Griselinoside

Details

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Internal ID 316b3203-0888-4f27-8612-2f5aef20b087
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name dimethyl (1R,4aR,7R,7aR)-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4,7-dicarboxylate
SMILES (Canonical) COC(=O)C1CC(=O)C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O
SMILES (Isomeric) COC(=O)[C@@H]1CC(=O)[C@@H]2[C@H]1[C@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
InChI InChI=1S/C18H24O12/c1-26-15(24)6-3-8(20)10-7(16(25)27-2)5-28-17(11(6)10)30-18-14(23)13(22)12(21)9(4-19)29-18/h5-6,9-14,17-19,21-23H,3-4H2,1-2H3/t6-,9-,10-,11+,12-,13+,14-,17-,18+/m1/s1
InChI Key USONHTFDCJKLKO-PHAJAEPKSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C18H24O12
Molecular Weight 432.40 g/mol
Exact Mass 432.12677620 g/mol
Topological Polar Surface Area (TPSA) 178.00 Ų
XlogP -2.40
Atomic LogP (AlogP) -2.79
H-Bond Acceptor 12
H-Bond Donor 4
Rotatable Bonds 5

Synonyms

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71035-06-8
dimethyl (1R,4aR,7R,7aR)-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4,7-dicarboxylate
Cyclopenta(c)pyran-4,7-dicarboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-5-oxo-, dimethyl ester, (1S-(1alpha,4aalpha,7alpha,7aalpha))-
DTXSID10991339
Dimethyl 1-(hexopyranosyloxy)-5-oxo-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4,7-dicarboxylate

2D Structure

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2D Structure of Griselinoside

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.5086 50.86%
Caco-2 - 0.8670 86.70%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.6940 69.40%
OATP2B1 inhibitior - 0.8607 86.07%
OATP1B1 inhibitior + 0.7730 77.30%
OATP1B3 inhibitior + 0.9563 95.63%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior - 0.7088 70.88%
P-glycoprotein inhibitior - 0.7089 70.89%
P-glycoprotein substrate - 0.7900 79.00%
CYP3A4 substrate + 0.6077 60.77%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8722 87.22%
CYP3A4 inhibition - 0.8641 86.41%
CYP2C9 inhibition - 0.8687 86.87%
CYP2C19 inhibition - 0.8940 89.40%
CYP2D6 inhibition - 0.9193 91.93%
CYP1A2 inhibition - 0.9036 90.36%
CYP2C8 inhibition - 0.6937 69.37%
CYP inhibitory promiscuity - 0.7868 78.68%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6717 67.17%
Eye corrosion - 0.9879 98.79%
Eye irritation - 0.9343 93.43%
Skin irritation - 0.7690 76.90%
Skin corrosion - 0.9514 95.14%
Ames mutagenesis - 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4757 47.57%
Micronuclear - 0.6100 61.00%
Hepatotoxicity - 0.7571 75.71%
skin sensitisation - 0.8790 87.90%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.8333 83.33%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity + 0.8388 83.88%
Acute Oral Toxicity (c) III 0.5240 52.40%
Estrogen receptor binding + 0.7448 74.48%
Androgen receptor binding + 0.5643 56.43%
Thyroid receptor binding - 0.6211 62.11%
Glucocorticoid receptor binding - 0.5820 58.20%
Aromatase binding - 0.6597 65.97%
PPAR gamma - 0.6008 60.08%
Honey bee toxicity - 0.7880 78.80%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.7600 76.00%
Fish aquatic toxicity - 0.4189 41.89%

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 96.90% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.47% 96.09%
CHEMBL2581 P07339 Cathepsin D 91.50% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 89.81% 94.73%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.80% 85.14%
CHEMBL3060 Q9Y345 Glycine transporter 2 87.29% 99.17%
CHEMBL5255 O00206 Toll-like receptor 4 83.98% 92.50%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.96% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.61% 97.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 81.53% 96.61%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.53% 89.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 80.78% 96.00%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 80.21% 96.90%

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.
Garcinia griffithii
Garcinia gummi-gutta
Griselinia littoralis
Verbena brasiliensis

Cross-Links

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PubChem 155589
LOTUS LTS0229479
wikiData Q105300626