1-(4-Amino-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

ID: ALA2021391

Chembl Id: CHEMBL2021391

Cas Number: 101062-04-8

PubChem CID: 122107

Max Phase: Preclinical

Molecular Formula: C9H13N3O4

Molecular Weight: 227.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H]1C[C@H](n2ccc(=O)[nH]c2=O)O[C@@H]1CO

Standard InChI:  InChI=1S/C9H13N3O4/c10-5-3-8(16-6(5)4-13)12-2-1-7(14)11-9(12)15/h1-2,5-6,8,13H,3-4,10H2,(H,11,14,15)/t5-,6+,8+/m0/s1

Standard InChI Key:  NDGYFDPAEFUDKS-SHYZEUOFSA-N

Alternative Forms

1. Parent:

   

   ALA2021391

   3'-Amino-2',3'-dideoxyuridine

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: 227.22

Molecular Weight (Monoisotopic): 227.0906

AlogP: -1.86

#Rotatable Bonds: 2

Polar Surface Area: 110.34

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.77

CX Basic pKa: 8.82

CX LogP: -1.94

CX LogD: -3.11

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.55

Np Likeness Score: 1.03

References

1. Lin TS, Gao YS, Mancini WR..  (1983)  Synthesis and biological activity of various 3'-azido and 3'-amino analogues of 5-substituted pyrimidine deoxyribonucleosides.,  26  (12): [PMID:6644738] [10.1021/jm00366a006]

2. Lin TS, Mancini WR..  (1983)  Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogues of pyrimidine deoxyribonucleoside.,  26  (4): [PMID:6834387] [10.1021/jm00358a016]

3. Chu CK, Schinazi RF, Ahn MK, Ullas GV, Gu ZP..  (1989)  Structure-activity relationships of pyrimidine nucleosides as antiviral agents for human immunodeficiency virus type 1 in peripheral blood mononuclear cells.,  32  (3): [PMID:2918508] [10.1021/jm00123a018]

4. Lin TS, Brubaker WF, Wang ZH, Park S, Prusoff WH..  (1986)  Antineoplastic activity of 3'-(chloroethyl)nitrosourea analogues of 2'-deoxyuridine and 2'-deoxy-5-fluorouridine.,  29  (5): [PMID:2939245] [10.1021/jm00155a044]

5. Krenitsky TA, Freeman GA, Shaver SR, Beacham LM, Hurlbert S, Cohn NK, Elwell LP, Selway JW..  (1983)  3'-Amino-2',3'-dideoxyribonucleosides of some pyrimidines: synthesis and biological activities.,  26  (6): [PMID:6854592] [10.1021/jm00360a019]

Source

Source(1):

• Scientific Literature