((3S,4R)-4-(2,4-difluorophenyl)-1-isopropylpyrrolidin-3-yl)((3S,4R,5R)-4-(4-fluorophenyl)-4-hydroxy-3,5-dimethylpiperidin-1-yl)methanone

ID: ALA1091633

PubChem CID: 46885974

Max Phase: Preclinical

Molecular Formula: C27H33F3N2O2

Molecular Weight: 474.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)N1C[C@@H](C(=O)N2C[C@@H](C)[C@](O)(c3ccc(F)cc3)[C@@H](C)C2)[C@H](c2ccc(F)cc2F)C1

Standard InChI:  InChI=1S/C27H33F3N2O2/c1-16(2)31-14-23(22-10-9-21(29)11-25(22)30)24(15-31)26(33)32-12-17(3)27(34,18(4)13-32)19-5-7-20(28)8-6-19/h5-11,16-18,23-24,34H,12-15H2,1-4H3/t17-,18+,23-,24+,27-/m0/s1

Standard InChI Key:  IYTUVFXIECWYAU-KYZOLGBSSA-N

Molfile:  

     RDKit          2D

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   17.8908  -20.2555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5396  -19.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2556  -18.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4309  -19.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0147  -18.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4235  -17.5709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   19.9552  -17.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5469  -16.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7177  -16.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3047  -17.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9215  -21.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9460  -19.0095    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.9627  -16.1506    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.7746  -17.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9532  -17.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5406  -18.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9556  -19.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7832  -19.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9500  -17.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1208  -19.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2948  -18.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8752  -19.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2804  -20.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1097  -20.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5256  -19.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5397  -16.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7375  -19.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8616  -21.1286    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.2229  -21.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6509  -21.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  1
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  9 10  2  0
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  2  3  1  0
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 28 29  2  0
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  4  9  1  6
 19 30  1  1
  6  7  2  0
 21 31  1  1
  2 15  1  0
 27 32  1  0
  6  8  1  0
 15 33  1  0
 10 16  1  0
 15 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091633

   ((3S,4R)-4-(2,4-difluorophenyl)-1-isopropylpyrrolidin-3-yl)((3S,4R,5R)-4-(4-fluorophenyl)-4-hydroxy-3,5-dimethylpiperidin-1-yl)methanone

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: 474.57

Molecular Weight (Monoisotopic): 474.2494

AlogP: 4.53

#Rotatable Bonds: 4

Polar Surface Area: 43.78

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.61

CX Basic pKa: 8.81

CX LogP: 4.24

CX LogD: 2.82

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.71

Np Likeness Score: -0.44

References

1. Lansdell MI, Hepworth D, Calabrese A, Brown AD, Blagg J, Burring DJ, Wilson P, Fradet D, Brown TB, Quinton F, Mistry N, Tang K, Mount N, Stacey P, Edmunds N, Adams C, Gaboardi S, Neal-Morgan S, Wayman C, Cole S, Phipps J, Lewis M, Verrier H, Gillon V, Feeder N, Heatherington A, Sultana S, Haughie S, Martin SW, Sudworth M, Tweedy S..  (2010)  Discovery of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans.,  53  (8): [PMID:20329799] [10.1021/jm9017866]

Source

Source(1):

• Scientific Literature