Grayanin

Details

• Internal ID: 2dc5ae2b-7fb6-4368-a7e1-b1a434360b2b
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Cyanogenic glycosides
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[(R)-cyano(phenyl)methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC=C(C=C1)C(C#N)OC2C(C(C(C(O2)COC(=O)C=CC3=CC(=C(C=C3)O)O)O)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)[C@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)/C=C/C3=CC(=C(C=C3)O)O)O)O)O
• InChI: InChI=1S/C23H23NO9/c24-11-17(14-4-2-1-3-5-14)32-23-22(30)21(29)20(28)18(33-23)12-31-19(27)9-7-13-6-8-15(25)16(26)10-13/h1-10,17-18,20-23,25-26,28-30H,12H2/b9-7+/t17-,18+,20+,21-,22+,23+/m0/s1
• InChI Key: HUKWADINTARKBT-DDYRGYEHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₃NO₉
• Molecular Weight: 457.40 g/mol
• Exact Mass: 457.13728131 g/mol
• Topological Polar Surface Area (TPSA): 170.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.74
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

• 110978-97-7
• Benzeneacetonitrile, alpha-((6-O-(3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)-beta-D-glucopyranosyl)oxy)-, (R-(E))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6800	68.00%
Caco-2	-	0.8891	88.91%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6196	61.96%
OATP2B1 inhibitior	-	0.8496	84.96%
OATP1B1 inhibitior	+	0.9066	90.66%
OATP1B3 inhibitior	+	0.9129	91.29%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7728	77.28%
P-glycoprotein inhibitior	-	0.5673	56.73%
P-glycoprotein substrate	-	0.8971	89.71%
CYP3A4 substrate	+	0.5890	58.90%
CYP2C9 substrate	-	0.8070	80.70%
CYP2D6 substrate	-	0.8643	86.43%
CYP3A4 inhibition	-	0.6673	66.73%
CYP2C9 inhibition	-	0.7630	76.30%
CYP2C19 inhibition	-	0.8231	82.31%
CYP2D6 inhibition	-	0.8645	86.45%
CYP1A2 inhibition	-	0.7811	78.11%
CYP2C8 inhibition	+	0.5926	59.26%
CYP inhibitory promiscuity	+	0.5293	52.93%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7389	73.89%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9178	91.78%
Skin irritation	-	0.8246	82.46%
Skin corrosion	-	0.9612	96.12%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8199	81.99%
Micronuclear	+	0.6707	67.07%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.7866	78.66%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.9495	94.95%
Acute Oral Toxicity (c)	III	0.7265	72.65%
Estrogen receptor binding	+	0.6179	61.79%
Androgen receptor binding	+	0.7190	71.90%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.6107	61.07%
PPAR gamma	+	0.6481	64.81%
Honey bee toxicity	-	0.5626	56.26%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5255	52.55%
Fish aquatic toxicity	+	0.8676	86.76%

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	99.76%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.97%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.59%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.09%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	95.91%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.91%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.74%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.35%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	90.95%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.84%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.78%	98.95%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	90.40%	83.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.64%	94.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.77%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.64%	99.17%
CHEMBL2535	P11166	Glucose transporter	88.39%	98.75%
CHEMBL226	P30542	Adenosine A1 receptor	86.48%	95.93%
CHEMBL3194	P02766	Transthyretin	84.96%	90.71%
CHEMBL5028	O14672	ADAM10	81.24%	97.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.06%	94.08%

Plants that contains it

• Prunus buergeriana
• Prunus grayana

Cross-Links

• PubChem: 6442904
• LOTUS: LTS0045444
• wikiData: Q105033856