2-[4-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyphenyl]acetonitrile

Details

• Internal ID: 4645136f-5fae-42e3-84a3-57321ea2bf90
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 2-[4-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyphenyl]acetonitrile
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC=C(C=C2)CC#N)O)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC2=CC=C(C=C2)CC#N)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C20H27NO10/c1-9-13(23)18(31-19-16(26)15(25)14(24)12(8-22)30-19)17(27)20(28-9)29-11-4-2-10(3-5-11)6-7-21/h2-5,9,12-20,22-27H,6,8H2,1H3/t9-,12-,13-,14-,15+,16-,17-,18+,19+,20-/m1/s1
• InChI Key: CKIYKMQZQIRHJO-CNTWJFQTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₇NO₁₀
• Molecular Weight: 441.40 g/mol
• Exact Mass: 441.16349606 g/mol
• Topological Polar Surface Area (TPSA): 182.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -2.22
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8086	80.86%
Caco-2	-	0.8673	86.73%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6144	61.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9130	91.30%
OATP1B3 inhibitior	+	0.9578	95.78%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4783	47.83%
P-glycoprotein inhibitior	-	0.7218	72.18%
P-glycoprotein substrate	-	0.8322	83.22%
CYP3A4 substrate	+	0.5864	58.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8157	81.57%
CYP3A4 inhibition	-	0.8286	82.86%
CYP2C9 inhibition	-	0.8600	86.00%
CYP2C19 inhibition	-	0.9143	91.43%
CYP2D6 inhibition	-	0.9138	91.38%
CYP1A2 inhibition	-	0.8943	89.43%
CYP2C8 inhibition	-	0.6554	65.54%
CYP inhibitory promiscuity	-	0.6817	68.17%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6657	66.57%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9643	96.43%
Skin irritation	-	0.8355	83.55%
Skin corrosion	-	0.9628	96.28%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7440	74.40%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8937	89.37%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.7894	78.94%
Acute Oral Toxicity (c)	III	0.6748	67.48%
Estrogen receptor binding	+	0.6074	60.74%
Androgen receptor binding	-	0.6306	63.06%
Thyroid receptor binding	+	0.6367	63.67%
Glucocorticoid receptor binding	-	0.4675	46.75%
Aromatase binding	+	0.6403	64.03%
PPAR gamma	+	0.6705	67.05%
Honey bee toxicity	-	0.5897	58.97%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5850	58.50%
Fish aquatic toxicity	-	0.7683	76.83%

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	96.59%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.89%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.63%	95.93%
CHEMBL2581	P07339	Cathepsin D	93.46%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.79%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.30%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.55%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	89.35%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.92%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.61%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.68%	96.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.12%	95.83%
CHEMBL3401	O75469	Pregnane X receptor	84.84%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.73%	97.36%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	83.29%	83.57%
CHEMBL4208	P20618	Proteasome component C5	82.54%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.18%	97.09%
CHEMBL1944	P08473	Neprilysin	81.18%	92.63%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.09%	94.80%

Plants that contains it

• Calamus draco
• Excoecaria acerifolia
• Garrya laurifolia
• Goupia glabra
• Laggera alata
• Medinilla magnifica
• Mesua ferrea
• Moringa oleifera
• Onobrychis bobrovii
• Papaver persicum
• Petteria ramentacea
• Senecio cathcartensis
• Sequoia sempervirens
• Syncarpha gnaphaloides

Cross-Links

• PubChem: 11419325
• NPASS: NPC244229
• LOTUS: LTS0008238
• wikiData: Q104962401