CID 5458474

Base Information

Chemical Name:CID 5458474
CAS No.:18791-21-4
Molecular Formula:C27H32N4O8
Molecular Weight:540.573
Hs Code.:
NSC Number:246134
Metabolomics Workbench ID:125847
ChEMBL ID:CHEMBL1966453
Mol file:18791-21-4.mol

Synonyms:pyridomycin

Suppliers and Price of CID 5458474

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
Pyridomycin
1000μg
$ 395.00

TRC
Pyridomycin
500μg
$ 245.00

Cayman Chemical
Pyridomycin ≥95%
2.5mg
$ 972.00

Cayman Chemical
Pyridomycin ≥95%
500μg
$ 299.00

Adipogen Life Sciences
Pyridomycin ≥98%(1H-NMR,HPLC)
1 mg
$ 290.00

Total 19 raw suppliers

Chemical Property of CID 5458474

Chemical Property:

Vapor Pressure:0mmHg at 25°C
Melting Point:222°
Refractive Index:1.6000 (estimate)
Boiling Point:951.1°Cat760mmHg
Flash Point:529°C
PSA：177.04000
Density:1.35g/cm³
LogP:1.89730
XLogP3:2.8
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:5
Exact Mass:540.22201399
Heavy Atom Count:39
Complexity:941

Purity/Quality:

99% ^*data from raw suppliers

Pyridomycin ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CCC(=C1C(=O)OC(C(C(=O)NC(C(C(C(=O)O1)C)O)CC2=CN=CC=C2)NC(=O)C3=C(C=CC=N3)O)C)C
Isomeric SMILES:CC/C(=C\1/C(=O)OC(C(C(=O)NC(C(C(C(=O)O1)C)O)CC2=CN=CC=C2)NC(=O)C3=C(C=CC=N3)O)C)/C
Description Pyridomycin is a structurally unusual antimycobacterial cyclodepsipeptide whose composition includes two rare moieties: 3-(3-pyridyl)-L-alanine and 2-hydroxy-3-methylpent-2-enoic acid. It inhibits NADH-dependent enoyl (Acyl-Carrier-Protein) reductase InhA, preventing mycolic acid synthesis in M. tuberculosis, including isoniazid-resistant strains (MICs = 0.31-0.63 μg/ml).
Uses Pyridomycin is a potent antibiotic active against mycobacteria and some Gram negative bacteria, originally isolated from Streptomyces abidoflavus by Umezawa group at the NIH Japan in 1953, and since isolated from different species and published under several names. The unusual 12-membered macrocyclic depsipeptide comprises three unique sub-units incorporating two substituted pyridines. Pyridomycin is thought to target NADH-dependent enoyl (acyl-carrier-protein) reductase InhA. Recent reports of activity against isoniazid-resistant mycobacteria has seen pyridomycin identified as a potential lead for new generation antibiotics. Pyridomycin is a potent antibiotic active against mycobacteria.

Technology Process of CID 5458474

There total 18 articles about CID 5458474 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

: 128829-10-7
3-Benzyloxy-pyridine-2-carboxylic acid {(5R,6S,9S,10S,11R)-10-hydroxy-5,11-dimethyl-2-[1-methyl-prop-(Z)-ylidene]-3,7,12-trioxo-9-pyridin-3-ylmethyl-1,4-dioxa-8-aza-cyclododec-6-yl}-amide

: 18791-21-4
pyridomicin

Guidance literature:: With hydrogen; palladium; In methanol;
DOI:10.1016/S0040-4039(00)70713-1

Reference yield:

: ((S)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol

: 18791-21-4
pyridomicin

Guidance literature:: Multi-step reaction with 15 steps

1: NaIO₄, RuCl₃ / CCl₄; acetonitrile; H₂O / 1 h / Ambient temperature

2: 83 percent / DCC,DMAP / ethyl acetate / 2 h / Ambient temperature

3: aq. TFA / 1 h / Ambient temperature

4: ethyl acetate; petroleum ether / 2.5 h / Ambient temperature

5: DCC, DMAP / ethyl acetate / 2.5 h / Ambient temperature

6: 1.) aq. HCl 2.) aq. TFA / 1 ) dioxane, 35 deg C, 12 h 2 ) rt., 20 min.

7: H₂ / Raney-Ni W-4 / methanol / 0.67 h / 35 °C

8: DCC, HOBt / dimethylformamide / 68 h / 2 °C

9: 95 percent / SOCl₂ / pyridine / 1 h / -30 °C

10: 84 percent / O₃/O₂ / CH₂Cl₂ / 0 h / -78 °C

11: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h

12: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C

13: H₂ / Pd-black / methanol / 0.5 h / Ambient temperature

15: 95 percent / H₂ / Pd-black / methanol

With hydrogenchloride; dmap; ruthenium trichloride; sodium periodate; thionyl chloride; hydrogen; oxygen; sodium hydride; benzotriazol-1-ol; ozone; dicyclohexyl-carbodiimide; trifluoroacetic acid; Raney-Ni W-4; palladium; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; Petroleum ether;
DOI:10.1016/S0040-4039(00)70713-1

Reference yield:

: 128829-04-9
(R)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid

: 18791-21-4
pyridomicin

Guidance literature:: Multi-step reaction with 14 steps

1: 83 percent / DCC,DMAP / ethyl acetate / 2 h / Ambient temperature

2: aq. TFA / 1 h / Ambient temperature

3: ethyl acetate; petroleum ether / 2.5 h / Ambient temperature

4: DCC, DMAP / ethyl acetate / 2.5 h / Ambient temperature

5: 1.) aq. HCl 2.) aq. TFA / 1 ) dioxane, 35 deg C, 12 h 2 ) rt., 20 min.

6: H₂ / Raney-Ni W-4 / methanol / 0.67 h / 35 °C

7: DCC, HOBt / dimethylformamide / 68 h / 2 °C

8: 95 percent / SOCl₂ / pyridine / 1 h / -30 °C

9: 84 percent / O₃/O₂ / CH₂Cl₂ / 0 h / -78 °C

10: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h

11: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C

12: H₂ / Pd-black / methanol / 0.5 h / Ambient temperature

14: 95 percent / H₂ / Pd-black / methanol

With hydrogenchloride; dmap; thionyl chloride; hydrogen; oxygen; sodium hydride; benzotriazol-1-ol; ozone; dicyclohexyl-carbodiimide; trifluoroacetic acid; Raney-Ni W-4; palladium; In tetrahydrofuran; pyridine; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; Petroleum ether;
DOI:10.1016/S0040-4039(00)70713-1