(Z,2R,3S)-N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]-2,3-dihydroxytetracos-17-enamide

Details

• Internal ID: 576363e5-e47c-48c7-a97b-3aaebe391504
• Taxonomy: Lipids and lipid-like molecules > Sphingolipids > Glycosphingolipids
• IUPAC Name: (Z,2R,3S)-N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]-2,3-dihydroxytetracos-17-enamide
• SMILES (Canonical): CCCCCCCCCCCCCCC(C(C(COC1C(C(C(C(O1)CO)O)O)O)NC(=O)C(C(CCCCCCCCCCCCCC=CCCCCCC)O)O)O)O
• SMILES (Isomeric): CCCCCCCCCCCCCC[C@H]([C@H]([C@H](CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)NC(=O)[C@@H]([C@H](CCCCCCCCCCCCC/C=C\CCCCCC)O)O)O)O
• InChI: InChI=1S/C48H93NO11/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-25-27-29-31-33-35-40(52)43(54)47(58)49-38(37-59-48-46(57)45(56)44(55)41(36-50)60-48)42(53)39(51)34-32-30-28-26-24-16-14-12-10-8-6-4-2/h13,15,38-46,48,50-57H,3-12,14,16-37H2,1-2H3,(H,49,58)/b15-13-/t38-,39+,40-,41+,42-,43+,44+,45-,46+,48+/m0/s1
• InChI Key: IUDRSGVTSFBWPF-JEUDDPGJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₉₃NO₁₁
• Molecular Weight: 860.30 g/mol
• Exact Mass: 859.67486278 g/mol
• Topological Polar Surface Area (TPSA): 209.00 Ų
• XlogP: 12.10
• Atomic LogP (AlogP): 7.42
• H-Bond Acceptor: 11
• H-Bond Donor: 9
• Rotatable Bonds: 41

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5955	59.55%
Caco-2	-	0.8629	86.29%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7759	77.59%
OATP2B1 inhibitior	-	0.5669	56.69%
OATP1B1 inhibitior	+	0.8154	81.54%
OATP1B3 inhibitior	+	0.9207	92.07%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8945	89.45%
P-glycoprotein inhibitior	+	0.6849	68.49%
P-glycoprotein substrate	-	0.6002	60.02%
CYP3A4 substrate	+	0.6507	65.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8690	86.90%
CYP3A4 inhibition	-	0.7519	75.19%
CYP2C9 inhibition	-	0.9321	93.21%
CYP2C19 inhibition	-	0.9108	91.08%
CYP2D6 inhibition	-	0.8519	85.19%
CYP1A2 inhibition	-	0.8906	89.06%
CYP2C8 inhibition	-	0.6660	66.60%
CYP inhibitory promiscuity	-	0.8718	87.18%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6977	69.77%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9051	90.51%
Skin irritation	-	0.7752	77.52%
Skin corrosion	-	0.9566	95.66%
Ames mutagenesis	-	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7408	74.08%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.7468	74.68%
skin sensitisation	-	0.8711	87.11%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.4564	45.64%
Acute Oral Toxicity (c)	III	0.6652	66.52%
Estrogen receptor binding	+	0.7673	76.73%
Androgen receptor binding	+	0.5231	52.31%
Thyroid receptor binding	-	0.5936	59.36%
Glucocorticoid receptor binding	+	0.5434	54.34%
Aromatase binding	+	0.6426	64.26%
PPAR gamma	+	0.6415	64.15%
Honey bee toxicity	-	0.8879	88.79%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5626	56.26%
Fish aquatic toxicity	-	0.4245	42.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	98.64%	99.17%
CHEMBL2581	P07339	Cathepsin D	98.63%	98.95%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	97.62%	97.29%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.27%	96.09%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	96.12%	92.86%
CHEMBL3359	P21462	Formyl peptide receptor 1	93.41%	93.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.11%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	92.18%	83.82%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	92.04%	92.08%
CHEMBL5255	O00206	Toll-like receptor 4	91.51%	92.50%
CHEMBL3401	O75469	Pregnane X receptor	90.99%	94.73%
CHEMBL4227	P25090	Lipoxin A4 receptor	90.63%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.73%	96.00%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	88.08%	85.94%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.62%	91.24%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	87.58%	95.58%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	87.52%	82.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.17%	94.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.80%	96.47%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.56%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.15%	89.34%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	84.85%	91.81%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.16%	96.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.97%	95.89%
CHEMBL4588	P22894	Matrix metalloproteinase 8	82.40%	94.66%
CHEMBL230	P35354	Cyclooxygenase-2	82.28%	89.63%
CHEMBL2514	O95665	Neurotensin receptor 2	82.15%	100.00%
CHEMBL2094135	Q96BI3	Gamma-secretase	81.59%	98.05%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.44%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.12%	89.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162959308
• LOTUS: LTS0144782
• wikiData: Q105120497