2-Bromo-5-hydroxy-3-methoxy-6-{2-(3-methyl-[1,2,4]oxadiazol-5-yl)-2-[4-(4-nitro-phenyl)-thiazol-2-ylamino]-ethylsulfanylmethyl}-benzoic acid methyl ester

ID: ALA157831

PubChem CID: 11456414

Max Phase: Preclinical

Molecular Formula: C24H22BrN5O7S2

Molecular Weight: 636.51

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ro-616653 | CHEMBL157831|Ro-616653|SCHEMBL8869564|BDBM50473498

Canonical SMILES:  COC(=O)c1c(Br)c(OC)cc(O)c1CSC[C@H](Nc1nc(-c2ccc([N+](=O)[O-])cc2)cs1)c1nc(C)no1

Standard InChI:  InChI=1S/C24H22BrN5O7S2/c1-12-26-22(37-29-12)17(28-24-27-16(11-39-24)13-4-6-14(7-5-13)30(33)34)10-38-9-15-18(31)8-19(35-2)21(25)20(15)23(32)36-3/h4-8,11,17,31H,9-10H2,1-3H3,(H,27,28)/t17-/m0/s1

Standard InChI Key:  RIXLZRBJGRFRFF-KRWDZBQOSA-N

Molfile:  

     RDKit          2D

 39 42  0  0  0  0  0  0  0  0999 V2000
    3.0111   -4.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0098   -5.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7228   -6.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4420   -5.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4389   -4.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7208   -4.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2948   -6.0348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5810   -5.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7214   -6.8612    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.7168   -3.5581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1513   -4.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1472   -3.5508    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8596   -3.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5761   -3.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1569   -6.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1576   -6.8597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8724   -7.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8709   -5.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5801   -4.3687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2966   -4.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2885   -3.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5437   -5.5605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3687   -5.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6304   -4.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9674   -4.2948    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.7707   -6.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3480   -6.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7513   -7.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5771   -7.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9979   -7.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5922   -6.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9850   -8.4485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8100   -8.4570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5651   -9.1585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0440   -3.4563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5930   -2.8406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1769   -2.1281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3709   -2.3037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4138   -2.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6 10  1  0
 14 21  1  1
  2  3  1  0
  5 11  1  0
  5  6  2  0
 20 22  2  0
 11 12  1  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 20  1  0
 13 14  1  0
  2  7  1  0
 26 27  2  0
  4 15  1  0
 27 28  1  0
  3  4  2  0
 28 29  2  0
 15 16  1  0
 29 30  1  0
  7  8  1  0
 30 31  2  0
 31 26  1  0
 23 26  1  0
 16 17  1  0
 15 18  2  0
 32 33  2  0
 32 34  1  0
 29 32  1  0
 21 35  2  0
  3  9  1  0
 14 19  1  0
  4  5  1  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 21  1  0
 19 20  1  0
 36 39  1  0
M  CHG  2  32   1  34  -1
M  END

Alternative Forms

1. Parent:

   

   ALA157831

   methyl 2-bromo-5-hydroxy-3-methoxy-6-[[(2R)-2-(3-methyl-1,2,4-oxadiazol-5-yl)-2-[[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amino]ethyl]sulfanylmethyl]benzoate

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: 636.51

Molecular Weight (Monoisotopic): 635.0144

AlogP: 5.76

#Rotatable Bonds: 11

Polar Surface Area: 162.74

Molecular Species: NEUTRAL

HBA: 13

HBD: 2

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.42

CX Basic pKa: 2.87

CX LogP: 5.91

CX LogD: 5.87

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.12

Np Likeness Score: -1.20

References

1. Rudolph J, Theis H, Hanke R, Endermann R, Johannsen L, Geschke F..  (2001)  seco-Cyclothialidines: new concise synthesis, inhibitory activity toward bacterial and human DNA topoisomerases, and antibacterial properties.,  44  (4): [PMID:11170652] [10.1021/jm0010623]

2. Brvar M, Perdih A, Oblak M, Masic LP, Solmajer T..  (2010)  In silico discovery of 2-amino-4-(2,4-dihydroxyphenyl)thiazoles as novel inhibitors of DNA gyrase B.,  20  (3): [PMID:20045642] [10.1016/j.bmcl.2009.12.060]

Source

Source(1):

• Scientific Literature