MiMeDB: Showing metabocard for L-Palmitoylcarnitine (MMDBc0031977)

Microbial

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:57:16 UTC

Update Date

2025-11-05 17:13:00 UTC

Metabolite ID

MMDBc0031977

Metabolite Identification

Common Name

L-Palmitoylcarnitine

Description

L-Palmitoylcarnitine is a fatty acylcarnitine, a chemical class involved in the transport of long-chain fatty acids into mitochondria for β-oxidation. Its chemical structure consists of a carnitine backbone esterified with palmitic acid, facilitating the transport of fatty acids across the mitochondrial membrane. In biological pathways, L-palmitoylcarnitine plays a critical role in lipid metabolism and energy production. It is generated from L-carnitine by the action of carnitine acyltransferases, particularly CPT1A, which is essential for the oxidation of fatty acids. Disruptions in this pathway can lead to abnormal accumulations of L-carnitine and decreased levels of L-palmitoylcarnitine, as observed in the substantia nigra pars compacta, impairing mitochondrial function (PMID:41130067 ). Additionally, L-palmitoylcarnitine levels are modulated by various factors, including gut microbiota balance and treatments affecting fatty acid metabolism (PMID:40848907 ). It has also been implicated in conditions such as MASLD, where its levels are elevated (PMID:40568565 ), and its modulation has been linked to the effects of dietary components like tea polyphenols (PMID:40188624 ). Overall, L-palmitoylcarnitine serves as a significant metabolite in energy metabolism and lipid homeostasis.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₂₃H₄₅NO₄

Average Mass

399.6077

Monoisotopic Mass

399.334858933

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h21H,5-20H2,1-4H3/t21-/m1/s1

InChI Key

XOMRRQXKHMYMOC-OAQYLSRUSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	188.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	50.9
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	621.1
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	929.3
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	952.4
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	323.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (retained)	2025-10-23	2958.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	476.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	331.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	805.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	171.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	198.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	257.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	8.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	336.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	635.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	523.3
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	2355.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	2365.1

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019706	L-Carnitine	L-Palmitoylcarnitine	Carnitine O-acetyltransferase, mitochondrial	N-Acetylation	PathBank	31602464

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/Eubacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal	Unknown
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Finocchiaro G, Taroni F, Rocchi M, Martin AL, Colombo I, Tarelli GT, DiDonato S: cDNA cloning, sequence analysis, and chromosomal localization of the gene for human carnitine palmitoyltransferase. Proc Natl Acad Sci U S A. 1991 Jan 15;88(2):661-5. doi: 10.1073/pnas.88.2.661. [PubMed:1988962 ]
Palmieri F: The mitochondrial transporter family (SLC25): physiological and pathological implications. Pflugers Arch. 2004 Feb;447(5):689-709. doi: 10.1007/s00424-003-1099-7. Epub 2003 Nov 4. [PubMed:14598172 ]
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 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for L-Palmitoylcarnitine (MMDBc0031977)

MOL for #<Metabolite:0x0000564323246208>

3D MOL for #<Metabolite:0x0000564323246208>

3D SDF for #<Metabolite:0x0000564323246208>

3D-SDF for #<Metabolite:0x0000564323246208>

PDB for #<Metabolite:0x0000564323246208>

3D PDB for #<Metabolite:0x0000564323246208>

SMILES for #<Metabolite:0x0000564323246208>

INCHI for #<Metabolite:0x0000564323246208>

Structure for #<Metabolite:0x0000564323246208>

3D Structure for #<Metabolite:0x0000564323246208>