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| Type | HazMat fee for 500 gram (Estimated) |
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Structure of 119785-99-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
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| CAS No. : | 119785-99-8 |
| Formula : | C30H42N7O18P3S |
| M.W : | 913.68 |
| SMILES Code : | NC1=C2C(N([C@H]3[C@H](O)[C@H](OP(O)(O)=O)[C@@H](COP(O)(OP(OCC(C)([C@H](C(NCCC(NCCSC(/C=C/C4=CC=C(O)C=C4)=O)=O)=O)O)C)(O)=O)=O)O3)C=N2)=NC=N1 |
| English Name : | (E)-S-(2-(3-((2R)-4-(((((((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)-2-hydroxy-3,3-dimethylbutanamido)propanamido)ethyl) 3-(4-hydroxyphenyl)prop-2-enethioate |
| MDL No. : | N/A |
| InChI Key : | DMZOKBALNZWDKI-MATMFAIHSA-N |
| Pubchem ID : | 6440013 |
| GHS Pictogram: | |
| Signal Word: | |
| Hazard Statements: | |
| Precautionary Statements: | |
| Class: | |
| UN#: | |
| Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With chalcone synthase | ||
| With recombinant type III polyketide synthase from Aquilaria sinensis In aq. phosphate buffer at 37℃; for 12h; Enzymatic reaction; | Enzyme reaction. General procedure: The enzyme reaction system contained 29 nmol of malonyl-CoA or methylmalonyl-CoA, 26 nmol of starter-CoA (4-coumaroyl-CoA, 4-hydroxyphenylpropionyl-CoA, or benzoyl-CoA) and 40 μg of the purified AsCHS in 500 μL of 100 mM KPB buffer (pH 7.0) was incub ated at 37 °C for 12 h and terminated by adding 50 μL of 20 % HCl. Then the reaction solution was extracted three times with 800 μL EtOAc. The combination of organic layer was dried by nitrogen and redissolved in 50 μL of MeOH and analyzed by HPLC on a Agilent Eclipse XDB C18 Column (250×4.6 mm I.D. 5 μm) with a flow rate of 1.0 mL/min and monitoring wave length at 280 nm. For the analysis of enzyme reaction products from 4-coumaroyl-CoA or 4-hydroxyphenylpropionyl-CoA and malonyl-CoA, the gradient elution was performed with H2O and acetonitrile: 0-10 min, 30% acetonitrile; 10-20 min, 30-60% acetonitrile, 20-25min, 60-70% acetonitrile, 25-30min, 70-80% acetonitrile, 30-35 min, 80-100 % acetonitrile, 35-40 min, 100 % acetonitrile. For the analysis of enzyme reaction products from benzoyl-CoA and malonyl-CoA, and the products from 4-hydroxy phenylpropionyl-CoA and methylmalonyl-CoA, the gradient elution was performed with aqueous acetonitrile containing 0.1 % formic acid: 0-5 min, 5-30 % acetonitrile; 5-15 min, 30-60 %a cetonitrile, 15-25 min, 60-70 % acetonitrile, 25-30 min, 70-80 % acetonitrile, 30-35 min, 80-100 % acetonitrile, 35-40 min, 100 % acetonitrile. The enzyme product of phloretin (11) and 2,4,6-trihydroxybenzophenone (13) were identified by comparision of their UV spectra and retention time on HPLC chromatogram to the authentic compounds. The products of enzyme reaction of 4-coumaroyl-CoA and malonyl-CoA were measured with HPLC-ESI-IT-TOF mass spectrometer, and identified by comparing their UV, MS data with those of reported in literature. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 91% | With ATP; magnesium chloride for 20h; Enzymatic reaction; | |
| With magnesium chloride at 30℃; for 0.0833333h; | ||
| With Tris-HCl buffer; magnesium chloride at 20℃; for 17h; |
| With recombinant 4-coumarate:CoA ligase | ||
| With Arabidopsis thaliana 4-coumaroyl-CoA ligase-(Gly-Ser-Gly)-Vitis vinifera stilbene synthase fusion protein; ATP; S-(hydrogen malonyl)coenzyme A In aq. phosphate buffer at 45℃; for 0.5h; Enzymatic reaction; | ||
| With Piper nigrum 4-coumarate:CoA ligase isoform 1; ATP; magnesium chloride In aq. buffer at 25℃; for 0.75h; Enzymatic reaction; | Enzyme kinetics study by UV spectrophotometry General procedure: The enzyme kinetic parameters were measured spectrophotometrically as described [22]. Each reaction contained 0.3 mM CoA, 2.5 mM MgCl2 and 2.5 mM ATP in 100 mM Tris-HCl (pH 7.5). For kinetic analyses, at least six concentrations of each substrate (coumaric, ferulic, 3,4-methylenedioxycinnamic, and piperic acids) ranging from 6.25 to 200 mM and 11 to 94 mg of each purified 4CL in a total volume of 1 ml reaction mixture were reacted in triplicate. For the assay of cinnamic acid, the acid concentration was between 15 mM and 600 mM and CoA was at 0.7 mM. The sample was set-up on ice and transferred to a water bath at 25°C to equilibrate temperature for 1 min. The reaction was started by addition of CoA. The formation of the thioester products were followed at 311 nm for cinnamoyl-, 333 nm for 4-coumaroyl-, 346 nm for feruloyl-, 346 nm for 3,4-methylenedioxycinnamoyl-, and 368 nm for piperoyl-CoA, and the concentration of these products were calculated using the corresponding extinction coefficients of 22, 21, 19, 19, and 30.8 mM-1 cm-1, respectively [18,23,24]. To estimate the formation of 3,4-methylenedioxycinnamoyl-CoA, the same extinction coefficient, and λmax as feruloyl-CoA were extrapolated. The reaction was followed for 15 min until the linearity of the reaction was maintained. The reaction at 50 mM substrate concentration was allowed to proceed for another 30 min and then the mixture was stood in a boiling water bath for 3 min before scanning on spectrophotometer. Negative control was run with the combined, boiled enzymes, each at the same concentration as the individual reaction. Piperonylic acid was allowed to react for 45 min without kinetic measurement. | |
| With magnesium(II); stilbene synthase (STS) from Pinus Sylvestris; tris hydrochloride; ATP at 20℃; for 12h; Enzymatic reaction; | ||
