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

ID: ALA221982

Chembl Id: CHEMBL221982

Cas Number: 27826-74-0

PubChem CID: 160155

Max Phase: Preclinical

Molecular Formula: C12H18N2O5

Molecular Weight: 270.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C12H18N2O5/c1-2-3-7-5-14(12(18)13-11(7)17)10-4-8(16)9(6-15)19-10/h5,8-10,15-16H,2-4,6H2,1H3,(H,13,17,18)/t8-,9+,10+/m0/s1

Standard InChI Key:  MBERTAKFBYOAHR-IVZWLZJFSA-N

Alternative Forms

1. Parent:

   

   ALA221982

   5-Propyl-2'-deoxyuridine

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: 270.29

Molecular Weight (Monoisotopic): 270.1216

AlogP: -0.87

#Rotatable Bonds: 4

Polar Surface Area: 104.55

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.95

CX Basic pKa: ┄

CX LogP: -0.23

CX LogD: -0.23

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.66

Np Likeness Score: 0.81

References

1. Bères J, Bentrude WG, Balzarini J, De Clercq E, Otvös L..  (1986)  Synthesis and antitumor and antiviral properties of 5-alkyl-2'-deoxyuridines, 3',5'-cyclic monophosphates, and neutral cyclic triesters.,  29  (4): [PMID:3959027] [10.1021/jm00154a012]

2. Helguera AM, Rodríguez-Borges JE, García-Mera X, Fernández F, Cordeiro MN..  (2007)  Probing the anticancer activity of nucleoside analogues: a QSAR model approach using an internally consistent training set.,  50  (7): [PMID:17341060] [10.1021/jm061445m]

3. Focher F, Lossani A, Verri A, Spadari S, Maioli A, Gambino JJ, Wright GE, Eberle R, Black DH, Medveczky P, Medveczky M, Shugar D..  (2007)  Sensitivity of monkey B virus (Cercopithecine herpesvirus 1) to antiviral drugs: role of thymidine kinase in antiviral activities of substrate analogs and acyclonucleosides.,  51  (6): [PMID:17438061] [10.1128/aac.01284-06]

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]

Source

Source(1):

• Scientific Literature