9-(2-phosphonylmethoxyethyl)diaminopurine

ID: ALA2074852

PubChem CID: 70682625

Max Phase: Preclinical

Molecular Formula: C9H14N5O4P

Molecular Weight: 287.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2ccn(CCOCP(=O)(O)O)c2n1

Standard InChI:  InChI=1S/C9H14N5O4P/c10-7-6-1-2-14(8(6)13-9(11)12-7)3-4-18-5-19(15,16)17/h1-2H,3-5H2,(H2,15,16,17)(H4,10,11,12,13)

Standard InChI Key:  OUZLVQKHYICBGG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   -6.4159    2.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1303    2.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8448    2.3571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8448    1.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1304    1.1196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4159    1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6313    1.2772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1464    1.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6312    2.6120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1304    3.5946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5593    1.1196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9536   -0.2946    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9536    0.5304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7786   -0.2946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9536   -1.1196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2391   -0.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5246   -0.2946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8102   -0.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0957   -0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  9  1  0
  1  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
  4 11  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2074852

   2-(2,4-Diaminopyrrolo[2,3-d]pyrimidin-7-yl)ethoxymethylphosphonic acid

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: 287.22

Molecular Weight (Monoisotopic): 287.0783

AlogP: -0.25

#Rotatable Bonds: 5

Polar Surface Area: 149.51

Molecular Species: ZWITTERION

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.50

CX Basic pKa: 9.35

CX LogP: -3.97

CX LogD: -4.06

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.43

Np Likeness Score: -0.71

References

1. Cihlar T, Lin DC, Pritchard JB, Fuller MD, Mendel DB, Sweet DH..  (1999)  The antiviral nucleotide analogs cidofovir and adefovir are novel substrates for human and rat renal organic anion transporter 1.,  56  (1): [PMID:10462545] [10.1124/mol.56.3.570]

Source

Source(1):

• TP-search Transporter Database