(3R,4R,4aS)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-8-one

Details

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Internal ID 299ef52e-5477-4ca8-9e8f-bdeb328339bd
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
IUPAC Name (3R,4R,4aS)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-8-one
SMILES (Canonical) C=CC1C2CCOC(=O)C2=COC1OC3C(C(C(C(O3)CO)O)O)O
SMILES (Isomeric) C=C[C@@H]1[C@@H]2CCOC(=O)C2=CO[C@@H]1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
InChI InChI=1S/C16H22O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2,6-8,10-13,15-20H,1,3-5H2/t7-,8+,10-,11-,12+,13-,15-,16+/m1/s1
InChI Key VSJGJMKGNMDJCI-BLZVUDKZSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C16H22O9
Molecular Weight 358.34 g/mol
Exact Mass 358.12638228 g/mol
Topological Polar Surface Area (TPSA) 135.00 Ų
XlogP -0.90
Atomic LogP (AlogP) -1.59
H-Bond Acceptor 9
H-Bond Donor 4
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3R,4R,4aS)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-8-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.6190 61.90%
Caco-2 - 0.8586 85.86%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.7627 76.27%
OATP2B1 inhibitior - 0.8592 85.92%
OATP1B1 inhibitior + 0.8558 85.58%
OATP1B3 inhibitior + 0.9304 93.04%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior - 0.8683 86.83%
P-glycoprotein inhibitior - 0.8876 88.76%
P-glycoprotein substrate - 0.9186 91.86%
CYP3A4 substrate + 0.5785 57.85%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8602 86.02%
CYP3A4 inhibition - 0.9284 92.84%
CYP2C9 inhibition - 0.8660 86.60%
CYP2C19 inhibition - 0.8277 82.77%
CYP2D6 inhibition - 0.8774 87.74%
CYP1A2 inhibition - 0.8514 85.14%
CYP2C8 inhibition - 0.6974 69.74%
CYP inhibitory promiscuity - 0.8641 86.41%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6851 68.51%
Eye corrosion - 0.9805 98.05%
Eye irritation - 0.9306 93.06%
Skin irritation - 0.7821 78.21%
Skin corrosion - 0.9451 94.51%
Ames mutagenesis - 0.6270 62.70%
Human Ether-a-go-go-Related Gene inhibition - 0.5940 59.40%
Micronuclear - 0.7741 77.41%
Hepatotoxicity - 0.7341 73.41%
skin sensitisation - 0.8399 83.99%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.7111 71.11%
Mitochondrial toxicity - 0.5750 57.50%
Nephrotoxicity + 0.5602 56.02%
Acute Oral Toxicity (c) III 0.4512 45.12%
Estrogen receptor binding + 0.5372 53.72%
Androgen receptor binding + 0.5640 56.40%
Thyroid receptor binding + 0.5772 57.72%
Glucocorticoid receptor binding - 0.5814 58.14%
Aromatase binding - 0.5091 50.91%
PPAR gamma + 0.6089 60.89%
Honey bee toxicity - 0.7952 79.52%
Biodegradation - 0.5500 55.00%
Crustacea aquatic toxicity - 0.6200 62.00%
Fish aquatic toxicity - 0.4064 40.64%

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
CHEMBL3137262 O60341 LSD1/CoREST complex 94.95% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.63% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.24% 95.56%
CHEMBL220 P22303 Acetylcholinesterase 88.22% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 86.91% 96.09%
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 86.78% 83.57%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 86.38% 86.92%
CHEMBL2581 P07339 Cathepsin D 85.87% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.73% 95.89%
CHEMBL226 P30542 Adenosine A1 receptor 82.91% 95.93%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.88% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.51% 86.33%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.18% 97.25%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.11% 89.00%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 81.00% 95.83%

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.
Gentiana algida
Gentiana macrophylla

Cross-Links

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PubChem 131704891
LOTUS LTS0043488
wikiData Q105292236