2-(2'-Hydroxytetracosanoylamino)-octadecane-1,3,4-triol, (2S,3S,4R,2'R)-

Details

• Internal ID: d3d9ff08-f670-4773-b05f-bdd408ecfc28
• Taxonomy: Lipids and lipid-like molecules > Sphingolipids > Ceramides > Phytoceramides
• IUPAC Name: (2R)-2-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]tetracosanamide
• SMILES (Canonical): CCCCCCCCCCCCCCCCCCCCCCC(C(=O)NC(CO)C(C(CCCCCCCCCCCCCC)O)O)O
• SMILES (Isomeric): CCCCCCCCCCCCCCCCCCCCCC[C@H](C(=O)N[C@@H](CO)[C@@H]([C@@H](CCCCCCCCCCCCCC)O)O)O
• InChI: InChI=1S/C42H85NO5/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-40(46)42(48)43-38(37-44)41(47)39(45)35-33-31-29-27-25-16-14-12-10-8-6-4-2/h38-41,44-47H,3-37H2,1-2H3,(H,43,48)/t38-,39+,40+,41-/m0/s1
• InChI Key: ZFUXWVVVWGWGPQ-QLLOZFISSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₈₅NO₅
• Molecular Weight: 684.10 g/mol
• Exact Mass: 683.64277481 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 15.80
• Atomic LogP (AlogP): 10.85
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 39

Synonyms

• 2-(2'-Hydroxytetracosanoylamino)-octadecane-1,3,4-triol
• N-(2R-hydroxytetracosanoyl)-phytoceramide
• WCK3J2NNE4
• 154801-30-6
• (2S,3S,4R,2'R)-2-(2'-Hydroxytetracosanoylamino)-octadecane-1,3,4-triol
• 2-(2'-Hydroxytetracosanoylamino)-octadecane-1,3,4-triol, (2S,3S,4R,2'R)-
• (2S,3S,4R,2'R)-2-(2'-Hydroxytetracosanoylamino)-octadecane-1,3,4-triol, (+)-
• Tetracosanamide, N-((1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadecyl)-2-hydroxy-, (2R)-
• N-(2R-hydroxytetracosanoyl)-4R-hydroxysphinganine
• N-(2R-hydroxytetracosanoyl)-4R-hydroxyl-octadecasphinganine
• (2S,3S,4R)-2-((2'R)-2'-Hydroxytetracosanoylamino)-1,3,4-octadecanetriol
• (2S,3S,4R)-2-[(2'R)-2'-hydroxytetracosanoylamino]-1,3,4-octadecanetriol
• UNII-WCK3J2NNE4
• DTXSID701152146
• LMSP02030026
• AKOS040760971
• FS-10418
• PD071072
• Cer(t18:0/24:0(2OH[R]))
• Cer(t18:0)/24:0(2OH[R]))
• (2R)-N-[(1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadecyl]-2-hydroxy-tetracosanamide
• (2S, 3S, 4R)-2-[(2R)-2-hydroxytetracosanoylamino]-1, 3, 4-octadecanetriol
• N-24:0(2R-OH) Phytosphingosine, N-(2'-(R)-hydroxylignoceroyl)-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	-	0.8569	85.69%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7869	78.69%
OATP2B1 inhibitior	-	0.5650	56.50%
OATP1B1 inhibitior	+	0.9372	93.72%
OATP1B3 inhibitior	+	0.9123	91.23%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9041	90.41%
BSEP inhibitior	+	0.6857	68.57%
P-glycoprotein inhibitior	-	0.4402	44.02%
P-glycoprotein substrate	-	0.6280	62.80%
CYP3A4 substrate	-	0.5125	51.25%
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	-	0.9406	94.06%
CYP inhibitory promiscuity	-	0.8621	86.21%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.7371	73.71%
Eye corrosion	-	0.9818	98.18%
Eye irritation	-	0.8588	85.88%
Skin irritation	-	0.9023	90.23%
Skin corrosion	-	0.9874	98.74%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5339	53.39%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	-	0.6259	62.59%
skin sensitisation	-	0.9157	91.57%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	-	0.7131	71.31%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	+	0.6109	61.09%
Acute Oral Toxicity (c)	III	0.6594	65.94%
Estrogen receptor binding	+	0.6740	67.40%
Androgen receptor binding	-	0.5836	58.36%
Thyroid receptor binding	-	0.5776	57.76%
Glucocorticoid receptor binding	+	0.5724	57.24%
Aromatase binding	+	0.5299	52.99%
PPAR gamma	+	0.5844	58.44%
Honey bee toxicity	-	0.9842	98.42%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5901	59.01%
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	99.48%	83.82%
CHEMBL2581	P07339	Cathepsin D	98.33%	98.95%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	97.92%	97.29%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	96.81%	92.86%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.87%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.69%	99.17%
CHEMBL3359	P21462	Formyl peptide receptor 1	92.41%	93.56%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	89.15%	91.81%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	88.52%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.86%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.40%	91.24%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	85.64%	92.08%
CHEMBL230	P35354	Cyclooxygenase-2	85.53%	89.63%
CHEMBL299	P17252	Protein kinase C alpha	85.20%	98.03%
CHEMBL2885	P07451	Carbonic anhydrase III	84.22%	87.45%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.70%	96.47%
CHEMBL2094135	Q96BI3	Gamma-secretase	83.32%	98.05%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.28%	96.95%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.62%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.30%	94.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.87%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	80.83%	94.73%

Plants that contains it

• Azadirachta indica
• Physalis philadelphica

Cross-Links

• PubChem: 10212035
• LOTUS: LTS0030129
• wikiData: Q105029155