Fosmidomycin sodium

ID: ALA2164257

Chembl Id: CHEMBL2164257

Cas Number: 66508-37-0

PubChem CID: 5141362

Product Number: F302004

Max Phase: Preclinical

Molecular Formula: C4H9NNaO5P

Molecular Weight: 183.10

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Fosmidomycin Sodium | Fosmidomycin Sodium Salt|Fosmidomycin Sodium|66508-37-0|(3-(Formylhydroxyamino)propyl)phosphonic acid monosodium salt|IYI1EW66CX|Phosphonic acid, (3-(formylhydroxyamino)propyl)-, monosodium salt|66508-37-0 (sodium)|FR 31564|FR-31564|Antibiotic FR 31564|UNII-IYI1EW66CX|SCHEMBL4432387|CHEMBL2164257|DTXSID10216711|FOSMIDOMYCIN SODIUM [JAN]|CHEBI:201600|FOSMIDOMYCIN MONOSODIUM SALT|AKOS030254266|FOSMIDOMYCIN MONOSODIUM SALT [MI]|HY-112853|CS-0067087|FT-0613838|Q27280957|sodium;Show More⌵

Canonical SMILES:  O=CN(O)CCCP(=O)([O-])O.[Na+]

Standard InChI:  InChI=1S/C4H10NO5P.Na/c6-4-5(7)2-1-3-11(8,9)10;/h4,7H,1-3H2,(H2,8,9,10);/q;+1/p-1

Standard InChI Key:  ZZPUYRHMTGOTEU-UHFFFAOYSA-M

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: 183.10

Molecular Weight (Monoisotopic): 183.0297

AlogP: -0.60

#Rotatable Bonds: 5

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: -2.21

CX LogD: -4.60

Aromatic Rings: 0

Heavy Atoms: 11

QED Weighted: 0.23

Np Likeness Score: 0.55

References

1. Brücher K, Illarionov B, Held J, Tschan S, Kunfermann A, Pein MK, Bacher A, Gräwert T, Maes L, Mordmüller B, Fischer M, Kurz T..  (2012)  α-Substituted β-oxa isosteres of fosmidomycin: synthesis and biological evaluation.,  55  (14): [PMID:22731758] [10.1021/jm300652f]

2. Konzuch S, Umeda T, Held J, Hähn S, Brücher K, Lienau C, Behrendt CT, Gräwert T, Bacher A, Illarionov B, Fischer M, Mordmüller B, Tanaka N, Kurz T..  (2014)  Binding modes of reverse fosmidomycin analogs toward the antimalarial target IspC.,  57  (21): [PMID:25254502] [10.1021/jm500850y]

3. Wang X, Edwards RL, Ball H, Johnson C, Haymond A, Girma M, Manikkam M, Brothers RC, McKay KT, Arnett SD, Osbourn DM, Alvarez S, Boshoff HI, Meyers MJ, Couch RD, Odom John AR, Dowd CS..  (2018)  MEPicides: α,β-Unsaturated Fosmidomycin Analogues as DXR Inhibitors against Malaria.,  61  (19): [PMID:30192536] [10.1021/acs.jmedchem.8b01026]

4. 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]

5. Courtens C, Risseeuw M, Caljon G, Cos P, Martin A, Van Calenbergh S..  (2019)  Phosphonodiamidate prodrugs of N-alkoxy analogs of a fosmidomycin surrogate as antimalarial and antitubercular agents.,  29  (9): [PMID:30857749] [10.1016/j.bmcl.2019.03.008]

6. Courtens C, Risseeuw M, Caljon G, Maes L, Cos P, Martin A, Van Calenbergh S..  (2019)  Double prodrugs of a fosmidomycin surrogate as antimalarial and antitubercular agents.,  29  (10): [PMID:30879839] [10.1016/j.bmcl.2019.03.009]

7. Lienau C, Gräwert T, Alves Avelar LA, Illarionov B, Held J, Knaab TC, Lungerich B, van Geelen L, Meier D, Geissler S, Cynis H, Riederer U, Buchholz M, Kalscheuer R, Bacher A, Mordmüller B, Fischer M, Kurz T..  (2019)  Novel reverse thia-analogs of fosmidomycin: Synthesis and antiplasmodial activity.,  181  [PMID:31382119] [10.1016/j.ejmech.2019.07.058]

8. Indorf P, Kubitza C, Scheidig AJ, Kunze T, Clement B..  (2020)  Drug Metabolism by the Mitochondrial Amidoxime Reducing Component (mARC): Rapid Assay and Identification of New Substrates.,  63  (12): [PMID:31790578] [10.1021/acs.jmedchem.9b01483]

9. 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