4-[Cyano-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethylidene]-6-methoxy-6-oxohex-2-enoic acid

Details

• Internal ID: 39a0a964-e34e-42b1-a617-496f265621ea
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Cyanogenic glycosides
• IUPAC Name: 4-[cyano-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethylidene]-6-methoxy-6-oxohex-2-enoic acid
• SMILES (Canonical): COC(=O)CC(=C(C#N)OC1C(C(C(C(O1)CO)O)O)O)C=CC(=O)O
• SMILES (Isomeric): COC(=O)CC(=C(C#N)OC1C(C(C(C(O1)CO)O)O)O)C=CC(=O)O
• InChI: InChI=1S/C15H19NO10/c1-24-11(20)4-7(2-3-10(18)19)8(5-16)25-15-14(23)13(22)12(21)9(6-17)26-15/h2-3,9,12-15,17,21-23H,4,6H2,1H3,(H,18,19)
• InChI Key: ZAGGPLANHIGDAL-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₉NO₁₀
• Molecular Weight: 373.31 g/mol
• Exact Mass: 373.10089580 g/mol
• Topological Polar Surface Area (TPSA): 187.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -2.22
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7758	77.58%
Caco-2	-	0.9136	91.36%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7300	73.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8708	87.08%
OATP1B3 inhibitior	+	0.9567	95.67%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6697	66.97%
P-glycoprotein inhibitior	-	0.9042	90.42%
P-glycoprotein substrate	-	0.8795	87.95%
CYP3A4 substrate	+	0.5824	58.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8698	86.98%
CYP3A4 inhibition	-	0.9477	94.77%
CYP2C9 inhibition	-	0.8676	86.76%
CYP2C19 inhibition	-	0.8934	89.34%
CYP2D6 inhibition	-	0.8941	89.41%
CYP1A2 inhibition	-	0.8632	86.32%
CYP2C8 inhibition	-	0.7170	71.70%
CYP inhibitory promiscuity	-	0.8966	89.66%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7834	78.34%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.9358	93.58%
Skin irritation	-	0.7967	79.67%
Skin corrosion	-	0.9454	94.54%
Ames mutagenesis	-	0.6270	62.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5318	53.18%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8864	88.64%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.6026	60.26%
Acute Oral Toxicity (c)	III	0.5500	55.00%
Estrogen receptor binding	+	0.5280	52.80%
Androgen receptor binding	-	0.5795	57.95%
Thyroid receptor binding	-	0.5827	58.27%
Glucocorticoid receptor binding	+	0.5711	57.11%
Aromatase binding	-	0.6063	60.63%
PPAR gamma	-	0.6030	60.30%
Honey bee toxicity	-	0.7016	70.16%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	-	0.7321	73.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.73%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.30%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.35%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.83%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.35%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.18%	91.11%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.73%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	84.23%	92.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.18%	95.83%

Plants that contains it

• Thalictrum aquilegiifolium

Cross-Links

• PubChem: 163010502
• LOTUS: LTS0009317
• wikiData: Q105369861