3'-Sulfogalactosylceramide

Details

• Internal ID: 310c5f7d-28ec-4f47-bf7e-511bb5adaa38
• Taxonomy: Lipids and lipid-like molecules > Sphingolipids > Glycosphingolipids
• IUPAC Name: [(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(E,2S,3R)-3-hydroxy-2-(tetracosanoylamino)octadec-4-enoxy]oxan-4-yl] hydrogen sulfate
• SMILES (Canonical): CCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)O)OS(=O)(=O)O)O)C(C=CCCCCCCCCCCCCC)O
• SMILES (Isomeric): CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)OS(=O)(=O)O)O)[C@@H](/C=C/CCCCCCCCCCCCC)O
• InChI: InChI=1S/C48H93NO11S/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-44(52)49-41(42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2)40-58-48-46(54)47(60-61(55,56)57)45(53)43(39-50)59-48/h35,37,41-43,45-48,50-51,53-54H,3-34,36,38-40H2,1-2H3,(H,49,52)(H,55,56,57)/b37-35+/t41-,42+,43+,45-,46+,47-,48+/m0/s1
• InChI Key: MEAZTWJVOWHKJM-CIAPRIGGSA-N
• Popularity: 18 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₉₃NO₁₁S
• Molecular Weight: 892.30 g/mol
• Exact Mass: 891.64693396 g/mol
• Topological Polar Surface Area (TPSA): 201.00 Ų
• XlogP: 15.20
• Atomic LogP (AlogP): 10.34
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 43

Synonyms

• 3'-Sulfogalactosylceramide
• Sulfoglycosphingolipids
• Tetracosanoyl-sulfatide
• tetracosanoyl sulfatide
• CHEBI:60361
• 3-O-Sulfogalactosylceramide (d18:1/24:0)
• 1-(3-O-sulfo-beta-D-galactosyl)-N-tetracosanoylsphingosine
• Tetracosanamide, N-((1S,2R,3E)-2-hydroxy-1-(((3-O-sulfo-beta-D-galactopyranosyl)oxy)methyl)-3-heptadecenyl)-
• Tetracosanamide, N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-beta-D-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-
• 3' Sulfogalactosylceramide
• Epitope ID:139424
• DTXSID901110847
• AKOS040756332
• [(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(E,2S,3R)-3-hydroxy-2-(tetracosanoylamino)octadec-4-enoxy]oxan-4-yl] hydrogen sulfate
• PD077234
• HY-145535
• CS-0375793
• C24 3'-sulfo Galactosylceramide (d18:1/24:0)
• Q27127214
• [(2R,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2S,3R,4E)-3-hydroxy-2-tetracosanamidooctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid
• [(2R,3S,4S,5R,6R)-3,5-Dihydroxy-2-(hydroxymethyl)-6-[(E,2S,3R)-3-hydroxy-2-(tetracosanoylamino)octadec-4-enoxy]oxan-4-yl]hydrogen sulfate
• [(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(E,2S,3R)-3-hydroxy-2-(tetracosanoylamino)octadec-4-enoxy]tetrahydropyran-4-yl] hydrogen sulfate
• N-[(1S,2R,3E)-2-Hydroxy-1-[[(3-O-sulfo-beta-D-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]tetracosanamide
• N-{(2S,3R,4E)-3-hydroxy-1-[(3-O-sulfo-beta-D-galactopyranosyl)oxy]octadec-4-en-2-yl}tetracosanamide
• Tetracosanamide, N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-b-D-galactopyranosyl)oxy]methyl]-3-heptadecenyl]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6333	63.33%
Caco-2	-	0.8591	85.91%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5194	51.94%
OATP2B1 inhibitior	-	0.5656	56.56%
OATP1B1 inhibitior	+	0.8133	81.33%
OATP1B3 inhibitior	+	0.9259	92.59%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8698	86.98%
P-glycoprotein inhibitior	+	0.7031	70.31%
P-glycoprotein substrate	-	0.5816	58.16%
CYP3A4 substrate	+	0.6497	64.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8645	86.45%
CYP3A4 inhibition	-	0.8275	82.75%
CYP2C9 inhibition	-	0.7941	79.41%
CYP2C19 inhibition	-	0.7427	74.27%
CYP2D6 inhibition	-	0.8777	87.77%
CYP1A2 inhibition	-	0.7937	79.37%
CYP2C8 inhibition	-	0.6278	62.78%
CYP inhibitory promiscuity	-	0.9389	93.89%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.5200	52.00%
Carcinogenicity (trinary)	Non-required	0.6187	61.87%
Eye corrosion	-	0.9753	97.53%
Eye irritation	-	0.9080	90.80%
Skin irritation	-	0.7651	76.51%
Skin corrosion	-	0.9063	90.63%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7833	78.33%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	-	0.7716	77.16%
skin sensitisation	-	0.8211	82.11%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6982	69.82%
Acute Oral Toxicity (c)	III	0.6013	60.13%
Estrogen receptor binding	+	0.7570	75.70%
Androgen receptor binding	-	0.5416	54.16%
Thyroid receptor binding	-	0.6020	60.20%
Glucocorticoid receptor binding	-	0.4635	46.35%
Aromatase binding	+	0.5807	58.07%
PPAR gamma	+	0.6557	65.57%
Honey bee toxicity	-	0.8125	81.25%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5634	56.34%
Fish aquatic toxicity	+	0.9132	91.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.26%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	98.20%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	96.55%	92.50%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	96.25%	97.29%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	94.74%	92.08%
CHEMBL3359	P21462	Formyl peptide receptor 1	94.61%	93.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.52%	96.09%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	94.16%	92.86%
CHEMBL230	P35354	Cyclooxygenase-2	93.86%	89.63%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	92.87%	91.81%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.46%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.41%	96.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	91.78%	94.33%
CHEMBL3401	O75469	Pregnane X receptor	91.52%	94.73%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	91.27%	85.94%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	91.08%	92.88%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	89.33%	82.50%
CHEMBL256	P0DMS8	Adenosine A3 receptor	88.82%	95.93%
CHEMBL340	P08684	Cytochrome P450 3A4	88.50%	91.19%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	87.73%	92.32%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	87.48%	96.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.48%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.09%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.16%	91.24%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.17%	95.50%
CHEMBL4588	P22894	Matrix metalloproteinase 8	84.53%	94.66%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.44%	95.83%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.07%	98.75%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.02%	96.90%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.97%	96.47%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.26%	96.95%

Plants that contains it

• Commelina communis

Cross-Links

• PubChem: 6451121
• NPASS: NPC268593