(1R,4S,6S,7R,11R)-6-methyl-1-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undecan-2-one

Details

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Internal ID 9e46dec6-057f-4cca-a3eb-b66b9ebf5cc6
Taxonomy Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
IUPAC Name (1R,4S,6S,7R,11R)-6-methyl-1-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undecan-2-one
SMILES (Canonical) CC1CC2C3C1COCC3(C(=O)O2)OC4C(C(C(C(O4)CO)O)O)O
SMILES (Isomeric) C[C@H]1C[C@H]2[C@H]3[C@@H]1COC[C@]3(C(=O)O2)O[C@H]4[C@H]([C@@H]([C@@H]([C@H](O4)CO)O)O)O
InChI InChI=1S/C16H24O9/c1-6-2-8-10-7(6)4-22-5-16(10,15(21)24-8)25-14-13(20)12(19)11(18)9(3-17)23-14/h6-14,17-20H,2-5H2,1H3/t6-,7+,8-,9+,10+,11+,12+,13-,14-,16-/m0/s1
InChI Key HWFAUXGDHAPNHM-NWESXJQGSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C16H24O9
Molecular Weight 360.36 g/mol
Exact Mass 360.14203234 g/mol
Topological Polar Surface Area (TPSA) 135.00 Ų
XlogP -1.40
Atomic LogP (AlogP) -2.23
H-Bond Acceptor 9
H-Bond Donor 4
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,4S,6S,7R,11R)-6-methyl-1-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[5.3.1.04,11]undecan-2-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5824 58.24%
Caco-2 - 0.8600 86.00%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.6721 67.21%
OATP2B1 inhibitior - 0.8575 85.75%
OATP1B1 inhibitior + 0.9156 91.56%
OATP1B3 inhibitior + 0.9582 95.82%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior - 0.8690 86.90%
P-glycoprotein inhibitior - 0.8773 87.73%
P-glycoprotein substrate - 0.7757 77.57%
CYP3A4 substrate + 0.6151 61.51%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8672 86.72%
CYP3A4 inhibition - 0.9495 94.95%
CYP2C9 inhibition - 0.9192 91.92%
CYP2C19 inhibition - 0.8721 87.21%
CYP2D6 inhibition - 0.9375 93.75%
CYP1A2 inhibition - 0.9202 92.02%
CYP2C8 inhibition - 0.8349 83.49%
CYP inhibitory promiscuity - 0.9437 94.37%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6289 62.89%
Eye corrosion - 0.9894 98.94%
Eye irritation - 0.9698 96.98%
Skin irritation - 0.7973 79.73%
Skin corrosion - 0.9556 95.56%
Ames mutagenesis - 0.5478 54.78%
Human Ether-a-go-go-Related Gene inhibition - 0.5626 56.26%
Micronuclear - 0.8300 83.00%
Hepatotoxicity - 0.6416 64.16%
skin sensitisation - 0.9083 90.83%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.6333 63.33%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity + 0.6262 62.62%
Acute Oral Toxicity (c) III 0.3710 37.10%
Estrogen receptor binding + 0.7611 76.11%
Androgen receptor binding - 0.5000 50.00%
Thyroid receptor binding + 0.5546 55.46%
Glucocorticoid receptor binding - 0.5162 51.62%
Aromatase binding + 0.6773 67.73%
PPAR gamma + 0.5441 54.41%
Honey bee toxicity - 0.6708 67.08%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.6300 63.00%
Fish aquatic toxicity + 0.8369 83.69%

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 94.97% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.37% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.93% 91.11%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 90.53% 86.92%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.94% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.43% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 84.56% 97.25%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.80% 86.33%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.95% 94.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 81.81% 96.77%
CHEMBL2581 P07339 Cathepsin D 81.29% 98.95%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 81.28% 91.24%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.96% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.57% 100.00%

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.
Gelsemium sempervirens

Cross-Links

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PubChem 163104345
LOTUS LTS0257896
wikiData Q105034633