Phosphoric acid mono-[5-(4-amino-5-methyl-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester

ID: ALA2311177

PubChem CID: 71720351

Max Phase: Preclinical

Molecular Formula: C10H16N3O8P

Molecular Weight: 337.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@@H]2O)c(=O)nc1N

Standard InChI:  InChI=1S/C10H16N3O8P/c1-4-2-13(10(16)12-8(4)11)9-7(15)6(14)5(21-9)3-20-22(17,18)19/h2,5-7,9,14-15H,3H2,1H3,(H2,11,12,16)(H2,17,18,19)/t5-,6-,7+,9-/m1/s1

Standard InChI Key:  NJQONZSFUKNYOY-JAGXHNFQSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    9.9061    2.4671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3045    1.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2418    3.6076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2418    2.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5452    2.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9035    0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2768    2.0034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5452    3.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9061    3.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2742    1.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6628    0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0811    1.3518    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.4805    1.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6528    2.4338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8789    1.1136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667    1.7653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9061    4.6395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3254   -0.0143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4795    0.7878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4946    2.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2366   -0.0226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1969    3.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  4  1  0
  4  1  1  0
  5  1  1  0
  6  2  1  0
  7  2  1  0
  8  5  2  0
  9  8  1  0
 10  7  1  0
 11  6  1  0
 12 15  1  0
 10 13  1  1
 14  4  2  0
 15 13  1  0
 16 12  2  0
 17  9  1  0
  6 18  1  1
 19 12  1  0
 20 12  1  0
 11 21  1  6
 22  8  1  0
  9  3  2  0
 10 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2311177

   1-(b-D-Arabinofuranosyl)cytosine 5'-monophosphate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 337.23

Molecular Weight (Monoisotopic): 337.0675

AlogP: -2.14

#Rotatable Bonds: 4

Polar Surface Area: 177.36

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.23

CX Basic pKa: ┄

CX LogP: -2.53

CX LogD: -6.06

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.38

Np Likeness Score: 1.29

References

1. Nakayama C, Wataya Y, Santi DV, Saneyoshi M, Ueda T..  (1981)  Interaction of 1-(5-phospho-beta-D-arabinofuranosyl)-5-substituted-uracils with thymidylate synthetase: mechanism-based inhibition by 1-(5-phospho-beta-D-arabinosyl)-5-fluorouracil.,  24  (10): [PMID:7328576] [10.1021/jm00142a008]

Source

Source(1):

• Scientific Literature