Phosphoric acid 3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester bis-(4-nitro-phenyl) ester

ID: ALA3144400

Chembl Id: CHEMBL3144400

PubChem CID: 90663931

Max Phase: Preclinical

Molecular Formula: C22H21N4O12P

Molecular Weight: 564.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(Oc3ccc([N+](=O)[O-])cc3)Oc3ccc([N+](=O)[O-])cc3)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C22H21N4O12P/c1-13-11-24(22(29)23-21(13)28)20-10-18(27)19(36-20)12-35-39(34,37-16-6-2-14(3-7-16)25(30)31)38-17-8-4-15(5-9-17)26(32)33/h2-9,11,18-20,27H,10,12H2,1H3,(H,23,28,29)/t18-,19+,20+/m0/s1

Standard InChI Key:  DSBOULKJHBPVBZ-XUVXKRRUSA-N

Alternative Forms

1. Parent:

   

   ALA3144400

   [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl bis(4-nitrophenyl) phosphate

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: 564.40

Molecular Weight (Monoisotopic): 564.0894

AlogP: 2.59

#Rotatable Bonds: 10

Polar Surface Area: 215.36

Molecular Species: NEUTRAL

HBA: 13

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.96

CX Basic pKa: ┄

CX LogP: 2.71

CX LogD: 2.71

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.21

Np Likeness Score: 0.16

References

1. Chawla RR, Freed JJ, Hampton A..  (1984)  Bis(m-nitrophenyl) and bis(p-nitrophenyl) esters and the phosphorodiamidate of thymidine 5'-phosphate as potential sources of intracellular thymidine 5'-phosphate in mouse cells in culture.,  27  (12): [PMID:6502604] [10.1021/jm00378a036]

Source

Source(1):

• Scientific Literature