(R)-(+)-4-pentenyl 2-[(2-furanylmethyl)(1H-imidazol-1-ylcarbonyl)amino]butanoate

ID: ALA2286351

PubChem CID: 70291915

Max Phase: Preclinical

Molecular Formula: C18H23N3O4

Molecular Weight: 345.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCCCOC(=O)[C@@H](CC)N(Cc1ccco1)C(=O)n1ccnc1

Standard InChI:  InChI=1S/C18H23N3O4/c1-3-5-6-11-25-17(22)16(4-2)21(13-15-8-7-12-24-15)18(23)20-10-9-19-14-20/h3,7-10,12,14,16H,1,4-6,11,13H2,2H3/t16-/m1/s1

Standard InChI Key:  WBTYBAGIHOISOQ-MRXNPFEDSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   12.7879   -3.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5003   -3.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2129   -3.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9279   -3.4659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2119   -2.2293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5003   -4.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7859   -4.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2148   -4.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2148   -5.5293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9293   -4.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5492   -6.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8041   -6.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6292   -6.7976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8841   -6.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7888   -2.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0714   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9852   -3.4715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1782   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7657   -4.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3177   -4.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6419   -3.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3568   -3.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0708   -3.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7858   -3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4998   -3.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  3  5  2  0
  2  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  1 15  1  0
  7 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 16  2  0
  4 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2286351

   (R)-(+)-pefurazoate

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: 345.40

Molecular Weight (Monoisotopic): 345.1689

AlogP: 3.23

#Rotatable Bonds: 9

Polar Surface Area: 77.57

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.55

CX LogP: 2.25

CX LogD: 2.25

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.40

Np Likeness Score: -0.81

References

1. TAKENAKA M, NISHIMURA T, HAYASHI K.  (2001)  Enantioselective Antifungal Activity of Pefurazoate against Pathogens of Rice Seed Diseases,  26  (4): [10.1584/jpestics.26.347]

2. TAKENAKA M, KIMURA S, TANAKA T, WADA T.  (1992)  Chiral Synthesis of Pefurazoate Enantiomers and Their Antifungal Activity to Gibberella fujikuroi,  17  (4): [10.1584/jpestics.17.4_205]

Source

Source(1):

• Scientific Literature