Structure of D-Glucamine
CAS No.: 488-43-7
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
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.
Synonyms: 1-Amino-1-deoxy-D-glucitol
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 488-43-7 |
Formula : | C6H15NO5 |
M.W : | 181.19 |
SMILES Code : | OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CN |
Synonyms : |
1-Amino-1-deoxy-D-glucitol
|
MDL No. : | MFCD00077776 |
InChI Key : | SDOFMBGMRVAJNF-SLPGGIOYSA-N |
Pubchem ID : | 452501 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 6.0 |
Molar Refractivity | 39.47 |
TPSA ? Topological Polar Surface Area: Calculated from |
127.17 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
-0.02 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-3.36 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-3.62 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-2.77 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-2.15 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-2.38 |
Log S (ESOL):? ESOL: Topological method implemented from |
1.48 |
Solubility | 5520.0 mg/ml ; 30.4 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (Ali)? Ali: Topological method implemented from |
1.26 |
Solubility | 3330.0 mg/ml ; 18.4 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
2.35 |
Solubility | 40600.0 mg/ml ; 224.0 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-9.79 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
3.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.12 |
* 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 |
---|---|---|
43 mg | Coupling steps. In a peptide synthesis vessel add the resin, add the amino acid solution, DIPEA, and PyBOP. Bubble argon for 1 hr. and wash 3× with DMF and IPA. Use 20% piperidine in DMF for Fmoc deprotection, 3×(10 min), before each amino acid coupling. Continue to complete all 9 coupling steps. At the end treat the resin with 2% hydrazine in DMF 3×(5 min) to cleave TFA protecting group on Pteroic acid, wash the resin with DMF (3×), IPA (3×), MeOH (3×), and bubble the resin with argon for 30 min. Cleavage step. Reagent: 92.5% TFA, 2.5% H2O, 2.5% triisopropylsilane, 2.5% ethanedithiol. Treat the resin with cleavage reagent 3×(10 min, 5 min, 5 min) with argon bubbling, drain, wash the resin once with cleavage reagent, and combine the solution. Rotavap until 5 ml remains and precipitate in diethyl ether (35 mL). Centrifuge, wash with diethyl ether, and dry. About half of the crude solid (-100 mg) was purified by HPLC. HPLC Purification step. Column: Waters Xterra Prep MS C18 10 mum 19×250 mm; Solvent A: 10 mM ammonium acetate, pH 5; Solvent B: ACN; Method: 5 min 0% B to 25 min 20% B 26 mL/min. Fractions containing the product was collected and freeze-dried to give 43 mg EC0488 (51% yield). 1H NMR and LC/MS (exact mass 1678.62) were consistent with the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The solid phase synthesis of N10-TFA protected EC1454 starts with resin bound trityl protected D-cysteine. The resin is suspended in dimethylformamide (DMF) and washed twice with DMF. EC0475 (glucamine modified L-glutamic acid), (Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP), and diisopropylethylamine (DIPEA) are added to reaction mixture. After at least 1 hour, a Kaiser test is performed to ensure the coupling is complete. The resin is washed three times with DMF, three times with IPA, and three times with DMF. The resin is slowly washed three times with piperidine in DMF, three times with DMF, and three times with IPA. A Kaiser test is performed to confirm deprotection. The resin is washed three times with DMF and the next amino acid in the sequence is coupled following the same process. Monomers are coupled in the following order: 1) EC0475, 2) <strong>[104091-08-9]Fmoc-D-Glu(OtBu)-OH</strong>, 3) EC0475, 4) <strong>[104091-08-9]Fmoc-D-Glu(OtBu)-OH</strong>, 5) EC0475, 6) Fmoc-D-Glu-OtBu, and 7) N10-TFA-Pte-OH. Once the final coupling is complete, the resin is washed three times with methanol and dried by passing argon through the resin at room temperature. The dried resin is suspended in a mixture of TFA, water, ethanedithiol, and triisopropylsilane. After 1 hour the resin is removed by filtration and washed with TFA. The product is precipitated by addition to cold ethyl ether, filtered, and washed with ether. The solids are dried under vacuum at room temperature and stored in a freezer. