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methyl (1S,4aS,6S,7R,7aS)-6-[(2S,3R,4S)-3-ethenyl-4-[(2S)-2-hydroxy-2-methoxyethyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]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 197b4550-99cb-406d-b8eb-b7464fef4d56
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-[(2S)-2-hydroxy-2-methoxyethyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]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)C4=COC(C(C4CC(O)OC)C=C)OC5C(C(C(C(O5)CO)O)O)O
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)CO)O)O)O)OC(=O)C4=CO[C@H]([C@@H]([C@@H]4C[C@@H](O)OC)C=C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
InChI InChI=1S/C34H50O20/c1-5-13-14(7-21(37)46-3)16(10-48-31(13)53-33-27(42)25(40)23(38)19(8-35)51-33)30(45)50-18-6-15-17(29(44)47-4)11-49-32(22(15)12(18)2)54-34-28(43)26(41)24(39)20(9-36)52-34/h5,10-15,18-28,31-43H,1,6-9H2,2-4H3/t12-,13+,14-,15+,18-,19+,20+,21-,22+,23+,24+,25-,26-,27+,28+,31-,32-,33-,34-/m0/s1
InChI Key JHDQHGCIJXUMCH-DPJQJATRSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C34H50O20
Molecular Weight 778.70 g/mol
Exact Mass 778.28954398 g/mol
Topological Polar Surface Area (TPSA) 299.00 Ų
XlogP -2.30
Atomic LogP (AlogP) -3.77
H-Bond Acceptor 20
H-Bond Donor 9
Rotatable Bonds 13

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-[(2S)-2-hydroxy-2-methoxyethyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]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 + 0.5511 55.11%
Caco-2 - 0.8825 88.25%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.8429 84.29%
Subcellular localzation Mitochondria 0.5609 56.09%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7043 70.43%
OATP1B3 inhibitior + 0.9373 93.73%
MATE1 inhibitior - 0.9412 94.12%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.5589 55.89%
P-glycoprotein inhibitior + 0.6481 64.81%
P-glycoprotein substrate + 0.5453 54.53%
CYP3A4 substrate + 0.6836 68.36%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8678 86.78%
CYP3A4 inhibition - 0.8510 85.10%
CYP2C9 inhibition - 0.9110 91.10%
CYP2C19 inhibition - 0.8945 89.45%
CYP2D6 inhibition - 0.9242 92.42%
CYP1A2 inhibition - 0.8969 89.69%
CYP2C8 inhibition + 0.6228 62.28%
CYP inhibitory promiscuity - 0.9386 93.86%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7214 72.14%
Eye corrosion - 0.9872 98.72%
Eye irritation - 0.9186 91.86%
Skin irritation - 0.7144 71.44%
Skin corrosion - 0.9406 94.06%
Ames mutagenesis - 0.5154 51.54%
Human Ether-a-go-go-Related Gene inhibition + 0.7685 76.85%
Micronuclear - 0.7300 73.00%
Hepatotoxicity - 0.6500 65.00%
skin sensitisation - 0.8572 85.72%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity + 0.6625 66.25%
Nephrotoxicity + 0.5305 53.05%
Acute Oral Toxicity (c) III 0.5561 55.61%
Estrogen receptor binding + 0.7925 79.25%
Androgen receptor binding + 0.6367 63.67%
Thyroid receptor binding - 0.5143 51.43%
Glucocorticoid receptor binding + 0.5957 59.57%
Aromatase binding + 0.5439 54.39%
PPAR gamma + 0.6954 69.54%
Honey bee toxicity - 0.7025 70.25%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.7100 71.00%
Fish aquatic toxicity + 0.7572 75.72%

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 98.66% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.64% 96.09%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 92.06% 86.92%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 90.73% 91.24%
CHEMBL2581 P07339 Cathepsin D 90.32% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 88.49% 94.73%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 88.43% 96.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.90% 97.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 87.25% 99.17%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.18% 85.14%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 86.21% 95.83%
CHEMBL340 P08684 Cytochrome P450 3A4 83.96% 91.19%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 83.25% 94.33%
CHEMBL5028 O14672 ADAM10 81.82% 97.50%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.69% 90.71%
CHEMBL4208 P20618 Proteasome component C5 81.34% 90.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.70% 86.33%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.66% 95.89%
CHEMBL5255 O00206 Toll-like receptor 4 80.34% 92.50%

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 163185295
LOTUS LTS0034651
wikiData Q105127897