(E)-(R)-4-((2R,4bS,7S,8aR)-7-Hydroxy-2,4b-dimethyl-1-oxo-tetradecahydro-phenanthren-2-yl)-hex-2-enoic acid 2-dimethylamino-ethyl ester

ID: ALA321090

PubChem CID: 44334168

Max Phase: Preclinical

Molecular Formula: C26H43NO4

Molecular Weight: 433.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](/C=C/C(=O)OCCN(C)C)[C@@]1(C)CCC2C(CC[C@@H]3C[C@@H](O)CC[C@]23C)C1=O

Standard InChI:  InChI=1S/C26H43NO4/c1-6-18(8-10-23(29)31-16-15-27(4)5)26(3)14-12-22-21(24(26)30)9-7-19-17-20(28)11-13-25(19,22)2/h8,10,18-22,28H,6-7,9,11-17H2,1-5H3/b10-8+/t18-,19-,20+,21?,22?,25+,26-/m1/s1

Standard InChI Key:  IJRWRMFNPYXLPH-ACVHBDGZSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  1  0  0  0  0  0999 V2000
    4.5750   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1292   -7.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -7.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1375   -6.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6125   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5750   -8.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -6.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -6.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -7.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -5.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042   -8.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4917   -5.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6875   -5.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7000   -7.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7125   -6.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875   -8.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -8.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2875   -4.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2417   -3.7250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2750   -4.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375   -8.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667   -6.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1375   -5.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4625   -4.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167   -8.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0500   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0625   -6.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8375   -3.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8500   -3.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6625   -6.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -8.7625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  1  1  0
  4  7  1  0
  5  3  1  0
  6  1  1  0
  7  8  1  0
  8  3  1  0
  9  1  1  0
 15 10  1  1
 11 16  1  0
 12 10  2  0
 13 12  1  0
 14  2  2  0
 15  4  1  0
 16  6  1  0
 17  6  1  0
 18 13  2  0
 19  9  1  0
 20 27  1  0
 21 13  1  0
 22 19  1  0
  1 23  1  1
  4 24  1  1
 25 21  1  0
 22 26  1  1
 27 25  1  0
 28 15  1  0
 29 20  1  0
 30 20  1  0
 31 28  1  0
  6 32  1  1
 22 17  1  0
  5 11  1  0
  2  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA321090

   2-(dimethylamino)ethyl (E,4R)-4-[(2R,4bS,7S,8aR)-7-hydroxy-2,4b-dimethyl-1-oxo-4,4a,5,6,7,8,8a,9,10,10a-decahydro-3H-phenanthren-2-yl]hex-2-enoate

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: 433.63

Molecular Weight (Monoisotopic): 433.3192

AlogP: 4.24

#Rotatable Bonds: 7

Polar Surface Area: 66.84

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.72

CX LogP: 4.90

CX LogD: 4.41

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.48

Np Likeness Score: 1.66

References

1. De Munari S, Barassi P, Cerri A, Fedrizzi G, Gobbini M, Mabilia M, Melloni P..  (1998)  A new approach to the design of novel inhibitors of Na+,K+-ATPase: 17alpha-substituted seco-D 5beta-androstane as cassaine analogues.,  41  (16): [PMID:9685243] [10.1021/jm980108d]

2. Gobbini M, Barassi P, Cerri A, De Munari S, Fedrizzi G, Santagostino M, Schiavone A, Torri M, Melloni P..  (2001)  17 alpha-O-(aminoalkyl)oxime derivatives of 3 beta,14 beta-dihydroxy-5 beta-androstane and 3 beta-hydroxy-14-oxoseco-D-5 beta-androstane as inhibitors of Na(+),K(+)-ATPase at the digitalis receptor.,  44  (23): [PMID:11689068] [10.1021/jm0109208]

Source

Source(1):

• Scientific Literature