(1S,4S,5S)-4,5-dihydroxy-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclopent-2-ene-1-carbonitrile

Details

• Internal ID: a3ea138f-81d6-4f22-a2bb-dbd86d66b839
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Cyanogenic glycosides
• IUPAC Name: (1S,4S,5S)-4,5-dihydroxy-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclopent-2-ene-1-carbonitrile
• SMILES (Canonical): C1=C(C(C(C1O)O)C#N)OC2C(C(C(C(O2)CO)O)O)O
• SMILES (Isomeric): C1=C([C@H]([C@@H]([C@H]1O)O)C#N)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O
• InChI: InChI=1S/C12H17NO8/c13-2-4-6(1-5(15)8(4)16)20-12-11(19)10(18)9(17)7(3-14)21-12/h1,4-5,7-12,14-19H,3H2/t4-,5+,7-,8+,9+,10+,11-,12-/m1/s1
• InChI Key: BTWZMPXQZXWWGU-FQDRLZQQSA-N
• Popularity: 0 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): 164.00 Ų
• XlogP: -2.80
• Atomic LogP (AlogP): -3.44
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8301	83.01%
Caco-2	-	0.9440	94.40%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6856	68.56%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.9132	91.32%
OATP1B3 inhibitior	+	0.9580	95.80%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9741	97.41%
P-glycoprotein inhibitior	-	0.9329	93.29%
P-glycoprotein substrate	-	0.9613	96.13%
CYP3A4 substrate	-	0.5275	52.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8441	84.41%
CYP3A4 inhibition	-	0.9169	91.69%
CYP2C9 inhibition	-	0.8711	87.11%
CYP2C19 inhibition	-	0.8663	86.63%
CYP2D6 inhibition	-	0.9162	91.62%
CYP1A2 inhibition	-	0.8420	84.20%
CYP2C8 inhibition	-	0.7635	76.35%
CYP inhibitory promiscuity	-	0.7576	75.76%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7043	70.43%
Eye corrosion	-	0.9853	98.53%
Eye irritation	-	0.9641	96.41%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9518	95.18%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4672	46.72%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8785	87.85%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.5799	57.99%
Acute Oral Toxicity (c)	III	0.4952	49.52%
Estrogen receptor binding	-	0.7218	72.18%
Androgen receptor binding	-	0.7044	70.44%
Thyroid receptor binding	+	0.6378	63.78%
Glucocorticoid receptor binding	-	0.5382	53.82%
Aromatase binding	-	0.5190	51.90%
PPAR gamma	-	0.5137	51.37%
Honey bee toxicity	-	0.6271	62.71%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7350	73.50%
Fish aquatic toxicity	-	0.8326	83.26%

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	95.70%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.48%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.61%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	85.95%	95.93%
CHEMBL3589	P55263	Adenosine kinase	84.70%	98.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.13%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	81.02%	94.73%

Plants that contains it

• Ryparosa kurrangii

Cross-Links

• PubChem: 163103587
• LOTUS: LTS0008530
• wikiData: Q104945915