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(Z)-3-[(1S,2S,4S,5S,6S,7S)-5-hydroxy-10-methoxycarbonyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,8-dioxatricyclo[4.4.0.02,4]dec-9-ene-5-carbonyl]oxy-2-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

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 53d2b805-c74b-4fa4-af4d-e5c9c59a4750
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
IUPAC Name (Z)-3-[(1S,2S,4S,5S,6S,7S)-5-hydroxy-10-methoxycarbonyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,8-dioxatricyclo[4.4.0.02,4]dec-9-ene-5-carbonyl]oxy-2-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
SMILES (Canonical) COC1=C(C=CC(=C1)C(=COC(=O)C2(C3C(C4C2O4)C(=COC3OC5C(C(C(C(O5)CO)O)O)O)C(=O)OC)O)C(=O)O)O
SMILES (Isomeric) COC1=C(C=CC(=C1)/C(=C/OC(=O)[C@@]2([C@@H]3[C@H]([C@H]4[C@@H]2O4)C(=CO[C@H]3O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C(=O)OC)O)/C(=O)O)O
InChI InChI=1S/C27H30O17/c1-38-13-5-9(3-4-12(13)29)10(22(33)34)7-41-26(36)27(37)16-15(20-21(27)43-20)11(23(35)39-2)8-40-24(16)44-25-19(32)18(31)17(30)14(6-28)42-25/h3-5,7-8,14-21,24-25,28-32,37H,6H2,1-2H3,(H,33,34)/b10-7-/t14-,15-,16-,17-,18+,19-,20+,21+,24+,25+,27+/m1/s1
InChI Key MHXHFEYHEPYROS-LINZIYSPSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C27H30O17
Molecular Weight 626.50 g/mol
Exact Mass 626.14829948 g/mol
Topological Polar Surface Area (TPSA) 261.00 Ų
XlogP -2.10
Atomic LogP (AlogP) -2.66
H-Bond Acceptor 16
H-Bond Donor 7
Rotatable Bonds 9

Synonyms

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BDBM50044559

2D Structure

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2D Structure of (Z)-3-[(1S,2S,4S,5S,6S,7S)-5-hydroxy-10-methoxycarbonyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,8-dioxatricyclo[4.4.0.02,4]dec-9-ene-5-carbonyl]oxy-2-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7390 73.90%
Caco-2 - 0.9037 90.37%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.5752 57.52%
OATP2B1 inhibitior - 0.5806 58.06%
OATP1B1 inhibitior + 0.7629 76.29%
OATP1B3 inhibitior + 0.9562 95.62%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior - 0.4743 47.43%
P-glycoprotein inhibitior - 0.4603 46.03%
P-glycoprotein substrate + 0.5769 57.69%
CYP3A4 substrate + 0.6856 68.56%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8629 86.29%
CYP3A4 inhibition - 0.8207 82.07%
CYP2C9 inhibition - 0.7612 76.12%
CYP2C19 inhibition - 0.7157 71.57%
CYP2D6 inhibition - 0.8790 87.90%
CYP1A2 inhibition - 0.7980 79.80%
CYP2C8 inhibition + 0.8004 80.04%
CYP inhibitory promiscuity - 0.6903 69.03%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6555 65.55%
Eye corrosion - 0.9866 98.66%
Eye irritation - 0.9182 91.82%
Skin irritation - 0.7614 76.14%
Skin corrosion - 0.9370 93.70%
Ames mutagenesis + 0.5263 52.63%
Human Ether-a-go-go-Related Gene inhibition + 0.6509 65.09%
Micronuclear + 0.5933 59.33%
Hepatotoxicity - 0.6750 67.50%
skin sensitisation - 0.7907 79.07%
Respiratory toxicity - 0.5111 51.11%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.7125 71.25%
Nephrotoxicity + 0.5962 59.62%
Acute Oral Toxicity (c) III 0.3810 38.10%
Estrogen receptor binding + 0.8072 80.72%
Androgen receptor binding + 0.6390 63.90%
Thyroid receptor binding + 0.5676 56.76%
Glucocorticoid receptor binding + 0.6332 63.32%
Aromatase binding - 0.5000 50.00%
PPAR gamma + 0.7297 72.97%
Honey bee toxicity - 0.7497 74.97%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.7366 73.66%
Fish aquatic toxicity + 0.8735 87.35%

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 99.01% 91.11%
CHEMBL3060 Q9Y345 Glycine transporter 2 94.22% 99.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.96% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.80% 96.09%
CHEMBL4208 P20618 Proteasome component C5 93.39% 90.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 90.25% 96.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.31% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.23% 89.00%
CHEMBL1951 P21397 Monoamine oxidase A 85.35% 91.49%
CHEMBL3401 O75469 Pregnane X receptor 85.13% 94.73%
CHEMBL3194 P02766 Transthyretin 85.03% 90.71%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 83.65% 95.83%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 82.89% 96.90%
CHEMBL2535 P11166 Glucose transporter 82.58% 98.75%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 82.55% 96.95%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 81.68% 86.92%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 80.62% 97.21%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 80.14% 89.62%
CHEMBL241 Q14432 Phosphodiesterase 3A 80.09% 92.94%

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.
Morinda citrifolia

Cross-Links

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PubChem 101135598
LOTUS LTS0103440
wikiData Q105164357