1-[2'-O-(N-Boc-12-aminododecanoyl)-beta-D-arabinofuranosyl]-5(E)-(2-bromovinyl)uracil

ID: ALA400232

Chembl Id: CHEMBL400232

PubChem CID: 44437476

Max Phase: Preclinical

Molecular Formula: C28H44BrN3O9

Molecular Weight: 646.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)NCCCCCCCCCCCC(=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/C28H44BrN3O9/c1-28(2,3)41-27(38)30-16-12-10-8-6-4-5-7-9-11-13-21(34)40-23-22(35)20(18-33)39-25(23)32-17-19(14-15-29)24(36)31-26(32)37/h14-15,17,20,22-23,25,33,35H,4-13,16,18H2,1-3H3,(H,30,38)(H,31,36,37)/b15-14+/t20-,22-,23+,25-/m1/s1

Standard InChI Key:  KDSMSKFGBACPTI-GGXOYMCQSA-N

Alternative Forms

1. Parent:

   

   ALA400232

   [(2R,3S,4R,5R)-2-[5-[(E)-2-bromoethenyl]-2,4-dioxopyrimidin-1-yl]-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] 12-[(2-methylpropan-2-yl)oxycarbonylamino]dodecanoate

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: 646.58

Molecular Weight (Monoisotopic): 645.2261

AlogP: 3.49

#Rotatable Bonds: 16

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: 3.69

CX LogD: 3.69

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.16

Np Likeness Score: 0.60

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