4-[(R)-1-((2R,4bS,7S,8aR)-7-Hydroxy-2,4b-dimethyl-1-oxo-tetradecahydro-phenanthren-2-yl)-propyl]-5H-furan-2-one

ID: ALA319670

PubChem CID: 44334165

Max Phase: Preclinical

Molecular Formula: C23H34O4

Molecular Weight: 374.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C1=CC(=O)OC1)[C@@]1(C)CCC2C(CC[C@@H]3C[C@@H](O)CC[C@]23C)C1=O

Standard InChI:  InChI=1S/C23H34O4/c1-4-18(14-11-20(25)27-13-14)23(3)10-8-19-17(21(23)26)6-5-15-12-16(24)7-9-22(15,19)2/h11,15-19,24H,4-10,12-13H2,1-3H3/t15-,16+,17?,18-,19?,22+,23-/m1/s1

Standard InChI Key:  RXAQOPSWCQZTHW-CIUKUSSFSA-N

Molfile:  

     RDKit          2D

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   -0.4750    2.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833    1.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0375    1.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5208    1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    1.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5875    2.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1000    2.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3875    3.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0375    0.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8625    3.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958    2.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5208    2.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542    3.2208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5625    1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0083    0.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1875    2.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375    1.1583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5250    0.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5625    0.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500    4.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0750    1.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4750    2.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0750    0.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0458    1.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5958    0.2708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4500    1.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417    1.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8875   -0.1667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6875    2.1833    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4 12  1  0
  5  2  1  0
  7  6  1  1
  7  1  1  0
  8  6  2  0
  9  3  1  0
 10  8  1  0
 11  1  1  0
 12 11  1  0
 13 16  1  0
 14  3  1  0
 15  5  1  0
 16  6  1  0
 17  2  2  0
 18 15  1  0
 19  9  1  0
 20 10  2  0
 21 14  1  0
  1 22  1  1
 23 21  1  0
  3 24  1  1
 23 25  1  1
 26  7  1  0
 27 26  1  0
  9 28  1  1
  7 29  1  6
  4  5  1  0
 10 13  1  0
 18  9  1  0
 23 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA319670

   3-[(1R)-1-[(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]propyl]-2H-furan-5-one

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: 374.52

Molecular Weight (Monoisotopic): 374.2457

AlogP: 4.06

#Rotatable Bonds: 3

Polar Surface Area: 63.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.13

CX Basic pKa: ┄

CX LogP: 4.36

CX LogD: 3.90

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: 2.58

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