N,5-Bis(3-methoxyphenyl)-N-methylthiophene-2-carboxamide

ID: ALA2324679

PubChem CID: 60196493

Max Phase: Preclinical

Molecular Formula: C20H19NO3S

Molecular Weight: 353.44

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H19NO3S/c1-21(15-7-5-9-17(13-15)24-3)20(22)19-11-10-18(25-19)14-6-4-8-16(12-14)23-2/h4-13H,1-3H3

Standard InChI Key:  BTXOYSPNQOWPQS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   14.8235  -23.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0037  -23.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6757  -23.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2851  -24.4604    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.9895  -24.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5497  -24.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5516  -25.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2544  -25.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9641  -25.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9664  -24.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2549  -23.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7380  -24.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4032  -23.9058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1516  -24.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3159  -23.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2377  -25.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9853  -25.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6470  -24.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5603  -24.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8167  -23.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8234  -25.2021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8463  -23.9082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1391  -24.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2182  -23.6132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1336  -22.8004    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
 22 23  1  0
  6 22  1  0
 24 25  1  0
 19 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2324679

   N,5-bis(3-methoxyphenyl)-N-methylthiophene-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: 353.44

Molecular Weight (Monoisotopic): 353.1086

AlogP: 4.71

#Rotatable Bonds: 5

Polar Surface Area: 38.77

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.17

CX LogD: 4.17

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.67

Np Likeness Score: -1.25

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