(1S,2S,3R,5S)-3-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(4-chlorophenylthio)cyclopentane-1,2-diol

ID: ALA4554624

PubChem CID: 135318312

Max Phase: Preclinical

Molecular Formula: C17H17ClN4O2S

Molecular Weight: 376.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ccn2[C@@H]1C[C@H](Sc2ccc(Cl)cc2)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C17H17ClN4O2S/c18-9-1-3-10(4-2-9)25-13-7-12(14(23)15(13)24)22-6-5-11-16(19)20-8-21-17(11)22/h1-6,8,12-15,23-24H,7H2,(H2,19,20,21)/t12-,13+,14+,15-/m1/s1

Standard InChI Key:  MHLOCKTYXIORPC-CBBWQLFWSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   33.5736  -15.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5724  -16.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2805  -16.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9901  -16.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9873  -15.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2787  -14.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6935  -14.9632    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.4064  -15.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3980  -16.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1700  -16.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6555  -15.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1836  -15.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7320  -16.6563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4144  -17.2223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.4727  -15.7970    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.7344  -15.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9599  -15.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7260  -16.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9477  -16.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7711  -17.2529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.3719  -17.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1520  -17.5556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.3249  -16.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1036  -16.5140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8644  -16.6056    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  8  7  1  1
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  9 13  1  6
 10 14  1  6
 11 15  1  1
 15 19  1  0
 18 16  1  0
 16 17  2  0
 17 15  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 23 24  1  0
  2 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4554624

   ---

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: 376.87

Molecular Weight (Monoisotopic): 376.0761

AlogP: 2.49

#Rotatable Bonds: 3

Polar Surface Area: 97.19

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.22

CX Basic pKa: 6.23

CX LogP: 2.00

CX LogD: 1.97

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.65

Np Likeness Score: -0.29

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