(2R)-N-[(Z,2S,3S,4R)-1-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxydocos-9-en-2-yl]-2-hydroxyhexadecanamide

Details

• Internal ID: c7a3a1f8-61e1-4c17-8cac-663faff14742
• Taxonomy: Lipids and lipid-like molecules > Sphingolipids > Glycosphingolipids
• IUPAC Name: (2R)-N-[(Z,2S,3S,4R)-1-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxydocos-9-en-2-yl]-2-hydroxyhexadecanamide
• SMILES (Canonical): CCCCCCCCCCCCCCC(C(=O)NC(COC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)O)O)O)O)O)C(C(CCCCC=CCCCCCCCCCCCC)O)O)O
• SMILES (Isomeric): CCCCCCCCCCCCCC[C@H](C(=O)N[C@@H](CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)O)O)[C@@H]([C@@H](CCCC/C=C\CCCCCCCCCCCC)O)O)O
• InChI: InChI=1S/C50H95NO15/c1-3-5-7-9-11-13-15-17-18-19-20-22-23-25-27-29-31-37(54)41(56)36(51-48(62)38(55)32-30-28-26-24-21-16-14-12-10-8-6-4-2)35-63-49-46(61)44(59)47(40(34-53)65-49)66-50-45(60)43(58)42(57)39(33-52)64-50/h22-23,36-47,49-50,52-61H,3-21,24-35H2,1-2H3,(H,51,62)/b23-22-/t36-,37+,38+,39+,40+,41-,42-,43-,44+,45+,46+,47+,49+,50-/m0/s1
• InChI Key: VAASXCGSKSOGMU-KJOKYILOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₉₅NO₁₅
• Molecular Weight: 950.30 g/mol
• Exact Mass: 949.67017132 g/mol
• Topological Polar Surface Area (TPSA): 268.00 Ų
• XlogP: 9.00
• Atomic LogP (AlogP): 4.71
• H-Bond Acceptor: 15
• H-Bond Donor: 11
• Rotatable Bonds: 40

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6705	67.05%
Caco-2	-	0.8718	87.18%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7539	75.39%
OATP2B1 inhibitior	-	0.5729	57.29%
OATP1B1 inhibitior	+	0.8288	82.88%
OATP1B3 inhibitior	+	0.9128	91.28%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9036	90.36%
P-glycoprotein inhibitior	+	0.6957	69.57%
P-glycoprotein substrate	-	0.5393	53.93%
CYP3A4 substrate	+	0.6793	67.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8690	86.90%
CYP3A4 inhibition	-	0.7109	71.09%
CYP2C9 inhibition	-	0.9315	93.15%
CYP2C19 inhibition	-	0.9126	91.26%
CYP2D6 inhibition	-	0.8447	84.47%
CYP1A2 inhibition	-	0.9178	91.78%
CYP2C8 inhibition	-	0.5825	58.25%
CYP inhibitory promiscuity	-	0.8395	83.95%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6595	65.95%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9061	90.61%
Skin irritation	-	0.7713	77.13%
Skin corrosion	-	0.9515	95.15%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7641	76.41%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.7450	74.50%
skin sensitisation	-	0.8792	87.92%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.6910	69.10%
Acute Oral Toxicity (c)	III	0.6834	68.34%
Estrogen receptor binding	+	0.7962	79.62%
Androgen receptor binding	+	0.5731	57.31%
Thyroid receptor binding	-	0.5852	58.52%
Glucocorticoid receptor binding	-	0.4776	47.76%
Aromatase binding	+	0.6067	60.67%
PPAR gamma	+	0.6791	67.91%
Honey bee toxicity	-	0.8022	80.22%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5902	59.02%
Fish aquatic toxicity	+	0.6828	68.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	98.92%	97.29%
CHEMBL3060	Q9Y345	Glycine transporter 2	98.55%	99.17%
CHEMBL2581	P07339	Cathepsin D	98.39%	98.95%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	97.08%	92.86%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.50%	96.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	95.43%	93.56%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	93.98%	95.58%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.69%	91.11%
CHEMBL5255	O00206	Toll-like receptor 4	93.20%	92.50%
CHEMBL3401	O75469	Pregnane X receptor	92.45%	94.73%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	92.14%	92.08%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.62%	91.24%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	90.36%	94.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.28%	96.47%
CHEMBL4227	P25090	Lipoxin A4 receptor	90.27%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.26%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.68%	96.00%
CHEMBL2094135	Q96BI3	Gamma-secretase	85.89%	98.05%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	85.76%	85.94%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	84.85%	91.81%
CHEMBL4040	P28482	MAP kinase ERK2	84.02%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.89%	89.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	83.50%	95.71%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.21%	82.50%
CHEMBL4588	P22894	Matrix metalloproteinase 8	82.15%	94.66%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.97%	96.38%
CHEMBL2514	O95665	Neurotensin receptor 2	81.89%	100.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.86%	92.88%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.43%	89.34%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	81.40%	97.47%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	80.56%	92.32%
CHEMBL3891	P07384	Calpain 1	80.51%	93.04%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11125896
• LOTUS: LTS0066159
• wikiData: Q105282586