acid	details

Enzyme Details

2. D-2-hydroxyglutarate dehydrogenase, mitochondrial

General function:: Energy production and conversion
Specific function:: Catalyzes the oxidation of D-2-hydroxyglutarate to alpha-ketoglutarate.
Gene Name:: D2HGDH
Uniprot ID:: Q1JPD3
Molecular weight:: 59056.0

Reactions

DHAP(18:0) + Octadecanol → DHAP(18:0e) + Stearic acid	details

Enzyme Details

3. Long-chain-fatty-acid--CoA ligase ACSBG1

General function:: Lipid transport and metabolism
Specific function:: Catalyzes the conversion of fatty acids such as long-chain and very long-chain fatty acids to their active form acyl-CoAs for both synthesis of cellular lipids, and degradation via beta-oxidation. Can activate diverse saturated, monosaturated and polyunsaturated fatty acids.
Gene Name:: ACSBG1
Uniprot ID:: Q2KHW5
Molecular weight:: 80585.0

Reactions

Stearic acid + Coenzyme A + Adenosine triphosphate → Stearoyl-CoA + Pyrophosphate + Adenosine monophosphate	details

Showing metabocard for Stearic acid (BMDB0000827)

Structure for BMDB0000827 (Stearic acid)

Enzymes

Reactions

Reactions

Reactions