L-isocoformycin

ID: ALA34023

PubChem CID: 44283248

Max Phase: Preclinical

Molecular Formula: C11H16N4O5

Molecular Weight: 284.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](n2cnc3c2NC=NC[C@@H]3O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C11H16N4O5/c16-2-6-8(18)9(19)11(20-6)15-4-14-7-5(17)1-12-3-13-10(7)15/h3-6,8-9,11,16-19H,1-2H2,(H,12,13)/t5-,6+,8+,9+,11+/m0/s1

Standard InChI Key:  YOOVTUPUBVHMPG-DANLAGSESA-N

Molfile:  

     RDKit          2D

 20 22  0  0  1  0  0  0  0  0999 V2000
    5.1167   -3.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -3.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -2.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -4.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7375   -2.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -3.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1667   -3.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8542   -4.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1000   -2.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9750   -2.7042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8125   -5.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8542   -5.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042   -1.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6917   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -3.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  1
  4  2  2  0
  5  7  2  0
  6  3  1  0
  7  1  1  0
  8  3  1  0
  9  2  1  0
 10  6  1  0
 11  8  1  0
 12  4  1  0
 13  9  1  0
 14 13  2  0
  6 15  1  6
 10 16  1  6
 12 17  1  1
 18 12  1  0
 11 19  1  1
 20 19  1  0
  4  5  1  0
 11 10  1  0
 18 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA34023

   (2R,3R,4S,5R)-2-[(8S)-8-hydroxy-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl]-5-(hydroxymethyl)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: 284.27

Molecular Weight (Monoisotopic): 284.1121

AlogP: -2.02

#Rotatable Bonds: 2

Polar Surface Area: 132.36

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.36

CX Basic pKa: 6.52

CX LogP: -2.84

CX LogD: -2.89

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.42

Np Likeness Score: 1.25

References

1. Cheviet T, Lefebvre-Tournier I, Wein S, Peyrottes S..  (2019)  Plasmodium Purine Metabolism and Its Inhibition by Nucleoside and Nucleotide Analogues.,  62  (18): [PMID:30964283] [10.1021/acs.jmedchem.9b00182]

Source

Source(1):

• Scientific Literature