Milk Composition Database: Showing metabocard for L-Acetylcarnitine (BMDB0000201)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:26:38 UTC

Update Date

2020-06-04 20:33:16 UTC

MCDB ID

BMDB0000201

Secondary Accession Numbers

BMDB00201

Metabolite Identification

Common Name

L-Acetylcarnitine

Description

L-Acetylcarnitine, also known as alcar or branigen, 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, L-acetylcarnitine is considered to be a fatty ester lipid molecule. L-Acetylcarnitine exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. L-Acetylcarnitine exists in all living species, ranging from bacteria to humans. L-Acetylcarnitine participates in a number of enzymatic reactions, within cattle. In particular, L-Acetylcarnitine and coenzyme A can be biosynthesized from acetyl-CoA and L-carnitine through the action of the enzyme carnitine O-acetyltransferase. In addition, L-Acetylcarnitine and L-carnitine can be converted into acetyl-CoA and coenzyme A; which is catalyzed by the enzyme carnitine O-acetyltransferase. In cattle, L-acetylcarnitine is involved in the metabolic pathway called the Beta oxidation OF very long chain fatty acids pathway. L-Acetylcarnitine has been found to be associated with several diseases known as colorectal cancer, crohn's disease, and 3-hydroxyacyl-coa dehydrogenase deficiency; also l-acetylcarnitine has been linked to several inborn metabolic disorders including very long chain acyl-coa dehydrogenase deficiency and 3-methyl-crotonyl-glycinuria.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(-)-Acetylcarnitine	ChEBI
(R)-Acetylcarnitine	ChEBI
Acetyl-L-(-)-carnitine	ChEBI
Acetyl-L-carnitine	ChEBI
L-Carnitine acetyl ester	ChEBI
L-O-Acetylcarnitine	ChEBI
O-Acetyl-(R)-carnitine	ChEBI
R-Acetylcarnitine	ChEBI
L-Acetylcarnitine	ChEBI
Branigen	MeSH, HMDB
Levocarnitine acetyl	MeSH, HMDB
Acetyl carnitine	MeSH, HMDB
Carnitine, acetyl	MeSH, HMDB
Alcar	MeSH, HMDB
Acetyl L carnitine	MeSH, HMDB
Acetylcarnitine, (R)-isomer	MeSH, HMDB
Medosan	MeSH, HMDB
ALC	HMDB
3-(Acetyloxy)-4-(trimethylammonio)butanoate	ChEBI, HMDB
Acetyl-DL-carnitine	ChEBI, HMDB
Acetylcarnitine	ChEBI, HMDB
DL-O-Acetylcarnitine	ChEBI, HMDB
3-(Acetyloxy)-4-(trimethylammonio)butanoic acid	Generator, HMDB
(+-)-Acetylcarnitine	HMDB
Acetyl-carnitine	HMDB
ALCAR	HMDB
Nicetile	HMDB
O-Acetyl-L-carnitine	HMDB
O-Acetylcarnitine	HMDB
(3R)-3-Acetyloxy-4-(trimethylazaniumyl)butanoate	HMDB
C2 Carnitine	HMDB

Chemical Formula

C₉H₁₇NO₄

Average Molecular Weight

203.238

Monoisotopic Molecular Weight

203.115758031

IUPAC Name

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

Traditional Name

acetyl-L-carnitine

CAS Registry Number

3040-38-8

SMILES

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

InChI Identifier

InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3/t8-/m1/s1

InChI Key

RDHQFKQIGNGIED-MRVPVSSYSA-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-acetylcarnitine (CHEBI:57589 )
O-acyl-L-carnitine (CHEBI:57589 )

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	-2.4	ALOGPS
logP	-4.4	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	-7	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	6	ChemAxon
Refractivity	72.64 m³·mol⁻¹	ChemAxon
Polarizability	20.82 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9100000000-c3bf4495e8c4abf714db	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-000i-9200000000-e3a84538f1dadc72bc00	2018-05-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-000i-9000000000-5d5d6858632925cf1c81	2018-05-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-001i-9000000000-b7dbd311ea9af892ad91	2018-05-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0pb9-3930000000-1af0468e51346890699f	2018-05-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-71230651236adb31fa6f	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-9050000000-2a63f200e23202870ebe	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2018-05-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2018-05-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2018-05-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2018-05-25	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected but not Quantified	Not Applicable	PMID: 23738862	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected and Quantified	48 +/- 3 uM	PMID: 30994344	details
Detected and Quantified	48 +/- 2 uM	PMID: 30994344	details
Detected and Quantified	48 +/- 5 uM	PMID: 30994344	details
Detected and Quantified	50 +/- 5 uM	PMID: 30994344	details
Detected and Quantified	37 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	39 +/- 2 uM	PMID: 30994344	details
Detected and Quantified	37 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	41 +/- 1 uM	PMID: 30994344	details
Detected and Quantified	51 +/- 13 uM	PMID: 29642378	details
Detected and Quantified	50 +/- 13 uM	PMID: 29642378	details
Detected and Quantified	46 +/- 7.4 uM	PMID: 29642378	details

External Links

HMDB ID

HMDB0304631

DrugBank ID

DB08842

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB093666

KNApSAcK ID

C00052178

Chemspider ID

5406074

KEGG Compound ID

Not Available

BioCyc ID

O-ACETYLCARNITINE

BiGG ID

Not Available

Wikipedia Link

Acetyl-L-carnitine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

57589

References

Synthesis Reference

Gu, Heng-da; Shi, Shuang; Yang, Ying; Shi, Zhao-xin; Yu, Zhan-long. Synthesis of acetyl-L-carnitine by direct acylation method. Shenyang Huagong Xueyuan Xuebao (2006), 20(2), 154-155, 160.

Material Safety Data Sheet (MSDS)

Not Available

General References

Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
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.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Showing metabocard for L-Acetylcarnitine (BMDB0000201)

Structure for BMDB0000201 (L-Acetylcarnitine)