4-Amino-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-iodo-1H-pyrimidin-2-one

ID: ALA2104340

Chembl Id: CHEMBL2104340

Max Phase: Phase

Molecular Formula: C9H12IN3O4

Molecular Weight: 353.12

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-527083

Canonical SMILES:  Nc1nc(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1I

Standard InChI:  InChI=1S/C9H12IN3O4/c10-4-2-13(9(16)12-8(4)11)7-1-5(15)6(3-14)17-7/h2,5-7,14-15H,1,3H2,(H2,11,12,16)/t5-,6+,7+/m0/s1

Standard InChI Key:  WEVJJMPVVFNAHZ-RRKCRQDMSA-N

Alternative Forms

1. Parent:

   

   ALA2104340

   IBACITABINE

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 353.12

Molecular Weight (Monoisotopic): 352.9873

AlogP: -0.93

#Rotatable Bonds: 2

Polar Surface Area: 110.60

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.89

CX Basic pKa: ┄

CX LogP: -0.91

CX LogD: -0.91

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.59

Np Likeness Score: 0.98

References

1. Hampton A, Chawla RR, Kappler F..  (1982)  Species- or isozyme-specific enzyme inhibitors. 5. Differential effects of thymidine substituents on affinity for rat thymidine kinase isozymes.,  25  (6): [PMID:7097717] [10.1021/jm00348a007]

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

3. Watanabe KA, Reichman U, Hirota K, Lopez C, Fox JJ..  (1979)  Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides.,  22  (1): [PMID:218006] [10.1021/jm00187a005]

4. Hampton A, Kappler F, Chawla RR..  (1979)  Design of species- or isozyme-specific enzyme inhibitors. 1. Effect of thymidine substituents on affinity for the thymidine site of hamster cytoplasmic thymidine kinase.,  22  (6): [PMID:458818] [10.1021/jm00192a005]

5. Lin TS, Prusoff WH..  (1978)  A novel synthesis and biological activity of several 5-halo-5'-amino analogues of deoxyribopyrimidine nucleosides.,  21  (1): [PMID:563459] [10.1021/jm00199a019]

6. Schinazi RF, Chen MS, Prusoff WH..  (1978)  Synthesis and biological activities of some uronic acids, uronates, uronamides, and urononitriles of pyrimidine nucleosides.,  21  (11): [PMID:214555] [10.1021/jm00209a010]

7. WHO Anatomical Therapeutic Chemical Classification, 

8. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

Source

Source(4):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification
• IMI-CARE SARS-CoV-2 Data