(20S)-21-(Bis(trifluoromethyl)hydroxymethyl)pregn-5-en-3beta,20-diol

ID: ALA3819473

Cas Number: 102586-30-1

PubChem CID: 97290924

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]2[C@@H](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-FJWDNACWSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3819473

   (1S)-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

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]

2. Castelli R, Taranto S, Furiassi L, Bozza N, Marseglia G, Ferlenghi F, Rivara S, Retini M, Bedini A, Spadoni G, Matarazzo S, Ronca R, Presta M, Mor M, Giacomini A..  (2021)  Chemical modification of NSC12 leads to a specific FGF-trap with antitumor activity in multiple myeloma.,  221  [PMID:34004471] [10.1016/j.ejmech.2021.113529]

Source

Source(1):

• Scientific Literature