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CAS No. : | 5852-10-8 | MDL No. : | MFCD00467589 |
Formula : | C12H10O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OOGKDHCQSZAEQI-UHFFFAOYSA-N |
M.W : | 234.20 | Pubchem ID : | 5393149 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 61.02 |
TPSA : | 87.74 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.06 cm/s |
Log Po/w (iLOGP) : | 1.32 |
Log Po/w (XLOGP3) : | 0.94 |
Log Po/w (WLOGP) : | 1.43 |
Log Po/w (MLOGP) : | 0.97 |
Log Po/w (SILICOS-IT) : | 2.16 |
Consensus Log Po/w : | 1.36 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.19 |
Solubility : | 1.52 mg/ml ; 0.00649 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.37 |
Solubility : | 1.0 mg/ml ; 0.00427 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.21 |
Solubility : | 0.145 mg/ml ; 0.000618 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.88 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 sulfuric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With quinoline; copper |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia at 270℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide | ||
With sodium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Stage #1: (7-hydroxy-4-methyl-2-oxochromen-3-yl)acetic acid With 1-hydroxy-pyrrolidine-2,5-dione; diisopropyl-carbodiimide In 1,4-dioxane at 20℃; for 2h; Stage #2: cytisine In 1,4-dioxane at 20℃; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With sodium hydroxide In water; isopropyl alcohol Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: concentrated sulfuric acid 2: aq. NaOH solution | ||
Multi-step reaction with 2 steps 1: concentrated sulfuric acid 2: ethanolic KOH-solution |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: concentrated sulfuric acid 2: aq. NaOH solution | ||
Multi-step reaction with 2 steps 1: concentrated sulfuric acid 2: ethanolic KOH-solution |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bovine serum albumin In dimethyl sulfoxide at 35℃; for 24h; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With sodium hydrogencarbonate In water; acetonitrile at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: Fmoc-(S)-2-aminohexanoic acid Automated synthesizer; Stage #2: With piperazine In ethanol; N,N-dimethyl-formamide Automated synthesizer; Stage #3: (7-hydroxy-4-methyl-2-oxochromen-3-yl)acetic acid; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; N-α-Fmoc-N-ε-(4,4-dimethylaminoazobenzene-4′carbonyl)-L-lysine; Fmoc-(tBu)Asp-OH; Fmoc-Glu(OtBu)-OH; Fmoc-Ile-OH; Fmoc-Thr(tBu)-OH; L-Asn(Trt); Fmoc-L-Gln(Trt)-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 6-[(9H-fluoren-9-ylmethoxy)carbonyl]amino}hexanoic acid Automated synthesizer; Stage #2: With piperazine In ethanol; N,N-dimethyl-formamide Automated synthesizer; Stage #3: (7-hydroxy-4-methyl-2-oxochromen-3-yl)acetic acid; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; N-α-Fmoc-N-ε-(4,4-dimethylaminoazobenzene-4′carbonyl)-L-lysine; Fmoc-(tBu)Asp-OH; Fmoc-Glu(OtBu)-OH; Fmoc-Ile-OH; Fmoc-Thr(tBu)-OH; L-Asn(Trt); Fmoc-L-Gln(Trt)-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N-α-Fmoc-N-ε-(4,4-dimethylaminoazobenzene-4′carbonyl)-L-lysine Automated synthesizer; Stage #2: With piperazine In ethanol; N,N-dimethyl-formamide Automated synthesizer; Stage #3: (7-hydroxy-4-methyl-2-oxochromen-3-yl)acetic acid; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-(tBu)Asp-OH; Fmoc-Glu(OtBu)-OH; Fmoc-Ile-OH; Fmoc-Thr(tBu)-OH; L-Asn(Trt); Fmoc-L-Gln(Trt)-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Stage #1: (7-hydroxy-4-methyl-2-oxochromen-3-yl)acetic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: aminolupinane In N,N-dimethyl-formamide at 50℃; | General Method for Synthesizing N-Acyl Lupinamine Derivatives 38-72 General procedure: A solution of 3-37 (1 mmol) in anhydrous DMF (1 mL) was treated with CDI (0.18 g, 1.1 mmol), stirred, held at room temperature for 2 h, treated with lupinamine (0.18 g, 1.05 mmol), stirred vigorously, heated (50°C) for 3-6 h (end of reaction determined by TLC), cooled to room temperature,and diluted with distilled H2O (10 mL). The resulting precipitate was filtered off and crystallized from EtOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Stage #1: (7-hydroxy-4-methyl-2-oxochromen-3-yl)acetic