ID: ALA324609

Max Phase: Preclinical

Molecular Formula: C7H14NO8P

Molecular Weight: 271.16

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC1(C)O[C@H](COP(=O)(O)O)[C@H](C(=O)NO)O1

Standard InChI:  InChI=1S/C7H14NO8P/c1-7(2)15-4(3-14-17(11,12)13)5(16-7)6(9)8-10/h4-5,10H,3H2,1-2H3,(H,8,9)(H2,11,12,13)/t4-,5-/m1/s1

Standard InChI Key:  DVFAQEVWJBLFDS-RFZPGFLSSA-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: 271.16

Molecular Weight (Monoisotopic): 271.0457

AlogP: -0.88

#Rotatable Bonds: 4

Polar Surface Area: 134.55

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 1.20

CX Basic pKa:

CX LogP: -1.38

CX LogD: -4.96

Aromatic Rings: 0

Heavy Atoms: 17

QED Weighted: 0.29

Np Likeness Score: 1.18

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. Ruda GF, Wong PE, Alibu VP, Norval S, Read KD, Barrett MP, Gilbert IH..  (2010)  Aryl phosphoramidates of 5-phospho erythronohydroxamic acid, a new class of potent trypanocidal compounds.,  53  (16): [PMID:20666371] [10.1021/jm1004754]

4. 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]

Source

Source(1):

• Scientific Literature