(2R,3S,5R)-5-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol

ID: ALA4540304

Cas Number: 166247-63-8

PubChem CID: 15289165

Product Number: D649745, Order Now?

Max Phase: Preclinical

Molecular Formula: C11H13IN4O3

Molecular Weight: 376.15

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(I)cn2[C@H]1C[C@H](O)[C@@H](CO)O1

Standard InChI:  InChI=1S/C11H13IN4O3/c12-5-2-16(8-1-6(18)7(3-17)19-8)11-9(5)10(13)14-4-15-11/h2,4,6-8,17-18H,1,3H2,(H2,13,14,15)/t6-,7+,8+/m0/s1

Standard InChI Key:  LIIIRHQRQZIIRT-XLPZGREQSA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   36.7808   -3.0298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.5148   -3.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5522   -2.7799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5622   -1.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7841   -1.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9936   -4.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2971   -2.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7409   -4.0569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5132   -5.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7376   -4.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2667   -1.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2501   -3.1900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.9646   -1.9779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.9613   -2.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2701   -0.7531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.7647   -5.9115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0739   -5.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1960   -6.1555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5359   -0.9379    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  1  1  0
  4  3  2  0
  5  7  2  0
  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  6  1  0
 10  8  1  0
 11  4  1  0
 12  3  1  0
 13 14  1  0
 14 12  2  0
 15 11  1  0
  9 16  1  6
 10 17  1  1
 18 17  1  0
  4  5  1  0
  9 10  1  0
 13 11  2  0
  5 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4540304

   7-Deaza-2'-deoxy-7-iodoadenosine

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: 376.15

Molecular Weight (Monoisotopic): 376.0032

AlogP: 0.26

#Rotatable Bonds: 2

Polar Surface Area: 106.42

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.89

CX Basic pKa: 5.81

CX LogP: 0.55

CX LogD: 0.54

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.65

Np Likeness Score: 0.74

References

1. Spurr SS, Bayle ED, Yu W, Li F, Tempel W, Vedadi M, Schapira M, Fish PV..  (2016)  New small molecule inhibitors of histone methyl transferase DOT1L with a nitrile as a non-traditional replacement for heavy halogen atoms.,  26  (18): [PMID:27485386] [10.1016/j.bmcl.2016.07.041]

Source

Source(1):

• Scientific Literature