Bovine Metabolome Database: Showing metabocard for L-Hexanoylcarnitine (BMDB0000756)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:36:06 UTC

Update Date

2020-06-04 19:25:50 UTC

BMDB ID

BMDB0000756

Secondary Accession Numbers

BMDB00756

Metabolite Identification

Common Name

L-Hexanoylcarnitine

Description

Hexanoylcarnitine, also known as (R)-caproylcarnitine or hexanoate, 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, hexanoylcarnitine is considered to be a fatty ester. Based on a literature review a significant number of articles have been published on Hexanoylcarnitine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-Caproylcarnitine	ChEBI
(R)-Hexanoylcarnitine	ChEBI
Hexanoyl-L-carnitine	ChEBI
L-Hexanoylcarnitine	ChEBI
O-Hexanoyl-(R)-carnitine	ChEBI
(R)-3-Carboxy-N,N,N-trimethyl-2-[(1-oxohexyl)oxy]-1-propanaminium inner salt	HMDB
Hexanoate	HMDB
Hexanoic acid	HMDB
Hexanoic acid ester with L-(3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt	HMDB
L-Carnitine hexanoyl ester	HMDB
L-Hexanoate	HMDB
L-Hexanoic acid	HMDB
L-Hexanoic acid ester with (3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt	HMDB
C6 Carnitine	HMDB
Hexanoylcarnitine	HMDB

Chemical Formula

C₁₃H₂₅NO₄

Average Molecular Weight

259.3419

Monoisotopic Molecular Weight

259.178358293

IUPAC Name

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

Traditional Name

L-carnitine hexanoyl ester

CAS Registry Number

22671-29-0

SMILES

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

InChI Identifier

InChI=1S/C13H25NO4/c1-5-6-7-8-13(17)18-11(9-12(15)16)10-14(2,3)4/h11H,5-10H2,1-4H3/t11-/m1/s1

InChI Key

VVPRQWTYSNDTEA-LLVKDONJSA-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:84834 )
Fatty acyl carnitines (LMFA07070001 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane

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	-1.7	ALOGPS
logP	-2.4	ChemAxon
logS	-4.9	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	10	ChemAxon
Refractivity	91.07 m³·mol⁻¹	ChemAxon
Polarizability	28.79 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)	splash10-03dr-6090000000-c19afe5acca5a4b0f82f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-8d30a3ad5fce9bf004f7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-a38bcb0bb25abdcaaa7c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0090000000-5c4e7ecd71d0ed800ae6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p9-9050000000-f92580b9643caf52768e	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, CD₃OD, experimental)	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, 100 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 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, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

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	0.05 +/- 0.01 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Liver	Detected and Quantified	0.3 +/- 0.1 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Longissimus Thoracis Muscle	Detected and Quantified	0.52 +/- 0.51 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	0.08 +/- 0.01 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Semimembranosus Muscle	Detected and Quantified	0.7 +/- 0.4 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	0.21 +/- 0.06 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000756

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022226

KNApSAcK ID

C00052313

Chemspider ID

2497478

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

3548

PubChem Compound

3246938

PDB ID

Not Available

ChEBI ID

84834

References

Synthesis Reference

Nakanishi, Toyofumi; Shimizu, Akira; Arimoto, Masao; Kanai, Michiko. Synthesis of acylcarnitines for differential diagnosis of metabolic disorders. Nippon Iyo Masu Supekutoru Gakkai Koenshu (1993), 18 129-32.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for L-Hexanoylcarnitine (BMDB0000756)

Structure for BMDB0000756 (L-Hexanoylcarnitine)