((2R,3S,5R)-5-(2,4-dioxo-5-(pyrrolidin-1-ylmethyl)-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate

ID: ALA3248470

Chembl Id: CHEMBL3248470

PubChem CID: 90655759

Max Phase: Preclinical

Molecular Formula: C14H22N3O8P

Molecular Weight: 391.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)cc1CN1CCCC1

Standard InChI:  InChI=1S/C14H22N3O8P/c18-10-5-12(25-11(10)8-24-26(21,22)23)17-7-9(13(19)15-14(17)20)6-16-3-1-2-4-16/h7,10-12,18H,1-6,8H2,(H,15,19,20)(H2,21,22,23)/t10-,11+,12+/m0/s1

Standard InChI Key:  QQUJSHBVJRSHAM-QJPTWQEYSA-N

Alternative Forms

1. Parent:

   

   ALA3248470

   [(2R,3S,5R)-5-[2,4-dioxo-5-(pyrrolidin-1-ylmethyl)pyrimidin-1-yl]-3-hydroxyoxolan-2-yl]methyl dihydrogen 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: 391.32

Molecular Weight (Monoisotopic): 391.1145

AlogP: -1.11

#Rotatable Bonds: 6

Polar Surface Area: 154.32

Molecular Species: ZWITTERION

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.23

CX Basic pKa: 8.67

CX LogP: -2.89

CX LogD: -4.05

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: 0.27

References

1. Edelman MS, Barfknecht RL, Huet-Rose R, Boguslawski S, Mertes MP..  (1977)  Thymidylate synthetase inhibitors. Synthesis of N-substituted 5-aminomethyl-2'-deoxyuridine 5'-phosphates.,  20  (5): [PMID:323484] [10.1021/jm00215a010]

Source

Source(1):

• Scientific Literature