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

ID: ALA4450954

PubChem CID: 155521551

Max Phase: Preclinical

Molecular Formula: C17H26N3O8P

Molecular Weight: 431.38

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(=O)[nH]c2=O)O1

Standard InChI:  InChI=1S/C17H26N3O8P/c1-10(2)27-15(22)11(3)19-29(24,25-4)26-9-13-7-12-8-17(12,28-13)20-6-5-14(21)18-16(20)23/h5-6,10-13H,7-9H2,1-4H3,(H,19,24)(H,18,21,23)/t11-,12-,13-,17+,29?/m0/s1

Standard InChI Key:  QJBQGZOWAGMCEM-VOCIQWDOSA-N

Molfile:  

 
     RDKit          2D

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    6.9147  -14.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9284  -15.2267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6446  -15.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3472  -15.2029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3336  -14.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6172  -13.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6584  -16.4424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0375  -13.9644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4733  -15.1176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8518  -15.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662  -16.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0552  -15.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8198  -14.6733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1757  -15.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9896  -16.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7707  -16.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4877  -16.9903    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0247  -14.4844    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.7908  -13.7014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4636  -15.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6685  -14.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2316  -15.2707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189  -15.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0017  -15.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2235  -16.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8110  -17.3919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407  -16.6910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4454  -17.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2626  -17.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0328  -18.1064    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  1  0
  5  6  1  0
  3  7  2  0
  5  8  2  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:

   

   ALA4450954

   ---

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: 431.38

Molecular Weight (Monoisotopic): 431.1458

AlogP: 0.70

#Rotatable Bonds: 9

Polar Surface Area: 137.95

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.70

CX Basic pKa: ┄

CX LogP: 0.07

CX LogD: 0.07

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: 0.20

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