Bovine Metabolome Database: Showing metabocard for Stearoylcarnitine (BMDB0000848)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:37:28 UTC

Update Date

2020-06-04 19:04:37 UTC

BMDB ID

BMDB0000848

Secondary Accession Numbers

BMDB00848

Metabolite Identification

Common Name

Stearoylcarnitine

Description

Stearoylcarnitine, also known as acylcarnitine C18:0, belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Thus, stearoylcarnitine is considered to be a fatty ester lipid molecule. Stearoylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, stearoylcarnitine is involved in the metabolic pathway called the mitochondrial Beta-oxidation OF long chain saturated fatty acids pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Stearoylcarnitine	ChEBI
(R)-Octadecanoylcarnitine	ChEBI
(R)-Stearoylcarnitine	ChEBI
Acylcarnitine C18:0	ChEBI
L-Stearoylcarnitine	ChEBI
O-Octadecanoyl-(R)-carnitine	ChEBI
O-Octadecanoyl-R-carnitine	ChEBI
O-Stearoyl-L-carnitine	ChEBI
Octadecanoylcarnitine	ChEBI
3-(Octadecanoyloxy)-4-(trimethylammonio)butanoate	HMDB
O-Octadecanoylcarnitine	HMDB
3-(Octadecanoyloxy)-4-(trimethylammonio)butanoic acid	HMDB
(R)-3-Carboxy-N,N,N-trimethyl-2-[(1-oxooctadecyl)oxy]-1-propanaminium inner salt	HMDB
L-(3-Carboxy-2-hydroxypropyl)trimethyl-ammonium stearate hydroxide inner salt	HMDB
L-Stearic acid ester with (3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt	HMDB
Octadecanoyl-L-carnitine	HMDB
Stearoyl-L-carnitine	HMDB
Stearoylcarnitine	ChEBI

Chemical Formula

C₂₅H₄₉NO₄

Average Molecular Weight

427.67

Monoisotopic Molecular Weight

427.366159062

IUPAC Name

(3R)-3-(octadecanoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

stearoylcarnitine

CAS Registry Number

1976-27-8

SMILES

CCCCCCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C25H49NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h23H,5-22H2,1-4H3/t23-/m1/s1

InChI Key

FNPHNLNTJNMAEE-HSZRJFAPSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-acyl-L-carnitine (CHEBI:84644 )
Fatty acyl carnitines (LMFA07070008 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane
Mitochondria

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	2.62	ALOGPS
logP	2.92	ChemAxon
logS	-7.7	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	146.28 m³·mol⁻¹	ChemAxon
Polarizability	54.7 Å³	ChemAxon
Number of Rings	0	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 GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0000900000-69f3d757e110ec8c3b98	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-2ea2540d550fb015d5e5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-6ab6988a50a1903532bb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000900000-c1f627ea020ee6c41402	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002r-9000500000-4ac5c177695cbcfccf15	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane
Mitochondria

Biospecimen Locations

Blood
Liver
Longissimus Thoracis Muscle
Placenta
Ruminal Fluid
Semimembranosus Muscle
Testis

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.021 +/- 0.008 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24630653	details
Liver	Detected and Quantified	0.008 +/- 0.001 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Longissimus Thoracis Muscle	Detected and Quantified	0.02 +/- 0.01 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	0.0067 +/- 0.0021 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Semimembranosus Muscle	Detected and Quantified	0.006 +/- 0.002 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	0.02 +/- 0.01 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000848

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022278

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

1585824

Wikipedia Link

Not Available

METLIN ID

5811

PubChem Compound

52922056

PDB ID

Not Available

ChEBI ID

84644

References

Synthesis Reference

Zhou, Qingzhong. Synthesis of branched-chain analogs of stearoyl carnitine and tests for their abilities to inhibited protein kinase C. Beijing Daxue Xuebao, Ziran Kexueban (1992), 28(2), 143-9.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Carnitine O-palmitoyltransferase 1, muscle isoform

General function:: Involved in carnitine O-palmitoyltransferase activity
Specific function:: Not Available
Gene Name:: CPT1B
Uniprot ID:: Q58DK1
Molecular weight:: 88512.0

Reactions

Stearoyl-CoA + L-Carnitine → Stearoylcarnitine + Coenzyme A	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

Stearoyl-CoA + L-Carnitine → Stearoylcarnitine + Coenzyme A	details

Showing metabocard for Stearoylcarnitine (BMDB0000848)

Structure for BMDB0000848 (Stearoylcarnitine)

Enzymes

Reactions

Reactions