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

ID: ALA156813

PubChem CID: 10555744

Max Phase: Preclinical

Molecular Formula: C23H22BrN3O8S2

Molecular Weight: 612.48

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BAY-507950 | CHEMBL156813|BAY-507950|BDBM50473499

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

Standard InChI:  InChI=1S/C23H22BrN3O8S2/c1-33-18-8-17(28)14(19(20(18)24)22(30)35-3)9-36-10-16(21(29)34-2)26-23-25-15(11-37-23)12-4-6-13(7-5-12)27(31)32/h4-8,11,16,28H,9-10H2,1-3H3,(H,25,26)/t16-/m0/s1

Standard InChI Key:  MULKVQPCLGZOFQ-INIZCTEOSA-N

Molfile:  

     RDKit          2D

 37 39  0  0  0  0  0  0  0  0999 V2000
    2.4798   -4.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785   -5.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1915   -6.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9108   -5.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9078   -4.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1896   -4.3818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7635   -6.0337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0496   -5.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1901   -6.8601    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.1857   -3.5567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6201   -4.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6161   -3.5495    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3286   -3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0450   -3.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6257   -6.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6265   -6.8585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3413   -7.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -5.6203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0492   -4.3674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7656   -4.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7574   -3.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0127   -5.5593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8377   -5.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0996   -4.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4364   -4.2935    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.2398   -6.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8171   -6.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2204   -7.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0463   -7.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4672   -7.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0614   -6.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4543   -8.4474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2792   -8.4560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0343   -9.1575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4733   -3.5364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7540   -2.3025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1857   -3.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6 10  1  0
 14 21  1  1
 20 22  2  0
  2  3  1  0
  5 11  1  0
  5  6  2  0
 11 12  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 20  1  0
  6  1  1  0
 12 13  1  0
 26 27  2  0
  1  2  2  0
 27 28  1  0
 13 14  1  0
 28 29  2  0
  2  7  1  0
 29 30  1  0
  4 15  1  0
 30 31  2  0
 31 26  1  0
 23 26  1  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 32 33  2  0
 32 34  1  0
 29 32  1  0
 16 17  1  0
 15 18  2  0
  3  9  1  0
 14 19  1  0
 21 35  1  0
  4  5  1  0
 21 36  2  0
 19 20  1  0
 35 37  1  0
M  CHG  2  32   1  34  -1
M  END

Alternative Forms

1. Parent:

   

   ALA156813

   methyl 2-bromo-5-hydroxy-3-methoxy-6-[[(2R)-3-methoxy-2-[[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amino]-3-oxopropyl]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: 612.48

Molecular Weight (Monoisotopic): 611.0032

AlogP: 4.87

#Rotatable Bonds: 11

Polar Surface Area: 150.12

Molecular Species: NEUTRAL

HBA: 12

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.42

CX Basic pKa: 1.27

CX LogP: 5.32

CX LogD: 5.28

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.17

Np Likeness Score: -0.81

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