[(1S,2S)-2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethyl]beta-D-glucopyranoside

Details

• Internal ID: bdc0f1b4-991e-4375-b313-f4c8ce80cae9
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(1S,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)C(C(CO)OC2C(C(C(C(O2)CO)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)[C@@H]([C@H](CO)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O
• InChI: InChI=1S/C16H24O10/c1-24-9-4-7(2-3-8(9)19)12(20)10(5-17)25-16-15(23)14(22)13(21)11(6-18)26-16/h2-4,10-23H,5-6H2,1H3/t10-,11+,12-,13+,14-,15+,16+/m0/s1
• InChI Key: UKYKCLFPJXHNON-ZWMPHZAGSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₁₀
• Molecular Weight: 376.36 g/mol
• Exact Mass: 376.13694696 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.39
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• [(1S,2S)-2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethyl]beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8407	84.07%
Caco-2	-	0.8820	88.20%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6129	61.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8817	88.17%
OATP1B3 inhibitior	+	0.9682	96.82%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9280	92.80%
P-glycoprotein inhibitior	-	0.9209	92.09%
P-glycoprotein substrate	-	0.8148	81.48%
CYP3A4 substrate	-	0.5095	50.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7966	79.66%
CYP3A4 inhibition	-	0.9135	91.35%
CYP2C9 inhibition	-	0.8692	86.92%
CYP2C19 inhibition	-	0.8622	86.22%
CYP2D6 inhibition	-	0.9229	92.29%
CYP1A2 inhibition	-	0.8887	88.87%
CYP2C8 inhibition	-	0.7151	71.51%
CYP inhibitory promiscuity	-	0.6649	66.49%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6491	64.91%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9476	94.76%
Skin irritation	-	0.8386	83.86%
Skin corrosion	-	0.9583	95.83%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6653	66.53%
Micronuclear	-	0.5841	58.41%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8703	87.03%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.8924	89.24%
Acute Oral Toxicity (c)	III	0.7549	75.49%
Estrogen receptor binding	-	0.5451	54.51%
Androgen receptor binding	-	0.6212	62.12%
Thyroid receptor binding	+	0.5825	58.25%
Glucocorticoid receptor binding	-	0.5574	55.74%
Aromatase binding	-	0.5276	52.76%
PPAR gamma	-	0.5500	55.00%
Honey bee toxicity	-	0.8246	82.46%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	-	0.6613	66.13%

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	98.99%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.05%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.34%	85.14%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	92.42%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.53%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.98%	96.00%
CHEMBL2581	P07339	Cathepsin D	88.74%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.52%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.53%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.75%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	84.39%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.32%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.70%	86.92%
CHEMBL4208	P20618	Proteasome component C5	82.69%	90.00%
CHEMBL1255126	O15151	Protein Mdm4	81.45%	90.20%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.18%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.14%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.01%	89.00%

Plants that contains it

• Alcea rosea
• Alpinia roxburghii
• Balanops australiana
• Davallia perdurans
• Euonymus tingens
• Euphorbia cornigera
• Gonzalezia decurrens
• Hylocomium splendens
• Iodes cirrhosa
• Kokoona reflexa
• Maesa ramentacea
• Miliusa balansae
• Millettia laurentii
• Monodora tenuifolia
• Ocimum tenuiflorum
• Pinus strobus
• Pinus sylvestris
• Pluchea odorata
• Salacia lehmbachii
• Salvia yosgadensis
• Sideritis brevibracteata
• Sideroxylon cubense

Cross-Links

• PubChem: 44577289
• NPASS: NPC65942
• LOTUS: LTS0268762
• wikiData: Q105274972