(1R,2S,3S,5S)-2-hydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-oxabicyclo[3.1.0]hexane-3-carbonitrile

Details

• Internal ID: e8c33d14-0f7d-4963-88c5-0e2f68eba6cd
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Cyanogenic glycosides
• IUPAC Name: (1R,2S,3S,5S)-2-hydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-oxabicyclo[3.1.0]hexane-3-carbonitrile
• InChI: InChI=1S/C12H17NO8/c13-3-12(1-4-9(19-4)10(12)18)21-11-8(17)7(16)6(15)5(2-14)20-11/h4-11,14-18H,1-2H2/t4-,5+,6+,7-,8+,9-,10-,11+,12-/m0/s1
• InChI Key: FNRGBSSYFROMOQ-MJSMJDDCSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₇NO₈
• Molecular Weight: 303.26 g/mol
• Exact Mass: 303.09541650 g/mol
• Topological Polar Surface Area (TPSA): 156.00 Ų
• XlogP: -2.60
• Atomic LogP (AlogP): -3.40
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9031	90.31%
Caco-2	-	0.9108	91.08%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5336	53.36%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.9250	92.50%
OATP1B3 inhibitior	+	0.9469	94.69%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9561	95.61%
P-glycoprotein inhibitior	-	0.9233	92.33%
P-glycoprotein substrate	-	0.9563	95.63%
CYP3A4 substrate	+	0.5456	54.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8122	81.22%
CYP3A4 inhibition	-	0.8754	87.54%
CYP2C9 inhibition	-	0.8689	86.89%
CYP2C19 inhibition	-	0.8261	82.61%
CYP2D6 inhibition	-	0.9210	92.10%
CYP1A2 inhibition	-	0.8427	84.27%
CYP2C8 inhibition	-	0.7724	77.24%
CYP inhibitory promiscuity	-	0.8511	85.11%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6413	64.13%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9709	97.09%
Skin irritation	-	0.8102	81.02%
Skin corrosion	-	0.9421	94.21%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4735	47.35%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8517	85.17%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.5637	56.37%
Acute Oral Toxicity (c)	III	0.4641	46.41%
Estrogen receptor binding	-	0.7995	79.95%
Androgen receptor binding	-	0.6888	68.88%
Thyroid receptor binding	+	0.6515	65.15%
Glucocorticoid receptor binding	+	0.5562	55.62%
Aromatase binding	+	0.6112	61.12%
PPAR gamma	+	0.5783	57.83%
Honey bee toxicity	-	0.5712	57.12%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6950	69.50%
Fish aquatic toxicity	-	0.9196	91.96%

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	97.19%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.46%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.82%	97.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	90.55%	95.83%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.56%	86.92%
CHEMBL221	P23219	Cyclooxygenase-1	86.79%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.71%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	84.20%	95.93%
CHEMBL1871	P10275	Androgen Receptor	83.87%	96.43%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.67%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.14%	95.89%

Plants that contains it

• Passiflora suberosa

Cross-Links

• PubChem: 162821264
• LOTUS: LTS0143843
• wikiData: Q104998460