(2Z)-2-[(2S,3R,4S,6R)-2-hydroxy-3,4-dimethoxy-6-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexylidene]acetonitrile

Details

• Internal ID: bd62af9f-371c-4185-8e7a-eb4edb81393e
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (2Z)-2-[(2S,3R,4S,6R)-2-hydroxy-3,4-dimethoxy-6-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexylidene]acetonitrile
• SMILES (Canonical): COC1CC(C(=CC#N)C(C1OC)O)OC2C(C(C(C(O2)CO)O)O)O
• SMILES (Isomeric): CO[C@H]1C[C@H](/C(=C\C#N)/[C@@H]([C@H]1OC)O)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)CO)O)O)O
• InChI: InChI=1S/C16H25NO9/c1-23-9-5-8(7(3-4-17)11(19)15(9)24-2)25-16-14(22)13(21)12(20)10(6-18)26-16/h3,8-16,18-22H,5-6H2,1-2H3/b7-3+/t8-,9+,10+,11+,12+,13-,14+,15+,16+/m1/s1
• InChI Key: KURSRHBVYUACKS-JICLZLQHSA-N
• Popularity: 21 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₅NO₉
• Molecular Weight: 375.37 g/mol
• Exact Mass: 375.15293138 g/mol
• Topological Polar Surface Area (TPSA): 162.00 Ų
• XlogP: -3.30
• Atomic LogP (AlogP): -2.58
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• CHEMBL2268556

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7373	73.73%
Caco-2	-	0.8824	88.24%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6361	63.61%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.8755	87.55%
OATP1B3 inhibitior	+	0.9519	95.19%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8709	87.09%
P-glycoprotein inhibitior	-	0.8334	83.34%
P-glycoprotein substrate	-	0.8170	81.70%
CYP3A4 substrate	+	0.5968	59.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8350	83.50%
CYP3A4 inhibition	-	0.8074	80.74%
CYP2C9 inhibition	-	0.8414	84.14%
CYP2C19 inhibition	-	0.8185	81.85%
CYP2D6 inhibition	-	0.8808	88.08%
CYP1A2 inhibition	-	0.8180	81.80%
CYP2C8 inhibition	-	0.7970	79.70%
CYP inhibitory promiscuity	-	0.6340	63.40%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7532	75.32%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9820	98.20%
Skin irritation	-	0.8167	81.67%
Skin corrosion	-	0.9594	95.94%
Ames mutagenesis	-	0.5128	51.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.6418	64.18%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8680	86.80%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.5887	58.87%
Acute Oral Toxicity (c)	III	0.6199	61.99%
Estrogen receptor binding	-	0.5300	53.00%
Androgen receptor binding	-	0.6617	66.17%
Thyroid receptor binding	+	0.6261	62.61%
Glucocorticoid receptor binding	-	0.5903	59.03%
Aromatase binding	+	0.5984	59.84%
PPAR gamma	-	0.5391	53.91%
Honey bee toxicity	-	0.6505	65.05%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.6243	62.43%

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	95.95%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.82%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	91.76%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.07%	97.09%
CHEMBL1871	P10275	Androgen Receptor	88.28%	96.43%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.83%	86.92%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.85%	95.83%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.60%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.39%	99.17%

Plants that contains it

• Ehretia philippinensis
• Simmondsia chinensis

Cross-Links

• PubChem: 76308614
• LOTUS: LTS0002839
• wikiData: Q104253427