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Chemical Structure| 55750-62-4 Chemical Structure| 55750-62-4

Structure of 55750-62-4

Chemical Structure| 55750-62-4

3-(Maleimido)propionic acid N-hydroxysuccinimide ester

CAS No.: 55750-62-4

Synonyms: BMPS

4.5 *For Research Use Only !

Cat. No.: A395905 Purity: 98%

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Product Details of [ 55750-62-4 ]

CAS No. :55750-62-4
Formula : C11H10N2O6
M.W : 266.21
SMILES Code : C(C(ON1C(CCC1=O)=O)=O)CN2C(C=CC2=O)=O
Synonyms :
BMPS
MDL No. :MFCD00043141
InChI Key :JKHVDAUOODACDU-UHFFFAOYSA-N
Pubchem ID :4620597

Safety of [ 55750-62-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 55750-62-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 0
Fraction Csp3 0.36
Num. rotatable bonds 5
Num. H-bond acceptors 6.0
Num. H-bond donors 0.0
Molar Refractivity 66.0
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

101.06 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.94
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-1.58
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-1.85
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.51
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.46
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.69

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.17
Solubility 182.0 mg/ml ; 0.684 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.03
Solubility 246.0 mg/ml ; 0.925 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.36
Solubility 116.0 mg/ml ; 0.438 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-9.05 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<0.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.85

Application In Synthesis of [ 55750-62-4 ]

* 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.

  • Downstream synthetic route of [ 55750-62-4 ]

[ 55750-62-4 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 55750-62-4 ]
  • [ 1615234-93-9 ]
  • [ 1263045-16-4 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; Referring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-blc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
0.227g With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; [0277] Referring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-boc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
  • 2
  • [ 55750-62-4 ]
  • [ 756525-91-4 ]
  • [ 1263045-16-4 ]
YieldReaction ConditionsOperation in experiment
0.227 g Synthesis of linker-drugReferring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-boc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
  • 3
  • [ 55750-62-4 ]
  • [ 474645-27-7 ]
  • C46H72N6O10 [ No CAS ]
  • 4
  • [ 55750-62-4 ]
  • [ 29390-67-8 ]
  • 6-deoxy-6-(3'-(N-maleimido)-propionamido)-β-cyclodextrin [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% In water; N,N-dimethyl-formamide; at 20℃; for 3h; 6-Amino-6-deoxy-P-cyclodextrin (1) was synthesized according to a literature method (Weihua, T., Siu-Choon, N., Nature Protocol, 2008, 3: 691-695). Compound 1 (115 mg, 0.10 mmol) was dissolved in deionised water (6 mL) and 3-(N-maleimido)-propionic acid N-hydroxysuccinimide ester (54 mg, 0.20 mg) was added in DMF (1.4 mL). The mixture was stirred for 3 h at room temperature, then the product (2) was precipitated with acetone and washed several times with acetone (yield 101 mg, 79%). HI -NMR (400 MHz, DMSO-d6): delta 6.97 (s, 2H), 5.73 (m, 14H), 4.82 (s, 7H), 4.67 (m, 7H), 3.82-3.47 (m, 30 H).; 13C-NMR (101 MHz, DMSO-d6): delta 171.1, 134.9, 102.4, 82.0, 73.5, 72.9, 72.5, 60.4.; ESI-MS (m/z): 1307.66 [M + Na]+.; Molecular weight: 1285.11894; molecular formula: C49H76N2O37
  • 5
  • [ 663921-15-1 ]
  • [ 55750-62-4 ]
  • [ 1263045-16-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; at 20℃; for 2h; Compound 3-11 (4.55 g, 18.7 mmol) was dissolved in 10 mL water, NaHCO3 (1.71 g, 20.4 mmol) was added and the mixture was stirred. CE-L-055 (4.55 g, 17 mmol) in 30 mL 1,2-dimethoxyethane was added dropwise slowly. The reaction mixture was stirred for 2 hours at room temperature. 50 mL water was added, the mixture was adjusted to pH 3-4 with 1 M dilute hydrochloric acid, and then extracted with EtOAc for 10 times (50 mL×10). The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to give the crude product, which was used directly for the next step. LCMS (ESI) m/z 417.2 (M+H)+.
 

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