5-[bis(3-methyl-5-oxo-1-phenyl-4,5-dihydro-4H-pyrazol-4-yl)methyl]-1-(2-deoxypentofuranosyl)pyrimidine-2,4(1H,3H)-dione

ID: ALA382253

PubChem CID: 15954514

Max Phase: Preclinical

Molecular Formula: C30H30N6O7

Molecular Weight: 586.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=NN(c2ccccc2)C(=O)C1C(c1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O)C1C(=O)N(c2ccccc2)N=C1C

Standard InChI:  InChI=1S/C30H30N6O7/c1-16-24(28(40)35(32-16)18-9-5-3-6-10-18)26(25-17(2)33-36(29(25)41)19-11-7-4-8-12-19)20-14-34(30(42)31-27(20)39)23-13-21(38)22(15-37)43-23/h3-12,14,21-26,37-38H,13,15H2,1-2H3,(H,31,39,42)/t21-,22+,23+,24?,25?,26?/m0/s1

Standard InChI Key:  ZRNMENLOYXEZTM-XWESOOCRSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA382253

   5-[bis(3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-yl)methyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

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: 586.61

Molecular Weight (Monoisotopic): 586.2176

AlogP: 1.34

#Rotatable Bonds: 7

Polar Surface Area: 169.89

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.64

CX Basic pKa: ┄

CX LogP: 1.05

CX LogD: 1.04

Aromatic Rings: 3

Heavy Atoms: 43

QED Weighted: 0.38

Np Likeness Score: 0.01

References

1. Fan X, Zhang X, Zhou L, Keith KA, Kern ER, Torrence PF..  (2006)  A pyrimidine-pyrazolone nucleoside chimera with potent in vitro anti-orthopoxvirus activity.,  16  (12): [PMID:16603351] [10.1016/j.bmcl.2006.03.043]

2. Prichard MN, Keith KA, Johnson MP, Harden EA, McBrayer A, Luo M, Qiu S, Chattopadhyay D, Fan X, Torrence PF, Kern ER..  (2007)  Selective phosphorylation of antiviral drugs by vaccinia virus thymidine kinase.,  51  (5): [PMID:17325220] [10.1128/aac.01447-06]

Source

Source(1):

• Scientific Literature