2-hydroxy-N-[3-hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8-dien-2-yl]hexadecanamide

Details

• Internal ID: 951eee24-dd85-4300-8cb3-432e8c83d1e4
• Taxonomy: Lipids and lipid-like molecules > Sphingolipids > Glycosphingolipids
• IUPAC Name: 2-hydroxy-N-[3-hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8-dien-2-yl]hexadecanamide
• SMILES (Canonical): CCCCCCCCCCCCCCC(C(=O)NC(COC1C(C(C(C(O1)CO)O)O)O)C(C=CCCC=CCCCCCCCCC)O)O
• SMILES (Isomeric): CCCCCCCCCCCCCCC(C(=O)NC(COC1C(C(C(C(O1)CO)O)O)O)C(C=CCCC=CCCCCCCCCC)O)O
• InChI: InChI=1S/C40H75NO9/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-33(43)32(31-49-40-38(47)37(46)36(45)35(30-42)50-40)41-39(48)34(44)29-27-25-23-21-18-16-14-12-10-8-6-4-2/h19-20,26,28,32-38,40,42-47H,3-18,21-25,27,29-31H2,1-2H3,(H,41,48)
• InChI Key: HOMYIYLRRDTKAA-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₇₅NO₉
• Molecular Weight: 714.00 g/mol
• Exact Mass: 713.54418297 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: 9.60
• Atomic LogP (AlogP): 6.13
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 32

Synonyms

• Glucosylceramide (plant)
• B0005-189738

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5446	54.46%
Caco-2	-	0.8690	86.90%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7599	75.99%
OATP2B1 inhibitior	-	0.5685	56.85%
OATP1B1 inhibitior	+	0.8186	81.86%
OATP1B3 inhibitior	+	0.9225	92.25%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8550	85.50%
P-glycoprotein inhibitior	+	0.6453	64.53%
P-glycoprotein substrate	-	0.6545	65.45%
CYP3A4 substrate	+	0.6495	64.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8690	86.90%
CYP3A4 inhibition	-	0.6831	68.31%
CYP2C9 inhibition	-	0.9257	92.57%
CYP2C19 inhibition	-	0.8752	87.52%
CYP2D6 inhibition	-	0.8066	80.66%
CYP1A2 inhibition	-	0.8743	87.43%
CYP2C8 inhibition	-	0.6327	63.27%
CYP inhibitory promiscuity	-	0.8687	86.87%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7098	70.98%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9140	91.40%
Skin irritation	-	0.7583	75.83%
Skin corrosion	-	0.9553	95.53%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7584	75.84%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	-	0.8450	84.50%
skin sensitisation	-	0.8789	87.89%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.4750	47.50%
Acute Oral Toxicity (c)	III	0.6732	67.32%
Estrogen receptor binding	+	0.7537	75.37%
Androgen receptor binding	-	0.5343	53.43%
Thyroid receptor binding	-	0.5962	59.62%
Glucocorticoid receptor binding	-	0.5533	55.33%
Aromatase binding	+	0.5485	54.85%
PPAR gamma	+	0.6288	62.88%
Honey bee toxicity	-	0.8637	86.37%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.5671	56.71%
Fish aquatic toxicity	-	0.4074	40.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.87%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	98.71%	99.17%
CHEMBL3359	P21462	Formyl peptide receptor 1	97.39%	93.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.85%	96.09%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	96.63%	92.86%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	96.57%	97.29%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.60%	91.11%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	93.17%	92.08%
CHEMBL5255	O00206	Toll-like receptor 4	92.49%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.79%	91.24%
CHEMBL3401	O75469	Pregnane X receptor	90.98%	94.73%
CHEMBL4227	P25090	Lipoxin A4 receptor	90.51%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	90.23%	94.33%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	89.94%	85.94%
CHEMBL221	P23219	Cyclooxygenase-1	89.76%	90.17%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.66%	96.47%
CHEMBL230	P35354	Cyclooxygenase-2	89.30%	89.63%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	89.17%	91.81%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.42%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.55%	96.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.80%	96.95%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	86.79%	82.50%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.18%	89.34%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.78%	92.88%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	84.17%	92.32%
CHEMBL2514	O95665	Neurotensin receptor 2	83.12%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.68%	91.19%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	82.67%	97.47%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.38%	89.50%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	81.73%	96.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.52%	97.21%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.55%	95.50%

Plants that contains it

• Allium sativum
• Capsicum annuum
• Dactylorhiza hatagirea
• Datura metel
• Dimocarpus fumatus
• Euphorbia nicaeensis
• Euphorbia platyphyllos
• Prunus dulcis
• Rosa chinensis var. spontanea
• Rourea minor

Cross-Links

• PubChem: 73156994
• LOTUS: LTS0121977
• wikiData: Q104399648