4,4,4-trifluoro-1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-3-(trifluoromethyl)butane-1,3-diol

ID: ALA3819333

PubChem CID: 127053051

Max Phase: Preclinical

Molecular Formula: C24H34F6O3

Molecular Weight: 484.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@@H]2C(O)CC(O)(C(F)(F)F)C(F)(F)F

Standard InChI:  InChI=1S/C24H34F6O3/c1-20-9-7-14(31)11-13(20)3-4-15-16-5-6-18(21(16,2)10-8-17(15)20)19(32)12-22(33,23(25,26)27)24(28,29)30/h3,14-19,31-33H,4-12H2,1-2H3/t14-,15-,16-,17-,18+,19?,20-,21-/m0/s1

Standard InChI Key:  OHKBOEWLASAFLW-STFFYOTPSA-N

Molfile:  

     RDKit          2D

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   -4.1792   -0.4015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9034    2.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5927    4.4532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2059    2.0675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1838    5.9682    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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    9.5458    1.9302    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.5099    1.3246    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6715   -0.8608    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3325    1.5372    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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 20 16  1  0
  8 21  1  1
  5 22  1  1
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  1 31  1  0
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  1 33  1  0
 13 34  1  1
 12 35  1  6
 17 36  1  6
 20 37  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3819333

   ---

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: 484.52

Molecular Weight (Monoisotopic): 484.2412

AlogP: 5.53

#Rotatable Bonds: 3

Polar Surface Area: 60.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.91

CX Basic pKa: ┄

CX LogP: 4.28

CX LogD: 4.16

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.36

Np Likeness Score: 1.83

References

1. Castelli R, Giacomini A, Anselmi M, Bozza N, Vacondio F, Rivara S, Matarazzo S, Presta M, Mor M, Ronca R..  (2016)  Synthesis, Structural Elucidation, and Biological Evaluation of NSC12, an Orally Available Fibroblast Growth Factor (FGF) Ligand Trap for the Treatment of FGF-Dependent Lung Tumors.,  59  (10): [PMID:27138345] [10.1021/acs.jmedchem.5b02021]

Source

Source(1):

• Scientific Literature