(2R,3S,5R)-2-((R)-8-Hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

ID: ALA284483

PubChem CID: 44326589

Max Phase: Phase

Molecular Formula: C11H16N4O5

Molecular Weight: 284.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Coformycin | NSC-277817 | CHEMBL284483|NSC277817|CHEMBL329608|BDBM50003602|(2R,3S,5R)-2-((R)-8-Hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol|2-(8-Hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol|2-(8-Hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol (Coformycin)|2-(8-Hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-5-hydroxymethyl-tetrahyShow More⌵

Canonical SMILES:  OC[C@H]1O[C@@H](n2cnc3c2N=CNC[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-/m1/s1

Standard InChI Key:  YOOVTUPUBVHMPG-LODYRLCVSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   -0.3795   -1.6716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8644   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795   -0.3367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0501   -0.0773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8545   -0.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2124   -1.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8545   -1.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0501   -1.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666   -2.7354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4051   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4051   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6344    0.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1495    1.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6755    1.1153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6344    1.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795    2.5674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4191    1.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4191    0.7028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0865    2.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8402    1.6772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
 10  1  1  0
  2  3  1  0
 12  3  1  6
 11  3  1  0
 11  4  1  0
  5  4  2  0
  5  6  1  0
  7  6  1  0
  7  8  1  0
  8 10  1  0
  8  9  1  1
 11 10  2  0
 12 18  1  0
 12 13  1  0
 13 15  1  0
 13 14  1  1
 15 17  1  0
 15 16  1  1
 17 19  1  6
 17 18  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA284483

   COFORMYCIN

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 284.27

Molecular Weight (Monoisotopic): 284.1121

AlogP: -2.21

#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: 12.37

CX Basic pKa: 8.30

CX LogP: -2.92

CX LogD: -3.81

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.42

Np Likeness Score: 1.19

References

1. Reayi A, Hosmane RS..  (2004)  Inhibition of adenosine deaminase by novel 5:7 fused heterocycles containing the imidazo[4,5-e][1,2,4]triazepine ring system: a structure-activity relationship study.,  47  (4): [PMID:14761206] [10.1021/jm0304257]

2. Bastian G, Bessodes M, Panzica RP, Abushanab E, Chen SF, Stoeckler JD, Parks RE..  (1981)  Adenosine deaminase inhibitors. Conversion of a single chiral synthon into erythro- and threo-9-(2-hydroxy-3-nonyl)adenines.,  24  (12): [PMID:7310814] [10.1021/jm00144a002]

3. Showalter HD, Putt SR, Borondy PE, Shillis JL..  (1983)  Adenosine deaminase inhibitors. Synthesis and biological evaluation of (+/-)-3,6,7,8-tetrahydro-3-[(2-hydroxyethoxy)methyl]imidazo[4,5-d] [1,3]diazepin-8-ol and some selected C-5 homologues of pentostatin.,  26  (10): [PMID:6604819] [10.1021/jm00364a022]

4. Andrews PR, Craik DJ, Martin JL..  (1984)  Functional group contributions to drug-receptor interactions.,  27  (12): [PMID:6094812] [10.1021/jm00378a021]

5. Antonini I, Cristalli G, Franchetti P, Grifantini M, Martelli S, Lupidi G, Riva F..  (1984)  Adenosine deaminase inhibitors. Synthesis of deaza analogues of erythro-9-(2-hydroxy-3-nonyl)adenine.,  27  (3): [PMID:6699873] [10.1021/jm00369a008]

6. Harriman GC, Poirot AF, Abushanab E, Midgett RM, Stoeckler JD..  (1992)  Adenosine deaminase inhibitors. Synthesis and biological evaluation of C1' and nor-C1' derivatives of (+)-erythro-9-(2(S)-hydroxy-3(R)-nonyl)adenine.,  35  (22): [PMID:1433220] [10.1021/jm00100a025]

7. Kasibhatla SR, Bookser BC, Xiao W, Erion MD..  (2001)  AMP deaminase inhibitors. 5. Design, synthesis, and SAR of a highly potent inhibitor series.,  44  (4): [PMID:11170651] [10.1021/jm000355t]

8. Chakraborty S, Shah NH, Fishbein JC, Hosmane RS..  (2012)  Investigations into specificity of azepinomycin for inhibition of guanase: discrimination between the natural heterocyclic inhibitor and its synthetic nucleoside analogues.,  22  (23): [PMID:23084905] [10.1016/j.bmcl.2012.09.053]

9. Unpublished dataset, 

10. 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]

11. Hou R, He Y, Yan G, Hou S, Xie Z, Liao C..  (2021)  Zinc enzymes in medicinal chemistry.,  226  [PMID:34624823] [10.1016/j.ejmech.2021.113877]

Source

Source(2):

• Scientific Literature
• Clinical Candidates