(2R,3S,4R,5R)-2-(1,8-diazaspiro[4.5]decan-1-ylmethyl)-5-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diol Hydrochloride

ID: ALA4524391

PubChem CID: 155520109

Max Phase: Preclinical

Molecular Formula: C19H29ClN6O3

Molecular Weight: 388.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.Nc1ncnc2c1ccn2[C@@H]1O[C@H](CN2CCCC23CCNCC3)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C19H28N6O3.ClH/c20-16-12-2-9-25(17(12)23-11-22-16)18-15(27)14(26)13(28-18)10-24-8-1-3-19(24)4-6-21-7-5-19;/h2,9,11,13-15,18,21,26-27H,1,3-8,10H2,(H2,20,22,23);1H/t13-,14-,15-,18-;/m1./s1

Standard InChI Key:  YYAPBRHULQSHKM-SRWXHXHESA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    7.9554  -20.3893    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7322  -21.7175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9398  -21.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7271  -22.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3035  -23.2973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0960  -23.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3119  -22.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892  -21.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4775  -21.3749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8942  -21.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6585  -21.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1698  -21.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7215  -20.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9331  -20.5337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8737  -22.4276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9861  -21.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0107  -19.5541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0707  -18.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5596  -18.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8351  -18.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7961  -19.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4807  -19.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2046  -19.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2397  -18.5836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5545  -18.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5899  -17.3319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3766  -20.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5769  -20.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1793  -21.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  7  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
 10  8  1  1
  9  8  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 11 15  1  6
 12 16  1  6
 13 17  1  1
 17 21  1  0
 20 18  1  0
 18 19  2  0
 19 17  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 25 26  1  0
  9 27  1  0
 27 28  1  0
 28 29  1  0
 29  2  1  0
  2  9  1  0
M  END

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: 388.47

Molecular Weight (Monoisotopic): 388.2223

AlogP: -0.15

#Rotatable Bonds: 3

Polar Surface Area: 121.69

Molecular Species: BASE

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.47

CX Basic pKa: 9.99

CX LogP: -0.60

CX LogD: -3.41

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.57

Np Likeness Score: 0.68

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