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methyl (1S,4aS,6S,7R,7aR)-6-[(2S,3S,4S)-4-(2-acetyloxyethyl)-3-ethenyl-2-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]oxy-7-methyl-1-[(2S,3S,4R,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 9e60e267-3965-4bf8-b95e-2232d07405a2
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1S,4aS,6S,7R,7aR)-6-[(2S,3S,4S)-4-(2-acetyloxyethyl)-3-ethenyl-2-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]oxy-7-methyl-1-[(2S,3S,4R,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(C4CCOC(=O)C)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]4CCOC(=O)C)C=C)O[C@H]5[C@H]([C@@H]([C@@H]([C@@H](O5)CO)O)O)O
InChI InChI=1S/C35H50O20/c1-5-15-16(6-7-48-14(3)38)18(11-49-32(15)54-34-28(43)26(41)24(39)21(9-36)52-34)31(46)51-20-8-17-19(30(45)47-4)12-50-33(23(17)13(20)2)55-35-29(44)27(42)25(40)22(10-37)53-35/h5,11-13,15-17,20-29,32-37,39-44H,1,6-10H2,2-4H3/t13-,15-,16-,17+,20-,21-,22+,23-,24+,25+,26+,27+,28-,29-,32-,33-,34-,35-/m0/s1
InChI Key HHQSMLRBHWUMDI-KWEUNCOGSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C35H50O20
Molecular Weight 790.80 g/mol
Exact Mass 790.28954398 g/mol
Topological Polar Surface Area (TPSA) 296.00 Ų
XlogP -1.70
Atomic LogP (AlogP) -3.17
H-Bond Acceptor 20
H-Bond Donor 8
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,3S,4S)-4-(2-acetyloxyethyl)-3-ethenyl-2-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]oxy-7-methyl-1-[(2S,3S,4R,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 - 0.5550 55.50%
Caco-2 - 0.8774 87.74%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.7099 70.99%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.6874 68.74%
OATP1B3 inhibitior + 0.9170 91.70%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.6936 69.36%
P-glycoprotein inhibitior + 0.6803 68.03%
P-glycoprotein substrate + 0.5554 55.54%
CYP3A4 substrate + 0.7011 70.11%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8859 88.59%
CYP3A4 inhibition - 0.9104 91.04%
CYP2C9 inhibition - 0.8798 87.98%
CYP2C19 inhibition - 0.8631 86.31%
CYP2D6 inhibition - 0.9230 92.30%
CYP1A2 inhibition - 0.8609 86.09%
CYP2C8 inhibition + 0.6820 68.20%
CYP inhibitory promiscuity - 0.9056 90.56%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7075 70.75%
Eye corrosion - 0.9860 98.60%
Eye irritation - 0.9160 91.60%
Skin irritation - 0.6989 69.89%
Skin corrosion - 0.9368 93.68%
Ames mutagenesis + 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7721 77.21%
Micronuclear - 0.8000 80.00%
Hepatotoxicity - 0.7290 72.90%
skin sensitisation - 0.8773 87.73%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.8111 81.11%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity + 0.6187 61.87%
Acute Oral Toxicity (c) III 0.5551 55.51%
Estrogen receptor binding + 0.8291 82.91%
Androgen receptor binding + 0.6614 66.14%
Thyroid receptor binding - 0.5111 51.11%
Glucocorticoid receptor binding + 0.6320 63.20%
Aromatase binding - 0.5000 50.00%
PPAR gamma + 0.7043 70.43%
Honey bee toxicity - 0.7148 71.48%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.6900 69.00%
Fish aquatic toxicity + 0.7491 74.91%

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 98.69% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.17% 96.09%
CHEMBL3401 O75469 Pregnane X receptor 89.27% 94.73%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 89.09% 86.92%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.07% 97.09%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 89.03% 91.24%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 88.96% 96.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 85.80% 99.17%
CHEMBL2581 P07339 Cathepsin D 84.58% 98.95%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 84.33% 95.83%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.03% 86.33%
CHEMBL5028 O14672 ADAM10 82.86% 97.50%
CHEMBL340 P08684 Cytochrome P450 3A4 81.96% 91.19%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.39% 89.00%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 81.36% 94.33%
CHEMBL5255 O00206 Toll-like receptor 4 81.31% 92.50%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 81.23% 95.50%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.90% 85.14%
CHEMBL4208 P20618 Proteasome component C5 80.27% 90.00%

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 fullonum

Cross-Links

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PubChem 162861857
LOTUS LTS0183798
wikiData Q105028489