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[(2R,3S,4R,5R,6S)-6-[[(3S,4R,4aR)-4-ethenyl-4a-hydroxy-8-oxo-3,4,5,6-tetrahydropyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)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 604508ba-32aa-4ea7-b9c7-26e45cd11644
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
IUPAC Name [(2R,3S,4R,5R,6S)-6-[[(3S,4R,4aR)-4-ethenyl-4a-hydroxy-8-oxo-3,4,5,6-tetrahydropyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
SMILES (Canonical) COC1=C(C=CC(=C1)C=CC(=O)OC2C(OC(C(C2O)O)OC3C(C4(CCOC(=O)C4=CO3)O)C=C)CO)O
SMILES (Isomeric) COC1=C(C=CC(=C1)/C=C/C(=O)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)O[C@H]3[C@@H]([C@@]4(CCOC(=O)C4=CO3)O)C=C)CO)O
InChI InChI=1S/C26H30O13/c1-3-14-24(36-12-15-23(32)35-9-8-26(14,15)33)39-25-21(31)20(30)22(18(11-27)37-25)38-19(29)7-5-13-4-6-16(28)17(10-13)34-2/h3-7,10,12,14,18,20-22,24-25,27-28,30-31,33H,1,8-9,11H2,2H3/b7-5+/t14-,18+,20+,21+,22+,24-,25-,26+/m0/s1
InChI Key YZIHSPLEUDRBMV-YXSMRIAXSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C26H30O13
Molecular Weight 550.50 g/mol
Exact Mass 550.16864101 g/mol
Topological Polar Surface Area (TPSA) 191.00 Ų
XlogP -0.30
Atomic LogP (AlogP) -0.50
H-Bond Acceptor 13
H-Bond Donor 5
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2R,3S,4R,5R,6S)-6-[[(3S,4R,4aR)-4-ethenyl-4a-hydroxy-8-oxo-3,4,5,6-tetrahydropyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)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 + 0.8001 80.01%
Caco-2 - 0.8942 89.42%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.7402 74.02%
OATP2B1 inhibitior - 0.8557 85.57%
OATP1B1 inhibitior + 0.8571 85.71%
OATP1B3 inhibitior + 0.9388 93.88%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.8319 83.19%
BSEP inhibitior - 0.6211 62.11%
P-glycoprotein inhibitior - 0.4511 45.11%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.7042 70.42%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8649 86.49%
CYP3A4 inhibition - 0.8433 84.33%
CYP2C9 inhibition - 0.7304 73.04%
CYP2C19 inhibition - 0.6632 66.32%
CYP2D6 inhibition - 0.8459 84.59%
CYP1A2 inhibition - 0.7037 70.37%
CYP2C8 inhibition + 0.7160 71.60%
CYP inhibitory promiscuity - 0.9048 90.48%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5677 56.77%
Eye corrosion - 0.9854 98.54%
Eye irritation - 0.9180 91.80%
Skin irritation - 0.7542 75.42%
Skin corrosion - 0.9316 93.16%
Ames mutagenesis - 0.6200 62.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5082 50.82%
Micronuclear - 0.5767 57.67%
Hepatotoxicity - 0.6191 61.91%
skin sensitisation - 0.7857 78.57%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity - 0.9001 90.01%
Acute Oral Toxicity (c) III 0.5386 53.86%
Estrogen receptor binding + 0.8004 80.04%
Androgen receptor binding + 0.6942 69.42%
Thyroid receptor binding - 0.5172 51.72%
Glucocorticoid receptor binding + 0.6854 68.54%
Aromatase binding + 0.6038 60.38%
PPAR gamma + 0.6907 69.07%
Honey bee toxicity - 0.6853 68.53%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.8264 82.64%

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 99.70% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 97.03% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 97.00% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.74% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.56% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 92.05% 96.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.95% 94.45%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 90.86% 92.62%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.31% 97.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 86.96% 85.14%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.74% 95.89%
CHEMBL4208 P20618 Proteasome component C5 85.67% 90.00%
CHEMBL2581 P07339 Cathepsin D 84.42% 98.95%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.47% 91.07%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.14% 97.14%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 81.92% 97.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.72% 100.00%
CHEMBL3401 O75469 Pregnane X receptor 80.94% 94.73%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.05% 99.17%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 101394760
NPASS NPC108701
LOTUS LTS0021928
wikiData Q105369251