Topramezone

ID: ALA3145388

Max Phase: Preclinical

Molecular Formula: C16H17N3O5S

Molecular Weight: 363.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(C(=O)c2c[nH]n(C)c2=O)ccc(S(C)(=O)=O)c1C1=NOCC1

Standard InChI:  InChI=1S/C16H17N3O5S/c1-9-10(15(20)11-8-17-19(2)16(11)21)4-5-13(25(3,22)23)14(9)12-6-7-24-18-12/h4-5,8,17H,6-7H2,1-3H3

Standard InChI Key:  BPPVUXSMLBXYGG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   10.7923   -3.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3798   -2.7399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8866   -3.8683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8866   -3.0433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1020   -2.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6173   -3.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1020   -4.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5563   -4.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8491   -4.9058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3798   -4.1715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5548   -4.1715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5548   -5.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7923   -4.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1423   -4.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3798   -5.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1423   -3.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1434   -6.3143    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.0479   -5.2999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8326   -5.5529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3173   -4.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8326   -4.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0479   -4.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3185   -6.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1374   -7.1374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9374   -6.5249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  3  7  1  0
  3  8  1  0
  7  9  2  0
  1  6  1  0
 10 11  2  0
 10 13  1  0
 11 14  1  0
 12 14  2  0
 12 15  1  0
 13 15  2  0
 11 16  1  0
 12 17  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 18 22  1  0
 14 20  1  0
  1 10  1  0
 17 23  1  0
 17 24  2  0
 17 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3145388

   ---

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: 363.40

Molecular Weight (Monoisotopic): 363.0889

AlogP: 0.78

#Rotatable Bonds: 4

Polar Surface Area: 110.59

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.70

CX Basic pKa: 1.74

CX LogP: -0.24

CX LogD: -1.23

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.81

Np Likeness Score: -0.62

References

1. Hausman NE, Singh S, Tranel PJ, Riechers DE, Kaundun SS, Polge ND, Thomas DA, Hager AG..  (2011)  Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States.,  67  (3): [PMID:21308951] [10.1002/ps.2100]

Source

Source(1):

• Scientific Literature