5-(2-Fluoro-3-methoxyphenyl)-N-(3-methoxyphenyl)-Nmethylthiophene-2-carboxamide

ID: ALA2324360

PubChem CID: 60165269

Max Phase: Preclinical

Molecular Formula: C20H18FNO3S

Molecular Weight: 371.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(N(C)C(=O)c2ccc(-c3cccc(OC)c3F)s2)c1

Standard InChI:  InChI=1S/C20H18FNO3S/c1-22(13-6-4-7-14(12-13)24-2)20(23)18-11-10-17(26-18)15-8-5-9-16(25-3)19(15)21/h4-12H,1-3H3

Standard InChI Key:  XXGYSORRVIEKQF-UHFFFAOYSA-N

Molfile:  

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   12.6376   -0.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3095   -1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9190   -2.1982    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.6234   -1.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1836   -2.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.5980   -2.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6003   -2.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8888   -1.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3719   -2.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0371   -1.6435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7855   -1.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.4506   -1.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4573   -2.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8842   -4.0962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5915   -4.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3047   -3.2844    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.8566   -1.3504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7720   -0.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 14 16  2  0
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  8 22  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA2324360

   5-(2-fluoro-3-methoxyphenyl)-N-(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: 371.43

Molecular Weight (Monoisotopic): 371.0991

AlogP: 4.85

#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: 4.31

CX LogD: 4.31

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.64

Np Likeness Score: -1.32

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. 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