Alpha-Galactosylceramide

Details

• Internal ID: 1637b5b1-2476-4c12-af48-f4ff47a95641
• Taxonomy: Lipids and lipid-like molecules > Sphingolipids > Glycosphingolipids
• IUPAC Name: N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide
• InChI: InChI=1S/C50H99NO9/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-45(54)51-42(41-59-50-49(58)48(57)47(56)44(40-52)60-50)46(55)43(53)38-36-34-32-30-28-16-14-12-10-8-6-4-2/h42-44,46-50,52-53,55-58H,3-41H2,1-2H3,(H,51,54)/t42-,43+,44+,46-,47-,48-,49+,50-/m0/s1
• InChI Key: VQFKFAKEUMHBLV-BYSUZVQFSA-N
• Popularity: 856 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₉₉NO₉
• Molecular Weight: 858.30 g/mol
• Exact Mass: 857.73198374 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: 16.00
• Atomic LogP (AlogP): 10.48
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 44

Synonyms

• alpha-GalCer
• alpha-Galactosyl Ceramide
• DTXSID40935847
• CHEBI:466659
• WX671898JF
• RGI-7000
• a-GalCer
• CHEBI:132148
• N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide
• N-((2S,3S,4R)-3,4-dihydroxy-1-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoctadecan-2-yl)hexacosanamide
• Alpha Galactosylceramide
• RefChem:794363
• DTXCID601766457
• 973-258-3
• 158021-47-7
• KRN7000
• Krn 7000
• Krn-7000
• .alpha.-galcer
• CCRIS 8968
• MFCD00939559
• AGL-582
• Galalpha-Cer(t18:0/26:0)
• 1-O-(alpha-D-galactosyl)-N-hexacosanoylphytosphingosine
• N-((2S,3S,4R)-3,4-dihydroxy-1-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)octadecan-2-yl)hexacosanamide
• 1-O-(alpha-D-galactopyranosyl)-N-hexacosanoylphytosphingosine
• N-[(2S,3S,4R)-1-(alpha-D-galactopyranosyloxy)-3,4-dihydroxyoctadecan-2-yl]hexacosanamide
• N-{(1S,2R,3S)-1-[(ALPHA-D-GALACTOPYRANOSYLOXY)METHYL]-2,3-DIHYDROXYHEPTADECYL}HEXACOSANAMIDE
• |A-Galactosylceramide
• C50H99NO9
• (2S,3S,4R)-1-O-(alpha-D-galactosyl)-N-hexacosanoyl-2-amino-1,3,4-octadecanetriol
• -Galactosylceramide
• a-Gal-Cer
• A-GALACTOSYLCERAMIDE
• UNII-WX671898JF
• VQFKFAKEUMHBLV-BYSUZVQFSA-N
• RGI-2001
• ??-Galactosylceramide
• |A-Galactosyl Ceramide
• alpha-GC(C26)
• alpha-GC (C26)
• -GalCer;KRN7000
• Epitope ID:130694
• Epitope ID:738312
• SCHEMBL512949
• CHEMBL384200
• orb1707685
• alpha-GalCer(t18:0/26:0)
• CHEMID158021477
• GLXC-20229
• GLXC-26234
• EX-A5755
• AKOS040741093
• DB12232
• MG15978
• AC-31508
• DA-49185
• NS00073040
• C16892
• alpha-Galactosylceramide(a-Gal-Cer) (synthetic)
• |A-Galactosyl Ceramide Supplier: Funakoshi Co. Ltd.
• Q27105159
• N-[(1S,2S,3R)-1-[(a-D-Galactopyranosyloxy)methyl]-2,3-dihydroxyheptadecyl]hexacosanamide
• (2S,3S,4R)-1-O-(alpha-D-Galactosyl)-N-hexacosanoyl-2-amino-1,3,4-octadecanetriol, >=95% (TLC)
• HEXACOSANAMIDE, N-((1S,2S,3R)-1-((.ALPHA.-D-GALACTOPYRANOSYLOXY)METHYL)-2,3-DIHYDROXYHEPTADECYL)-
• Hexacosanamide, N-(1-((alpha-D-galactopyranosyloxy)methyl)-2,3-dihdyroxyheptadecyl)-, (1S-(1R*,2R*,3S*))-
• hexacosanamide, N-[(1S,2S,3R)-1-[(alpha-D-galactopyranosyloxy)methyl]-2,3-dihydroxyheptadecyl]-
• Hexacosanamide, N-[(1S,2S,3R)-1-[(alpha-D-galactopyranosyloxy)methyl]-2,3-dihydroxyheptadecyl]- (9CI)
• Hexacosanamide, N-[1-[(alpha-D-galactopyranosyloxy)methyl]-2,3-dihydroxyheptadecyl]-, [1S-(1R*,2R*,3S*)]-
• N-((2S,3S,4R)-3,4-dihydroxy-1-(3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)octadecan-2-yl)hexaicosanamide
• N-[(1S,2S,3R)-2,3-dihydroxy-1-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]heptadecyl]hexacosanamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6881	68.81%
