Isopropyl ((((1R,3S,5S)-1-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-oxabicyclo[3.1.0]hexan-3 yl)methoxy)(phenoxy)phosphoryl)-L-alaninate

ID: ALA4466009

PubChem CID: 155531856

Max Phase: Preclinical

Molecular Formula: C17H27N4O7P

Molecular Weight: 430.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COP(=O)(N[C@@H](C)C(=O)OC(C)C)OC[C@@H]1C[C@H]2C[C@@]2(n2ccc(N)nc2=O)O1

Standard InChI:  InChI=1S/C17H27N4O7P/c1-10(2)27-15(22)11(3)20-29(24,25-4)26-9-13-7-12-8-17(12,28-13)21-6-5-14(18)19-16(21)23/h5-6,10-13H,7-9H2,1-4H3,(H,20,24)(H2,18,19,23)/t11-,12-,13-,17+,29?/m0/s1

Standard InChI Key:  GMTMECRWKCZUTK-VOCIQWDOSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   16.9026   -3.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9163   -3.8479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6325   -4.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3351   -3.8241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3215   -3.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6051   -2.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6463   -5.0636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0254   -2.5856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4612   -3.7388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8396   -4.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1541   -5.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0431   -4.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8077   -3.2945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1636   -4.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9775   -4.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7586   -4.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4756   -5.6115    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0126   -3.1056    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.7787   -2.3226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4515   -3.6997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6564   -3.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2195   -3.8920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8068   -4.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9896   -4.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2114   -5.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7989   -6.0131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0286   -5.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4333   -6.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2504   -6.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0207   -6.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  3  7  2  0
  5  8  1  0
 14  9  1  0
  9 10  1  0
 10 11  1  0
 11 15  1  0
 14  2  1  1
 10 12  1  1
 12 13  1  0
 15 14  1  0
 16 15  1  0
 14 16  1  0
 15 17  1  1
 13 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4466009

   ---

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: 430.40

Molecular Weight (Monoisotopic): 430.1617

AlogP: 0.99

#Rotatable Bonds: 9

Polar Surface Area: 144.00

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.46

CX Basic pKa: ┄

CX LogP: -0.31

CX LogD: -0.31

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: 0.28

References

1. Rico L, Hanessian S..  (2019)  Synthesis of 1',2'-methano-2',3'-dideoxynucleosides as potential antivirals.,  29  (4): [PMID:30612845] [10.1016/j.bmcl.2018.12.054]

Source

Source(1):

• Scientific Literature