| With 4-coumarate:CoA ligase from Nicotiana tabacum; ATP; magnesium chloride In aq. buffer at 25℃; for 1h; Enzymatic reaction; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With recombinant type III polyketide synthase from Aquilaria sinensis In aq. phosphate buffer at 37℃; for 12h; Enzymatic reaction; | Enzyme reaction. General procedure: The enzyme reaction system contained 29 nmol of malonyl-CoA or methylmalonyl-CoA, 26 nmol of starter-CoA (4-coumaroyl-CoA, 4-hydroxyphenylpropionyl-CoA, or benzoyl-CoA) and 40 μg of the purified AsCHS in 500 μL of 100 mM KPB buffer (pH 7.0) was incub ated at 37 °C for 12 h and terminated by adding 50 μL of 20 % HCl. Then the reaction solution was extracted three times with 800 μL EtOAc. The combination of organic layer was dried by nitrogen and redissolved in 50 μL of MeOH and analyzed by HPLC on a Agilent Eclipse XDB C18 Column (250×4.6 mm I.D. 5 μm) with a flow rate of 1.0 mL/min and monitoring wave length at 280 nm. For the analysis of enzyme reaction products from 4-coumaroyl-CoA or 4-hydroxyphenylpropionyl-CoA and malonyl-CoA, the gradient elution was performed with H2O and acetonitrile: 0-10 min, 30% acetonitrile; 10-20 min, 30-60% acetonitrile, 20-25min, 60-70% acetonitrile, 25-30min, 70-80% acetonitrile, 30-35 min, 80-100 % acetonitrile, 35-40 min, 100 % acetonitrile. For the analysis of enzyme reaction products from benzoyl-CoA and malonyl-CoA, and the products from 4-hydroxy phenylpropionyl-CoA and methylmalonyl-CoA, the gradient elution was performed with aqueous acetonitrile containing 0.1 % formic acid: 0-5 min, 5-30 % acetonitrile; 5-15 min, 30-60 %a cetonitrile, 15-25 min, 60-70 % acetonitrile, 25-30 min, 70-80 % acetonitrile, 30-35 min, 80-100 % acetonitrile, 35-40 min, 100 % acetonitrile. The enzyme product of phloretin (11) and 2,4,6-trihydroxybenzophenone (13) were identified by comparision of their UV spectra and retention time on HPLC chromatogram to the authentic compounds. The products of enzyme reaction of 4-coumaroyl-CoA and malonyl-CoA were measured with HPLC-ESI-IT-TOF mass spectrometer, and identified by comparing their UV, MS data with those of reported in literature. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 16 % | With wild type crystal structure of piper methysticum styrylpyrone synthase 1 in complex with p-coumaroyl-CoA In aq. phosphate buffer at 37℃; Enzymatic reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: iron(II) sulfate; (+)-sodium L-ascorbate; α-ketoglutarate; recombinant Angelica sinensis p-coumaroyl-CoA 2′-hydroxylase / aq. acetate buffer / 30 min / 20 °C / pH 4.5 / Enzymatic reaction 2: recombinant Angelica sinensis umbelliferone 8-prenyltransferase; magnesium chloride / aq. buffer / 5 h / 25 °C / pH 8.5 / Enzymatic reaction 3: NADPH / aq. buffer / 2 h / 27 °C / pH 7 / Enzymatic reaction |
Tags: 119785-99-8 | (E)-S-(2-(3-((2R)-4-(((((((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)-2-hydroxy-3,3-dimethylbutanamido)propanamido)ethyl) 3-(4-hydroxyphenyl)prop-2-enethioate | Esters | Purines | Tetrahydrofurans | Benzene Compounds | Nucleotides and Derivatives | Organic Building Blocks | Heterocyclic Building Blocks | Nucleosides & Nucleotides
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| Code | Phrase |
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| P378 | |
| P380 | Evacuate area. |
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| P391 | Collect spillage. Hazardous to the aquatic environment |
| P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
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| P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
| P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
| P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
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| P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
| P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
| P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
| P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
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| P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
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| P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
| P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
| P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
| P370 + P376 | In case of fire: Stop leak if safe to Do so. |
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| H311 | Toxic in contact with skin |
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| H314 | Causes severe skin burns and eye damage |
| H315 | Causes skin irritation |
| H316 | Causes mild skin irritation |
| H317 | May cause an allergic skin reaction |
| H318 | Causes serious eye damage |
| H319 | Causes serious eye irritation |
| H320 | Causes eye irritation |
| H330 | Fatal if inhaled |
| H331 | Toxic if inhaled |
| H332 | Harmful if inhaled |
| H333 | May be harmful if inhaled |
| H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
| H335 | May cause respiratory irritation |
| H336 | May cause drowsiness or dizziness |
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| H341 | Suspected of causing genetic defects |
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| H351 | Suspected of causing cancer |
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| H361d | Suspected of damaging the unborn child |
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| H410 | Very toxic to aquatic life with long-lasting effects |
| H411 | Toxic to aquatic life with long-lasting effects |
| H412 | Harmful to aquatic life with long-lasting effects |
| H413 | May cause long-lasting harmful effects to aquatic life |
| H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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