N-(1-((2R,4R,5R)-3,3-Difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)-3-mercaptopropanamide

ID: ALA4569800

PubChem CID: 155551879

Max Phase: Preclinical

Molecular Formula: C12H15F2N3O5S

Molecular Weight: 351.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCS)Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)C2(F)F)c(=O)n1

Standard InChI:  InChI=1S/C12H15F2N3O5S/c13-12(14)9(20)6(5-18)22-10(12)17-3-1-7(16-11(17)21)15-8(19)2-4-23/h1,3,6,9-10,18,20,23H,2,4-5H2,(H,15,16,19,21)/t6-,9-,10-/m1/s1

Standard InChI Key:  MODDLRRNEHNQAD-BDODKLCJSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    3.0171   -8.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248   -8.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4326   -8.8148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4326   -9.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248  -10.0414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0171   -9.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248  -10.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3857  -11.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1318  -12.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3178  -12.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0639  -11.3408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9064  -12.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0877  -12.8258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5433  -12.8258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1791  -11.5533    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9660  -10.7624    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.1441  -10.0412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248   -7.5845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4323   -7.1772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4323   -6.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248   -5.9511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248   -5.1324    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1438   -7.5845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  2  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  1  6  2  0
  7  5  1  1
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
 10 12  1  1
 12 13  1  0
  9 14  1  6
  8 15  1  0
  8 16  1  0
  4 17  2  0
  2 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 19 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4569800

   ---

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: 351.33

Molecular Weight (Monoisotopic): 351.0700

AlogP: -0.61

#Rotatable Bonds: 5

Polar Surface Area: 113.68

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.08

CX Basic pKa: ┄

CX LogP: -0.86

CX LogD: -0.86

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.53

Np Likeness Score: 0.19

References

1. Jiang Z, Pflug K, Usama SM, Kuai D, Yan X, Sitcheran R, Burgess K..  (2019)  Cyanine-Gemcitabine Conjugates as Targeted Theranostic Agents for Glioblastoma Tumor Cells.,  62  (20): [PMID:31469566] [10.1021/acs.jmedchem.9b01147]

Source

Source(1):

• Scientific Literature