(1R,3r,5S)-tert-butyl 3-(3-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-ylamino)-9-azabicyclo[3.3.1]nonane-9-carboxylate

ID: ALA4556786

PubChem CID: 155557168

Max Phase: Preclinical

Molecular Formula: C20H29N5O3

Molecular Weight: 387.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1c(N[C@H]2C[C@H]3CCC[C@@H](C2)N3C(=O)OC(C)(C)C)nc2cc[nH]c2c1=O

Standard InChI:  InChI=1S/C20H29N5O3/c1-20(2,3)28-19(27)25-13-6-5-7-14(25)11-12(10-13)22-18-23-15-8-9-21-16(15)17(26)24(18)4/h8-9,12-14,21H,5-7,10-11H2,1-4H3,(H,22,23)/t12-,13+,14-

Standard InChI Key:  WUNZQLHREXLEQA-BTTYYORXSA-N

Molfile:  

 
     RDKit          2D

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   16.4099  -11.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.8039  -10.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1069  -10.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9207  -11.2467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9196  -12.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6194  -12.4710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3290  -12.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6176  -10.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3234  -11.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9257  -10.7093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5988   -9.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7920  -10.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0339  -12.4679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2157  -12.4701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6192  -13.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5083  -12.0609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5144  -11.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1074  -11.2309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8070  -12.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0734  -10.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0972   -9.9975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3624  -11.1898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6751  -10.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9641  -11.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6988   -9.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9707  -10.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7966  -10.0292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6946  -12.7490    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9 15  2  0
  7 16  1  0
  8 17  1  0
 18 16  1  6
 18 19  1  0
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  4 20  1  0
  3 20  1  0
  3 21  1  0
 20 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
  4 29  1  1
  3 30  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4556786

   ---

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: 387.48

Molecular Weight (Monoisotopic): 387.2270

AlogP: 2.99

#Rotatable Bonds: 2

Polar Surface Area: 92.25

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.01

CX Basic pKa: 6.19

CX LogP: 1.90

CX LogD: 1.87

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.83

Np Likeness Score: -0.49

References

1. Huang L, Li H, Li L, Niu L, Seupel R, Wu C, Cheng W, Chen C, Ding B, Brennan PE, Yang S..  (2019)  Discovery of Pyrrolo[3,2- d]pyrimidin-4-one Derivatives as a New Class of Potent and Cell-Active Inhibitors of P300/CBP-Associated Factor Bromodomain.,  62  (9): [PMID:30998845] [10.1021/acs.jmedchem.9b00096]

Source

Source(1):

• Scientific Literature