ID: ALA538118

Max Phase: Preclinical

Molecular Formula: C8H13N4O9P

Molecular Weight: 340.19

Molecule Type: Small molecule

Representations

Synonyms (1): 5-Aminoimidazole Ribonucleotide Carboxylase
Synonyms from Alternative Forms(1):

Canonical SMILES:  Nc1c([N+](=O)[O-])ncn1[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C8H13N4O9P/c9-6-7(12(15)16)10-2-11(6)8-5(14)4(13)3(21-8)1-20-22(17,18)19/h2-5,8,13-14H,1,9H2,(H2,17,18,19)/t3-,4-,5-,8-/m1/s1

Standard InChI Key:  YVRCVGZPIYHJLU-AFCXAGJDSA-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: 340.19

Molecular Weight (Monoisotopic): 340.0420

AlogP: -1.90

#Rotatable Bonds: 5

Polar Surface Area: 203.43

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.21

CX Basic pKa: 2.79

CX LogP: -2.84

CX LogD: -4.91

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.23

Np Likeness Score: 0.73

References

1. Firestine SM, Davisson VJ..  (1993)  A tight binding inhibitor of 5-aminoimidazole ribonucleotide carboxylase.,  36  (22): [PMID:8230140] [10.1021/jm00074a033]

2. Firestine SM, Wu W, Youn H, Davisson VJ..  (2009)  Interrogating the mechanism of a tight binding inhibitor of AIR carboxylase.,  17  (2): [PMID:19095456] [10.1016/j.bmc.2008.11.057]

3. Kim A, Wolf NM, Zhu T, Johnson ME, Deng J, Cook JL, Fung LW..  (2015)  Identification of Bacillus anthracis PurE inhibitors with antimicrobial activity.,  23  (7): [PMID:25737087] [10.1016/j.bmc.2015.02.016]

4. Lei H, Jones C, Zhu T, Patel K, Wolf NM, Fung LW, Lee H, Johnson ME..  (2016)  Identification of B. anthracis N(5)-carboxyaminoimidazole ribonucleotide mutase (PurE) active site binding compounds via fragment library screening.,  24  (4): [PMID:26740153] [10.1016/j.bmc.2015.12.029]

Source

Source(1):

• Scientific Literature