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[(2R,3S,4S,5R,6S)-6-[[(1S,4aR,5R,7aR)-5-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,7a-dihydro-1H-cyclopenta[c]pyran-4a-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate

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 4723d642-64af-46a4-9cec-984688fc2cc7
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name [(2R,3S,4S,5R,6S)-6-[[(1S,4aR,5R,7aR)-5-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,7a-dihydro-1H-cyclopenta[c]pyran-4a-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
SMILES (Canonical) C1=CC(=CC=C1C=CC(=O)OCC2C(C(C(C(O2)OC34C=COC(C3C(=CC4O)CO)OC5C(C(C(C(O5)CO)O)O)O)O)O)O)O
SMILES (Isomeric) C1=CC(=CC=C1/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@]34C=CO[C@H]([C@@H]3C(=C[C@H]4O)CO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)O
InChI InChI=1S/C30H38O17/c31-10-14-9-18(34)30(7-8-42-27(20(14)30)46-28-25(40)23(38)21(36)16(11-32)44-28)47-29-26(41)24(39)22(37)17(45-29)12-43-19(35)6-3-13-1-4-15(33)5-2-13/h1-9,16-18,20-29,31-34,36-41H,10-12H2/b6-3+/t16-,17-,18-,20+,21-,22-,23+,24+,25-,26-,27+,28+,29+,30+/m1/s1
InChI Key OKFCVICEPQRZSV-NZTXADQGSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C30H38O17
Molecular Weight 670.60 g/mol
Exact Mass 670.21089974 g/mol
Topological Polar Surface Area (TPSA) 275.00 Ų
XlogP -3.90
Atomic LogP (AlogP) -3.89
H-Bond Acceptor 17
H-Bond Donor 10
Rotatable Bonds 10

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2R,3S,4S,5R,6S)-6-[[(1S,4aR,5R,7aR)-5-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,7a-dihydro-1H-cyclopenta[c]pyran-4a-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6418 64.18%
Caco-2 - 0.8932 89.32%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8714 87.14%
Subcellular localzation Mitochondria 0.6644 66.44%
OATP2B1 inhibitior - 0.8560 85.60%
OATP1B1 inhibitior + 0.8148 81.48%
OATP1B3 inhibitior + 0.9518 95.18%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.5000 50.00%
P-glycoprotein inhibitior - 0.4586 45.86%
P-glycoprotein substrate - 0.5839 58.39%
CYP3A4 substrate + 0.6809 68.09%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8685 86.85%
CYP3A4 inhibition - 0.9340 93.40%
CYP2C9 inhibition - 0.8426 84.26%
CYP2C19 inhibition - 0.6853 68.53%
CYP2D6 inhibition - 0.8557 85.57%
CYP1A2 inhibition - 0.8308 83.08%
CYP2C8 inhibition + 0.7658 76.58%
CYP inhibitory promiscuity - 0.6249 62.49%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5881 58.81%
Eye corrosion - 0.9896 98.96%
Eye irritation - 0.9134 91.34%
Skin irritation - 0.7750 77.50%
Skin corrosion - 0.9527 95.27%
Ames mutagenesis - 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7163 71.63%
Micronuclear - 0.5567 55.67%
Hepatotoxicity - 0.7375 73.75%
skin sensitisation - 0.7967 79.67%
Respiratory toxicity + 0.5778 57.78%
Reproductive toxicity + 0.8000 80.00%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity - 0.7153 71.53%
Acute Oral Toxicity (c) III 0.4195 41.95%
Estrogen receptor binding + 0.7343 73.43%
Androgen receptor binding + 0.6851 68.51%
Thyroid receptor binding - 0.4888 48.88%
Glucocorticoid receptor binding + 0.5586 55.86%
Aromatase binding + 0.5575 55.75%
PPAR gamma + 0.6648 66.48%
Honey bee toxicity - 0.6977 69.77%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.8165 81.65%

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 98.82% 91.11%
CHEMBL226 P30542 Adenosine A1 receptor 96.84% 95.93%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.05% 96.09%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 94.03% 89.67%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.87% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.69% 86.33%
CHEMBL1951 P21397 Monoamine oxidase A 90.99% 91.49%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.79% 97.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 90.38% 96.00%
CHEMBL3194 P02766 Transthyretin 87.69% 90.71%
CHEMBL3401 O75469 Pregnane X receptor 86.67% 94.73%
CHEMBL3060 Q9Y345 Glycine transporter 2 85.91% 99.17%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 85.04% 86.92%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 84.27% 95.83%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 83.75% 94.45%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 82.99% 89.62%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.56% 95.56%
CHEMBL5678 P34947 G protein-coupled receptor kinase 5 81.04% 88.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 81.03% 95.89%
CHEMBL1937 Q92769 Histone deacetylase 2 80.04% 94.75%

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.
Stachys byzantina

Cross-Links

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PubChem 162914869
LOTUS LTS0111590
wikiData Q105193507