Psychosine

Details

• Internal ID: 1f8febb1-ddcb-4ccb-8a40-210d8ae201b2
• Taxonomy: Lipids and lipid-like molecules > Sphingolipids > Glycosphingolipids
• IUPAC Name: (2R,3R,4S,5R,6R)-2-[(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• InChI: InChI=1S/C24H47NO7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)18(25)17-31-24-23(30)22(29)21(28)20(16-26)32-24/h14-15,18-24,26-30H,2-13,16-17,25H2,1H3/b15-14+/t18-,19+,20+,21-,22-,23+,24+/m0/s1
• InChI Key: HHJTWTPUPVQKNA-PIIMIWFASA-N
• Popularity: 397 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₄₇NO₇
• Molecular Weight: 461.60 g/mol
• Exact Mass: 461.33525284 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 1.75
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 18

Synonyms

• Galactosylsphingosine
• 2238-90-6
• Sphingosine galactoside
• 1-beta-D-galactosphingosine
• 1-beta-D-Galactosylsphingosine
• erythro-Psychosine
• O-Galactosylsphingosine
• CHEBI:16874
• 1-O-beta-D-galactosylsphingosine
• 1-O-beta-D-galactopyranosylsphingosine
• (2R,3R,4S,5R,6R)-2-[(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• (2S,3R,4E)-2-amino-1-(beta-D-galactopyranosyloxy)-3-hydroxyoctadec-4-ene
• beta-D-Galactopyranoside, 2-amino-3-hydroxy-4-octadecenyl, (R-(R*,S*-(E)))-
• beta-psychosine
• Epitope ID:151082
• SCHEMBL242696
• BG5A25U68L
• GTPL5548
• ?-Galactosyl erythro-Sphingosine
• 1-beta-D-galactosyl-sphing-4-enine
• AKOS037645023
• AS-56228
• HY-136490
• CS-0129786
• C01747
• 2-amino-3-hydroxy-4-octadecenyl Galactopyranoside
• Galactopyranoside, 2-amino-3-hydroxy-4-octadecenyl
• Q25106489
• Psychosine from bovine brain, lyophilized powder, >=98% (TLC)
• (2S,3R,4E)-2-Amino-3-hydroxy-4-octadecen-1-yl beta-D-galactopyranoside
• (2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl beta-D-galactopyranoside
• (E)-DL-erythro-b-D-2-amino-3-hydroxy-4-octadecenyl Galactopyranoside
• (E)-DL-erythro-beta-delta-2-amino-3-hydroxy-4-octadecenyl Galactopyranoside
• [R-[R*,S*-(E)]]-2-amino-3-hydroxy-4-octadecenyl b-D-Galactopyranoside
• beta-D-Galactopyranoside, (2S,3R,4E)-2-amino-3-hydroxy-4-octadecen-1-yl
• beta-D-Galactopyranoside, (2S,3R,4E)-2-amino-3-hydroxy-4-octadecenyl
• Galactopyranoside, 2-amino-3-hydroxy-4-octadecenyl, (E)-DL-erythro-beta-D-
• [R-[R*,S*-(E)]]-2-amino-3-hydroxy-4-octadecenyl b-delta-Galactopyranoside
• (2R,3R,4S,5R,6R)-2-[(E)-2-amino-3-hydroxyoctadec-4-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• (2R,3R,4S,5R,6R)-2-[(E,2S,3R)-2-amino-3-hydroxy-octadec-4-enoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6846	68.46%
Caco-2	-	0.8681	86.81%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Lysosomes	0.4906	49.06%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.8581	85.81%
OATP1B3 inhibitior	+	0.9286	92.86%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8892	88.92%
P-glycoprotein inhibitior	-	0.6329	63.29%
P-glycoprotein substrate	-	0.8822	88.22%
CYP3A4 substrate	+	0.5441	54.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7967	79.67%
CYP3A4 inhibition	-	0.8604	86.04%
CYP2C9 inhibition	-	0.9337	93.37%
CYP2C19 inhibition	-	0.8239	82.39%
CYP2D6 inhibition	-	0.7982	79.82%
CYP1A2 inhibition	-	0.8125	81.25%
CYP2C8 inhibition	-	0.7078	70.78%
CYP inhibitory promiscuity	-	0.9231	92.31%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6748	67.48%
Eye corrosion	-	0.9816	98.16%
Eye irritation	-	0.9494	94.94%
Skin irritation	-	0.7284	72.84%
Skin corrosion	-	0.9223	92.23%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7632	76.32%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8641	86.41%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.7873	78.73%
Acute Oral Toxicity (c)	III	0.6523	65.23%
Estrogen receptor binding	+	0.5814	58.14%
Androgen receptor binding	-	0.6264	62.64%
Thyroid receptor binding	-	0.5721	57.21%
Glucocorticoid receptor binding	-	0.6143	61.43%
Aromatase binding	+	0.5524	55.24%
PPAR gamma	+	0.5905	59.05%
Honey bee toxicity	-	0.8835	88.35%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5386	53.86%
Fish aquatic toxicity	-	0.5981	59.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	97.84%	97.29%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.43%	96.09%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	97.18%	92.86%
CHEMBL3060	Q9Y345	Glycine transporter 2	97.08%	99.17%
CHEMBL2581	P07339	Cathepsin D	95.63%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.19%	91.11%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	94.07%	92.08%
CHEMBL3359	P21462	Formyl peptide receptor 1	92.59%	93.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	91.15%	100.00%
CHEMBL2885	P07451	Carbonic anhydrase III	88.98%	87.45%
CHEMBL230	P35354	Cyclooxygenase-2	88.53%	89.63%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	87.97%	85.94%
CHEMBL3401	O75469	Pregnane X receptor	87.43%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.57%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.42%	97.36%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.95%	96.95%
CHEMBL4581	P52732	Kinesin-like protein 1	85.80%	93.18%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.78%	96.47%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	85.31%	95.58%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	85.25%	82.50%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.31%	89.34%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.31%	100.00%
CHEMBL1907	P15144	Aminopeptidase N	82.88%	93.31%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	82.41%	96.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.23%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	82.05%	95.93%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	81.99%	92.32%
CHEMBL2996	Q05655	Protein kinase C delta	81.39%	97.79%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5280458
• LOTUS: LTS0189437
• wikiData: Q25106489