(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-4,4,8,10,14-pentamethyl-3-(4-(trifluoromethoxy)benzyloxy)-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)tetradecahydro-1H-cyclopenta[a]phenanthren-6(10H)-one

ID: ALA4250526

PubChem CID: 145982890

Max Phase: Preclinical

Molecular Formula: C38H55F3O5

Molecular Weight: 648.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CCC[C@](C)([C@H]2CC[C@]3(C)[C@@H]2[C@H](O)C[C@@H]2[C@@]4(C)CC[C@H](OCc5ccc(OC(F)(F)F)cc5)C(C)(C)[C@@H]4C(=O)C[C@]23C)O1

Standard InChI:  InChI=1S/C38H55F3O5/c1-32(2)16-9-17-37(8,46-32)25-14-19-35(6)30(25)26(42)20-28-34(5)18-15-29(33(3,4)31(34)27(43)21-36(28,35)7)44-22-23-10-12-24(13-11-23)45-38(39,40)41/h10-13,25-26,28-31,42H,9,14-22H2,1-8H3/t25-,26+,28+,29-,30-,31-,34+,35+,36+,37+/m0/s1

Standard InChI Key:  YTVVIRMXLLFOAP-GGVVMKIBSA-N

Molfile:  

     RDKit          2D

 50 55  0  0  0  0  0  0  0  0999 V2000
    7.8913  -16.4676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8954  -15.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1815  -16.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7927  -10.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5067  -10.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5056   -9.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1896  -14.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1896  -15.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8990  -14.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6084  -14.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6050  -15.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3112  -15.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0253  -15.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3181  -14.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0249  -14.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0417  -12.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3234  -13.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7444  -13.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7355  -14.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5109  -14.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0005  -13.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5252  -12.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7894  -12.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5960  -12.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8576  -11.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3163  -10.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2445  -11.5733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4784  -15.6515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5970  -16.0549    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6011  -13.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3110  -14.8291    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3066  -16.4725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0168  -13.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0517  -11.9648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7308  -14.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7390  -12.3817    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3445  -12.9595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4972  -12.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7693  -15.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0630  -15.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3552  -15.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6493  -15.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6515  -16.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3655  -16.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0685  -16.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9457  -16.8888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2361  -16.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5303  -16.8953    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.2323  -15.6663    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.5229  -16.0714    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  7  8  1  0
  7  9  1  0
  8  2  1  0
  2 11  1  0
 10  9  1  0
 10 11  1  0
 10 14  1  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
 14 15  1  0
 14 17  1  0
 15 19  1  0
 18 16  1  0
 16 17  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 23 24  1  0
 23 27  1  0
 24 25  1  0
 25 26  1  0
 26  5  1  0
  5 27  1  0
 22 23  1  0
  8 28  1  1
 11 29  1  6
 10 30  1  1
 14 31  1  6
 12 32  2  0
 15 33  1  1
 16 34  1  1
 19 35  1  6
 18 36  1  1
 22 37  1  6
 23 38  1  1
 28 39  1  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 42 43  2  0
 43 44  1  0
 44 45  2  0
 45 40  1  0
 43 46  1  0
 46 47  1  0
 47 48  1  0
 47 49  1  0
 47 50  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4250526

   ---

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: 648.85

Molecular Weight (Monoisotopic): 648.4002

AlogP: 9.04

#Rotatable Bonds: 5

Polar Surface Area: 64.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 8.50

CX LogD: 8.50

Aromatic Rings: 1

Heavy Atoms: 46

QED Weighted: 0.35

Np Likeness Score: 1.94

References

1. Wu Q, Chen P, Tu G, Li M, Pan B, Guo Y, Zhai J, Fu H..  (2018)  Synthesis and evaluation of panaxatriol derivatives as Na+, K+-ATPase inhibitors.,  28  (17): [PMID:30049579] [10.1016/j.bmcl.2018.07.027]

Source

Source(1):

• Scientific Literature