[(2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (2S)-2-amino-3-(4-hydroxyphenyl)propanoate

Details

• Internal ID: 78721682-e716-4560-9ba7-cfd8cf46fa1e
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Alpha amino acid esters > Alpha-amino acyl ester of carbohydrates
• IUPAC Name: [(2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (2S)-2-amino-3-(4-hydroxyphenyl)propanoate
• SMILES (Canonical): C1=CC(=CC=C1CC(C(=O)OC2C(C(C(OC2OC3(C(C(C(O3)CO)O)O)CO)CO)O)O)N)O
• SMILES (Isomeric): C1=CC(=CC=C1C[C@@H](C(=O)O[C@@H]2[C@H]([C@@H]([C@H](O[C@@H]2O[C@]3([C@H]([C@@H]([C@H](O3)CO)O)O)CO)CO)O)O)N)O
• InChI: InChI=1S/C21H31NO13/c22-11(5-9-1-3-10(26)4-2-9)19(31)33-17-16(29)14(27)12(6-23)32-20(17)35-21(8-25)18(30)15(28)13(7-24)34-21/h1-4,11-18,20,23-30H,5-8,22H2/t11-,12+,13+,14+,15+,16-,17+,18-,20+,21-/m0/s1
• InChI Key: VMEPGASCAOVEGW-YFOMKJGISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₁NO₁₃
• Molecular Weight: 505.50 g/mol
• Exact Mass: 505.17954004 g/mol
• Topological Polar Surface Area (TPSA): 242.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -4.57
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7423	74.23%
Caco-2	-	0.9041	90.41%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Nucleus	0.3425	34.25%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.8700	87.00%
OATP1B3 inhibitior	+	0.9423	94.23%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6957	69.57%
P-glycoprotein inhibitior	-	0.7358	73.58%
P-glycoprotein substrate	-	0.7498	74.98%
CYP3A4 substrate	+	0.6089	60.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8190	81.90%
CYP3A4 inhibition	-	0.9127	91.27%
CYP2C9 inhibition	-	0.9272	92.72%
CYP2C19 inhibition	-	0.8739	87.39%
CYP2D6 inhibition	-	0.8165	81.65%
CYP1A2 inhibition	-	0.8926	89.26%
CYP2C8 inhibition	+	0.5313	53.13%
CYP inhibitory promiscuity	-	0.8249	82.49%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6280	62.80%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.9606	96.06%
Skin irritation	-	0.8061	80.61%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7603	76.03%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8497	84.97%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.8540	85.40%
Acute Oral Toxicity (c)	III	0.5665	56.65%
Estrogen receptor binding	+	0.7315	73.15%
Androgen receptor binding	+	0.5998	59.98%
Thyroid receptor binding	+	0.5172	51.72%
Glucocorticoid receptor binding	+	0.5469	54.69%
Aromatase binding	+	0.6570	65.70%
PPAR gamma	+	0.7564	75.64%
Honey bee toxicity	-	0.6363	63.63%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7250	72.50%
Fish aquatic toxicity	-	0.7979	79.79%

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	98.02%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.26%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.97%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.62%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.33%	99.17%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	90.16%	94.97%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	90.13%	85.00%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	89.96%	97.53%
CHEMBL340	P08684	Cytochrome P450 3A4	89.59%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.30%	97.09%
CHEMBL3437	Q16853	Amine oxidase, copper containing	88.53%	94.00%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	88.40%	92.29%
CHEMBL226	P30542	Adenosine A1 receptor	88.12%	95.93%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	87.45%	89.67%
CHEMBL3401	O75469	Pregnane X receptor	85.44%	94.73%
CHEMBL2514	O95665	Neurotensin receptor 2	84.96%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.90%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.83%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.32%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	84.30%	91.49%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.21%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.89%	95.56%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.66%	93.10%
CHEMBL3891	P07384	Calpain 1	81.45%	93.04%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.73%	94.23%

Plants that contains it

• Ipomoea batatas

Cross-Links

• PubChem: 11843135
• LOTUS: LTS0186615
• wikiData: Q105288953