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methyl (1S,4aS,6S,7R,7aR)-6-[(2S,3R,4R)-3-ethenyl-4-[[(2R,4S)-4-(hydroxymethyl)-1,3-dioxolan-2-yl]methyl]-2-[(2S,3R,4S,5R,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,5R,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 873efc4e-5868-4282-ac62-99ed72e1fbe2
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1S,4aS,6S,7R,7aR)-6-[(2S,3R,4R)-3-ethenyl-4-[[(2R,4S)-4-(hydroxymethyl)-1,3-dioxolan-2-yl]methyl]-2-[(2S,3R,4S,5R,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,5R,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(C4CC5OCC(O5)CO)C=C)OC6C(C(C(C(O6)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]5OC[C@@H](O5)CO)C=C)O[C@H]6[C@@H]([C@H]([C@H]([C@H](O6)CO)O)O)O
InChI InChI=1S/C36H52O21/c1-4-15-16(6-23-49-10-14(7-37)52-23)18(11-50-33(15)56-35-29(44)27(42)25(40)21(8-38)54-35)32(47)53-20-5-17-19(31(46)48-3)12-51-34(24(17)13(20)2)57-36-30(45)28(43)26(41)22(9-39)55-36/h4,11-17,20-30,33-45H,1,5-10H2,2-3H3/t13-,14-,15+,16+,17+,20-,21+,22+,23+,24-,25-,26-,27-,28-,29+,30+,33-,34-,35-,36-/m0/s1
InChI Key BDKGRKLZWISWKI-QAORRUDASA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C36H52O21
Molecular Weight 820.80 g/mol
Exact Mass 820.30010866 g/mol
Topological Polar Surface Area (TPSA) 309.00 Ų
XlogP -2.60
Atomic LogP (AlogP) -4.00
H-Bond Acceptor 21
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,7aR)-6-[(2S,3R,4R)-3-ethenyl-4-[[(2R,4S)-4-(hydroxymethyl)-1,3-dioxolan-2-yl]methyl]-2-[(2S,3R,4S,5R,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,5R,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 + 0.5977 59.77%
Caco-2 - 0.8828 88.28%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.7579 75.79%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7030 70.30%
OATP1B3 inhibitior + 0.9546 95.46%
MATE1 inhibitior - 0.9412 94.12%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.7892 78.92%
P-glycoprotein inhibitior + 0.6604 66.04%
P-glycoprotein substrate + 0.6131 61.31%
CYP3A4 substrate + 0.7013 70.13%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8693 86.93%
CYP3A4 inhibition - 0.8134 81.34%
CYP2C9 inhibition - 0.9175 91.75%
CYP2C19 inhibition - 0.8574 85.74%
CYP2D6 inhibition - 0.9261 92.61%
CYP1A2 inhibition - 0.8896 88.96%
CYP2C8 inhibition + 0.7216 72.16%
CYP inhibitory promiscuity - 0.8815 88.15%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7103 71.03%
Eye corrosion - 0.9865 98.65%
Eye irritation - 0.9164 91.64%
Skin irritation - 0.7327 73.27%
Skin corrosion - 0.9426 94.26%
Ames mutagenesis + 0.6946 69.46%
Human Ether-a-go-go-Related Gene inhibition + 0.7541 75.41%
Micronuclear - 0.7400 74.00%
Hepatotoxicity - 0.7216 72.16%
skin sensitisation - 0.8558 85.58%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.8333 83.33%
Mitochondrial toxicity + 0.6875 68.75%
Nephrotoxicity - 0.7465 74.65%
Acute Oral Toxicity (c) III 0.4563 45.63%
Estrogen receptor binding + 0.8160 81.60%
Androgen receptor binding + 0.6435 64.35%
Thyroid receptor binding - 0.5376 53.76%
Glucocorticoid receptor binding + 0.5707 57.07%
Aromatase binding - 0.4933 49.33%
PPAR gamma + 0.6902 69.02%
Honey bee toxicity - 0.6678 66.78%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6600 66.00%
Fish aquatic toxicity + 0.9615 96.15%

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 98.92% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.06% 96.09%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 95.35% 86.92%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 90.00% 96.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.86% 97.09%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 88.05% 91.24%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 87.02% 95.83%
CHEMBL2243 O00519 Anandamide amidohydrolase 86.92% 97.53%
CHEMBL5028 O14672 ADAM10 85.53% 97.50%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.79% 99.17%
CHEMBL5255 O00206 Toll-like receptor 4 83.75% 92.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.37% 89.00%
CHEMBL3401 O75469 Pregnane X receptor 83.29% 94.73%
CHEMBL4208 P20618 Proteasome component C5 83.24% 90.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.61% 91.07%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.72% 86.33%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 81.38% 94.33%
CHEMBL4040 P28482 MAP kinase ERK2 80.00% 83.82%

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.
Dipsacus inermis

Cross-Links

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PubChem 154496492
LOTUS LTS0248560
wikiData Q104924332