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[(2R,3R,4S,5R,6R)-5-acetyloxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (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 f6825ca3-2b01-4396-896c-70059620cf45
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
IUPAC Name [(2R,3R,4S,5R,6R)-5-acetyloxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
SMILES (Canonical) CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C)OCCC3=CC(=C(C=C3)O)O)CO)OC(=O)C=CC4=CC=C(C=C4)O)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]([C@H](O[C@H]([C@@H]2OC(=O)C)OCCC3=CC(=C(C=C3)O)O)CO)OC(=O)/C=C/C4=CC=C(C=C4)O)O)O)O
InChI InChI=1S/C31H38O15/c1-15-24(38)25(39)26(40)30(42-15)46-28-27(45-23(37)10-6-17-3-7-19(34)8-4-17)22(14-32)44-31(29(28)43-16(2)33)41-12-11-18-5-9-20(35)21(36)13-18/h3-10,13,15,22,24-32,34-36,38-40H,11-12,14H2,1-2H3/b10-6+/t15-,22+,24-,25+,26+,27+,28-,29+,30-,31+/m0/s1
InChI Key XWAGWSCLKIGRPW-RHHHWDBBSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C31H38O15
Molecular Weight 650.60 g/mol
Exact Mass 650.22107050 g/mol
Topological Polar Surface Area (TPSA) 231.00 Ų
XlogP 0.40
Atomic LogP (AlogP) -0.15
H-Bond Acceptor 15
H-Bond Donor 7
Rotatable Bonds 11

Synonyms

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orb2893501

2D Structure

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2D Structure of [(2R,3R,4S,5R,6R)-5-acetyloxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (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 - 0.8373 83.73%
Caco-2 - 0.8977 89.77%
Blood Brain Barrier - 0.7000 70.00%
Human oral bioavailability - 0.9000 90.00%
Subcellular localzation Mitochondria 0.7684 76.84%
OATP2B1 inhibitior - 0.8592 85.92%
OATP1B1 inhibitior + 0.8690 86.90%
OATP1B3 inhibitior + 0.9366 93.66%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.9010 90.10%
P-glycoprotein inhibitior - 0.4538 45.38%
P-glycoprotein substrate - 0.5442 54.42%
CYP3A4 substrate + 0.6758 67.58%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8729 87.29%
CYP3A4 inhibition - 0.8012 80.12%
CYP2C9 inhibition - 0.6940 69.40%
CYP2C19 inhibition - 0.8573 85.73%
CYP2D6 inhibition - 0.9190 91.90%
CYP1A2 inhibition - 0.8568 85.68%
CYP2C8 inhibition + 0.7666 76.66%
CYP inhibitory promiscuity - 0.7570 75.70%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9200 92.00%
Carcinogenicity (trinary) Non-required 0.7213 72.13%
Eye corrosion - 0.9908 99.08%
Eye irritation - 0.9237 92.37%
Skin irritation - 0.8586 85.86%
Skin corrosion - 0.9519 95.19%
Ames mutagenesis - 0.6200 62.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8060 80.60%
Micronuclear - 0.6467 64.67%
Hepatotoxicity - 0.8875 88.75%
skin sensitisation - 0.8452 84.52%
Respiratory toxicity - 0.6000 60.00%
Reproductive toxicity + 0.5667 56.67%
Mitochondrial toxicity - 0.5625 56.25%
Nephrotoxicity - 0.8289 82.89%
Acute Oral Toxicity (c) III 0.7934 79.34%
Estrogen receptor binding + 0.8027 80.27%
Androgen receptor binding - 0.5000 50.00%
Thyroid receptor binding + 0.5224 52.24%
Glucocorticoid receptor binding + 0.6167 61.67%
Aromatase binding - 0.5315 53.15%
PPAR gamma + 0.6852 68.52%
Honey bee toxicity - 0.6365 63.65%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.5200 52.00%
Fish aquatic toxicity + 0.8673 86.73%

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 99.65% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.34% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.97% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.26% 89.00%
CHEMBL3401 O75469 Pregnane X receptor 94.43% 94.73%
CHEMBL3060 Q9Y345 Glycine transporter 2 94.31% 99.17%
CHEMBL2581 P07339 Cathepsin D 94.12% 98.95%
CHEMBL1951 P21397 Monoamine oxidase A 94.12% 91.49%
CHEMBL3194 P02766 Transthyretin 92.31% 90.71%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 91.50% 86.92%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 89.28% 95.89%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 88.45% 96.00%
CHEMBL226 P30542 Adenosine A1 receptor 87.95% 95.93%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.40% 94.45%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 85.19% 85.00%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 85.07% 91.71%
CHEMBL3004 P33527 Multidrug resistance-associated protein 1 83.09% 96.37%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 82.98% 89.67%
CHEMBL4208 P20618 Proteasome component C5 81.78% 90.00%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 81.63% 94.80%
CHEMBL3714130 P46095 G-protein coupled receptor 6 81.62% 97.36%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 81.51% 94.62%
CHEMBL2085 P14174 Macrophage migration inhibitory factor 80.29% 80.78%

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.
Cistanche mongolica

Cross-Links

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PubChem 21629995
LOTUS LTS0061627
wikiData Q105343284