(2R)-2-(3-hydroxy-4-methoxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile

Details

• Internal ID: 7b7b957d-1f05-4c34-beed-fc17f29b3ec0
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Cyanogenic glycosides
• IUPAC Name: (2R)-2-(3-hydroxy-4-methoxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
• SMILES (Canonical): COC1=C(C=C(C=C1)C(C#N)OC2C(C(C(C(O2)COC3C(C(C(C(O3)CO)O)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)[C@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C21H29NO13/c1-31-10-3-2-8(4-9(10)24)11(5-22)33-21-19(30)17(28)15(26)13(35-21)7-32-20-18(29)16(27)14(25)12(6-23)34-20/h2-4,11-21,23-30H,6-7H2,1H3/t11-,12+,13+,14+,15+,16-,17-,18+,19+,20+,21+/m0/s1
• InChI Key: UCDZCGGWKCRURM-SJLSZISSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₉NO₁₃
• Molecular Weight: 503.50 g/mol
• Exact Mass: 503.16388998 g/mol
• Topological Polar Surface Area (TPSA): 232.00 Ų
• XlogP: -3.10
• Atomic LogP (AlogP): -3.39
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9180	91.80%
Caco-2	-	0.8963	89.63%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5649	56.49%
OATP2B1 inhibitior	-	0.8617	86.17%
OATP1B1 inhibitior	+	0.9023	90.23%
OATP1B3 inhibitior	+	0.9656	96.56%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8273	82.73%
P-glycoprotein inhibitior	-	0.7120	71.20%
P-glycoprotein substrate	-	0.6907	69.07%
CYP3A4 substrate	+	0.5668	56.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8007	80.07%
CYP3A4 inhibition	-	0.8709	87.09%
CYP2C9 inhibition	-	0.8426	84.26%
CYP2C19 inhibition	-	0.8588	85.88%
CYP2D6 inhibition	-	0.8939	89.39%
CYP1A2 inhibition	-	0.8703	87.03%
CYP2C8 inhibition	-	0.5619	56.19%
CYP inhibitory promiscuity	-	0.6256	62.56%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6783	67.83%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9438	94.38%
Skin irritation	-	0.8431	84.31%
Skin corrosion	-	0.9562	95.62%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7900	79.00%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8738	87.38%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.7039	70.39%
Acute Oral Toxicity (c)	III	0.5355	53.55%
Estrogen receptor binding	+	0.7295	72.95%
Androgen receptor binding	-	0.6224	62.24%
Thyroid receptor binding	+	0.5444	54.44%
Glucocorticoid receptor binding	-	0.5805	58.05%
Aromatase binding	+	0.6981	69.81%
PPAR gamma	+	0.6590	65.90%
Honey bee toxicity	-	0.6404	64.04%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6749	67.49%
Fish aquatic toxicity	-	0.8614	86.14%

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	98.53%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.33%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.25%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.67%	86.92%
CHEMBL2581	P07339	Cathepsin D	90.06%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.10%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.90%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.70%	86.33%
CHEMBL2535	P11166	Glucose transporter	86.78%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	86.14%	94.73%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.53%	94.80%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.62%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.31%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.90%	89.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.81%	93.65%
CHEMBL1871	P10275	Androgen Receptor	82.52%	96.43%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.99%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.32%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.18%	95.89%

Plants that contains it

• Hydrangea macrophylla

Cross-Links

• PubChem: 101474173
• LOTUS: LTS0013426
• wikiData: Q105269843