N-Palmitoylsphingosine

Details

• Internal ID: e49d4b54-5989-4742-8d72-e6c0e897128a
• Taxonomy: Lipids and lipid-like molecules > Sphingolipids > Ceramides > Long-chain ceramides
• IUPAC Name: N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide
• SMILES (Canonical): CCCCCCCCCCCCCCCC(=O)NC(CO)C(C=CCCCCCCCCCCCCC)O
• SMILES (Isomeric): CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H](/C=C/CCCCCCCCCCCCC)O
• InChI: InChI=1S/C34H67NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(37)32(31-36)35-34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36-37H,3-26,28,30-31H2,1-2H3,(H,35,38)/b29-27+/t32-,33+/m0/s1
• InChI Key: YDNKGFDKKRUKPY-TURZORIXSA-N
• Popularity: 214 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₆₇NO₃
• Molecular Weight: 537.90 g/mol
• Exact Mass: 537.51209500 g/mol
• Topological Polar Surface Area (TPSA): 69.60 Ų
• XlogP: 12.90
• Atomic LogP (AlogP): 9.56
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 30

Synonyms

• N-Palmitoylsphingosine
• 24696-26-2
• N-(hexadecanoyl)-sphing-4-enine
• C16-ceramide
• Cer(d18:1/16:0)
• N-palmitoyl-sphingosine
• C16 Cer
• N-acylsphingosine
• N-(palmitoyl)-ceramide
• N-(hexadecanoyl)-ceramide
• N-(1,3-dihydroxyoctadec-4-en-2-yl)hexadecanamide
• CHEMBL35292
• CHEBI:72959
• N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide
• Hexadecanamide,N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-
• N-((E,2s,3r)-1,3-Dihydroxyoctadec-4-En-2-Yl)palmitamide
• C16 Ceramide (N-Palmitoylsphingosine, D-erythro)
• N-palmitoyl-D-erythro-sphingosine
• Ceramide d34:1
• N-(palmitoyl)ceramide
• N-hexadecanoylsphingosine
• N-(hexadecanoyl)ceramide
• N-palmitoylsphing-4-enine
• N-hexadecanoylsphing-4-enine
• sphing-4-enine-16-ceramide
• BSPBio_001281
• BML3-D03
• N-(hexadecanoyl)sphing-4-enine
• Ceramide (d18:1/16:0)
• SCHEMBL10298591
• SCHEMBL16027983
• Ceramide (18:1/16:0)
• YDNKGFDKKRUKPY-TURZORIXSA-N
• DTXSID301317974
• HMS1361A03
• HMS1791A03
• HMS1989A03
• HMS3402A03
• CUA24306
• BDBM50289523
• LMSP02010004
• AKOS040755906
• IDI1_033751
• NCGC00161362-01
• NCGC00161362-02
• NCGC00161362-03
• BP-28815
• HY-100354
• CS-0018668
• N-Palmitoyl-D-sphingosine, >=98.0% (TLC)
• J-015630
• N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide
• C16 Ceramide (d18:1/16:0), N-palmitoyl-D-erythro-sphingosine, powder
• Hexadecanoic acid ((E)-(1S,2R)-2-hydroxy-1-hydroxymethyl-heptadec-3-enyl)-amide
• N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)heptadec-3-en-1-yl]hexadecanamide
• N-Palmitoyl-D-erythro-sphingosine;N-Hexadecanoyl-D-erythro-sphingosine;N-Palmitoyl ceramide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9660	96.60%
Caco-2	-	0.8398	83.98%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8225	82.25%
OATP2B1 inhibitior	+	0.5745	57.45%
OATP1B1 inhibitior	+	0.8563	85.63%
OATP1B3 inhibitior	+	0.9278	92.78%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8629	86.29%
BSEP inhibitior	+	0.7934	79.34%
P-glycoprotein inhibitior	-	0.4724	47.24%
P-glycoprotein substrate	-	0.8483	84.83%
CYP3A4 substrate	-	0.5413	54.13%
CYP2C9 substrate	-	0.6095	60.95%
CYP2D6 substrate	-	0.8417	84.17%
CYP3A4 inhibition	-	0.7704	77.04%
CYP2C9 inhibition	+	0.5000	50.00%
CYP2C19 inhibition	-	0.8536	85.36%
CYP2D6 inhibition	+	0.8449	84.49%
CYP1A2 inhibition	+	0.8704	87.04%
CYP2C8 inhibition	-	0.8976	89.76%
CYP inhibitory promiscuity	-	0.6867	68.67%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.7039	70.39%
Eye corrosion	-	0.9685	96.85%
Eye irritation	-	0.7904	79.04%
Skin irritation	-	0.8416	84.16%
Skin corrosion	-	0.9765	97.65%
Ames mutagenesis	-	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6673	66.73%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.6165	61.65%
skin sensitisation	-	0.9342	93.42%
Respiratory toxicity	-	0.8000	80.00%
Reproductive toxicity	-	0.7451	74.51%
Mitochondrial toxicity	-	0.8125	81.25%
Nephrotoxicity	+	0.5429	54.29%
Acute Oral Toxicity (c)	III	0.5901	59.01%
Estrogen receptor binding	+	0.5949	59.49%
Androgen receptor binding	-	0.8679	86.79%
Thyroid receptor binding	-	0.5519	55.19%
Glucocorticoid receptor binding	-	0.5580	55.80%
Aromatase binding	-	0.6009	60.09%
PPAR gamma	+	0.5740	57.40%
Honey bee toxicity	-	0.9730	97.30%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	+	0.6034	60.34%
Fish aquatic toxicity	-	0.4656	46.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL230	P35354	Cyclooxygenase-2	99.32%	89.63%
CHEMBL2581	P07339	Cathepsin D	98.75%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	98.62%	99.17%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	96.68%	97.29%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	94.91%	92.86%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	94.78%	92.08%
CHEMBL3359	P21462	Formyl peptide receptor 1	92.92%	93.56%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	91.23%	85.94%
CHEMBL299	P17252	Protein kinase C alpha	88.78%	98.03%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	88.47%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.09%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	87.93%	90.17%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	86.88%	91.81%
CHEMBL2664	P23526	Adenosylhomocysteinase	86.60%	86.67%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.29%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.15%	96.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.15%	89.34%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.90%	94.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.70%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.21%	96.47%
CHEMBL256	P0DMS8	Adenosine A3 receptor	83.49%	95.93%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.48%	91.24%
CHEMBL340	P08684	Cytochrome P450 3A4	83.16%	91.19%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	82.93%	96.67%
CHEMBL5255	O00206	Toll-like receptor 4	82.87%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.39%	100.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.36%	92.88%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	81.99%	96.00%
CHEMBL1781	P11387	DNA topoisomerase I	81.43%	97.00%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	81.11%	92.29%
CHEMBL4040	P28482	MAP kinase ERK2	81.06%	83.82%
CHEMBL3401	O75469	Pregnane X receptor	80.87%	94.73%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	80.35%	89.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.18%	96.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5283564
• LOTUS: LTS0111846
• wikiData: Q24300403