Caco-2	-	0.8593	85.93%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7698	76.98%
OATP2B1 inhibitior	-	0.5589	55.89%
OATP1B1 inhibitior	+	0.8787	87.87%
OATP1B3 inhibitior	+	0.9204	92.04%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8112	81.12%
P-glycoprotein inhibitior	+	0.6605	66.05%
P-glycoprotein substrate	-	0.6460	64.60%
CYP3A4 substrate	+	0.6273	62.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8733	87.33%
CYP3A4 inhibition	-	0.8312	83.12%
CYP2C9 inhibition	-	0.9349	93.49%
CYP2C19 inhibition	-	0.9192	91.92%
CYP2D6 inhibition	-	0.8712	87.12%
CYP1A2 inhibition	-	0.9021	90.21%
CYP2C8 inhibition	-	0.8029	80.29%
CYP inhibitory promiscuity	-	0.8912	89.12%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7091	70.91%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.8972	89.72%
Skin irritation	-	0.8013	80.13%
Skin corrosion	-	0.9615	96.15%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3946	39.46%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8811	88.11%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.6408	64.08%
Acute Oral Toxicity (c)	III	0.6707	67.07%
Estrogen receptor binding	+	0.7481	74.81%
Androgen receptor binding	-	0.6876	68.76%
Thyroid receptor binding	-	0.5782	57.82%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6387	63.87%
PPAR gamma	+	0.6449	64.49%
Honey bee toxicity	-	0.9047	90.47%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5239	52.39%
Fish aquatic toxicity	-	0.6228	62.28%

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	99.62%	83.82%
CHEMBL2581	P07339	Cathepsin D	98.55%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	98.50%	99.17%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	97.45%	97.29%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.48%	96.09%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	95.07%	92.86%
CHEMBL5255	O00206	Toll-like receptor 4	94.76%	92.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.19%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	91.80%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.66%	93.56%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	90.61%	92.08%
CHEMBL230	P35354	Cyclooxygenase-2	90.56%	89.63%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	89.73%	85.94%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.86%	96.47%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.82%	91.24%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	87.39%	82.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.05%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.24%	96.00%
CHEMBL2094135	Q96BI3	Gamma-secretase	84.51%	98.05%
CHEMBL256	P0DMS8	Adenosine A3 receptor	84.39%	95.93%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.38%	94.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.64%	100.00%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	83.49%	91.81%
CHEMBL299	P17252	Protein kinase C alpha	82.40%	98.03%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.12%	95.89%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	81.58%	95.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.29%	95.50%
CHEMBL2514	O95665	Neurotensin receptor 2	80.64%	100.00%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	80.55%	96.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.47%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.16%	97.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 2826713
• LOTUS: LTS0068802
• wikiData: Q27105159