4-(hydroxy(methyl)amino)-4-oxobutylphosphonic acid

ID: ALA258981

Chembl Id: CHEMBL258981

PubChem CID: 9794471

Max Phase: Preclinical

Molecular Formula: C5H12NO5P

Molecular Weight: 197.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(O)C(=O)CCCP(=O)(O)O

Standard InChI:  InChI=1S/C5H12NO5P/c1-6(8)5(7)3-2-4-12(9,10)11/h8H,2-4H2,1H3,(H2,9,10,11)

Standard InChI Key:  OXDGJHZVDJQJCC-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA258981

   4-[Hydroxy(methyl)amino]-4-oxobutyl phosphonic acid

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: 197.13

Molecular Weight (Monoisotopic): 197.0453

AlogP: -0.21

#Rotatable Bonds: 4

Polar Surface Area: 98.07

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 1.81

CX Basic pKa:

CX LogP: -1.87

CX LogD: -4.26

Aromatic Rings: 0

Heavy Atoms: 12

QED Weighted: 0.33

Np Likeness Score: 0.01

References

1. Haemers T, Wiesner J, Giessmann D, Verbrugghen T, Hillaert U, Ortmann R, Jomaa H, Link A, Schlitzer M, Van Calenbergh S..  (2008)  Synthesis of beta- and gamma-oxa isosteres of fosmidomycin and FR900098 as antimalarial candidates.,  16  (6): [PMID:18158249] [10.1016/j.bmc.2007.12.001]

2. Ponaire S, Zinglé C, Tritsch D, Grosdemange-Billiard C, Rohmer M..  (2012)  Growth inhibition of Mycobacterium smegmatis by prodrugs of deoxyxylulose phosphate reducto-isomerase inhibitors, promising anti-mycobacterial agents.,  51  [PMID:22405649] [10.1016/j.ejmech.2012.02.031]

3. Zinglé C, Kuntz L, Tritsch D, Grosdemange-Billiard C, Rohmer M..  (2012)  Modifications around the hydroxamic acid chelating group of fosmidomycin, an inhibitor of the metalloenzyme 1-deoxyxylulose 5-phosphate reductoisomerase (DXR).,  22  (21): [PMID:23025997] [10.1016/j.bmcl.2012.09.021]

4. Nguyen-Trung AT, Tritsch D, Grosdemange-Billiard C, Rohmer M..  (2013)  Synthesis of tetrazole analogues of phosphonohydroxamic acids: an attempt to improve the inhibitory activity against the DXR.,  23  (6): [PMID:23414808] [10.1016/j.bmcl.2013.01.080]

5. Chofor R, Sooriyaarachchi S, Risseeuw MD, Bergfors T, Pouyez J, Johny C, Haymond A, Everaert A, Dowd CS, Maes L, Coenye T, Alex A, Couch RD, Jones TA, Wouters J, Mowbray SL, Van Calenbergh S..  (2015)  Synthesis and bioactivity of β-substituted fosmidomycin analogues targeting 1-deoxy-D-xylulose-5-phosphate reductoisomerase.,  58  (7): [PMID:25781377] [10.1021/jm5014264]

6. Munier M, Tritsch D, Krebs F, Esque J, Hemmerlin A, Rohmer M, Stote RH, Grosdemange-Billiard C..  (2017)  Synthesis and biological evaluation of phosphate isosters of fosmidomycin and analogs as inhibitors of Escherichia coli and Mycobacterium smegmatis 1-deoxyxylulose 5-phosphate reductoisomerases.,  25  (2): [PMID:27955925] [10.1016/j.bmc.2016.11.040]

7. Courtens C, Risseeuw M, Caljon G, Cos P, Van Calenbergh S..  (2018)  Acyloxybenzyl and Alkoxyalkyl Prodrugs of a Fosmidomycin Surrogate as Antimalarial and Antitubercular Agents.,  9  (10): [PMID:30344904] [10.1021/acsmedchemlett.8b00223]

8. Kesharwani S, Sundriyal S..  (2021)  Non-hydroxamate inhibitors of 1-deoxy-d-xylulose 5-phosphate reductoisomerase (DXR): A critical review and future perspective.,  213  [PMID:33303239] [10.1016/j.ejmech.2020.113055]

Source

Source(1):

• Scientific Literature