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

ID: ALA1915964

PubChem CID: 56649596

Max Phase: Preclinical

Molecular Formula: C20H18FNO3S

Molecular Weight: 371.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(-c2ccc(C(=O)N(C)Cc3cccc(O)c3)s2)c1F

Standard InChI:  InChI=1S/C20H18FNO3S/c1-22(12-13-5-3-6-14(23)11-13)20(24)18-10-9-17(26-18)15-7-4-8-16(25-2)19(15)21/h3-11,23H,12H2,1-2H3

Standard InChI Key:  VLNQSUWHVVGANO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -3.4826   -8.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0289   -8.4597    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4501   -7.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6447   -8.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6318   -9.1967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632   -7.9482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7840   -8.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8210  -10.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5312  -10.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152   -9.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6085  -10.8402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7645   -9.4840    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1963  -10.3110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9109  -10.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
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 15 17  1  0
  4  5  1  0
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  2  3  1  0
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  8  9  1  0
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  9 10  2  0
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M  END

Alternative Forms

1. Parent:

   

   ALA1915964

   5-(2-Fluoro-3-methoxyphenyl)-N-(3-hydroxybenzyl)-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: 4.54

#Rotatable Bonds: 5

Polar Surface Area: 49.77

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.41

CX Basic pKa: ┄

CX LogP: 4.23

CX LogD: 4.23

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -1.06

References

1. Xu K, Al-Soud YA, Wetzel M, Hartmann RW, Marchais-Oberwinkler S..  (2011)  Triazole ring-opening leads to the discovery of potent nonsteroidal 17β-hydroxysteroid dehydrogenase type 2 inhibitors.,  46  (12): [PMID:22037253] [10.1016/j.ejmech.2011.10.010]

2. 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]

3. 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]

Source

Source(1):

• Scientific Literature