[5-hydroxy-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-7-yl]methyl acetate

Details

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Internal ID 6f67531f-9228-4d1b-803c-86246ae5087c
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name [5-hydroxy-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-7-yl]methyl acetate
SMILES (Canonical) CC(=O)OCC1CC(C2C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O
SMILES (Isomeric) CC(=O)OCC1CC(C2C1C(OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
InChI InChI=1S/C17H26O10/c1-7(19)25-6-8-4-10(20)9-2-3-24-16(12(8)9)27-17-15(23)14(22)13(21)11(5-18)26-17/h2-3,8-18,20-23H,4-6H2,1H3/t8?,9?,10?,11-,12?,13-,14+,15-,16?,17+/m1/s1
InChI Key WULASHYSJRHJKR-OGRUUTKISA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C17H26O10
Molecular Weight 390.40 g/mol
Exact Mass 390.15259702 g/mol
Topological Polar Surface Area (TPSA) 155.00 Ų
XlogP -1.60
Atomic LogP (AlogP) -2.15
H-Bond Acceptor 10
H-Bond Donor 5
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [5-hydroxy-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-7-yl]methyl acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.4816 48.16%
Caco-2 - 0.8804 88.04%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.5808 58.08%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8105 81.05%
OATP1B3 inhibitior + 0.9623 96.23%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior - 0.7837 78.37%
P-glycoprotein inhibitior - 0.8621 86.21%
P-glycoprotein substrate - 0.8530 85.30%
CYP3A4 substrate + 0.6025 60.25%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8783 87.83%
CYP3A4 inhibition - 0.9572 95.72%
CYP2C9 inhibition - 0.9692 96.92%
CYP2C19 inhibition - 0.9281 92.81%
CYP2D6 inhibition - 0.9224 92.24%
CYP1A2 inhibition - 0.9165 91.65%
CYP2C8 inhibition - 0.8078 80.78%
CYP inhibitory promiscuity - 0.9061 90.61%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7130 71.30%
Eye corrosion - 0.9915 99.15%
Eye irritation - 0.9800 98.00%
Skin irritation - 0.7943 79.43%
Skin corrosion - 0.9506 95.06%
Ames mutagenesis - 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5232 52.32%
Micronuclear - 0.7841 78.41%
Hepatotoxicity - 0.6927 69.27%
skin sensitisation - 0.9113 91.13%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.7000 70.00%
Mitochondrial toxicity - 0.5250 52.50%
Nephrotoxicity + 0.4612 46.12%
Acute Oral Toxicity (c) III 0.4945 49.45%
Estrogen receptor binding + 0.6263 62.63%
Androgen receptor binding - 0.6208 62.08%
Thyroid receptor binding - 0.5853 58.53%
Glucocorticoid receptor binding - 0.7082 70.82%
Aromatase binding + 0.6144 61.44%
PPAR gamma - 0.5497 54.97%
Honey bee toxicity - 0.8475 84.75%
Biodegradation - 0.5000 50.00%
Crustacea aquatic toxicity - 0.6758 67.58%
Fish aquatic toxicity - 0.5000 50.00%

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 98.39% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.26% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.81% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.20% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.10% 94.45%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 89.96% 97.21%
CHEMBL3401 O75469 Pregnane X receptor 89.34% 94.73%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.24% 85.14%
CHEMBL5255 O00206 Toll-like receptor 4 84.50% 92.50%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 84.16% 96.95%
CHEMBL218 P21554 Cannabinoid CB1 receptor 83.88% 96.61%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.31% 89.00%
CHEMBL226 P30542 Adenosine A1 receptor 82.12% 95.93%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 81.85% 94.33%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 80.72% 96.21%

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.
Elaeagnus angustifolia
Hippophae rhamnoides
Peganum harmala

Cross-Links

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PubChem 5317967
NPASS NPC306813