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methyl (1S,6S,7R)-6-[2-[(2S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]acetyl]oxy-7-methyl-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-carboxylate

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID e4ed27e5-8a98-4ece-b8d1-7dfc8835d758
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1S,6S,7R)-6-[2-[(2S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]acetyl]oxy-7-methyl-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-carboxylate
SMILES (Canonical) CC1C(CC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)CC4C(C(OC=C4C(=O)OC)OC5C(C(C(C(O5)CO)O)O)O)C=C
SMILES (Isomeric) C[C@H]1[C@H](CC2C1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC(=O)CC4C([C@@H](OC=C4C(=O)OC)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C=C
InChI InChI=1S/C34H48O20/c1-5-13-14(16(29(44)46-3)10-48-31(13)53-33-27(42)25(40)23(38)19(8-35)51-33)7-21(37)50-18-6-15-17(30(45)47-4)11-49-32(22(15)12(18)2)54-34-28(43)26(41)24(39)20(9-36)52-34/h5,10-15,18-20,22-28,31-36,38-43H,1,6-9H2,2-4H3/t12-,13?,14?,15?,18-,19+,20+,22?,23+,24+,25-,26-,27+,28+,31-,32-,33-,34-/m0/s1
InChI Key SALKJJXIOWSSIF-STTDBXLJSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C34H48O20
Molecular Weight 776.70 g/mol
Exact Mass 776.27389392 g/mol
Topological Polar Surface Area (TPSA) 296.00 Ų
XlogP -2.20
Atomic LogP (AlogP) -3.56
H-Bond Acceptor 20
H-Bond Donor 8
Rotatable Bonds 12

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1S,6S,7R)-6-[2-[(2S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]acetyl]oxy-7-methyl-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-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.4685 46.85%
Caco-2 - 0.8791 87.91%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.8429 84.29%
Subcellular localzation Mitochondria 0.6742 67.42%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior - 0.3541 35.41%
OATP1B3 inhibitior + 0.9141 91.41%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.7327 73.27%
P-glycoprotein inhibitior + 0.6775 67.75%
P-glycoprotein substrate - 0.5210 52.10%
CYP3A4 substrate + 0.6806 68.06%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8859 88.59%
CYP3A4 inhibition - 0.9018 90.18%
CYP2C9 inhibition - 0.9042 90.42%
CYP2C19 inhibition - 0.8789 87.89%
CYP2D6 inhibition - 0.9289 92.89%
CYP1A2 inhibition - 0.8821 88.21%
CYP2C8 inhibition + 0.5958 59.58%
CYP inhibitory promiscuity - 0.9160 91.60%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.7544 75.44%
Eye corrosion - 0.9869 98.69%
Eye irritation - 0.9148 91.48%
Skin irritation - 0.7318 73.18%
Skin corrosion - 0.9487 94.87%
Ames mutagenesis + 0.5246 52.46%
Human Ether-a-go-go-Related Gene inhibition + 0.7450 74.50%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.7091 70.91%
skin sensitisation - 0.8613 86.13%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.8222 82.22%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity + 0.5264 52.64%
Acute Oral Toxicity (c) III 0.4546 45.46%
Estrogen receptor binding + 0.7904 79.04%
Androgen receptor binding + 0.6413 64.13%
Thyroid receptor binding - 0.5128 51.28%
Glucocorticoid receptor binding + 0.5983 59.83%
Aromatase binding + 0.5215 52.15%
PPAR gamma + 0.6941 69.41%
Honey bee toxicity - 0.7397 73.97%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6900 69.00%
Fish aquatic toxicity + 0.8940 89.40%

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 98.09% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.22% 91.11%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 94.47% 86.92%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 86.93% 91.24%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.77% 97.09%
CHEMBL4208 P20618 Proteasome component C5 86.15% 90.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 86.10% 96.00%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 85.37% 95.83%
CHEMBL5028 O14672 ADAM10 84.59% 97.50%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.47% 99.17%
CHEMBL3401 O75469 Pregnane X receptor 83.04% 94.73%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.20% 89.00%
CHEMBL5255 O00206 Toll-like receptor 4 82.01% 92.50%
CHEMBL2581 P07339 Cathepsin D 81.67% 98.95%
CHEMBL340 P08684 Cytochrome P450 3A4 81.18% 91.19%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.00% 86.33%

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.
Loasa acerifolia
Loasa placei

Cross-Links

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PubChem 102586546
LOTUS LTS0122690
wikiData Q104392945