2-(6-Amino-purin-9-yl)-5-iodomethyl-tetrahydro-furan-3,4-diol

ID: ALA603180

PubChem CID: 46874771

Max Phase: Preclinical

Molecular Formula: C10H12IN5O3

Molecular Weight: 377.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2C1O[C@H](CI)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C10H12IN5O3/c11-1-4-6(17)7(18)10(19-4)16-3-15-5-8(12)13-2-14-9(5)16/h2-4,6-7,10,17-18H,1H2,(H2,12,13,14)/t4-,6-,7-,10?/m1/s1

Standard InChI Key:  FUWWLIOFNXNKQR-VTHZCTBJSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    3.8833   -4.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7083   -4.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9651   -4.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2958   -3.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6308   -4.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460   -3.7613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2332   -4.3136    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    3.3975   -5.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1924   -5.4680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5750   -2.7708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -2.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -2.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5750   -1.9083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -2.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042   -1.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042   -2.8958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -2.0708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -2.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042   -1.2583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  5  1  1  0
  1  2  1  0
  5  6  1  1
  6  7  1  0
  2  3  1  0
  1  8  1  6
  3  4  1  0
  2  9  1  6
 11 10  1  0
 12 11  2  0
 13 14  2  0
 14 10  1  0
 15 12  1  0
 16 11  1  0
 17 18  1  0
 18 16  2  0
 19 15  1  0
 13 12  1  0
 17 15  2  0
  3 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA603180

   (3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(iodomethyl)oxolane-3,4-diol

Molecule Features

Natural Product: Yes

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: 377.14

Molecular Weight (Monoisotopic): 376.9985

AlogP: -0.54

#Rotatable Bonds: 2

Polar Surface Area: 119.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.47

CX Basic pKa: 3.94

CX LogP: -0.28

CX LogD: -0.28

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.48

Np Likeness Score: 1.00

References

1. Sufrin JR, Spiess AJ, Kramer DL, Libby PR, Porter CW..  (1989)  Synthesis and antiproliferative effects of novel 5'-fluorinated analogues of 5'-deoxy-5'-(methylthio)adenosine.,  32  (5): [PMID:2496231] [10.1021/jm00125a012]

2. Young RC, Jones M, Milliner KJ, Rana KK, Ward JG..  (1990)  Purine derivatives as competitive inhibitors of human erythrocyte membrane phosphatidylinositol 4-kinase.,  33  (8): [PMID:2165159] [10.1021/jm00170a005]

Source

Source(1):

• Scientific Literature