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methyl (1S,4aS,6S,7R,7aS)-6-[(2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]oxy-7-methyl-1-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)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 1f2cabab-2bb5-423e-a208-b2a628c82971
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1S,4aS,6S,7R,7aS)-6-[(2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]oxy-7-methyl-1-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)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)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C4=COC(C(C4CC=O)C=C)OC5C(C(C(C(O5)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
SMILES (Isomeric) C[C@H]1[C@H](C[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)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C4=CO[C@H]([C@@H]([C@@H]4CC=O)C=C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
InChI InChI=1S/C49H62O27/c1-12-29-30(13-14-50)32(16-64-46(29)75-48-42(70-27(9)57)40(68-25(7)55)38(66-23(5)53)35(73-48)18-62-21(3)51)45(60)72-34-15-31-33(44(59)61-11)17-65-47(37(31)20(34)2)76-49-43(71-28(10)58)41(69-26(8)56)39(67-24(6)54)36(74-49)19-63-22(4)52/h12,14,16-17,20,29-31,34-43,46-49H,1,13,15,18-19H2,2-11H3/t20-,29+,30-,31+,34-,35+,36+,37+,38+,39+,40-,41-,42+,43+,46-,47-,48-,49-/m0/s1
InChI Key YWOADMLJMDWHTM-SDSRGVLNSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C49H62O27
Molecular Weight 1083.00 g/mol
Exact Mass 1082.34784670 g/mol
Topological Polar Surface Area (TPSA) 335.00 Ų
XlogP 0.90
Atomic LogP (AlogP) 1.03
H-Bond Acceptor 27
H-Bond Donor 0
Rotatable Bonds 20

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1S,4aS,6S,7R,7aS)-6-[(2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]oxy-7-methyl-1-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)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 + 0.9591 95.91%
Caco-2 - 0.8546 85.46%
Blood Brain Barrier + 0.8250 82.50%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.6490 64.90%
OATP2B1 inhibitior - 0.7161 71.61%
OATP1B1 inhibitior + 0.7294 72.94%
OATP1B3 inhibitior + 0.8913 89.13%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.9957 99.57%
P-glycoprotein inhibitior + 0.7689 76.89%
P-glycoprotein substrate + 0.5638 56.38%
CYP3A4 substrate + 0.7108 71.08%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8855 88.55%
CYP3A4 inhibition - 0.6531 65.31%
CYP2C9 inhibition - 0.9088 90.88%
CYP2C19 inhibition - 0.6961 69.61%
CYP2D6 inhibition - 0.9378 93.78%
CYP1A2 inhibition - 0.7715 77.15%
CYP2C8 inhibition + 0.6995 69.95%
CYP inhibitory promiscuity - 0.6242 62.42%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6749 67.49%
Eye corrosion - 0.9749 97.49%
Eye irritation - 0.8985 89.85%
Skin irritation - 0.7097 70.97%
Skin corrosion - 0.9390 93.90%
Ames mutagenesis + 0.5500 55.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7654 76.54%
Micronuclear - 0.6100 61.00%
Hepatotoxicity - 0.5557 55.57%
skin sensitisation - 0.6809 68.09%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.8000 80.00%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity + 0.5858 58.58%
Acute Oral Toxicity (c) III 0.5143 51.43%
Estrogen receptor binding + 0.8150 81.50%
Androgen receptor binding + 0.6967 69.67%
Thyroid receptor binding + 0.5620 56.20%
Glucocorticoid receptor binding + 0.7624 76.24%
Aromatase binding + 0.6599 65.99%
PPAR gamma + 0.7515 75.15%
Honey bee toxicity - 0.7265 72.65%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.9100 91.00%

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 98.36% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.01% 91.11%
CHEMBL4208 P20618 Proteasome component C5 92.69% 90.00%
CHEMBL3401 O75469 Pregnane X receptor 90.66% 94.73%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 88.99% 86.92%
CHEMBL340 P08684 Cytochrome P450 3A4 88.96% 91.19%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 87.98% 94.80%
CHEMBL5255 O00206 Toll-like receptor 4 87.02% 92.50%
CHEMBL5028 O14672 ADAM10 86.53% 97.50%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.98% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.98% 97.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 80.14% 96.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.13% 94.45%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 163037194
LOTUS LTS0233503
wikiData Q105366981