acid; N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-methoxybenzenesulfonamide With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 1.16667h; Inert atmosphere; Stage #2: With dmap In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; | 4.1.1 N-((2S,3R)-3-hydroxy-4-((N-isobutyl-4-methoxyphenyl)sulfonamido)-1-phenylbutan-2-yl)-2-oxo-2H-chromene-6-carboxamide (6a) General procedure: N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI, 0.029g, 0.15mmol) and 1-hydroxybenzotriazole (HOBt, 0.015g, 0.11mmol) were sequentially added in batches to a stirring solution of 2-oxo-2H-chromene-6-carboxylic acid (4a, 0.019g, 0.10mmol) and N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4- methoxybenzenesulfonamide (9, 0.043g, 0.105mmol) in dry DMF (1mL) at 0°C under an argon atmosphere. The reaction mixture was stirred for 10minat 0°C and then additional 1h at room temperature. 4-Dimethylaminopyridine (DMAP, 0.0024g, 0.020mmol) was added and the reaction mixture was stirred for another 2h at room temperature. The solvent was removed under reduced pressure. Water (4mL) was added to the residue and extracted with ethyl acetate (3×4mL). The combined organic phases were dried over Na2SO4, and evaporated, in vacuo. The residue was purified by chromatography on a silica gel column (30×6cm). Elution with 1:1 to 2:3 hexanes-ethyl acetate gave 6a as pale yellow crystalline powder: yield 0.050g (87%); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | Stage #1: (7-hydroxy-4-methyl-2-oxochromen-3-yl)acetic acid; N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 1.16667h; Inert atmosphere; Stage #2: With dmap In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; | 4.1.1 N-((2S,3R)-3-hydroxy-4-((N-isobutyl-4-methoxyphenyl)sulfonamido)-1-phenylbutan-2-yl)-2-oxo-2H-chromene-6-carboxamide (6a) General procedure: N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI, 0.029g, 0.15mmol) and 1-hydroxybenzotriazole (HOBt, 0.015g, 0.11mmol) were sequentially added in batches to a stirring solution of 2-oxo-2H-chromene-6-carboxylic acid (4a, 0.019g, 0.10mmol) and N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4- methoxybenzenesulfonamide (9, 0.043g, 0.105mmol) in dry DMF (1mL) at 0°C under an argon atmosphere. The reaction mixture was stirred for 10minat 0°C and then additional 1h at room temperature. 4-Dimethylaminopyridine (DMAP, 0.0024g, 0.020mmol) was added and the reaction mixture was stirred for another 2h at room temperature. The solvent was removed under reduced pressure. Water (4mL) was added to the residue and extracted with ethyl acetate (3×4mL). The combined organic phases were dried over Na2SO4, and evaporated, in vacuo. The residue was purified by chromatography on a silica gel column (30×6cm). Elution with 1:1 to 2:3 hexanes-ethyl acetate gave 6a as pale yellow crystalline powder: yield 0.050g (87%); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | Stage #1: (7-hydroxy-4-methyl-2-oxochromen-3-yl)acetic acid; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 1.16667h; Inert atmosphere; Stage #2: With dmap In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; | 4.1.1 N-((2S,3R)-3-hydroxy-4-((N-isobutyl-4-methoxyphenyl)sulfonamido)-1-phenylbutan-2-yl)-2-oxo-2H-chromene-6-carboxamide (6a) General procedure: N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI, 0.029g, 0.15mmol) and 1-hydroxybenzotriazole (HOBt, 0.015g, 0.11mmol) were sequentially added in batches to a stirring solution of 2-oxo-2H-chromene-6-carboxylic acid (4a, 0.019g, 0.10mmol) and N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4- methoxybenzenesulfonamide (9, 0.043g, 0.105mmol) in dry DMF (1mL) at 0°C under an argon atmosphere. The reaction mixture was stirred for 10minat 0°C and then additional 1h at room temperature. 4-Dimethylaminopyridine (DMAP, 0.0024g, 0.020mmol) was added and the reaction mixture was stirred for another 2h at room temperature. The solvent was removed under reduced pressure. Water (4mL) was added to the residue and extracted with ethyl acetate (3×4mL). The combined organic phases were dried over Na2SO4, and evaporated, in vacuo. The residue was purified by chromatography on a silica gel column (30×6cm). Elution with 1:1 to 2:3 hexanes-ethyl acetate gave 6a as pale yellow crystalline powder: yield 0.050g (87%); |
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