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[ CAS No. 13139-14-5 ] {[proInfo.proName]}

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Chemical Structure| 13139-14-5
Chemical Structure| 13139-14-5
Structure of 13139-14-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 13139-14-5 ]

CAS No. :13139-14-5 MDL No. :MFCD00065595
Formula : C16H20N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :NFVNYBJCJGKVQK-ZDUSSCGKSA-N
M.W :304.34 Pubchem ID :83169
Synonyms :

Calculated chemistry of [ 13139-14-5 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.38
Num. rotatable bonds : 7
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 83.2
TPSA : 91.42 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.68
Log Po/w (XLOGP3) : 1.97
Log Po/w (WLOGP) : 2.69
Log Po/w (MLOGP) : 1.37
Log Po/w (SILICOS-IT) : 2.28
Consensus Log Po/w : 2.0

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.81
Solubility : 0.473 mg/ml ; 0.00155 mol/l
Class : Soluble
Log S (Ali) : -3.52
Solubility : 0.0929 mg/ml ; 0.000305 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.05
Solubility : 0.0272 mg/ml ; 0.0000893 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.94

Safety of [ 13139-14-5 ]

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:

Application In Synthesis of [ 13139-14-5 ]

* 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.

  • Upstream synthesis route of [ 13139-14-5 ]
  • Downstream synthetic route of [ 13139-14-5 ]

[ 13139-14-5 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 53267-93-9 ]
  • [ 13139-14-5 ]
  • [ 37169-36-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 74, p. 60354 - 60364
  • 2
  • [ 13139-14-5 ]
  • [ 5022-65-1 ]
Reference: [1] Patent: WO2018/33724, 2018, A1,
  • 3
  • [ 100-39-0 ]
  • [ 13139-14-5 ]
  • [ 57229-67-1 ]
YieldReaction ConditionsOperation in experiment
81% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12 h; Inert atmosphere To a solution of methyl (S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoate (2 g, 6.57 mmol) in DMF (27 mL) were addedK2CO3 (2.27 g, 16.5 mmol) and benzyl bromide (811 μL, 6.83 mmol).The mixture was stirred at r.t. for 12h. The reaction was quenchedwith sat. aq NH4Cl, diluted with EtOAc(10 mL), and the layers wereseparated. The aqueous layer was extracted with EtOAc (3 × 10 mL),and the combined organic layers were washed with brine (3 × 15 mL),dried (Na2SO4), filtered, and concentrated in vacuo. A white powderwas obtained after recrystallization from cyclohexane (2.1 g, 81percent);mp 140 °C. Spectroscopic data were consistent with the previouslyreported values.1H NMR (250 MHz, CDCl3): δ = 8.00 (br s, 1 H), 7.56 (d, J = 8.3 Hz, 1 H),7.38–7.30 (m, 4 H), 7.29–7.17 (m, 3 H), 7.16–7.07 (m, 1 H), 6.81 (s, 1H), 5.09 (d, J = 3.7 Hz, 2 H), 4.79–4.61 (m, 1 H), 3.29 (d, J = 5.3 Hz, 2 H),1.43 (s, 9 H).
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 10, p. 1594 - 1597
[2] Journal of Organic Chemistry, 2014, vol. 79, # 23, p. 11549 - 11557
[3] Tetrahedron Letters, 2009, vol. 50, # 26, p. 3645 - 3647
[4] Synthesis (Germany), 2017, vol. 49, # 2, p. 391 - 396
[5] Carbohydrate Research, 1981, vol. 89, p. 229 - 236
[6] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 8, p. 1272 - 1280
[7] Chemistry - A European Journal, 2017, vol. 23, # 50, p. 12120 - 12124
[8] Journal of Medicinal Chemistry, 1993, vol. 36, # 14, p. 2044 - 2045
[9] Journal of Medicinal Chemistry, 1994, vol. 37, # 9, p. 1269 - 1274
  • 4
  • [ 13139-14-5 ]
  • [ 100-51-6 ]
  • [ 57229-67-1 ]
Reference: [1] ChemMedChem, 2015, vol. 10, # 2, p. 296 - 303
[2] Organic Letters, 2003, vol. 5, # 6, p. 853 - 856
[3] Chemical Biology and Drug Design, 2017, vol. 89, # 1, p. 38 - 46
  • 5
  • [ 13139-14-5 ]
  • [ 57229-67-1 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 40, p. 7301 - 7304
  • 6
  • [ 4530-20-5 ]
  • [ 15761-38-3 ]
  • [ 13734-34-4 ]
  • [ 15260-10-3 ]
  • [ 23680-31-1 ]
  • [ 18942-46-6 ]
  • [ 54613-99-9 ]
  • [ 13139-14-5 ]
  • [ 65420-40-8 ]
  • [ 38916-34-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 17, p. 5981 - 5987
  • 7
  • [ 13139-14-5 ]
  • [ 142880-36-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 2, p. 199 - 223
  • 8
  • [ 13139-14-5 ]
  • [ 229639-48-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 12, p. 2571 - 2578
[2] Angewandte Chemie - International Edition, 1999, vol. 38, # 9, p. 1223 - 1226
[3] Helvetica Chimica Acta, 2000, vol. 83, # 1, p. 16 - 33
  • 9
  • [ 186581-53-3 ]
  • [ 13139-14-5 ]
  • [ 229639-48-9 ]
Reference: [1] Journal of Peptide Science, 2015, vol. 21, # 12, p. 893 - 904
[2] Organic Syntheses, 2002, vol. 79, p. 154 - 154
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