N-(3-Methoxyphenyl)-N-methyl-5-m-tolylthiophene-2-carboxamide

ID: ALA2324690

PubChem CID: 60196704

Max Phase: Preclinical

Molecular Formula: C20H19NO2S

Molecular Weight: 337.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(N(C)C(=O)c2ccc(-c3cccc(C)c3)s2)c1

Standard InChI:  InChI=1S/C20H19NO2S/c1-14-6-4-7-15(12-14)18-10-11-19(24-18)20(22)21(2)16-8-5-9-17(13-16)23-3/h4-13H,1-3H3

Standard InChI Key:  BABRITZRSIMSNK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    4.5508   -5.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7310   -5.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4030   -6.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125   -6.7753    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7169   -6.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2771   -6.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2789   -7.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9817   -7.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6914   -7.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6937   -6.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9822   -6.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4653   -6.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1305   -6.2206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8790   -6.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0433   -5.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9650   -7.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7126   -7.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3744   -7.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2876   -6.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5441   -6.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5508   -7.5169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5689   -6.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9455   -5.9280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8609   -5.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
 10  3  1  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 14  1  0
 12 21  2  0
  6 22  1  0
 23 24  1  0
 19 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2324690

   N-(3-methoxyphenyl)-N-methyl-5-m-tolylthiophene-2-carboxamide

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: 337.44

Molecular Weight (Monoisotopic): 337.1136

AlogP: 5.01

#Rotatable Bonds: 4

Polar Surface Area: 29.54

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.84

CX LogD: 4.84

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: -1.57

References

1. Marchais-Oberwinkler S, Xu K, Wetzel M, Perspicace E, Negri M, Meyer A, Odermatt A, Möller G, Adamski J, Hartmann RW..  (2013)  Structural optimization of 2,5-thiophene amides as highly potent and selective 17β-hydroxysteroid dehydrogenase type 2 inhibitors for the treatment of osteoporosis.,  56  (1): [PMID:23145773] [10.1021/jm3014053]

2. Perspicace E, Cozzoli L, Gargano EM, Hanke N, Carotti A, Hartmann RW, Marchais-Oberwinkler S..  (2014)  Novel, potent and selective 17β-hydroxysteroid dehydrogenase type 2 inhibitors as potential therapeutics for osteoporosis with dual human and mouse activities.,  83  [PMID:24974351] [10.1016/j.ejmech.2014.06.036]

3. Gargano EM, Perspicace E, Hanke N, Carotti A, Marchais-Oberwinkler S, Hartmann RW..  (2014)  Metabolic stability optimization and metabolite identification of 2,5-thiophene amide 17β-hydroxysteroid dehydrogenase type 2 inhibitors.,  87  [PMID:25259513] [10.1016/j.ejmech.2014.09.061]

Source

Source(1):

• Scientific Literature