(2S)-2-[(2R,3R,4R,5S,6R)-6-hydroperoxy-3,4,5-trihydroxyoxan-2-yl]oxy-2-(4-hydroxyphenyl)acetonitrile

Details

• Internal ID: c941bb98-3458-4c7e-884b-b3eb38f2d0dd
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (2S)-2-[(2R,3R,4R,5S,6R)-6-hydroperoxy-3,4,5-trihydroxyoxan-2-yl]oxy-2-(4-hydroxyphenyl)acetonitrile
• SMILES (Canonical): C1=CC(=CC=C1C(C#N)OC2C(C(C(C(O2)OO)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)OO)O)O)O)O
• InChI: InChI=1S/C13H15NO8/c14-5-8(6-1-3-7(15)4-2-6)20-12-10(17)9(16)11(18)13(21-12)22-19/h1-4,8-13,15-19H/t8-,9-,10-,11+,12-,13-/m1/s1
• InChI Key: KNDPSAIVRFVRBF-JOLBHGKHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₅NO₈
• Molecular Weight: 313.26 g/mol
• Exact Mass: 313.07976644 g/mol
• Topological Polar Surface Area (TPSA): 153.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.77
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6600	66.00%
Caco-2	-	0.8517	85.17%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5708	57.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8859	88.59%
OATP1B3 inhibitior	+	0.9418	94.18%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9560	95.60%
P-glycoprotein inhibitior	-	0.9088	90.88%
P-glycoprotein substrate	-	0.9335	93.35%
CYP3A4 substrate	-	0.5284	52.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8119	81.19%
CYP3A4 inhibition	-	0.5127	51.27%
CYP2C9 inhibition	-	0.8315	83.15%
CYP2C19 inhibition	-	0.8446	84.46%
CYP2D6 inhibition	-	0.9017	90.17%
CYP1A2 inhibition	-	0.7002	70.02%
CYP2C8 inhibition	-	0.6520	65.20%
CYP inhibitory promiscuity	+	0.5378	53.78%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8909	89.09%
Carcinogenicity (trinary)	Non-required	0.6676	66.76%
Eye corrosion	-	0.9647	96.47%
Eye irritation	-	0.8551	85.51%
Skin irritation	-	0.7168	71.68%
Skin corrosion	-	0.9156	91.56%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5961	59.61%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	-	0.6322	63.22%
skin sensitisation	-	0.7518	75.18%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.6202	62.02%
Acute Oral Toxicity (c)	III	0.6434	64.34%
Estrogen receptor binding	-	0.7923	79.23%
Androgen receptor binding	+	0.5730	57.30%
Thyroid receptor binding	+	0.5962	59.62%
Glucocorticoid receptor binding	+	0.5547	55.47%
Aromatase binding	-	0.5210	52.10%
PPAR gamma	+	0.5224	52.24%
Honey bee toxicity	-	0.4697	46.97%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6450	64.50%
Fish aquatic toxicity	-	0.4153	41.53%

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	97.61%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.42%	96.09%
CHEMBL242	Q92731	Estrogen receptor beta	88.44%	98.35%
CHEMBL2581	P07339	Cathepsin D	87.79%	98.95%
CHEMBL2535	P11166	Glucose transporter	85.74%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	83.30%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.12%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.51%	89.62%

Plants that contains it

• Macadamia ternifolia
• Sorghum bicolor

Cross-Links

• PubChem: 17751003
• NPASS: NPC171156