(1S,2S,3Z,4R,6S)-3-(Cyanomethylene)-4-(beta-D-glucopyranosyloxy)-2,6-dihydroxycyclohexyl 3-methyl-2-butenoate

Details

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Internal ID e519e8db-d3e8-4003-9431-d6088d60c1aa
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
IUPAC Name [3-(cyanomethylidene)-2,6-dihydroxy-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexyl] 3-methylbut-2-enoate
SMILES (Canonical) CC(=CC(=O)OC1C(CC(C(=CC#N)C1O)OC2C(C(C(C(O2)CO)O)O)O)O)C
SMILES (Isomeric) CC(=CC(=O)OC1C(CC(C(=CC#N)C1O)OC2C(C(C(C(O2)CO)O)O)O)O)C
InChI InChI=1S/C19H27NO10/c1-8(2)5-13(23)30-18-10(22)6-11(9(3-4-20)14(18)24)28-19-17(27)16(26)15(25)12(7-21)29-19/h3,5,10-12,14-19,21-22,24-27H,6-7H2,1-2H3
InChI Key FETVEFSIUIGFMX-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C19H27NO10
Molecular Weight 429.40 g/mol
Exact Mass 429.16349606 g/mol
Topological Polar Surface Area (TPSA) 190.00 Ų
XlogP -2.30
Atomic LogP (AlogP) -2.38
H-Bond Acceptor 11
H-Bond Donor 6
Rotatable Bonds 5

Synonyms

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(1S,2S,3Z,4R,6S)-3-(Cyanomethylene)-4-(beta-D-glucopyranosyloxy)-2,6-dihydroxycyclohexyl 3-methyl-2-butenoate
156368-85-3

2D Structure

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2D Structure of (1S,2S,3Z,4R,6S)-3-(Cyanomethylene)-4-(beta-D-glucopyranosyloxy)-2,6-dihydroxycyclohexyl 3-methyl-2-butenoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.5687 56.87%
Caco-2 - 0.9014 90.14%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8571 85.71%
Subcellular localzation Mitochondria 0.7772 77.72%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8507 85.07%
OATP1B3 inhibitior + 0.9507 95.07%
MATE1 inhibitior - 0.9212 92.12%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.8725 87.25%
P-glycoprotein inhibitior - 0.7376 73.76%
P-glycoprotein substrate - 0.7498 74.98%
CYP3A4 substrate + 0.6309 63.09%
CYP2C9 substrate - 0.6049 60.49%
CYP2D6 substrate - 0.8836 88.36%
CYP3A4 inhibition - 0.8479 84.79%
CYP2C9 inhibition - 0.8578 85.78%
CYP2C19 inhibition - 0.8634 86.34%
CYP2D6 inhibition - 0.8650 86.50%
CYP1A2 inhibition - 0.8605 86.05%
CYP2C8 inhibition - 0.7546 75.46%
CYP inhibitory promiscuity - 0.7414 74.14%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.7673 76.73%
Eye corrosion - 0.9883 98.83%
Eye irritation - 0.9713 97.13%
Skin irritation - 0.8123 81.23%
Skin corrosion - 0.9513 95.13%
Ames mutagenesis - 0.6978 69.78%
Human Ether-a-go-go-Related Gene inhibition - 0.5355 53.55%
Micronuclear - 0.6800 68.00%
Hepatotoxicity - 0.6642 66.42%
skin sensitisation - 0.8439 84.39%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.6667 66.67%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity + 0.4664 46.64%
Acute Oral Toxicity (c) III 0.5967 59.67%
Estrogen receptor binding + 0.6811 68.11%
Androgen receptor binding - 0.6187 61.87%
Thyroid receptor binding + 0.5265 52.65%
Glucocorticoid receptor binding + 0.5397 53.97%
Aromatase binding + 0.6254 62.54%
PPAR gamma + 0.5297 52.97%
Honey bee toxicity - 0.5424 54.24%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5655 56.55%
Fish aquatic toxicity - 0.5507 55.07%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.09% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.92% 91.11%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 90.87% 96.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.93% 85.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.22% 89.00%
CHEMBL2581 P07339 Cathepsin D 88.90% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.55% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.52% 97.09%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 85.13% 95.83%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.65% 100.00%
CHEMBL5255 O00206 Toll-like receptor 4 83.79% 92.50%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 83.63% 86.92%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.77% 99.17%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 81.74% 95.50%
CHEMBL3401 O75469 Pregnane X receptor 81.53% 94.73%
CHEMBL5028 O14672 ADAM10 81.46% 97.50%
CHEMBL253 P34972 Cannabinoid CB2 receptor 80.78% 97.25%

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.
Ehretia philippinensis

Cross-Links

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PubChem 85141478
LOTUS LTS0126836
wikiData Q104994194