WF-3161
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| Category | Antibiotics |
| Catalog number | BBF-01622 |
| CAS | 86402-37-1 |
| Molecular Weight | 568.7 |
| Molecular Formula | C31H44N4O6 |
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Description
WF-3161 is an antitumor antibiotic produced by a strain of fungus, Petriella guttulata. It inhibited the growth of Trichophyton asteroides.
Specification
| Synonyms | Antibiotic WF 3161; WF 3161; Antibiotic FR 900261; WF-3161 |
| IUPAC Name | (3S,6R,9S,12S)-6-benzyl-3-(2-methylpropyl)-9-[6-(oxiran-2-yl)-6-oxohexyl]-1,4,7,10-tetrazabicyclo[10.4.0]hexadecane-2,5,8,11-tetrone |
| Canonical SMILES | CC(C)CC1C(=O)N2CCCCC2C(=O)NC(C(=O)NC(C(=O)N1)CC3=CC=CC=C3)CCCCCC(=O)C4CO4 |
| InChI | InChI=1S/C31H44N4O6/c1-20(2)17-24-31(40)35-16-10-9-14-25(35)30(39)32-22(13-7-4-8-15-26(36)27-19-41-27)28(37)33-23(29(38)34-24)18-21-11-5-3-6-12-21/h3,5-6,11-12,20,22-25,27H,4,7-10,13-19H2,1-2H3,(H,32,39)(H,33,37)(H,34,38)/t22-,23+,24-,25-,27?/m0/s1 |
| InChI Key | DYQZJCUKWTVTLH-HTUOISEFSA-N |
Properties
| Appearance | Crystal |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 181-183°C |
Reference Reading
1. Structure and solution conformation of the cytostatic cyclic tetrapeptide WF-3161, cyclo[L-leucyl-L-pipecolyl-L-(2-amino-8-oxo-9, 10-epoxydecanoyl)-D-phenylalanyl]
M Kawai, R S Pottorf, D H Rich J Med Chem. 1986 Nov;29(11):2409-11. doi: 10.1021/jm00161a046.
The sequence and configuration of amino acids in the cytostatic cyclic tetrapeptide WF-3161 are established as cyclo(L-Leu-L-Pip-L-Aoe-D-Phe) where Pip = pipecolic acid and Aoe = 2-amino-8-oxo-9,10-epoxydecanoic acid. In chloroform, WF-3161 adopts a conformation with a possible gamma-turn between Leu NH and Aoe C = O and a cis amide bond between Leu and Pip. The torsion angles for this conformation are L-Aoe, phi, -95 degrees, psi, +85 degrees, omega, -155 degrees; D-Phe, phi, +120 degrees, psi, -80 degrees, omega, -175 degrees; L-Leu, phi, -145 degrees, psi, +35 degrees, omega, -10 degrees; L-Pip, phi, +20 degrees, psi, -135 degrees, omega, -170 degrees. The cis,trans,trans,trans amide bond sequence is related to the dimethyl sulfoxide conformation of chlamydocin, another cytostatic cyclic tetrapeptide.
2. Studies on WF-3161, a new antitumor antibiotic
K Umehara, K Nakahara, S Kiyoto, M Iwami, M Okamoto, H Tanaka, M Kohsaka, H Aoki, H Imanaka J Antibiot (Tokyo). 1983 May;36(5):478-83. doi: 10.7164/antibiotics.36.478.
WF-3161 is an antitumor antibiotic produced by a strain of fungus, Petriella guttulata. The antibiotic was purified by solvent extraction and a combination of silica gel and reverse phase column chromatography. The chemical structure of the antibiotic (C31H44N4O6, mp 181-183 degrees C) was found to be a cyclic tetrapeptide consisting of phenylalanine, leucine, pipecolinic acid and 2-amino-8-oxo-9,10-epoxydecanoic acid. WF-3161 inhibited the growth of Trichophyton asteroides. It prolonged survival period of mice bearing leukemia P-388 with a high therapeutic index.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
