(3R,4R,5S)-3-(Adenin-9)-yl-4,5-bis(hydroxymethyl)-1-iodo-cyclopent-1-ene

ID: ALA4546313

PubChem CID: 155553278

Max Phase: Preclinical

Molecular Formula: C12H14IN5O2

Molecular Weight: 387.18

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@H]1C=C(I)[C@H](CO)[C@H]1CO

Standard InChI:  InChI=1S/C12H14IN5O2/c13-8-1-9(7(3-20)6(8)2-19)18-5-17-10-11(14)15-4-16-12(10)18/h1,4-7,9,19-20H,2-3H2,(H2,14,15,16)/t6-,7-,9+/m1/s1

Standard InChI Key:  OXOKFWPGJXDFKA-BHNWBGBOSA-N

Molfile:  

 
     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    6.4875   -3.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2336   -4.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9016   -4.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5685   -4.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3125   -3.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3532   -4.7327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6884   -4.7309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0202   -4.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4345   -5.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6103   -5.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1997   -6.2281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6120   -6.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4393   -6.9378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8463   -6.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6715   -6.2216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9026   -5.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1885   -6.2051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4491   -4.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8352   -4.1869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0017   -3.0304    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  4  5  1  0
  5  1  2  0
  6 10  1  0
  9  7  1  0
  7  8  2  0
  8  6  1  0
  4  6  1  6
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 14 15  1  0
  3 16  1  6
 16 17  1  0
  2 18  1  1
 18 19  1  0
  1 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4546313

   ---

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: 387.18

Molecular Weight (Monoisotopic): 387.0192

AlogP: 0.50

#Rotatable Bonds: 3

Polar Surface Area: 110.08

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.11

CX LogP: -0.81

CX LogD: -0.81

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.66

Np Likeness Score: 0.60

References

1. Kumamoto H, Imoto S, Amano M, Kuwata-Higashi N, Baba M, Mitsuya H, Odanaka Y, Shimbara Matsubayashi S, Tanaka H, Haraguchi K..  (2018)  Synthesis, Anti-HBV, and Anti-HIV Activities of 3'-Halogenated Bis(hydroxymethyl)-cyclopentenyladenines.,  9  (12): [PMID:30613328] [10.1021/acsmedchemlett.8b00374]

Source

Source(1):

• Scientific Literature