(8R,9S,13S,14R,15S)-N-ethyl-3-(3-(4-fluoropiperidin-1-yl)propoxy)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-15-carboxamide

ID: ALA4520503

PubChem CID: 71276381

Max Phase: Preclinical

Molecular Formula: C29H41FN2O3

Molecular Weight: 484.66

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCNC(=O)[C@H]1CC(=O)[C@@]2(C)CC[C@@H]3c4ccc(OCCCN5CCC(F)CC5)cc4CC[C@H]3[C@H]12

Standard InChI:  InChI=1S/C29H41FN2O3/c1-3-31-28(34)25-18-26(33)29(2)12-9-23-22-8-6-21(17-19(22)5-7-24(23)27(25)29)35-16-4-13-32-14-10-20(30)11-15-32/h6,8,17,20,23-25,27H,3-5,7,9-16,18H2,1-2H3,(H,31,34)/t23-,24-,25+,27-,29-/m1/s1

Standard InChI Key:  STCAZOUTSRLMGA-YFGKGCBZSA-N

Molfile:  

 
     RDKit          2D

 38 42  0  0  0  0  0  0  0  0999 V2000
   36.3569  -28.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0710  -28.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3638  -26.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0745  -27.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0914  -25.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3692  -26.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8021  -26.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7888  -27.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5675  -27.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0637  -26.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5890  -25.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0666  -26.5835    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   36.3568  -27.8093    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   37.7807  -27.8258    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   37.7972  -25.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6548  -28.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6599  -27.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9533  -26.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2411  -27.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2400  -28.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9472  -28.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5278  -28.6266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8164  -28.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1041  -28.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3927  -28.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3935  -27.3904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.8073  -28.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2507  -28.6585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.6079  -28.2390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.8518  -29.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6524  -29.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8582  -25.1607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1061  -26.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1089  -26.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3999  -25.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6863  -26.1603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6818  -26.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4038  -24.9344    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 17  3  1  0
 16  1  1  0
  1  2  1  0
  2  4  1  0
  3  4  1  0
  3  6  1  0
  4  8  1  0
  7  5  1  0
  5  6  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
  4 12  1  1
  3 13  1  6
  8 14  1  6
  7 15  1  1
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
  9 27  1  6
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 11 32  2  0
 26 33  1  0
 26 37  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 35 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4520503

   (8R,9S,13S,14R,15S)-N-ethyl-3-[3-(4-fluoropiperidin-1-yl)propoxy]-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-15-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 484.66

Molecular Weight (Monoisotopic): 484.3101

AlogP: 4.68

#Rotatable Bonds: 7

Polar Surface Area: 58.64

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.80

CX LogP: 3.74

CX LogD: 2.33

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.57

Np Likeness Score: 0.10

References

1. Ledneczki I, Némethy Z, Tapolcsányi P, Éles J, Greiner I, Gábor E, Varga B, Balázs O, Román V, Lévay G, Mahó S..  (2019)  Discovery of novel steroidal histamine H3 receptor antagonists/inverse agonists. Part 2. Versatile steroidal carboxamide derivatives.,  29  (20): [PMID:31492518] [10.1016/j.bmcl.2019.126643]

Source

Source(1):

• Scientific Literature