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[(2S,3R,4R,5S,6S)-4-acetyloxy-5-hydroxy-2-[[(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl]oxy]-6-methyloxan-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 0a33173f-2b0d-4ece-932c-3c8c05365c04
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
IUPAC Name [(2S,3R,4R,5S,6S)-4-acetyloxy-5-hydroxy-2-[[(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl]oxy]-6-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
SMILES (Canonical) CC1C(C(C(C(O1)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)OC(=O)C=CC6=CC=C(C=C6)O)OC(=O)C)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@H]3C=CO[C@H]([C@@H]3[C@@]4([C@H]2O4)CO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)OC(=O)/C=C/C6=CC=C(C=C6)O)OC(=O)C)O
InChI InChI=1S/C32H40O17/c1-13-21(38)26(44-14(2)35)27(46-19(37)8-5-15-3-6-16(36)7-4-15)31(43-13)47-25-17-9-10-42-29(20(17)32(12-34)28(25)49-32)48-30-24(41)23(40)22(39)18(11-33)45-30/h3-10,13,17-18,20-31,33-34,36,38-41H,11-12H2,1-2H3/b8-5+/t13-,17-,18+,20+,21-,22+,23-,24+,25-,26+,27+,28-,29-,30-,31-,32+/m0/s1
InChI Key LHEWQIBORVAWFM-FIBGQUEGSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C32H40O17
Molecular Weight 696.60 g/mol
Exact Mass 696.22654980 g/mol
Topological Polar Surface Area (TPSA) 253.00 Ų
XlogP -1.40
Atomic LogP (AlogP) -2.20
H-Bond Acceptor 17
H-Bond Donor 7
Rotatable Bonds 10

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2S,3R,4R,5S,6S)-4-acetyloxy-5-hydroxy-2-[[(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl]oxy]-6-methyloxan-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 - 0.4897 48.97%
Caco-2 - 0.8850 88.50%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.6439 64.39%
OATP2B1 inhibitior - 0.8604 86.04%
OATP1B1 inhibitior + 0.7942 79.42%
OATP1B3 inhibitior + 0.9547 95.47%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.5742 57.42%
P-glycoprotein inhibitior + 0.6056 60.56%
P-glycoprotein substrate + 0.5665 56.65%
CYP3A4 substrate + 0.7065 70.65%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8786 87.86%
CYP3A4 inhibition - 0.8978 89.78%
CYP2C9 inhibition - 0.8882 88.82%
CYP2C19 inhibition - 0.8528 85.28%
CYP2D6 inhibition - 0.9305 93.05%
CYP1A2 inhibition - 0.9008 90.08%
CYP2C8 inhibition + 0.7177 71.77%
CYP inhibitory promiscuity - 0.7892 78.92%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5864 58.64%
Eye corrosion - 0.9888 98.88%
Eye irritation - 0.9191 91.91%
Skin irritation - 0.7803 78.03%
Skin corrosion - 0.9398 93.98%
Ames mutagenesis - 0.6100 61.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4187 41.87%
Micronuclear + 0.5233 52.33%
Hepatotoxicity - 0.8375 83.75%
skin sensitisation - 0.8014 80.14%
Respiratory toxicity - 0.5111 51.11%
Reproductive toxicity + 0.7889 78.89%
Mitochondrial toxicity + 0.7125 71.25%
Nephrotoxicity - 0.5843 58.43%
Acute Oral Toxicity (c) III 0.4601 46.01%
Estrogen receptor binding + 0.7380 73.80%
Androgen receptor binding + 0.5643 56.43%
Thyroid receptor binding + 0.5192 51.92%
Glucocorticoid receptor binding + 0.6014 60.14%
Aromatase binding - 0.5338 53.38%
PPAR gamma + 0.6986 69.86%
Honey bee toxicity - 0.6690 66.90%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.8514 85.14%

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 99.38% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.15% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 96.26% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.17% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.63% 96.09%
CHEMBL1951 P21397 Monoamine oxidase A 91.76% 91.49%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 91.64% 96.00%
CHEMBL2581 P07339 Cathepsin D 91.26% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 89.76% 94.73%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.84% 85.14%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 88.07% 95.89%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 87.47% 89.67%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.14% 94.45%
CHEMBL3060 Q9Y345 Glycine transporter 2 85.73% 99.17%
CHEMBL3714130 P46095 G-protein coupled receptor 6 85.21% 97.36%
CHEMBL4208 P20618 Proteasome component C5 82.76% 90.00%
CHEMBL1937 Q92769 Histone deacetylase 2 80.73% 94.75%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 80.42% 86.92%

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 163021135
LOTUS LTS0161587
wikiData Q105151733