(E,Z)10,13-Dimethyl-tetradecahydro-cyclopenta[a]phenanthrene-3,6,17-trione 3-[O-(2-dimethylamino-ethyl)-oxime]

ID: ALA3137925

PubChem CID: 15838421

Max Phase: Preclinical

Molecular Formula: C23H36N2O3

Molecular Weight: 388.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CCO/N=C1\CC[C@@]2(C)[C@H](C1)C(=O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12

Standard InChI:  InChI=1S/C23H36N2O3/c1-22-9-7-15(24-28-12-11-25(3)4)13-19(22)20(26)14-16-17-5-6-21(27)23(17,2)10-8-18(16)22/h16-19H,5-14H2,1-4H3/b24-15+/t16-,17-,18-,19+,22+,23-/m0/s1

Standard InChI Key:  VQTACRZXPYUKHZ-WZSOWKKOSA-N

Molfile:  

     RDKit          2D

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   12.8543   -8.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5859   -7.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1412   -8.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5662   -8.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4262   -9.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1393   -9.7154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8554   -9.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3730   -7.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8728   -6.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1484   -7.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7162   -8.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3541   -8.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7184   -9.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0054   -9.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2936   -9.7193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1321  -10.5404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8489   -7.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6387   -6.2246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0043   -8.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4240   -7.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4311   -9.7231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5805   -9.3077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5765   -6.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8644   -9.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1514   -9.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7181   -9.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4405  -10.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4190  -10.1246    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1371   -8.8878    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8472   -7.6557    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5697   -8.9044    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0
  3 10  1  0
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  4 11  1  0
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  5 13  1  0
  6 14  1  0
 15 20  1  0
 16 15  2  0
 17  7  2  0
 18 13  1  0
 19  9  2  0
 20 12  1  0
  1 21  1  1
 22 26  1  0
 23 16  1  0
  3 24  1  1
 25 23  1  0
 26 25  1  0
 27 22  1  0
 28 22  1  0
  6 29  1  6
 14 15  1  0
  2  8  1  0
  5  3  1  0
 18  9  1  0
  4 30  1  6
  2 31  1  1
  5 32  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3137925

   (3E,5S,8R,9S,10R,13S,14S)-3-[2-(dimethylamino)ethoxyimino]-10,13-dimethyl-1,2,4,5,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-6,17-dione

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: 388.55

Molecular Weight (Monoisotopic): 388.2726

AlogP: 3.71

#Rotatable Bonds: 4

Polar Surface Area: 58.97

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.12

CX LogP: 3.46

CX LogD: 3.27

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: 1.45

References

1. De Munari S, Cerri A, Gobbini M, Almirante N, Banfi L, Carzana G, Ferrari P, Marazzi G, Micheletti R, Schiavone A, Sputore S, Torri M, Zappavigna MP, Melloni P..  (2003)  Structure-based design and synthesis of novel potent Na+,K+ -ATPase inhibitors derived from a 5alpha,14alpha-androstane scaffold as positive inotropic compounds.,  46  (17): [PMID:12904068] [10.1021/jm030830y]

Source

Source(1):

• Scientific Literature