L-Palmitoylcarnitine

Details

• Internal ID: 37db7c4e-30b4-4535-9db2-eeaf4b525591
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters > Acyl carnitines
• IUPAC Name: (3R)-3-hexadecanoyloxy-4-(trimethylazaniumyl)butanoate
• SMILES (Canonical): CCCCCCCCCCCCCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C
• SMILES (Isomeric): CCCCCCCCCCCCCCCC(=O)O[C@H](CC(=O)[O-])C[N+](C)(C)C
• InChI: 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
• Popularity: 467 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₄₅NO₄
• Molecular Weight: 399.60 g/mol
• Exact Mass: 399.33485892 g/mol
• Topological Polar Surface Area (TPSA): 66.40 Ų
• XlogP: 7.70
• Atomic LogP (AlogP): 4.23
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 19

Synonyms

• Palmitoyl-L-carnitine
• 2364-67-2
• O-palmitoyl-L-carnitine
• Hexadecanoyl-L-carnitine
• Palmityl-L-carnitine
• L-Carnitine palmitoyl ester
• PALMITOYLCARNITINE
• O-hexadecanoyl-R-carnitine
• Hexadecenoyl carnitine
• CHEBI:17490
• L(-)-Palmitylcarnitine
• Palmitoyl-(-)-carnitine
• Palmitoyl carnitine, (-)-
• palmitoyl carnitine
• CHEMBL3392050
• 1G38O5K038
• (3R)-3-hexadecanoyloxy-4-(trimethylazaniumyl)butanoate
• Ammonium, (3-carboxy-2-hydroxypropyl)trimethyl-, hydroxide, inner salt, palmitate, L-
• Palmitylcarnitine
• (3R)-3-(hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate
• D-Palmitylcarnitine
• hexadecanoylcarnitine
• Palmitoyl d-carnitine
• (+)-Palmitoylcarnitine
• Palmitoyl-L-(-)-carnitin
• UNII-1G38O5K038
• Palmitoyl-L-(-)-carnitin [German]
• L-Palmitoyl carnitine
• L-palmitoyl-L-carnitine
• (-)-palmitoyl carnitine
• O-hexadecanoyl-L-carnitine
• O-hexadecanoyl-(R)-carnitine
• SCHEMBL116634
• XOMRRQXKHMYMOC-OAQYLSRUSA-N
• DTXSID101019091
• BDBM50537024
• CAR(16:0)
• LMFA07070004
• AKOS037645114
• AS-57239
• PD101999
• XP165791
• Palmitoyl-L-carnitine, >=97.0% (TLC)
• HY-113147
• CS-0062278
• C16 Carnitine, palmitoyl L-carnitine, powder
• C02990
• (3R)-3-palmitoyloxy-4-(trimethylammonio)butanoate
• (3R)-3-hexadecanoyloxy-4-(trimethylammonio)butanoate
• (3S)-3-palmitoyloxy-4-(trimethylammonio)butanoic acid
• Q27102424
• (3S)-3-hexadecanoyloxy-4-(trimethylammonio)butanoic acid
• 3-carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-1-Propanaminium
• 1-PROPANAMINIUM, 3-CARBOXY-N,N,N-TRIMETHYL-2-((1-OXOHEXADECYL)OXY)-, INNER SALT, (2R)-
• 1-PROPANAMINIUM, 3-CARBOXY-N,N,N-TRIMETHYL-2-((1-OXOHEXADECYL)OXY)-, INNER SALT, (R)-
• PALMITIC ACID, ESTER WITH (3-CARBOXY-2-HYDROXYPROPYL)TRIMETHYLAMMONIUM HYDROXIDE INNER SALT, L-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9656	96.56%
Caco-2	+	0.5117	51.17%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6531	65.31%
OATP2B1 inhibitior	-	0.8537	85.37%
OATP1B1 inhibitior	+	0.8936	89.36%
OATP1B3 inhibitior	+	0.9444	94.44%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.6003	60.03%
P-glycoprotein inhibitior	-	0.5818	58.18%
P-glycoprotein substrate	-	0.7841	78.41%
CYP3A4 substrate	-	0.5374	53.74%
CYP2C9 substrate	-	0.5924	59.24%
CYP2D6 substrate	-	0.8522	85.22%
CYP3A4 inhibition	-	0.8480	84.80%
CYP2C9 inhibition	-	0.9212	92.12%
CYP2C19 inhibition	-	0.9065	90.65%
CYP2D6 inhibition	-	0.9121	91.21%
CYP1A2 inhibition	-	0.8752	87.52%
CYP2C8 inhibition	-	0.6586	65.86%
CYP inhibitory promiscuity	-	0.9589	95.89%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5923	59.23%
Carcinogenicity (trinary)	Non-required	0.6533	65.33%
Eye corrosion	-	0.8946	89.46%
Eye irritation	+	0.7078	70.78%
Skin irritation	-	0.8097	80.97%
Skin corrosion	-	0.9359	93.59%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5510	55.10%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.7518	75.18%
skin sensitisation	-	0.9045	90.45%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	-	0.8667	86.67%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.6973	69.73%
Acute Oral Toxicity (c)	III	0.6962	69.62%
Estrogen receptor binding	-	0.4857	48.57%
Androgen receptor binding	-	0.7225	72.25%
Thyroid receptor binding	+	0.5350	53.50%
Glucocorticoid receptor binding	-	0.4743	47.43%
Aromatase binding	-	0.5960	59.60%
PPAR gamma	+	0.5374	53.74%
Honey bee toxicity	-	0.9559	95.59%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	+	0.8065	80.65%
Fish aquatic toxicity	+	0.7408	74.08%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3060	Q9Y345	Glycine transporter 2	600 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.47%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.31%	96.09%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	94.66%	92.86%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	92.38%	92.08%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.47%	96.95%
CHEMBL230	P35354	Cyclooxygenase-2	90.73%	89.63%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	90.65%	97.29%
CHEMBL299	P17252	Protein kinase C alpha	90.15%	98.03%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	89.55%	95.17%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	89.21%	91.81%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.83%	94.45%
CHEMBL5255	O00206	Toll-like receptor 4	86.57%	92.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.16%	97.21%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	85.12%	85.94%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.08%	93.56%
CHEMBL321	P14780	Matrix metalloproteinase 9	83.56%	92.12%
CHEMBL3238	P23786	Carnitine palmitoyltransferase 2	83.35%	94.05%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.80%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.93%	94.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11953816
• LOTUS: LTS0183906
• wikiData: Q27102424