(2R)-N-[(E,2S,3R)-3,8-dihydroxy-9-methylidene-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadec-4-en-2-yl]-2-hydroxyoctadecanamide

Details

• Internal ID: 5bfab2b6-a35e-4429-a088-e9a557f8cc7c
• Taxonomy: Lipids and lipid-like molecules > Sphingolipids > Glycosphingolipids > Simple glycosylceramides > Glycosyl-N-acylsphingosines
• IUPAC Name: (2R)-N-[(E,2S,3R)-3,8-dihydroxy-9-methylidene-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadec-4-en-2-yl]-2-hydroxyoctadecanamide
• SMILES (Canonical): CCCCCCCCCCCCCCCCC(C(=O)NC(COC1C(C(C(C(O1)CO)O)O)O)C(C=CCCC(C(=C)CCCCCCCCC)O)O)O
• SMILES (Isomeric): CCCCCCCCCCCCCCCC[C@H](C(=O)N[C@@H](COC1C(C(C(C(O1)CO)O)O)O)[C@@H](/C=C/CCC(C(=C)CCCCCCCCC)O)O)O
• InChI: InChI=1S/C43H81NO10/c1-4-6-8-10-12-13-14-15-16-17-18-20-22-24-30-37(48)42(52)44-34(32-53-43-41(51)40(50)39(49)38(31-45)54-43)36(47)29-26-25-28-35(46)33(3)27-23-21-19-11-9-7-5-2/h26,29,34-41,43,45-51H,3-25,27-28,30-32H2,1-2H3,(H,44,52)/b29-26+/t34-,35?,36+,37+,38?,39?,40?,41?,43?/m0/s1
• InChI Key: YGHZUFAKQVBOFS-ZIXZZZIXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₈₁NO₁₀
• Molecular Weight: 772.10 g/mol
• Exact Mass: 771.58604778 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: 10.30
• Atomic LogP (AlogP): 6.28
• H-Bond Acceptor: 10
• H-Bond Donor: 8
• Rotatable Bonds: 35

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5456	54.56%
Caco-2	-	0.8727	87.27%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7482	74.82%
OATP2B1 inhibitior	-	0.5695	56.95%
OATP1B1 inhibitior	+	0.8376	83.76%
OATP1B3 inhibitior	+	0.9273	92.73%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7819	78.19%
P-glycoprotein inhibitior	+	0.6673	66.73%
P-glycoprotein substrate	-	0.5758	57.58%
CYP3A4 substrate	+	0.6650	66.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8690	86.90%
CYP3A4 inhibition	-	0.6415	64.15%
CYP2C9 inhibition	-	0.8864	88.64%
CYP2C19 inhibition	-	0.8301	83.01%
CYP2D6 inhibition	-	0.8286	82.86%
CYP1A2 inhibition	-	0.8271	82.71%
CYP2C8 inhibition	-	0.5736	57.36%
CYP inhibitory promiscuity	-	0.8492	84.92%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6841	68.41%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9090	90.90%
Skin irritation	-	0.7470	74.70%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7656	76.56%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	-	0.7627	76.27%
skin sensitisation	-	0.8522	85.22%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5578	55.78%
Acute Oral Toxicity (c)	III	0.6746	67.46%
Estrogen receptor binding	+	0.7813	78.13%
Androgen receptor binding	+	0.5600	56.00%
Thyroid receptor binding	-	0.5717	57.17%
Glucocorticoid receptor binding	-	0.5315	53.15%
Aromatase binding	+	0.6177	61.77%
PPAR gamma	+	0.6112	61.12%
Honey bee toxicity	-	0.8172	81.72%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5634	56.34%
Fish aquatic toxicity	+	0.8070	80.70%

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	99.80%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	98.66%	99.17%
CHEMBL2581	P07339	Cathepsin D	98.60%	98.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	97.22%	93.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.40%	96.09%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	96.25%	85.94%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.00%	91.11%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	95.98%	92.08%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	95.67%	92.86%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	95.30%	97.29%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	94.54%	91.24%
CHEMBL5255	O00206	Toll-like receptor 4	94.38%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	91.69%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.55%	96.47%
CHEMBL3401	O75469	Pregnane X receptor	90.32%	94.73%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	90.06%	94.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.45%	97.25%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	89.27%	82.50%
CHEMBL230	P35354	Cyclooxygenase-2	88.00%	89.63%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.92%	92.88%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.88%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.72%	96.61%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.30%	96.00%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	85.82%	92.32%
CHEMBL2514	O95665	Neurotensin receptor 2	83.05%	100.00%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	82.82%	91.81%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.79%	89.34%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.96%	95.50%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	81.41%	95.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.29%	91.19%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.07%	96.21%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	80.94%	96.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.83%	95.89%
CHEMBL3776	Q14790	Caspase-8	80.10%	97.06%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.07%	96.90%

Plants that contains it

• Azadirachta indica
• Owenia cepiodora

Cross-Links

• PubChem: 139584286
• LOTUS: LTS0184226
• wikiData: Q105103321