(1S)-1alpha-(beta-D-Glucopyranosyloxy)-1,4aalpha,5,6,7,7aalpha-hexahydrocyclopenta[c]pyran-4,7alpha-dicarboxylic acid 4-beta-D-glucopyranosyl 7-methyl ester

Details

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Internal ID 53fb84e2-e72e-4db4-a503-33052d9ef251
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name 7-O-methyl 4-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4,7-dicarboxylate
SMILES (Canonical) COC(=O)C1CCC2C1C(OC=C2C(=O)OC3C(C(C(C(O3)CO)O)O)O)OC4C(C(C(C(O4)CO)O)O)O
SMILES (Isomeric) COC(=O)[C@H]1CC[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
InChI InChI=1S/C23H34O16/c1-34-19(32)8-3-2-7-9(20(33)38-22-17(30)15(28)13(26)10(4-24)36-22)6-35-21(12(7)8)39-23-18(31)16(29)14(27)11(5-25)37-23/h6-8,10-18,21-31H,2-5H2,1H3/t7-,8+,10-,11-,12+,13-,14-,15+,16+,17-,18-,21+,22+,23+/m1/s1
InChI Key QBDNAUYUWVKDHB-HNMQKENPSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C23H34O16
Molecular Weight 566.50 g/mol
Exact Mass 566.18468499 g/mol
Topological Polar Surface Area (TPSA) 251.00 Ų
XlogP -3.30
Atomic LogP (AlogP) -4.80
H-Bond Acceptor 16
H-Bond Donor 8
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S)-1alpha-(beta-D-Glucopyranosyloxy)-1,4aalpha,5,6,7,7aalpha-hexahydrocyclopenta[c]pyran-4,7alpha-dicarboxylic acid 4-beta-D-glucopyranosyl 7-methyl ester

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.6551 65.51%
Caco-2 - 0.8995 89.95%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.7734 77.34%
OATP2B1 inhibitior - 0.8671 86.71%
OATP1B1 inhibitior + 0.7178 71.78%
OATP1B3 inhibitior + 0.9583 95.83%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior - 0.7695 76.95%
P-glycoprotein inhibitior - 0.6235 62.35%
P-glycoprotein substrate - 0.7877 78.77%
CYP3A4 substrate + 0.6244 62.44%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8683 86.83%
CYP3A4 inhibition - 0.9603 96.03%
CYP2C9 inhibition - 0.8621 86.21%
CYP2C19 inhibition - 0.8509 85.09%
CYP2D6 inhibition - 0.9131 91.31%
CYP1A2 inhibition - 0.8474 84.74%
CYP2C8 inhibition - 0.5843 58.43%
CYP inhibitory promiscuity - 0.8453 84.53%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6157 61.57%
Eye corrosion - 0.9863 98.63%
Eye irritation - 0.9308 93.08%
Skin irritation - 0.7667 76.67%
Skin corrosion - 0.9396 93.96%
Ames mutagenesis - 0.6270 62.70%
Human Ether-a-go-go-Related Gene inhibition + 0.6451 64.51%
Micronuclear - 0.7700 77.00%
Hepatotoxicity - 0.7977 79.77%
skin sensitisation - 0.8870 88.70%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.7556 75.56%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity + 0.5182 51.82%
Acute Oral Toxicity (c) III 0.5371 53.71%
Estrogen receptor binding + 0.7500 75.00%
Androgen receptor binding + 0.6250 62.50%
Thyroid receptor binding - 0.5942 59.42%
Glucocorticoid receptor binding - 0.4819 48.19%
Aromatase binding - 0.5157 51.57%
PPAR gamma - 0.4903 49.03%
Honey bee toxicity - 0.8489 84.89%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity - 0.6400 64.00%
Fish aquatic toxicity - 0.6203 62.03%

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 97.55% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.26% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.42% 97.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 86.62% 99.17%
CHEMBL3401 O75469 Pregnane X receptor 85.55% 94.73%
CHEMBL5255 O00206 Toll-like receptor 4 85.49% 92.50%
CHEMBL218 P21554 Cannabinoid CB1 receptor 84.62% 96.61%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 84.31% 96.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 84.28% 97.25%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 81.53% 91.24%

Cross-Links

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PubChem 101673970
NPASS NPC159003
LOTUS LTS0053181
wikiData Q105217745