5-(4-bromophenyl)-6-((3S,4S)-3,4,5-trihydroxypentyl)pyrimidine-2,4-diamine

ID: ALA388840

Chembl Id: CHEMBL388840

PubChem CID: 44423943

Max Phase: Preclinical

Molecular Formula: C15H19BrN4O3

Molecular Weight: 383.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c(-c2ccc(Br)cc2)c(CC[C@H](O)[C@@H](O)CO)n1

Standard InChI:  InChI=1S/C15H19BrN4O3/c16-9-3-1-8(2-4-9)13-10(19-15(18)20-14(13)17)5-6-11(22)12(23)7-21/h1-4,11-12,21-23H,5-7H2,(H4,17,18,19,20)/t11-,12-/m0/s1

Standard InChI Key:  IUAGAKHMGONNCS-RYUDHWBXSA-N

Alternative Forms

1. Parent:

   

   ALA388840

   (2S,3S)-5-[2,6-diamino-5-(4-bromophenyl)pyrimidin-4-yl]pentane-1,2,3-triol

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: 383.25

Molecular Weight (Monoisotopic): 382.0641

AlogP: 0.72

#Rotatable Bonds: 6

Polar Surface Area: 138.51

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.34

CX Basic pKa: 7.70

CX LogP: 0.66

CX LogD: 0.19

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.50

Np Likeness Score: 0.39

References

1. El-Hamamsy MH, Smith AW, Thompson AS, Threadgill MD..  (2007)  Structure-based design, synthesis and preliminary evaluation of selective inhibitors of dihydrofolate reductase from Mycobacterium tuberculosis.,  15  (13): [PMID:17451962] [10.1016/j.bmc.2007.04.011]

Source

Source(1):

• Scientific Literature