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere; | D-Glucamine (282 mg, 1.56 mmol), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (592 mg, 1.56 mmol) and diisopropylethylamine (0.542 mL, 3.90 mmol) were added successively to a solution of 4-bromophenoxyacetic acid 16 (300 mg, 1.30 mmol) in anhydrous dimethylformamide (20 mL). The mixture was stirred at room temperature for 16 h under inert atmosphere. The progress of the reaction was monitored by TLC. After this time, reaction was complete. A 0.1 M aqueous solution of hydrochloric acid (10 mL) was added to this mixture and then the solvent was removed under reduced pressure a pale yellow solid corresponding to compound 20. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The solid phase synthesis of N?-TFA protected EC1454 starts with resin bound trityl protected D-cysteine. The resin is suspended in dimethylformamide (DMF) and washed twice with DMF. EC0475 (glucamine modified L-glutamic acid), (l3enzotriazol- 1 -yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyI3OP), and diisopropylethylamine (DIPEA) are added to reaction mixture. After at least 1 hour, a Kaiser test is performed to ensure the coupling is complete. The resin is washed three times with DMF, three times with IPA, and three times with DMF. The resin is slowly washed three times with piperidine in DMF, three times with DMF, and three times with IPA. A Kaiser test is performed to confirm deprotection. The resin is washed three times with DMF and the next amino acid in the sequence is coupled following the same process. Monomers are coupled in the following order: 1) EC0475, 2) Fmoc-DGlu(Otl3u)-OH, 3) EC0475, 4) <strong>[104091-08-9]Fmoc-D-Glu(OtBu)-OH</strong>, 5) EC0475, 6) Fmoc-D-Glu-Otl3u, and 7) N?-TFA-Pte-OH. Once the final coupling is complete, the resin is washed three times with methanol and dried by passing argon through the resin at room temperature. The dried resin is suspended in a mixture of TFA, water, ethanedithiol, and triisopropylsilane. After 1 hour the resin is removed by filtration and washed with TFA. The product is precipitated by addition to cold ethyl ether, filtered, and washed with ether. The solids are dried under vacuum at room tempera- tare and stored in a freezer. |
A627563 [55700-83-9]
(2R,3R,4R)-5-Aminopentane-1,2,3,4-tetraol
Similarity: 1.00
A533596 [42015-13-4]
(2R,3S,4R,5S)-6-Aminohexane-1,2,3,4,5-pentaol
Similarity: 1.00
A533596 [42015-13-4]
(2R,3S,4R,5S)-6-Aminohexane-1,2,3,4,5-pentaol
Similarity: 1.00
A533596 [42015-13-4]
(2R,3S,4R,5S)-6-Aminohexane-1,2,3,4,5-pentaol
Similarity: 1.00
A621688 [2165350-89-8]
Potassium (2S,3S,4R,5R)-1-amino-3,4,5,6-tetrahydroxyhexan-2-olate
Similarity: 0.95
A627563 [55700-83-9]
(2R,3R,4R)-5-Aminopentane-1,2,3,4-tetraol
Similarity: 1.00
A533596 [42015-13-4]
(2R,3S,4R,5S)-6-Aminohexane-1,2,3,4,5-pentaol
Similarity: 1.00
A621688 [2165350-89-8]
Potassium (2S,3S,4R,5R)-1-amino-3,4,5,6-tetrahydroxyhexan-2-olate
Similarity: 0.95
A143753 [554-62-1]
(2S,3S,4R)-2-Aminooctadecane-1,3,4-triol
Similarity: 0.88
A627563 [55700-83-9]
(2R,3R,4R)-5-Aminopentane-1,2,3,4-tetraol
Similarity: 1.00
A533596 [42015-13-4]
(2R,3S,4R,5S)-6-Aminohexane-1,2,3,4,5-pentaol
Similarity: 1.00
A621688 [2165350-89-8]
Potassium (2S,3S,4R,5R)-1-amino-3,4,5,6-tetrahydroxyhexan-2-olate
Similarity: 0.95
A143753 [554-62-1]
(2S,3S,4R)-2-Aminooctadecane-1,3,4-triol
Similarity: 0.88