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[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl (1S,4aR,7R,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-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 379a992f-68fc-452f-8600-7469acee9edc
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl (1S,4aR,7R,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C28H36O17/c29-7-15-18(32)20(34)23(37)27(43-15)45-25-17-13(5-6-28(17,39)10-30)14(8-41-25)24(38)40-9-16-19(33)21(35)22(36)26(44-16)42-12-3-1-11(31)2-4-12/h1-6,8,13,15-23,25-27,29-37,39H,7,9-10H2/t13-,15+,16+,17+,18+,19+,20-,21-,22+,23+,25-,26+,27-,28-/m0/s1
InChI Key SWPCUCSDISESSE-ZVISEQGLSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C28H36O17
Molecular Weight 644.60 g/mol
Exact Mass 644.19524968 g/mol
Topological Polar Surface Area (TPSA) 275.00 Ų
XlogP -3.50
Atomic LogP (AlogP) -4.30
H-Bond Acceptor 17
H-Bond Donor 10
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl (1S,4aR,7R,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-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 + 0.6835 68.35%
Caco-2 - 0.9001 90.01%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.5952 59.52%
OATP2B1 inhibitior - 0.8561 85.61%
OATP1B1 inhibitior + 0.8156 81.56%
OATP1B3 inhibitior + 0.9503 95.03%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.6626 66.26%
P-glycoprotein inhibitior - 0.4549 45.49%
P-glycoprotein substrate - 0.7358 73.58%
CYP3A4 substrate + 0.6774 67.74%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8578 85.78%
CYP3A4 inhibition - 0.9306 93.06%
CYP2C9 inhibition - 0.8744 87.44%
CYP2C19 inhibition - 0.7299 72.99%
CYP2D6 inhibition - 0.8265 82.65%
CYP1A2 inhibition - 0.8395 83.95%
CYP2C8 inhibition + 0.6625 66.25%
CYP inhibitory promiscuity - 0.7717 77.17%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5897 58.97%
Eye corrosion - 0.9908 99.08%
Eye irritation - 0.9098 90.98%
Skin irritation - 0.7619 76.19%
Skin corrosion - 0.9496 94.96%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6456 64.56%
Micronuclear - 0.5567 55.67%
Hepatotoxicity - 0.8375 83.75%
skin sensitisation - 0.7921 79.21%
Respiratory toxicity + 0.5778 57.78%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity - 0.5658 56.58%
Acute Oral Toxicity (c) III 0.4299 42.99%
Estrogen receptor binding + 0.7575 75.75%
Androgen receptor binding + 0.6252 62.52%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.5693 56.93%
Aromatase binding + 0.5782 57.82%
PPAR gamma + 0.6727 67.27%
Honey bee toxicity - 0.7653 76.53%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.6850 68.50%
Fish aquatic toxicity + 0.7486 74.86%

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 96.97% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.81% 91.11%
CHEMBL4208 P20618 Proteasome component C5 92.58% 90.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.33% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.36% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.61% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.84% 95.89%
CHEMBL226 P30542 Adenosine A1 receptor 85.02% 95.93%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.75% 99.17%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 83.44% 94.45%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.08% 95.89%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.84% 94.00%
CHEMBL2581 P07339 Cathepsin D 81.54% 98.95%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 81.50% 86.92%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 81.39% 94.62%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 81.35% 95.83%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 80.81% 85.00%
CHEMBL3891 P07384 Calpain 1 80.50% 93.04%
CHEMBL5255 O00206 Toll-like receptor 4 80.11% 92.50%

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.
Vaccinium dunalianum

Cross-Links

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PubChem 162879139
LOTUS LTS0088141
wikiData Q105262786