2-Amino-9-((6-bromobenzo[d][1,3]dioxol-5-yl)methyl)-6-chloro-9H-purin-8-ol

ID: ALA4869481

PubChem CID: 155920143

Max Phase: Preclinical

Molecular Formula: C13H9BrClN5O3

Molecular Weight: 398.60

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nc(Cl)c2nc(O)n(Cc3cc4c(cc3Br)OCO4)c2n1

Standard InChI:  InChI=1S/C13H9BrClN5O3/c14-6-2-8-7(22-4-23-8)1-5(6)3-20-11-9(17-13(20)21)10(15)18-12(16)19-11/h1-2H,3-4H2,(H,17,21)(H2,16,18,19)

Standard InChI Key:  JGUUSDOBVPWHAQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   18.4019   -2.6579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4008   -3.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1088   -3.8864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1070   -2.2490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8156   -2.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8205   -3.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6048   -3.7273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0848   -3.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5970   -2.3954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6927   -3.8855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1046   -1.4318    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.8619   -4.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6622   -4.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9145   -5.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9973   -4.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1984   -4.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2582   -5.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7143   -5.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1247   -6.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9223   -6.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0047   -5.3303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9381   -3.2856    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   21.7993   -2.6459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  2 10  1  0
  4 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  2  0
 14 18  1  0
 17 15  1  0
 15 16  2  0
 16 13  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 16 22  1  0
  8 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4869481

   ---

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: 398.60

Molecular Weight (Monoisotopic): 396.9577

AlogP: 2.31

#Rotatable Bonds: 2

Polar Surface Area: 108.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.52

CX Basic pKa: 1.43

CX LogP: 3.10

CX LogD: 3.10

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.64

Np Likeness Score: -0.82

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]

2. Kang S, Kang BH..  (2022)  Structure, Function, and Inhibitors of the Mitochondrial Chaperone TRAP1.,  65  (24.0): [PMID:36507721] [10.1021/acs.jmedchem.2c01633]

Source

Source(1):

• Scientific Literature