1-[2'-O-(N-boc-4-aminobutanoyl)-beta-D-arabinofuranosyl]-5(E)-(2-bromovinyl)uracil

ID: ALA398594

Chembl Id: CHEMBL398594

PubChem CID: 44437473

Max Phase: Preclinical

Molecular Formula: C20H28BrN3O9

Molecular Weight: 534.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)NCCCC(=O)O[C@H]1[C@H](O)[C@@H](CO)O[C@H]1n1cc(/C=C/Br)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C20H28BrN3O9/c1-20(2,3)33-19(30)22-8-4-5-13(26)32-15-14(27)12(10-25)31-17(15)24-9-11(6-7-21)16(28)23-18(24)29/h6-7,9,12,14-15,17,25,27H,4-5,8,10H2,1-3H3,(H,22,30)(H,23,28,29)/b7-6+/t12-,14-,15+,17-/m1/s1

Standard InChI Key:  MQFTYOSSTNGEII-LKFLUANLSA-N

Alternative Forms

1. Parent:

   

   ALA398594

   [(2R,3S,4R,5R)-2-[5-[(E)-2-bromoethenyl]-2,4-dioxopyrimidin-1-yl]-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] 4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate

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: 534.36

Molecular Weight (Monoisotopic): 533.1009

AlogP: 0.37

#Rotatable Bonds: 8

Polar Surface Area: 169.18

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.74

CX Basic pKa: ┄

CX LogP: 0.14

CX LogD: 0.14

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.27

Np Likeness Score: 0.66

References

1. Ciliberti N, Manfredini S, Angusti A, Durini E, Solaroli N, Vertuani S, Buzzoni L, Bonache MC, Ben-Shalom E, Karlsson A, Saada A, Balzarini J..  (2007)  Novel selective human mitochondrial kinase inhibitors: design, synthesis and enzymatic activity.,  15  (8): [PMID:17324575] [10.1016/j.bmc.2007.01.049]

Source

Source(1):

• Scientific Literature