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

ID: ALA4547524

PubChem CID: 132200704

Max Phase: Preclinical

Molecular Formula: C22H24F2N4O3

Molecular Weight: 430.46

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H24F2N4O3/c1-11-14-3-5-28(22(14)27-10-26-11)16-8-18(20(30)19(16)29)31-17-7-13(21(23)24)6-12-2-4-25-9-15(12)17/h3,5-7,10,16,18-21,25,29-30H,2,4,8-9H2,1H3/t16-,18+,19+,20-/m1/s1

Standard InChI Key:  MKDAOQCQTOXOMQ-BTHPGYMESA-N

Molfile:  

 
     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   29.8316   -5.9734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1199   -5.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5366   -5.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3009   -5.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8123   -5.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3639   -4.5193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5756   -4.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5161   -6.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6285   -5.2416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6532   -3.7550    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7132   -2.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2021   -3.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4776   -2.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4386   -3.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1232   -3.9760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.8471   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8822   -2.7846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.1969   -2.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2324   -1.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6978   -4.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7121   -5.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4235   -5.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3990   -4.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1070   -4.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8001   -4.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7913   -3.5362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0832   -3.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3840   -3.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0117   -6.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2969   -5.6257    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.0262   -6.8388    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
M  END

Alternative Forms

1. Parent:

   

   ALA4547524

   ---

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: 430.46

Molecular Weight (Monoisotopic): 430.1816

AlogP: 2.44

#Rotatable Bonds: 4

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: 8.33

CX LogP: 1.25

CX LogD: 0.27

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.59

Np Likeness Score: 0.40

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