(R)-(beta-D-Glucopyranosyloxy)(3-hydroxyphenyl)acetonitrile

Details

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Internal ID a9add97c-f88c-46ac-958a-6145a30b1664
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Cyanogenic glycosides
IUPAC Name (2R)-2-(3-hydroxyphenyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
SMILES (Canonical) C1=CC(=CC(=C1)O)C(C#N)OC2C(C(C(C(O2)CO)O)O)O
SMILES (Isomeric) C1=CC(=CC(=C1)O)[C@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
InChI InChI=1S/C14H17NO7/c15-5-9(7-2-1-3-8(17)4-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2/t9-,10+,11+,12-,13+,14+/m0/s1
InChI Key KCVXNPDAHDGXFD-GMDXDWKASA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C14H17NO7
Molecular Weight 311.29 g/mol
Exact Mass 311.10050188 g/mol
Topological Polar Surface Area (TPSA) 143.00 Ų
XlogP -0.90
Atomic LogP (AlogP) -1.23
H-Bond Acceptor 8
H-Bond Donor 5
Rotatable Bonds 4

Synonyms

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41753-54-2
(R)-(beta-D-Glucopyranosyloxy)(3-hydroxyphenyl)acetonitrile
EINECS 255-533-3
DTXSID10961956
(Hexopyranosyloxy)(3-hydroxyphenyl)acetonitrile

2D Structure

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2D Structure of (R)-(beta-D-Glucopyranosyloxy)(3-hydroxyphenyl)acetonitrile

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.8843 88.43%
Caco-2 - 0.8817 88.17%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.6176 61.76%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9141 91.41%
OATP1B3 inhibitior + 0.9416 94.16%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior - 0.9304 93.04%
P-glycoprotein inhibitior - 0.8965 89.65%
P-glycoprotein substrate - 0.8871 88.71%
CYP3A4 substrate + 0.5301 53.01%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8159 81.59%
CYP3A4 inhibition - 0.7601 76.01%
CYP2C9 inhibition - 0.8384 83.84%
CYP2C19 inhibition - 0.8579 85.79%
CYP2D6 inhibition - 0.9090 90.90%
CYP1A2 inhibition - 0.8878 88.78%
CYP2C8 inhibition - 0.6978 69.78%
CYP inhibitory promiscuity - 0.6054 60.54%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6928 69.28%
Eye corrosion - 0.9915 99.15%
Eye irritation - 0.9428 94.28%
Skin irritation - 0.8374 83.74%
Skin corrosion - 0.9653 96.53%
Ames mutagenesis - 0.6400 64.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7053 70.53%
Micronuclear - 0.6100 61.00%
Hepatotoxicity - 0.7500 75.00%
skin sensitisation - 0.8525 85.25%
Respiratory toxicity + 0.5444 54.44%
Reproductive toxicity + 0.6111 61.11%
Mitochondrial toxicity - 0.6750 67.50%
Nephrotoxicity - 0.7538 75.38%
Acute Oral Toxicity (c) III 0.8047 80.47%
Estrogen receptor binding - 0.7716 77.16%
Androgen receptor binding - 0.5629 56.29%
Thyroid receptor binding - 0.4875 48.75%
Glucocorticoid receptor binding - 0.4906 49.06%
Aromatase binding - 0.6565 65.65%
PPAR gamma + 0.5376 53.76%
Honey bee toxicity + 0.5522 55.22%
Biodegradation - 0.6000 60.00%
Crustacea aquatic toxicity - 0.6450 64.50%
Fish aquatic toxicity - 0.7476 74.76%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 98.59% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.68% 96.09%
CHEMBL2581 P07339 Cathepsin D 94.11% 98.95%
CHEMBL226 P30542 Adenosine A1 receptor 93.11% 95.93%
CHEMBL3401 O75469 Pregnane X receptor 91.24% 94.73%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.62% 99.17%
CHEMBL2535 P11166 Glucose transporter 88.23% 98.75%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.29% 86.33%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 85.31% 95.89%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 85.29% 99.15%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.80% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.16% 89.00%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 81.62% 94.23%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 81.37% 94.80%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 81.10% 96.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Oxyanthus speciosus
Sambucus nigra

Cross-Links

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PubChem 92323
NPASS NPC238413
LOTUS LTS0234225
wikiData Q82943508