16-beta-(4-((6-chloro-2-fluoro-9H-purin-9-yl)methyl)-1H-1,2,3-triazol-1-yl)-androsta-3-beta-ol-5-en-17-one

ID: ALA4533668

PubChem CID: 155547353

Max Phase: Preclinical

Molecular Formula: C27H31ClFN7O2

Molecular Weight: 540.04

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)[C@@H](n3cc(Cn4cnc5c(Cl)nc(F)nc54)nn3)C[C@@H]12

Standard InChI:  InChI=1S/C27H31ClFN7O2/c1-26-7-5-16(37)9-14(26)3-4-17-18(26)6-8-27(2)19(17)10-20(22(27)38)36-12-15(33-34-36)11-35-13-30-21-23(28)31-25(29)32-24(21)35/h3,12-13,16-20,37H,4-11H2,1-2H3/t16-,17+,18-,19-,20-,26-,27-/m0/s1

Standard InChI Key:  JMLSYJIEHZYFPY-DVCZEVKNSA-N

Molfile:  

 
     RDKit          2D

 41 47  0  0  0  0  0  0  0  0999 V2000
   31.2442   -4.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9478   -4.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6556   -4.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6556   -5.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9478   -6.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2442   -5.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5361   -6.1601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3633   -6.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0670   -5.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0670   -4.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3633   -4.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3634   -3.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0671   -3.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7749   -3.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7748   -4.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5505   -4.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0377   -4.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5725   -3.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7804   -2.6798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.8530   -4.1138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2607   -3.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0708   -3.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1525   -4.3844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.4008   -4.7110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.6507   -3.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4385   -3.2267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.0142   -2.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7496   -3.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6240   -3.8223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.8119   -3.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4580   -2.5863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4198   -1.7571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.6843   -1.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9800   -1.8161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.6843   -0.5565    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   42.1661   -2.9939    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.7749   -2.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6556   -4.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0620   -4.1190    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   33.3563   -5.3448    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   34.7678   -5.3448    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  1  6  1  0
  6  7  1  1
  4  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  3 11  1  0
 11 12  1  0
 13 12  1  0
 14 13  1  0
 15 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
 18 17  1  0
 14 18  1  0
 18 19  2  0
 17 20  1  1
 21 20  1  0
 21 22  2  0
 22 23  1  0
 24 23  2  0
 20 24  1  0
 22 25  1  0
 25 26  1  0
 27 26  1  0
 27 28  2  0
 28 29  1  0
 30 29  2  0
 26 30  1  0
 28 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 27 34  1  0
 33 35  1  0
 31 36  1  0
 14 37  1  1
  3 38  1  1
 10 39  1  1
 11 40  1  6
 15 41  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4533668

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 540.04

Molecular Weight (Monoisotopic): 539.2212

AlogP: 4.30

#Rotatable Bonds: 3

Polar Surface Area: 111.61

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 0.23

CX LogP: 4.23

CX LogD: 4.23

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.30

Np Likeness Score: 0.48

References

1. Zhao JW, Wu ZH, Guo JW, Huang MJ, You YZ, Liu HM, Huang LH..  (2019)  Synthesis and anti-gastric cancer activity evaluation of novel triazole nucleobase analogues containing steroidal/coumarin/quinoline moieties.,  181  [PMID:31404863] [10.1016/j.ejmech.2019.07.023]

Source

Source(1):

• Scientific Literature