(S)-N-(4-(4,4-dimethylcyclohexyloxy)-5-fluoro-2-methoxybenzyl)pyrrolidine-2-carboxamide

ID: ALA1091105

Cas Number: 1224048-09-2

PubChem CID: 46830177

Product Number: S669260, Order Now?

Max Phase: Preclinical

Molecular Formula: C21H31FN2O3

Molecular Weight: 378.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC2CCC(C)(C)CC2)c(F)cc1CNC(=O)[C@@H]1CCCN1

Standard InChI:  InChI=1S/C21H31FN2O3/c1-21(2)8-6-15(7-9-21)27-19-12-18(26-3)14(11-16(19)22)13-24-20(25)17-5-4-10-23-17/h11-12,15,17,23H,4-10,13H2,1-3H3,(H,24,25)/t17-/m0/s1

Standard InChI Key:  FGJOAGVKQWXJAD-KRWDZBQOSA-N

Molfile:  

     RDKit          2D

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    6.8891  -15.8982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6039  -16.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3203  -15.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3175  -15.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6021  -14.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0304  -14.6520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7464  -15.0618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4593  -14.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1750  -15.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4562  -13.8216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1533  -15.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9301  -16.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4344  -15.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9692  -14.8243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1757  -14.6585    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.0355  -16.3091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0367  -17.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1743  -16.3101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4601  -15.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4647  -15.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547  -14.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0375  -15.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0349  -15.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7494  -16.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167  -14.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2333  -15.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 10  1  0
  3  4  2  0
  1 16  1  0
  7  8  1  0
  4 17  1  0
 17 18  1  0
  8  9  1  0
  2 19  1  0
  4  5  1  0
 19 20  1  0
 20 21  1  0
 10  9  1  1
  2  3  1  0
  9 11  2  0
 10 12  1  0
  5  6  2  0
 20 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  6  1  1  0
 23 26  1  0
  1  2  2  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091105

   (S)-N-(4-((4,4-Dimethylcyclohexyl)oxy)-5-fluoro-2-methoxybenzyl)pyrrolidine-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: 378.49

Molecular Weight (Monoisotopic): 378.2319

AlogP: 3.55

#Rotatable Bonds: 6

Polar Surface Area: 59.59

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.78

CX Basic pKa: 9.80

CX LogP: 3.26

CX LogD: 0.91

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.79

Np Likeness Score: -0.09

References

1. Liu KK, Lefker BA, Dombroski MA, Chiang P, Cornelius P, Patterson TA, Zeng Y, Santucci S, Tomlinson E, Gibbons CP, Marala R, Brown JA, Kong JX, Lee E, Werner W, Wenzel Z, Giragossian C, Chen H, Coffey SB..  (2010)  Orally active and brain permeable proline amides as highly selective 5HT2c agonists for the treatment of obesity.,  20  (7): [PMID:20202843] [10.1016/j.bmcl.2010.01.107]

Source

Source(1):

• Scientific Literature