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Chemical Structure| 4125-98-8 Chemical Structure| 4125-98-8

Structure of N-Me-Ile-OH
CAS No.: 4125-98-8

Chemical Structure| 4125-98-8

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Product Details of [ 4125-98-8 ]

CAS No. :4125-98-8
Formula : C7H15NO2
M.W : 145.20
SMILES Code : [H][C@](C)(CC)[C@]([H])(NC)C(O)=O
MDL No. :MFCD00037755
InChI Key :KSPIYJQBLVDRRI-WDSKDSINSA-N
Pubchem ID :5288628

Safety of [ 4125-98-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 4125-98-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 0
Fraction Csp3 0.86
Num. rotatable bonds 4
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 40.34
TPSA ?

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

49.33 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.53
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

-1.67
Log Po/w (WLOGP)?

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

0.71
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.

-1.47
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

0.32
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.12

Water Solubility

Log S (ESOL):?

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

0.58
Solubility 547.0 mg/ml ; 3.77 mol/l
Class?

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

Highly soluble
Log S (Ali)?

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

1.15
Solubility 2030.0 mg/ml ; 14.0 mol/l
Class?

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

Highly 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

-0.95
Solubility 16.4 mg/ml ; 0.113 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

Yes
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.

-8.37 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

1.0
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

0.0 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<1.0
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)

1.79

Application In Synthesis of [ 4125-98-8 ]

* 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 [ 4125-98-8 ]

[ 4125-98-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 4125-98-8 ]
  • [ 82911-69-1 ]
  • [ 138775-22-1 ]
  • 2
  • pembamide [ No CAS ]
  • [ 56-41-7 ]
  • [ 72-18-4 ]
  • [ 2480-23-1 ]
  • [ 73-32-5 ]
  • [ 4125-98-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; at 110℃; for 18h; Compound 1 (0.4 mg) was hydrolyzed with 0.5 mL of 6N HCl at 110 C for 18 h. Excess aqueous HCl was removed under a N2 stream.
  • 3
  • urumamide [ No CAS ]
  • [ 3913-67-5 ]
  • [ 72-18-4 ]
  • [ 17407-56-6 ]
  • [ 2480-23-1 ]
  • [ 61-90-5 ]
  • [ 3060-46-6 ]
  • [ 4125-98-8 ]
  • [ 147-85-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; at 110℃; for 24h; Urumamide (1) (0.7 mg) was treated with 9 N HCl (100 L) for 24 h at 110 C. The hydrolyzed product was evaporated to dryness and could be separated into each component by HPLC. [Cosmosil 5C18-PAQ (4.6 × 250 mm); flowrate, 1.0 mL/min; detection at 215 nm; solvent H2O. Retention times (min) of components: N-Me-Ala (tR = 3.0 min), Pro(tR = 3.2 min), Val (tR = 3.4 min), N-Me-Val (tR = 3.7 min), Leu (tR = 4.8 min), N-Me-Ile (tR = 5.3 min), N-Me-Leu (tR =6.0 min)].
  • 4
  • odobromoamide [ No CAS ]
  • [ 72-18-4 ]
  • [ 17407-55-5 ]
  • [ 2480-23-1 ]
  • [ 4125-98-8 ]
  • [ 147-85-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; at 105℃; for 12h; Absolute Configurations of Amino Acid Residues in 1.Odobromoamide (1, 1.2 mg) was treated with 5 M HCl (0.5mL) at 105 C for 12 h. The hydrolysate was concentrated todryness and partitioned between H2O and EtOAc. The aqueouslayer was subjected to HPLC [Cosmosil HILIC (4.6 250mm), MeCN/10 mM AcONH4 = 85:15 at 1.0 mL/min, UV detection at 215 nm] to yield N-Me-Ile, N-Me-Val, Hmba, Val andPro. Each amino acid expect for Hmba was added with 0.1%solution of Nα-(5-fluoro-2,4-dinitrophenyl)-L-alaninamide (LFDAA, Marfey’s reagent, 200 L) in acetone and 0.5 MNaHCO3 (100 L) followed by heating at 40 C for 90 min.After cooling to room temperature, the reaction mixture wasneutralized with 2 M HCl (25 L) and diluted with MeOH(300 L). The solution was subjected to reversed-phase HPLC[Cosmosil 5C18-AR-II (4.6 250 mm), MeOH/20 mM AcONa = 60:40 (solvent A) or 50:50 (solvent B) at 1.0 mL/min,UV detection at 340 nm]. The L-FDAA derivatives of standardamino acids were prepared by the same procedure. The retention times (min) of the authentic standards were as follows: LN-Me-Ile (6.6), L-allo-N-Me-Ile (6.9), D-N-Me-Ile (11.6), Dallo-N-Me-Ile (12.2), L-N-Me-Val (5.3) and D-N-Me-Val (8.5)in solvent A, L-Val (6.8), D-Val (18.3), L-Pro (4.9) and D-Pro(6.5) in solvent B. The retention times and ESIMS product ions(m/z [M+Na]+) of the L-FDAA derivatives of N-Me-Ile and NMe-Val from the hydrolysate were 6.6 min (420.1) and 5.3 min(406.1) in solvent A, respectively, proving the configurationsof N-Me-Ile and N-Me-Val were L. The retention times andESIMS product ions (m/z [M+Na]+) of the L-FDAA derivatives of Val and Pro from the hydrolysate were 6.8 min (392.1)and 4.9 min (390.1) in solvent B, respectively, proving theconfigurations of Val and Pro were L
 

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