methyl (1S,3R,6S,7S,7aR)-6-hydroxy-3-methoxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Details

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Internal ID e08fbf21-8325-4123-9665-4818da33e7ab
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
IUPAC Name methyl (1S,3R,6S,7S,7aR)-6-hydroxy-3-methoxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
SMILES (Canonical) CC1C(CC2=C(C(OC(C12)OC3C(C(C(C(O3)CO)O)O)O)OC)C(=O)OC)O
SMILES (Isomeric) C[C@@H]1[C@H](CC2=C([C@@H](O[C@H]([C@H]12)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC)C(=O)OC)O
InChI InChI=1S/C18H28O11/c1-6-8(20)4-7-10(6)17(28-16(26-3)11(7)15(24)25-2)29-18-14(23)13(22)12(21)9(5-19)27-18/h6,8-10,12-14,16-23H,4-5H2,1-3H3/t6-,8+,9-,10-,12-,13+,14-,16-,17+,18+/m1/s1
InChI Key PSQQPRMLISSRFV-VYVLMKMUSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C18H28O11
Molecular Weight 420.40 g/mol
Exact Mass 420.16316171 g/mol
Topological Polar Surface Area (TPSA) 164.00 Ų
XlogP -2.20
Atomic LogP (AlogP) -2.38
H-Bond Acceptor 11
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 methyl (1S,3R,6S,7S,7aR)-6-hydroxy-3-methoxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7880 78.80%
Caco-2 - 0.8226 82.26%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.8571 85.71%
Subcellular localzation Mitochondria 0.6357 63.57%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8340 83.40%
OATP1B3 inhibitior + 0.9250 92.50%
MATE1 inhibitior - 0.8812 88.12%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior - 0.9229 92.29%
P-glycoprotein inhibitior - 0.8329 83.29%
P-glycoprotein substrate - 0.7005 70.05%
CYP3A4 substrate + 0.5971 59.71%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8819 88.19%
CYP3A4 inhibition - 0.9168 91.68%
CYP2C9 inhibition - 0.9246 92.46%
CYP2C19 inhibition - 0.9211 92.11%
CYP2D6 inhibition - 0.8962 89.62%
CYP1A2 inhibition - 0.8659 86.59%
CYP2C8 inhibition - 0.7967 79.67%
CYP inhibitory promiscuity - 0.8867 88.67%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6781 67.81%
Eye corrosion - 0.9884 98.84%
Eye irritation - 0.9535 95.35%
Skin irritation - 0.6847 68.47%
Skin corrosion - 0.9479 94.79%
Ames mutagenesis - 0.6545 65.45%
Human Ether-a-go-go-Related Gene inhibition - 0.6954 69.54%
Micronuclear - 0.7000 70.00%
Hepatotoxicity - 0.7500 75.00%
skin sensitisation - 0.8834 88.34%
Respiratory toxicity - 0.5222 52.22%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity - 0.5834 58.34%
Acute Oral Toxicity (c) III 0.5390 53.90%
Estrogen receptor binding + 0.6247 62.47%
Androgen receptor binding - 0.5360 53.60%
Thyroid receptor binding + 0.5314 53.14%
Glucocorticoid receptor binding - 0.5964 59.64%
Aromatase binding - 0.5066 50.66%
PPAR gamma + 0.5433 54.33%
Honey bee toxicity - 0.8468 84.68%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.7700 77.00%
Fish aquatic toxicity - 0.4102 41.02%

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 97.62% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.24% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.44% 85.14%
CHEMBL2581 P07339 Cathepsin D 88.73% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 84.68% 94.73%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.62% 97.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.41% 99.17%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 83.52% 94.33%
CHEMBL5255 O00206 Toll-like receptor 4 81.43% 92.50%
CHEMBL226 P30542 Adenosine A1 receptor 80.58% 95.93%

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.
Phlomis aurea

Cross-Links

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PubChem 101085900
LOTUS LTS0172372
wikiData Q105214347