N-tetracosanoylphytosphingosine

Details

• Internal ID: 8d067ebb-6622-459c-9d1b-3aba0a4ee1a1
• Taxonomy: Lipids and lipid-like molecules > Sphingolipids > Ceramides > Phytoceramides
• IUPAC Name: N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]tetracosanamide
• SMILES (Canonical): CCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(CO)C(C(CCCCCCCCCCCCCC)O)O
• SMILES (Isomeric): CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@@H]([C@@H](CCCCCCCCCCCCCC)O)O
• InChI: InChI=1S/C42H85NO4/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-27-29-31-33-35-37-41(46)43-39(38-44)42(47)40(45)36-34-32-30-28-26-16-14-12-10-8-6-4-2/h39-40,42,44-45,47H,3-38H2,1-2H3,(H,43,46)/t39-,40+,42-/m0/s1
• InChI Key: ZESJDNWGTANZCC-LFVSMIGWSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₈₅NO₄
• Molecular Weight: 668.10 g/mol
• Exact Mass: 667.64786019 g/mol
• Topological Polar Surface Area (TPSA): 89.80 Ų
• XlogP: 16.60
• Atomic LogP (AlogP): 11.88
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 39

Synonyms

• 34437-74-6
• N-(tetracosanoyl)-4R-hydroxysphinganine
• ceramide-2 (phytosphingosine:N-C24:0)
• N-(tetracosanoyl)-phytoceramide
• Cer(t18:0/24:0)
• N-[(1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadecyl]-tetracosanamide
• C24 Phytoceramide (t18:0/24:0)
• ceramide B (C24)
• ceramide-2 (C24)
• cer2_24
• N-(lignoceroyl)-phytosphingosine
• SCHEMBL22910827
• CHEBI:52979
• N-(tetracosanoyl)phytosphingosine
• DTXSID901216287
• N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]tetracosanamide
• N-tetracosanoyl-4-hydroxysphinganine
• LMSP02030004
• ceramide N(C24:0)P(C:18:0)
• AKOS040756338
• N-(tetracosanoyl)-4-hydroxysphinganine
• N-tetracosanoyl-(4R)-hydroxysphinganine
• C24 Phytosphingosine (t18:0/24:0)
• Q27104803
• (2S,3S,4R)-2-Tetracosanoylamino-1,3,4-octadecanetriol
• (2S,3S,4R)-N-tetracosanoyl-2-amino-1,3,4-octadecanetriol
• N-24:0 Phytosphingosine, N-lignoceroyl-phytosphingosine (Saccharomyces Cerevisiae), powder

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8206	82.06%
Caco-2	-	0.8504	85.04%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7869	78.69%
OATP2B1 inhibitior	+	0.5747	57.47%
OATP1B1 inhibitior	+	0.9345	93.45%
OATP1B3 inhibitior	+	0.9123	91.23%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9041	90.41%
BSEP inhibitior	+	0.7740	77.40%
P-glycoprotein inhibitior	-	0.4545	45.45%
P-glycoprotein substrate	-	0.6698	66.98%
CYP3A4 substrate	-	0.5247	52.47%
CYP2C9 substrate	-	0.6124	61.24%
CYP2D6 substrate	-	0.8374	83.74%
CYP3A4 inhibition	-	0.8748	87.48%
CYP2C9 inhibition	-	0.7451	74.51%
CYP2C19 inhibition	-	0.8790	87.90%
CYP2D6 inhibition	-	0.5735	57.35%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	-	0.9504	95.04%
CYP inhibitory promiscuity	-	0.8621	86.21%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.7371	73.71%
Eye corrosion	-	0.9818	98.18%
Eye irritation	-	0.8364	83.64%
Skin irritation	-	0.9023	90.23%
Skin corrosion	-	0.9874	98.74%
Ames mutagenesis	-	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5316	53.16%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	-	0.6209	62.09%
skin sensitisation	-	0.9157	91.57%
Respiratory toxicity	-	0.8222	82.22%
Reproductive toxicity	-	0.7131	71.31%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	+	0.6448	64.48%
Acute Oral Toxicity (c)	III	0.6594	65.94%
Estrogen receptor binding	+	0.6650	66.50%
Androgen receptor binding	-	0.7930	79.30%
Thyroid receptor binding	-	0.5479	54.79%
Glucocorticoid receptor binding	+	0.5910	59.10%
Aromatase binding	-	0.4879	48.79%
PPAR gamma	+	0.6115	61.15%
Honey bee toxicity	-	0.9842	98.42%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.6104	61.04%
Fish aquatic toxicity	-	0.6854	68.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.63%	83.82%
CHEMBL2581	P07339	Cathepsin D	98.51%	98.95%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	97.88%	97.29%
CHEMBL230	P35354	Cyclooxygenase-2	97.64%	89.63%
CHEMBL3060	Q9Y345	Glycine transporter 2	97.46%	99.17%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	95.22%	92.86%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.94%	96.09%
CHEMBL299	P17252	Protein kinase C alpha	92.13%	98.03%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	89.33%	92.08%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	89.19%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.04%	93.56%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	88.26%	91.81%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	87.43%	85.94%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.03%	96.47%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.65%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	83.14%	94.73%
CHEMBL5255	O00206	Toll-like receptor 4	82.83%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.35%	91.24%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.57%	95.17%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.24%	100.00%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	81.19%	92.29%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.14%	90.71%
CHEMBL256	P0DMS8	Adenosine A3 receptor	80.68%	95.93%
CHEMBL1944495	P28065	Proteasome subunit beta type-9	80.35%	97.50%

Plants that contains it

• Physalis philadelphica

Cross-Links

• PubChem: 10462091
• LOTUS: LTS0234825
• wikiData: Q27104803