(1S,2S,3R,5S)-3-(4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(6-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinolin-8-yloxy)cyclopentane-1,2-diol

ID: ALA4579108

PubChem CID: 132200649

Max Phase: Preclinical

Molecular Formula: C22H23F3N4O3

Molecular Weight: 448.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ncnc2c1ccn2[C@@H]1C[C@H](Oc2cc(C(F)(F)F)cc3c2CNCC3)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C22H23F3N4O3/c1-11-14-3-5-29(21(14)28-10-27-11)16-8-18(20(31)19(16)30)32-17-7-13(22(23,24)25)6-12-2-4-26-9-15(12)17/h3,5-7,10,16,18-20,26,30-31H,2,4,8-9H2,1H3/t16-,18+,19+,20-/m1/s1

Standard InChI Key:  QDHALPIIHPGYSX-BTHPGYMESA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   12.5303   -5.4245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8186   -5.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2353   -5.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9996   -5.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5109   -4.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0626   -3.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2743   -4.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2148   -6.0796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3272   -4.6927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3518   -3.2061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4119   -1.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9007   -2.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1762   -2.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1373   -2.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8218   -3.4271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5457   -3.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5809   -2.2356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8956   -1.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9311   -0.9839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3965   -4.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4107   -5.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1221   -5.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0976   -3.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8057   -4.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4988   -3.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4899   -2.9873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7819   -2.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0827   -3.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7104   -5.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9955   -5.0768    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.7248   -6.2899    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.9974   -5.8772    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  1
  2  1  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  3  1  0
  4  8  1  6
  5  9  1  6
  6 10  1  1
 10 14  1  0
 13 11  1  0
 11 12  2  0
 12 10  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 18 19  1  0
  2 24  2  0
 23 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 21 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4579108

   ---

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: 448.45

Molecular Weight (Monoisotopic): 448.1722

AlogP: 2.52

#Rotatable Bonds: 3

Polar Surface Area: 92.43

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.97

CX Basic pKa: 8.29

CX LogP: 1.74

CX LogD: 0.80

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.57

Np Likeness Score: 0.33

References

1. Lin H, Luengo JI..  (2019)  Nucleoside protein arginine methyltransferase 5 (PRMT5) inhibitors.,  29  (11): [PMID:30956011] [10.1016/j.bmcl.2019.03.042]

Source

Source(1):

• Scientific Literature