(1S,2R,3aR,4S,6aR)-4-((2-amino-3-bromoquinolin-7-yl)methyl)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)octahydropentalene-1,6a-diol

ID: ALA4846178

PubChem CID: 156705377

Max Phase: Preclinical

Molecular Formula: C24H25BrN6O2

Molecular Weight: 509.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nc2cc(C[C@@H]3CC[C@@]4(O)[C@@H]3C[C@@H](n3ccc5c(N)ncnc53)[C@@H]4O)ccc2cc1Br

Standard InChI:  InChI=1S/C24H25BrN6O2/c25-17-9-14-2-1-12(8-18(14)30-22(17)27)7-13-3-5-24(33)16(13)10-19(20(24)32)31-6-4-15-21(26)28-11-29-23(15)31/h1-2,4,6,8-9,11,13,16,19-20,32-33H,3,5,7,10H2,(H2,27,30)(H2,26,28,29)/t13-,16+,19+,20-,24+/m0/s1

Standard InChI Key:  CUHBMWWZOQHSJP-CVXUCQRBSA-N

Molfile:  

 
     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
    7.5094  -18.7113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3191  -17.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5363  -17.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7803  -18.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2795  -18.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5843  -19.7353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3897  -19.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8893  -19.2018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5817  -18.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8417  -19.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0821  -17.8061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0759  -18.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5765  -19.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0375  -20.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8216  -19.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7945  -19.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7665  -20.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5312  -20.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4343  -20.9209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1503  -19.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3927  -19.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7497  -19.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9927  -19.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2824  -20.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5280  -20.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8823  -20.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1242  -20.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0105  -21.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611  -21.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167  -21.4930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5511  -22.6123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2535  -21.6066    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.4645  -20.4848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5718  -18.7252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0
  4  2  1  0
  2  3  2  0
  3  1  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
 10  1  1  1
  9 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 10  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 14 19  1  6
 16 20  1  1
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 26  2  0
 25 24  2  0
 24 21  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 29 31  1  0
 28 32  1  0
 15 33  1  6
 13 34  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4846178

   ---

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: 509.41

Molecular Weight (Monoisotopic): 508.1222

AlogP: 3.21

#Rotatable Bonds: 3

Polar Surface Area: 136.10

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.14

CX Basic pKa: 6.25

CX LogP: 2.97

CX LogD: 2.94

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: 0.74

References

1. Quiroz RV, Reutershan MH, Schneider SE, Sloman D, Lacey BM, Swalm BM, Yeung CS, Gibeau C, Spellman DS, Rankic DA, Chen D, Witter D, Linn D, Munsell E, Feng G, Xu H, Hughes JME, Lim J, Saurí J, Geddes K, Wan M, Mansueto MS, Follmer NE, Fier PS, Siliphaivanh P, Daublain P, Palte RL, Hayes RP, Lee S, Kawamura S, Silverman S, Sanyal S, Henderson TJ, Ye Y, Gao Y, Nicholson B, Machacek MR..  (2021)  The Discovery of Two Novel Classes of 5,5-Bicyclic Nucleoside-Derived PRMT5 Inhibitors for the Treatment of Cancer.,  64  (7.0): [PMID:33755451] [10.1021/acs.jmedchem.0c02083]

Source

Source(1):

• Scientific Literature