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methyl (1S,4aS,5R,7S,7aS)-5-hydroxy-7-[3-(4-hydroxyphenyl)propanoyloxy]-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[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 3534522a-d620-4b1f-aa30-13aea1c35d8c
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1S,4aS,5R,7S,7aS)-5-hydroxy-7-[3-(4-hydroxyphenyl)propanoyloxy]-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
SMILES (Canonical) CC1(CC(C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)OC(=O)CCC4=CC=C(C=C4)O
SMILES (Isomeric) C[C@@]1(C[C@H]([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)O)OC(=O)CCC4=CC=C(C=C4)O
InChI InChI=1S/C26H34O13/c1-26(39-17(30)8-5-12-3-6-13(28)7-4-12)9-15(29)18-14(23(34)35-2)11-36-24(19(18)26)38-25-22(33)21(32)20(31)16(10-27)37-25/h3-4,6-7,11,15-16,18-22,24-25,27-29,31-33H,5,8-10H2,1-2H3/t15-,16-,18+,19-,20-,21+,22-,24+,25+,26+/m1/s1
InChI Key XEXWMGIDWXELLE-RCVSRHDUSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C26H34O13
Molecular Weight 554.50 g/mol
Exact Mass 554.19994113 g/mol
Topological Polar Surface Area (TPSA) 202.00 Ų
XlogP -0.50
Atomic LogP (AlogP) -1.15
H-Bond Acceptor 13
H-Bond Donor 6
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1S,4aS,5R,7S,7aS)-5-hydroxy-7-[3-(4-hydroxyphenyl)propanoyloxy]-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[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 + 0.7443 74.43%
Caco-2 - 0.8847 88.47%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.7157 71.57%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7266 72.66%
OATP1B3 inhibitior + 0.9169 91.69%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8375 83.75%
BSEP inhibitior + 0.7194 71.94%
P-glycoprotein inhibitior - 0.6066 60.66%
P-glycoprotein substrate + 0.5852 58.52%
CYP3A4 substrate + 0.7045 70.45%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8717 87.17%
CYP3A4 inhibition - 0.8240 82.40%
CYP2C9 inhibition - 0.8469 84.69%
CYP2C19 inhibition - 0.8636 86.36%
CYP2D6 inhibition - 0.9041 90.41%
CYP1A2 inhibition - 0.8181 81.81%
CYP2C8 inhibition + 0.7404 74.04%
CYP inhibitory promiscuity - 0.8958 89.58%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6052 60.52%
Eye corrosion - 0.9908 99.08%
Eye irritation - 0.9411 94.11%
Skin irritation - 0.6842 68.42%
Skin corrosion - 0.9397 93.97%
Ames mutagenesis - 0.6337 63.37%
Human Ether-a-go-go-Related Gene inhibition + 0.6917 69.17%
Micronuclear - 0.7100 71.00%
Hepatotoxicity - 0.8448 84.48%
skin sensitisation - 0.8752 87.52%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.5074 50.74%
Acute Oral Toxicity (c) I 0.5425 54.25%
Estrogen receptor binding + 0.8252 82.52%
Androgen receptor binding + 0.6745 67.45%
Thyroid receptor binding + 0.5290 52.90%
Glucocorticoid receptor binding + 0.7267 72.67%
Aromatase binding + 0.5771 57.71%
PPAR gamma + 0.6524 65.24%
Honey bee toxicity - 0.7064 70.64%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.7200 72.00%
Fish aquatic toxicity + 0.8954 89.54%

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 99.11% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 99.06% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.34% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.97% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 90.66% 95.89%
CHEMBL3060 Q9Y345 Glycine transporter 2 89.72% 99.17%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.27% 85.14%
CHEMBL2581 P07339 Cathepsin D 88.20% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.77% 97.09%
CHEMBL3437 Q16853 Amine oxidase, copper containing 87.53% 94.00%
CHEMBL4208 P20618 Proteasome component C5 87.02% 90.00%
CHEMBL3401 O75469 Pregnane X receptor 86.53% 94.73%
CHEMBL5255 O00206 Toll-like receptor 4 85.38% 92.50%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 85.31% 95.50%
CHEMBL220 P22303 Acetylcholinesterase 84.49% 94.45%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 83.45% 95.83%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 83.27% 96.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.64% 89.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 81.66% 95.89%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.29% 94.00%

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.
Barleria lupulina

Cross-Links

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PubChem 154497405
LOTUS LTS0223938
wikiData Q105326822