4-(2-Hydroxy-3-isopropylamino-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester

ID: ALA53849

Cas Number: 279231-65-1

PubChem CID: 489104

Max Phase: Preclinical

Molecular Formula: C18H25NO5

Molecular Weight: 335.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1oc2cccc(OCC(O)CNC(C)C)c2c1C

Standard InChI:  InChI=1S/C18H25NO5/c1-5-22-18(21)17-12(4)16-14(7-6-8-15(16)24-17)23-10-13(20)9-19-11(2)3/h6-8,11,13,19-20H,5,9-10H2,1-4H3

Standard InChI Key:  QVJVMNUTCGTBCH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    3.0074   -0.9743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2648    1.4826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8279   -2.4895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0654   -1.7751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6938    2.3076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1227    1.4826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504    0.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1635   -0.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359   -0.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8279   -1.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504    1.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2404   -1.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214    0.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359    1.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214    1.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9704   -0.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9793    1.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6938    1.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2404   -3.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4083    1.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8279   -3.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8372    1.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5517    1.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8372    0.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 17  1  0
  3 12  1  0
  3 19  1  0
  4 12  2  0
  5 18  1  0
  6 20  1  0
  6 22  1  0
  7  8  1  0
  7  9  1  0
  7 11  2  0
  8 10  2  0
  8 16  1  0
  9 13  2  0
 10 12  1  0
 11 14  1  0
 13 15  1  0
 14 15  2  0
 17 18  1  0
 18 20  1  0
 19 21  1  0
 22 23  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA53849

   Ethyl 4-[2-hydroxy-3-(isopropylamino)propoxy]-3-methyl-1-benzofuran-2-carboxylate

2. Alternative Forms:

   

   ALA53849

   Ethyl 4-(2-hydroxy-3-(isopropylamino)propoxy)-3-methylbenzofuran-2-carboxylate hydrochloride

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 335.40

Molecular Weight (Monoisotopic): 335.1733

AlogP: 2.66

#Rotatable Bonds: 8

Polar Surface Area: 80.93

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.67

CX LogP: 2.55

CX LogD: 0.32

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: -0.51

References

1. Masubuchi M, Kawasaki K, Ebiike H, Ikeda Y, Tsujii S, Sogabe S, Fujii T, Sakata K, Shiratori Y, Aoki Y, Ohtsuka T, Shimma N..  (2001)  Design and synthesis of novel benzofurans as a new class of antifungal agents targeting fungal N-myristoyltransferase. Part 1.,  11  (14): [PMID:11459642] [10.1016/s0960-894x(01)00319-5]

2. Deokar HS, Puranik P, Kulkarni VM.  (2009)  QSAR analysis of N-myristoyltransferase inhibitors: antifungal activity of benzofurans,  18  (3): [10.1007/s00044-008-9120-5]

Source

Source(1):

• Scientific Literature