2-Amino-4-chloro-7-(2-chloro-5-(trifluoromethyl)benzyl)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

ID: ALA4870963

PubChem CID: 162767113

Max Phase: Preclinical

Molecular Formula: C14H9Cl2F3N4O

Molecular Weight: 377.15

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nc(Cl)c2c(n1)N(Cc1cc(C(F)(F)F)ccc1Cl)C(=O)C2

Standard InChI:  InChI=1S/C14H9Cl2F3N4O/c15-9-2-1-7(14(17,18)19)3-6(9)5-23-10(24)4-8-11(16)21-13(20)22-12(8)23/h1-3H,4-5H2,(H2,20,21,22)

Standard InChI Key:  SHDZNBAQAWUOQS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   36.7530  -10.2685    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   37.3349  -10.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5479  -10.0555    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.1992   -9.9012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1981  -10.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9061  -11.1297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9043   -9.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6130   -9.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6178  -10.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4022  -10.9706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8822  -10.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3943   -9.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4900  -11.1288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9019   -8.6751    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.6592  -11.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4595  -11.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7118  -12.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7946  -11.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9957  -11.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0555  -12.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5116  -12.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6993  -10.2969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.1674  -13.2990    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   38.1366  -11.0153    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  5 13  1  0
  7 14  1  0
 10 15  1  0
 15 16  1  0
 16 17  2  0
 17 21  1  0
 20 18  1  0
 18 19  2  0
 19 16  1  0
 20 21  2  0
 11 22  2  0
 17 23  1  0
 18  2  1  0
  2 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4870963

   ---

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: 377.15

Molecular Weight (Monoisotopic): 376.0106

AlogP: 3.47

#Rotatable Bonds: 2

Polar Surface Area: 72.11

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.06

CX Basic pKa: 1.88

CX LogP: 3.49

CX LogD: 3.49

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.81

Np Likeness Score: -1.43

References

1. Yang S, Yoon NG, Kim D, Park E, Kim SY, Lee JH, Lee C, Kang BH, Kang S..  (2021)  Design and Synthesis of TRAP1 Selective Inhibitors: H-Bonding with Asn171 Residue in TRAP1 Increases Paralog Selectivity.,  12  (7.0): [PMID:34267888] [10.1021/acsmedchemlett.1c00213]

Source

Source(1):

• Scientific Literature