(6R)-5-(acetylamino)-3,5-dideoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-beta-L-threo-hex-2-ulopyranonosyl-(2->6)-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranose

Details

• Internal ID: 4dda5789-18d1-4a22-b0bd-0e8180c12fe4
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > N-acylneuraminic acids and derivatives > N-acylneuraminic acids
• IUPAC Name: (2R,4S,5R,6R)-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-2-[[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-2-yl]methoxy]oxane-2-carboxylic acid
• SMILES (Canonical): CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)OCC2C(C(C(C(O2)OC3C(OC(C(C3O)O)O)CO)O)O)O)O
• SMILES (Isomeric): CC(=O)N[C@@H]1[C@H](C[C@@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)O)OC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)O)O)CO)O)O)O)O
• InChI: InChI=1S/C23H39NO19/c1-6(27)24-11-7(28)2-23(22(37)38,43-19(11)12(30)8(29)3-25)39-5-10-13(31)14(32)17(35)21(41-10)42-18-9(4-26)40-20(36)16(34)15(18)33/h7-21,25-26,28-36H,2-5H2,1H3,(H,24,27)(H,37,38)/t7-,8+,9+,10+,11+,12+,13-,14-,15+,16+,17+,18+,19+,20+,21-,23+/m0/s1
• InChI Key: TYALNJQZQRNQNQ-JLYOMPFMSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₉NO₁₉
• Molecular Weight: 633.60 g/mol
• Exact Mass: 633.21162801 g/mol
• Topological Polar Surface Area (TPSA): 335.00 Ų
• XlogP: -7.80
• Atomic LogP (AlogP): -8.22
• H-Bond Acceptor: 18
• H-Bond Donor: 13
• Rotatable Bonds: 11

Synonyms

• CHEMBL3764071
• Neu5Acalpha2-6Galbeta1-4Glcbeta
• 6'-SL
• alpha-Neu5Ac-(2->6)-beta-D-Gal-(1->4)-beta-D-Glc
• alpha-Neup5Ac-(2->6)-beta-D-Galp-(1->4)-beta-D-Glcp
• alpha-D-N-acetylneuraminyl-(2->6)-beta-D-galactosyl-(1->4)-beta-D-glucose
• (6R)-5-(acetylamino)-3,5-dideoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-beta-L-threo-hex-2-ulopyranonosyl-(2->6)-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranose
• 5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranonosyl-(2->6)-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranose
• CHEBI:71943
• CHEBI:85039
• BDBM50230649
• Q27454966
• alpha-Neup5Gc-(2->6)-beta-D-Galp-(1->4)-beta-D-Glcp

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9898	98.98%
Caco-2	-	0.9095	90.95%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5760	57.60%
OATP2B1 inhibitior	-	0.7225	72.25%
OATP1B1 inhibitior	+	0.7893	78.93%
OATP1B3 inhibitior	+	0.9477	94.77%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8289	82.89%
P-glycoprotein inhibitior	-	0.5519	55.19%
P-glycoprotein substrate	+	0.5057	50.57%
CYP3A4 substrate	+	0.6686	66.86%
CYP2C9 substrate	-	0.8069	80.69%
CYP2D6 substrate	-	0.8749	87.49%
CYP3A4 inhibition	-	0.9577	95.77%
CYP2C9 inhibition	-	0.9347	93.47%
CYP2C19 inhibition	-	0.9211	92.11%
CYP2D6 inhibition	-	0.9400	94.00%
CYP1A2 inhibition	-	0.9481	94.81%
CYP2C8 inhibition	-	0.6257	62.57%
CYP inhibitory promiscuity	-	0.9221	92.21%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6501	65.01%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9345	93.45%
Skin irritation	-	0.8355	83.55%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7140	71.40%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.6553	65.53%
skin sensitisation	-	0.8993	89.93%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.5971	59.71%
Acute Oral Toxicity (c)	III	0.5343	53.43%
Estrogen receptor binding	+	0.7386	73.86%
Androgen receptor binding	+	0.5548	55.48%
Thyroid receptor binding	-	0.6042	60.42%
Glucocorticoid receptor binding	-	0.4870	48.70%
Aromatase binding	+	0.6364	63.64%
PPAR gamma	+	0.5292	52.92%
Honey bee toxicity	-	0.7382	73.82%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	-	0.8374	83.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.44%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.96%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.42%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.88%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.72%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	89.07%	94.73%
CHEMBL2581	P07339	Cathepsin D	88.40%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.63%	94.45%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.41%	91.24%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.84%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	86.81%	91.19%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.70%	95.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.53%	95.50%
CHEMBL226	P30542	Adenosine A1 receptor	85.20%	95.93%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.92%	96.47%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.65%	95.83%
CHEMBL5255	O00206	Toll-like receptor 4	83.25%	92.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.88%	98.75%
CHEMBL4040	P28482	MAP kinase ERK2	81.66%	83.82%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.38%	97.36%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.96%	82.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.12%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.10%	99.17%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 44611588
• LOTUS: LTS0146390
• wikiData: Q27454966