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methyl (1S,4aR,6S,7R,7aS)-4a,7-dihydroxy-6-[(2S)-2-hydroxypropoxy]-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[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 5ec322f8-88e9-4d80-be22-c4c1ae5db1b8
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1S,4aR,6S,7R,7aS)-4a,7-dihydroxy-6-[(2S)-2-hydroxypropoxy]-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
SMILES (Canonical) CC(COC1CC2(C(C1(C)O)C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)O
SMILES (Isomeric) C[C@@H](CO[C@H]1C[C@]2([C@@H]([C@@]1(C)O)[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
InChI InChI=1S/C20H32O13/c1-8(22)6-30-11-4-20(28)9(16(26)29-3)7-31-18(15(20)19(11,2)27)33-17-14(25)13(24)12(23)10(5-21)32-17/h7-8,10-15,17-18,21-25,27-28H,4-6H2,1-3H3/t8-,10+,11-,12+,13-,14+,15+,17-,18-,19-,20-/m0/s1
InChI Key KNWPUFRWLDYCQJ-VKTYGPIQSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H32O13
Molecular Weight 480.50 g/mol
Exact Mass 480.18429107 g/mol
Topological Polar Surface Area (TPSA) 205.00 Ų
XlogP -2.90
Atomic LogP (AlogP) -3.52
H-Bond Acceptor 13
H-Bond Donor 7
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1S,4aR,6S,7R,7aS)-4a,7-dihydroxy-6-[(2S)-2-hydroxypropoxy]-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[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 + 0.7035 70.35%
Caco-2 - 0.8287 82.87%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.6222 62.22%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8328 83.28%
OATP1B3 inhibitior + 0.9232 92.32%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.8477 84.77%
P-glycoprotein inhibitior - 0.7701 77.01%
P-glycoprotein substrate - 0.6085 60.85%
CYP3A4 substrate + 0.6645 66.45%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8734 87.34%
CYP3A4 inhibition - 0.9424 94.24%
CYP2C9 inhibition - 0.9295 92.95%
CYP2C19 inhibition - 0.9125 91.25%
CYP2D6 inhibition - 0.9419 94.19%
CYP1A2 inhibition - 0.9053 90.53%
CYP2C8 inhibition - 0.7073 70.73%
CYP inhibitory promiscuity - 0.9363 93.63%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6345 63.45%
Eye corrosion - 0.9901 99.01%
Eye irritation - 0.9488 94.88%
Skin irritation - 0.6403 64.03%
Skin corrosion - 0.9445 94.45%
Ames mutagenesis - 0.6200 62.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4437 44.37%
Micronuclear - 0.8000 80.00%
Hepatotoxicity - 0.7620 76.20%
skin sensitisation - 0.8856 88.56%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.5875 58.75%
Nephrotoxicity - 0.6979 69.79%
Acute Oral Toxicity (c) III 0.4190 41.90%
Estrogen receptor binding + 0.6799 67.99%
Androgen receptor binding + 0.5667 56.67%
Thyroid receptor binding + 0.5574 55.74%
Glucocorticoid receptor binding + 0.5852 58.52%
Aromatase binding + 0.7184 71.84%
PPAR gamma + 0.5252 52.52%
Honey bee toxicity - 0.7862 78.62%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.8100 81.00%
Fish aquatic toxicity + 0.8262 82.62%

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 98.87% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.67% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.34% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.16% 94.45%
CHEMBL2581 P07339 Cathepsin D 92.27% 98.95%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 88.74% 96.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 86.74% 97.25%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 85.59% 91.24%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.46% 97.09%
CHEMBL3401 O75469 Pregnane X receptor 84.10% 94.73%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.73% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.41% 95.89%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 83.37% 94.33%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.09% 97.14%
CHEMBL218 P21554 Cannabinoid CB1 receptor 82.60% 96.61%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.07% 99.17%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.69% 92.62%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.26% 86.33%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.16% 100.00%

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.
Fridericia elegans

Cross-Links

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PubChem 162875518
LOTUS LTS0084561
wikiData Q105143634