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[ CAS No. 16136-58-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 16136-58-6
Chemical Structure| 16136-58-6
Chemical Structure| 16136-58-6
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Product Details of [ 16136-58-6 ]

CAS No. :16136-58-6 MDL No. :MFCD00005801
Formula : C10H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :MAHAMBLNIDMREX-UHFFFAOYSA-N
M.W : 175.18 Pubchem ID :27695
Synonyms :

Calculated chemistry of [ 16136-58-6 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.16
TPSA : 42.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.62
Log Po/w (XLOGP3) : 2.0
Log Po/w (WLOGP) : 1.88
Log Po/w (MLOGP) : 1.38
Log Po/w (SILICOS-IT) : 1.3
Consensus Log Po/w : 1.63

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.63
Solubility : 0.408 mg/ml ; 0.00233 mol/l
Class : Soluble
Log S (Ali) : -2.51
Solubility : 0.537 mg/ml ; 0.00307 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.21
Solubility : 1.07 mg/ml ; 0.0061 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.3

Safety of [ 16136-58-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16136-58-6 ]

* 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 [ 16136-58-6 ]
  • Downstream synthetic route of [ 16136-58-6 ]

[ 16136-58-6 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 37493-34-8 ]
  • [ 16136-58-6 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With lithium hydroxide; water In tetrahydrofuran at 23℃;
Stage #2: With hydrogenchloride In water
To a solution of 1-methyl-1H-indole-2-carboxylic acid methyl ester (250 mg, 1.32 mmol) in THF/H2O (2:1, 15 mL) at 23° C. was added LiOH.H2O (291 mg, 6.94 mmol) and the reaction mixture was stirred overnight. The reaction mixture was concentrated in vacuo and partitioned between H2O (100 mL) and ethyl ether (100 mL). The aqueous layer was acidified to pH 2-3 with 1.0 N HCl, then extracted with ethyl acetate (2.x.100 mL). The organic layer was dried (MgSO4) and concentrated to yield 1-methyl-1H-indole-2-carboxylic acid (210 mg, 91percent).
Reference: [1] Tetrahedron, 2004, vol. 60, # 44, p. 10039 - 10047
[2] Journal of Organic Chemistry, 2016, vol. 81, # 16, p. 7288 - 7300
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 11, p. 2093 - 2100
[4] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5298 - 5310
[5] Patent: US2006/211603, 2006, A1, . Location in patent: Page/Page column 71
[6] Archiv der Pharmazie, 1996, vol. 329, # 3, p. 120 - 124
[7] Organic Letters, 2005, vol. 7, # 21, p. 4777 - 4779
  • 2
  • [ 932-32-1 ]
  • [ 127-17-3 ]
  • [ 16136-58-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2004, vol. 43, # 34, p. 4526 - 4528
  • 3
  • [ 124-38-9 ]
  • [ 16136-58-6 ]
Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 27, p. 8706 - 8707
  • 4
  • [ 18450-24-3 ]
  • [ 16136-58-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 24, p. 3938 - 3942
[2] European Journal of Medicinal Chemistry, 1995, vol. 30, # 12, p. 963 - 972
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 22, p. 9222 - 9241
[4] Tetrahedron, 1998, vol. 54, # 37, p. 11079 - 11094
[5] Journal of Organic Chemistry, 2012, vol. 77, # 16, p. 6959 - 6969
[6] Tetrahedron, 2016, vol. 72, # 22, p. 3014 - 3021
  • 5
  • [ 545432-27-7 ]
  • [ 16136-58-6 ]
Reference: [1] Synlett, 2003, # 2, p. 173 - 178
  • 6
  • [ 1202-04-6 ]
  • [ 16136-58-6 ]
Reference: [1] Organic Letters, 2005, vol. 7, # 21, p. 4777 - 4779
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5298 - 5310
[3] Archiv der Pharmazie, 1996, vol. 329, # 3, p. 120 - 124
[4] Journal of Organic Chemistry, 2016, vol. 81, # 16, p. 7288 - 7300
[5] Advanced Synthesis and Catalysis, 2018, vol. 360, # 11, p. 2093 - 2100
  • 7
  • [ 3770-50-1 ]
  • [ 16136-58-6 ]
Reference: [1] Archiv der Pharmazie, 2015, vol. 348, # 1, p. 34 - 45
[2] Tetrahedron, 1998, vol. 54, # 37, p. 11079 - 11094
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 22, p. 9222 - 9241
  • 8
  • [ 1477-50-5 ]
  • [ 16136-58-6 ]
Reference: [1] Organic Letters, 2005, vol. 7, # 21, p. 4777 - 4779
[2] Archiv der Pharmazie, 2015, vol. 348, # 1, p. 34 - 45
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 11, p. 2093 - 2100
  • 9
  • [ 603-76-9 ]
  • [ 124-38-9 ]
  • [ 16136-58-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 32, p. 8416 - 8420[2] Angew. Chem., 2014, vol. 126, # 32, p. 8556 - 8560,5
  • 10
  • [ 81777-11-9 ]
  • [ 16136-58-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5298 - 5310
  • 11
  • [ 603-76-9 ]
  • [ 16136-58-6 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 375,377
  • 12
  • [ 27421-51-8 ]
  • [ 16136-58-6 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 17, p. 3931 - 3943
  • 13
  • [ 3265-26-7 ]
  • [ 16136-58-6 ]
Reference: [1] Tetrahedron, 1989, vol. 45, # 11, p. 3351 - 3362
  • 14
  • [ 118618-61-4 ]
  • [ 16136-58-6 ]
Reference: [1] Synlett, 2003, # 2, p. 173 - 178
  • 15
  • [ 124-38-9 ]
  • [ 128746-62-3 ]
  • [ 16136-58-6 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 40, p. 7135 - 7137
  • 16
  • [ 58881-45-1 ]
  • [ 16136-58-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 11, p. 2093 - 2100
  • 17
  • [ 3265-26-7 ]
  • [ 16136-58-6 ]
Reference: [1] Chemische Berichte, 1884, vol. 17, p. 561
[2] Chemische Berichte, 1883, vol. 16, p. 2241
[3] Chemische Berichte, 1925, vol. 58, p. 781
[4] Chemische Berichte, 1925, vol. 58, p. 781
  • 18
  • [ 603-76-9 ]
  • [ 124-38-9 ]
  • [ 32387-21-6 ]
  • [ 16136-58-6 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 92, p. 14360 - 14363
  • 19
  • [ 90-12-0 ]
  • [ 13867-00-0 ]
  • [ 16136-58-6 ]
Reference: [1] Canadian Journal of Research, Section B: Chemical Sciences, 1947, vol. 25, p. 1,12
  • 20
  • [ 603-76-9 ]
  • [ 109-72-8 ]
  • [ 60-29-7 ]
  • [ 124-38-9 ]
  • [ 16136-58-6 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 375,377
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