(2S)-3-(hydroxymethyl)-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-3-enenitrile

Details

• Internal ID: 5a91892d-a115-447c-926d-f4c7f724930a
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Cyanogenic glycosides
• IUPAC Name: (2S)-3-(hydroxymethyl)-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-3-enenitrile
• SMILES (Canonical): C=C(CO)C(C#N)OC1C(C(C(C(O1)CO)O)O)O
• SMILES (Isomeric): C=C(CO)[C@@H](C#N)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O
• InChI: InChI=1S/C11H17NO7/c1-5(3-13)6(2-12)18-11-10(17)9(16)8(15)7(4-14)19-11/h6-11,13-17H,1,3-4H2/t6-,7-,8+,9+,10-,11-/m1/s1
• InChI Key: MQTLCYHUTVTHFO-VFZPANTDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₇NO₇
• Molecular Weight: 275.25 g/mol
• Exact Mass: 275.10050188 g/mol
• Topological Polar Surface Area (TPSA): 143.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -2.76
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9132	91.32%
Caco-2	-	0.9108	91.08%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6595	65.95%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.9276	92.76%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9381	93.81%
P-glycoprotein inhibitior	-	0.9320	93.20%
P-glycoprotein substrate	-	0.9578	95.78%
CYP3A4 substrate	+	0.5128	51.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8375	83.75%
CYP3A4 inhibition	-	0.8603	86.03%
CYP2C9 inhibition	-	0.8420	84.20%
CYP2C19 inhibition	-	0.8087	80.87%
CYP2D6 inhibition	-	0.8949	89.49%
CYP1A2 inhibition	-	0.8579	85.79%
CYP2C8 inhibition	-	0.8530	85.30%
CYP inhibitory promiscuity	-	0.7740	77.40%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7323	73.23%
Eye corrosion	-	0.9812	98.12%
Eye irritation	-	0.9611	96.11%
Skin irritation	-	0.8198	81.98%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5134	51.34%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8408	84.08%
Respiratory toxicity	-	0.7222	72.22%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.6472	64.72%
Acute Oral Toxicity (c)	III	0.4717	47.17%
Estrogen receptor binding	-	0.7502	75.02%
Androgen receptor binding	-	0.6659	66.59%
Thyroid receptor binding	+	0.5820	58.20%
Glucocorticoid receptor binding	-	0.5759	57.59%
Aromatase binding	+	0.5949	59.49%
PPAR gamma	-	0.5219	52.19%
Honey bee toxicity	+	0.6361	63.61%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.8700	87.00%
Fish aquatic toxicity	-	0.7799	77.99%

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	93.58%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.44%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	88.06%	95.93%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.03%	86.92%
CHEMBL3589	P55263	Adenosine kinase	87.73%	98.05%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.41%	95.83%
CHEMBL4040	P28482	MAP kinase ERK2	81.29%	83.82%

Plants that contains it

• Anacardium occidentale
• Cardiospermum grandiflorum
• Ginkgo biloba

Cross-Links

• PubChem: 6324886
• NPASS: NPC10568