(2S,3S,4R,5R,6R)-3-[(2S,3R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid

Details

• Internal ID: aa67fe20-9156-44e4-8214-09ab563d64ad
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Sugar acids and derivatives > Glucuronic acid derivatives
• IUPAC Name: (2S,3S,4R,5R,6R)-3-[(2S,3R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): CC(=O)NC1CC(C(OC1OC2C(C(C(OC2C(=O)O)O)O)O)CO)O
• SMILES (Isomeric): CC(=O)N[C@@H]1C[C@@H]([C@H](O[C@H]1O[C@H]2[C@@H]([C@H]([C@@H](O[C@@H]2C(=O)O)O)O)O)CO)O
• InChI: InChI=1S/C14H23NO11/c1-4(17)15-5-2-6(18)7(3-16)24-14(5)26-10-8(19)9(20)13(23)25-11(10)12(21)22/h5-11,13-14,16,18-20,23H,2-3H2,1H3,(H,15,17)(H,21,22)/t5-,6+,7-,8-,9-,10+,11+,13-,14+/m1/s1
• InChI Key: WCDDVEOXEIYWFB-VXORFPGASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₃NO₁₁
• Molecular Weight: 381.33 g/mol
• Exact Mass: 381.12711055 g/mol
• Topological Polar Surface Area (TPSA): 195.00 Ų
• XlogP: -3.50
• Atomic LogP (AlogP): -4.13
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

• SCHEMBL20516522

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9706	97.06%
Caco-2	-	0.9267	92.67%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5194	51.94%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.8222	82.22%
OATP1B3 inhibitior	+	0.9383	93.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9829	98.29%
P-glycoprotein inhibitior	-	0.8573	85.73%
P-glycoprotein substrate	-	0.8047	80.47%
CYP3A4 substrate	+	0.6063	60.63%
CYP2C9 substrate	-	0.8069	80.69%
CYP2D6 substrate	-	0.8749	87.49%
CYP3A4 inhibition	-	0.9430	94.30%
CYP2C9 inhibition	-	0.9213	92.13%
CYP2C19 inhibition	-	0.9418	94.18%
CYP2D6 inhibition	-	0.9444	94.44%
CYP1A2 inhibition	-	0.9585	95.85%
CYP2C8 inhibition	-	0.8861	88.61%
CYP inhibitory promiscuity	-	0.8990	89.90%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6437	64.37%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9871	98.71%
Skin irritation	-	0.8302	83.02%
Skin corrosion	-	0.9556	95.56%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4044	40.44%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	-	0.5915	59.15%
skin sensitisation	-	0.9089	90.89%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.6004	60.04%
Acute Oral Toxicity (c)	III	0.5764	57.64%
Estrogen receptor binding	+	0.5459	54.59%
Androgen receptor binding	-	0.5231	52.31%
Thyroid receptor binding	+	0.5444	54.44%
Glucocorticoid receptor binding	-	0.6282	62.82%
Aromatase binding	-	0.5482	54.82%
PPAR gamma	-	0.5365	53.65%
Honey bee toxicity	-	0.6443	64.43%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.8305	83.05%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.78%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.39%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.30%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	89.05%	91.19%
CHEMBL226	P30542	Adenosine A1 receptor	88.81%	95.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.57%	99.17%
CHEMBL2581	P07339	Cathepsin D	86.86%	98.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.53%	94.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.20%	96.95%
CHEMBL1951	P21397	Monoamine oxidase A	83.81%	91.49%
CHEMBL5255	O00206	Toll-like receptor 4	83.18%	92.50%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	82.96%	95.58%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.30%	95.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.28%	91.24%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.34%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	81.08%	94.73%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.61%	89.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.38%	95.83%

Plants that contains it

• Litchi chinensis

Cross-Links

• PubChem: 6852395
• NPASS: NPC215949