4-[6-Amino-8-(3-fluoro-phenyl)-9-methyl-9H-purin-2-yl]-2-methyl-but-3-yn-2-ol

ID: ALA300624

PubChem CID: 10616023

Max Phase: Preclinical

Molecular Formula: C17H16FN5O

Molecular Weight: 325.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(-c2cccc(F)c2)nc2c(N)nc(C#CC(C)(C)O)nc21

Standard InChI:  InChI=1S/C17H16FN5O/c1-17(2,24)8-7-12-20-14(19)13-16(21-12)23(3)15(22-13)10-5-4-6-11(18)9-10/h4-6,9,24H,1-3H3,(H2,19,20,21)

Standard InChI Key:  UWDBBNIVTAVDGD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    6.3125   -6.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8792   -6.9250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3125   -6.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2250   -6.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8792   -5.9542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8000   -7.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8000   -5.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -6.1500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -6.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -7.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -7.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8250   -6.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6875   -7.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1500   -5.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -5.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0750   -7.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7500   -6.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0875   -5.4917    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -7.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1000   -7.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7000   -7.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542   -7.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750   -8.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0250   -6.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  1  2  0
  7  3  2  0
  8  9  2  0
  9  6  1  0
 10  9  1  0
 11 10  3  0
 12  4  1  0
 13 11  1  0
 14 12  1  0
 15  7  1  0
 16  2  1  0
 17 14  2  0
 18 17  1  0
 19 13  1  0
 20 12  2  0
 21 20  1  0
 22 13  1  0
 23 13  1  0
 24 21  2  0
  5  4  2  0
  7  8  1  0
 24 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA300624

   4-[6-Amino-8-(3-fluoro-phenyl)-9-methyl-9H-purin-2-yl]-2-methyl-but-3-yn-2-ol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 325.35

Molecular Weight (Monoisotopic): 325.1339

AlogP: 1.87

#Rotatable Bonds: 1

Polar Surface Area: 89.85

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.52

CX Basic pKa: 3.59

CX LogP: 2.90

CX LogD: 2.90

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: -0.94

References

1. Harada H, Asano O, Hoshino Y, Yoshikawa S, Matsukura M, Kabasawa Y, Niijima J, Kotake Y, Watanabe N, Kawata T, Inoue T, Horizoe T, Yasuda N, Minami H, Nagata K, Murakami M, Nagaoka J, Kobayashi S, Tanaka I, Abe S..  (2001)  2-Alkynyl-8-aryl-9-methyladenines as novel adenosine receptor antagonists: their synthesis and structure-activity relationships toward hepatic glucose production induced via agonism of the A(2B) receptor.,  44  (2): [PMID:11170626] [10.1021/jm990499b]

Source

Source(1):

• Scientific Literature