MiMeDB: Showing metabocard for L-Acetylcarnitine (MMDBc0000501)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:39:12 UTC

Update Date

2022-12-15 22:51:41 UTC

Metabolite ID

MMDBc0000501

Metabolite Identification

Common Name

L-Acetylcarnitine

Description

O-acetylcarnitinium 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. O-acetylcarnitinium is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 17-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-SEP-20         0                                  
HETATM    1  C   UNK     0      -0.537  -0.372   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.797  -1.144   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.131  -0.372   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.465  -1.144   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.131   1.168   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.537   1.168   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.871   1.935   0.000  0.00  0.00           N+1
HETATM    8  C   UNK     0      -3.212   1.164   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.871   3.476   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.465   2.855   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.856  -1.164   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.856  -2.704   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.522  -3.476   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -3.189  -3.476   0.000  0.00  0.00           O+0
CONECT    1    2    6   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    1   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

Synonyms

Value	Source
O-Acetyl-L-carnitine	ChEBI
O-Acetylcarnitine	ChEBI
(-)-Acetylcarnitine	ChEBI
(R)-Acetylcarnitine	ChEBI
Acetyl-L-(-)-carnitine	ChEBI
Acetyl-L-carnitine	ChEBI
L-Acetylcarnitine	ChEBI
L-Carnitine acetyl ester	ChEBI
L-O-Acetylcarnitine	ChEBI
O-Acetyl-(R)-carnitine	ChEBI
R-Acetylcarnitine	ChEBI
Branigen	MeSH
Levocarnitine acetyl	MeSH
Acetyl carnitine	MeSH
Carnitine, acetyl	MeSH
Alcar	MeSH
Acetyl L carnitine	MeSH
Acetylcarnitine, (R)-isomer	MeSH
Medosan	MeSH
ALC	HMDB
3-(Acetyloxy)-4-(trimethylammonio)butanoate	ChEBI
Acetyl-DL-carnitine	ChEBI
Acetylcarnitine	ChEBI
DL-O-Acetylcarnitine	ChEBI
3-(Acetyloxy)-4-(trimethylammonio)butanoic acid	Generator
(+-)-Acetylcarnitine	HMDB
Acetyl-carnitine	HMDB
ALCAR	HMDB
Nicetile	HMDB
(3R)-3-Acetyloxy-4-(trimethylazaniumyl)butanoate	HMDB
C2 Carnitine	HMDB
Acylcarnitine C2:0	HMDB
C2:0 Carnitine	HMDB

Molecular Formula

C₉H₁₈NO₄

Average Mass

204.2435

Monoisotopic Mass

204.123583069

IUPAC Name

[(2R)-2-(acetyloxy)-3-carboxypropyl]trimethylazanium

Traditional Name

(+-)-acetylcarnitine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

RDHQFKQIGNGIED-MRVPVSSYSA-O

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 derivative
Carboxylic acid
Organic nitrogen compound
Amine
Organic salt
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

quaternary ammonium ion (CHEBI:15960 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-4.4	ChemAxon
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	61.8 m³·mol⁻¹	ChemAxon
Polarizability	21.16 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	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	splash10-0596-9400000000-d53cbc72a0b9e219206d	2016-09-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-000i-9200000000-e3a84538f1dadc72bc00	2020-09-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-000i-9000000000-5d5d6858632925cf1c81	2020-09-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-001i-9000000000-b7dbd311ea9af892ad91	2020-09-17	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0pb9-3930000000-1af0468e51346890699f	2020-09-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2020-09-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2020-09-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2020-09-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2020-09-17	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane
Mitochondria
Peroxisome

Biospecimen Locations

Blood
Brain
Feces
Neuron
Placenta
Prostate
Saliva
Semen
Skeletal Muscle
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000548	L-Carnitine	L-Acetylcarnitine	carnitine O-acetyltransferase	VMH; KEGG	11257506 3759988
MMDBr0000549	L-Acetylcarnitine	L-Carnitine	carnitine O-acetyltransferase	VMH; KEGG	3759988
MMDBr0000550	L-Carnitine	L-Acetylcarnitine	carnitine O-acetyltransferase	VMH; KEGG	7829107
MMDBr0000551	L-Carnitine	L-Acetylcarnitine	carnitine O-acetyltransferase	VMH; KEGG	11257506 7829107

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1	Human ; Human supragingival plaque; Human saliva; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Brain	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Semen	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	22932811
Human Urine	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Not Specified	Normal	HMDB	22727327
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	26476344
Human Feces	Detected but not Quantified	Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529
Human Urine	Detected but not Quantified	Adult (>18 years old)	Male	Normal	HMDB	17022649
Human Urine	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	21177801
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000201

DrugBank ID

DB08842

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB093666

KNApSAcK ID

Not Available

Chemspider ID

388815

KEGG Compound ID

C02571

BioCyc ID

O-ACETYLCARNITINE

BiGG ID

Not Available

Wikipedia Link

Acetyl-L-carnitine

METLIN ID

Not Available

PubChem Compound

439756

PDB ID

Not Available

ChEBI ID

57589

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Lysiak W, Toth PP, Suelter CH, Bieber LL: Quantitation of the efflux of acylcarnitines from rat heart, brain, and liver mitochondria. J Biol Chem. 1986 Oct 15;261(29):13698-703. [PubMed:3759988 ]
Corti O, Finocchiaro G, Rossi E, Zuffardi O, DiDonato S: Molecular cloning of cDNAs encoding human carnitine acetyltransferase and mapping of the corresponding gene to chromosome 9q34.1. Genomics. 1994 Sep 1;23(1):94-9. doi: 10.1006/geno.1994.1463. [PubMed:7829107 ]
Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for L-Acetylcarnitine (MMDBc0000501)

MOL for #<Metabolite:0x00007fdb08289390>

3D MOL for #<Metabolite:0x00007fdb08289390>

3D SDF for #<Metabolite:0x00007fdb08289390>

3D-SDF for #<Metabolite:0x00007fdb08289390>

PDB for #<Metabolite:0x00007fdb08289390>

3D PDB for #<Metabolite:0x00007fdb08289390>

SMILES for #<Metabolite:0x00007fdb08289390>

INCHI for #<Metabolite:0x00007fdb08289390>

Structure for #<Metabolite:0x00007fdb08289390>

3D Structure for #<Metabolite:0x00007fdb08289390>