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

ID: ALA4585734

PubChem CID: 132190245

Max Phase: Preclinical

Molecular Formula: C21H24N4O3

Molecular Weight: 380.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ncnc2c1ccn2[C@@H]1C[C@H](Oc2cccc3c2CNCC3)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C21H24N4O3/c1-12-14-6-8-25(21(14)24-11-23-12)16-9-18(20(27)19(16)26)28-17-4-2-3-13-5-7-22-10-15(13)17/h2-4,6,8,11,16,18-20,22,26-27H,5,7,9-10H2,1H3/t16-,18+,19+,20-/m1/s1

Standard InChI Key:  SFDOALJIDJMJFX-BTHPGYMESA-N

Molfile:  

 
     RDKit          2D

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   40.0094  -22.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.2977  -22.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7144  -22.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4787  -22.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9900  -22.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5417  -21.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7534  -21.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6939  -23.4511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.8063  -22.0642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.8309  -20.5776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.8910  -19.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3798  -19.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6553  -19.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6164  -20.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3009  -20.7986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.0248  -20.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0600  -19.6071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.3747  -19.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4101  -18.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8756  -21.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8898  -22.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6012  -22.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5767  -21.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2847  -21.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9778  -21.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9690  -20.3588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.2610  -19.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5618  -20.3774    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA4585734

   ---

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: 380.45

Molecular Weight (Monoisotopic): 380.1848

AlogP: 1.50

#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: 8.42

CX LogP: 0.86

CX LogD: -0.20

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.64

Np Likeness Score: 0.55

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