ID: ALA116018

Max Phase: Preclinical

Molecular Formula: C4H10NO8P

Molecular Weight: 231.10

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(NO)[C@H](O)[C@H](O)COP(=O)(O)O

Standard InChI:  InChI=1S/C4H10NO8P/c6-2(1-13-14(10,11)12)3(7)4(8)5-9/h2-3,6-7,9H,1H2,(H,5,8)(H2,10,11,12)/t2-,3-/m1/s1

Standard InChI Key:  JJQQOJRGUHNREK-PWNYCUMCSA-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: 231.10

Molecular Weight (Monoisotopic): 231.0144

AlogP: -2.68

#Rotatable Bonds: 5

Polar Surface Area: 156.55

Molecular Species: ACID

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.47

CX Basic pKa:

CX LogP: -3.08

CX LogD: -6.42

Aromatic Rings: 0

Heavy Atoms: 14

QED Weighted: 0.17

Np Likeness Score: 1.09

References

1. Dardonville C, Rinaldi E, Barrett MP, Brun R, Gilbert IH, Hanau S..  (2004)  Selective inhibition of Trypanosoma brucei 6-phosphogluconate dehydrogenase by high-energy intermediate and transition-state analogues.,  47  (13): [PMID:15189039] [10.1021/jm031066i]

2. Ruda GF, Campbell G, Alibu VP, Barrett MP, Brenk R, Gilbert IH..  (2010)  Virtual fragment screening for novel inhibitors of 6-phosphogluconate dehydrogenase.,  18  (14): [PMID:20598892] [10.1016/j.bmc.2010.05.077]

3. Yep A, Sorenson RJ, Wilson MR, Showalter HD, Larsen SD, Keller PR, Woodard RW..  (2011)  Enediol mimics as inhibitors of the D-arabinose 5-phosphate isomerase (KdsD) from Francisella tularensis.,  21  (9): [PMID:21236668] [10.1016/j.bmcl.2010.12.066]

4. Gabrielli L, Merlo S, Airoldi C, Sperandeo P, Gianera S, Polissi A, Nicotra F, Holler TP, Woodard RW, Cipolla L..  (2014)  Arabinose 5-phosphate isomerase as a target for antibacterial design: studies with substrate analogues and inhibitors.,  22  (8): [PMID:24680056] [10.1016/j.bmc.2013.08.012]

5. Gonzalez SN,Mills JJ,Maugeri D,Olaya C,Laguera BL,Enders JR,Sherman J,Rodriguez A,Pierce JG,Cazzulo JJ,D'Antonio EL.  (2021)  Design, synthesis, and evaluation of substrate - analogue inhibitors of Trypanosoma cruzi ribose 5-phosphate isomerase type B.,  32  [PMID:33249135] [10.1016/j.bmcl.2020.127723]

Source

Source(1):

• Scientific Literature