ID: ALA375035

Max Phase: Preclinical

Molecular Formula: C11H13BrN2O6

Molecular Weight: 349.14

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=c1[nH]c(=O)n([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)cc1/C=C/Br

Standard InChI:  InChI=1S/C11H13BrN2O6/c12-2-1-5-3-14(11(19)13-9(5)18)10-8(17)7(16)6(4-15)20-10/h1-3,6-8,10,15-17H,4H2,(H,13,18,19)/b2-1+/t6-,7-,8-,10-/m1/s1

Standard InChI Key:  GCQYYIHYQMVWLT-YPLKXGEDSA-N

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

Properties

Molecular Weight: 349.14

Molecular Weight (Monoisotopic): 347.9957

AlogP: -1.49

#Rotatable Bonds: 3

Polar Surface Area: 124.78

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.74

CX Basic pKa:

CX LogP: -1.40

CX LogD: -1.40

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.53

Np Likeness Score: 1.30

References

1. De Clercq E, Desgranges C, Herdewijn P, Sim IS, Jones AS, McLean MJ, Walker RT..  (1986)  Synthesis and antiviral activity of (E)-5-(2-bromovinyl)uracil and (E)-5-(2-bromovinyl)uridine.,  29  (2): [PMID:3005566] [10.1021/jm00152a008]

2. Onishi T, Mukai C, Nakagawa R, Sekiyama T, Aoki M, Suzuki K, Nakazawa H, Ono N, Ohmura Y, Iwayama S, Okunishi M, Tsuji T..  (2000)  Synthesis and antiviral activity of novel anti-VZV 5-substituted uracil nucleosides with a cyclopropane sugar moiety.,  43  (2): [PMID:10649983] [10.1021/jm9904194]

3. Reefschläger J, Pein CD, Cech D..  (1988)  Synthesis and biological activities of 4-O-(difluoromethyl)-5-substituted-uracil nucleoside analogues.,  31  (2): [PMID:2828623] [10.1021/jm00397a022]

4. Kitano K, Machida H, Miura S, Ohrui H..  (1999)  Synthesis of novel 4'-C-methyl-pyrimidine nucleosides and their biological activities.,  9  (6): [PMID:10206544] [10.1016/s0960-894x(99)00090-6]

Source

Source(1):

• Scientific Literature