WF-3681
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01624 |
| CAS | 105364-56-5 |
| Molecular Weight | 248.23 |
| Molecular Formula | C13H12O5 |
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Description
WF-3681 is an aldose reductase inhibitor produced by Chaetomella raphigera Swift No. 3681.
Specification
| Synonyms | WF 3681 |
| IUPAC Name | 3-(4-hydroxy-5-oxo-3-phenyl-2H-furan-2-yl)propanoic acid |
| Canonical SMILES | C1=CC=C(C=C1)C2=C(C(=O)OC2CCC(=O)O)O |
| InChI | InChI=1S/C13H12O5/c14-10(15)7-6-9-11(12(16)13(17)18-9)8-4-2-1-3-5-8/h1-5,9,16H,6-7H2,(H,14,15) |
| InChI Key | PPZVSYXNLXFYAD-UHFFFAOYSA-N |
Properties
| Appearance | Crystal |
| Melting Point | 177-179°C |
Reference Reading
1. Structure of WF-3681, 3-(2,5-dihydro-4-hydroxy-5-oxo-3-phenyl-2-furyl)propionic acid
J I Clark, C R Kissinger, S Turley Acta Crystallogr C . 1988 Mar 15;44 ( Pt 3):512-4. doi: 10.1107/s010827018700845x.
C13H12O5, Mr = 248.24, monoclinic, C2/c, a = 18.757 (8), b = 7.282 (2), c = 17.511 (8) A, beta = 91.20 (3) degrees, V = 2391 (3) A3, Z = 8, Dx = 1.379 Mg m-3, lambda(Cu K alpha) = 1.54178 A, mu = 0.859 mm-1, F(000) = 1040, T = 293 K. Final R = 0.054 for 1409 unique observed reflections. The molecule contains two planar regions which differ in orientation by 5.7 degrees. Distances from the carbonyl carbons to the center of the phenyl ring are not in the range found in the crystal structures of other potent aldose reductase inhibitor molecules.
2. Studies on WF-3681, a novel aldose reductase inhibitor. I. Taxonomy, fermentation, isolation and characterization
M Nishikawa, M Okuhara, T Namiki, K Yoshida, Y Tsurumi J Antibiot (Tokyo) . 1987 Oct;40(10):1394-9. doi: 10.7164/antibiotics.40.1394.
WF-3681 was isolated from a cultured filtrate of Chaetomella raphigera as a novel inhibitor of aldose reductase. It was extracted with ethyl acetate and then purified with silica gel chromatography. Its molecular formula was determined to be C13H12O5 by elemental analysis and high resolution electron impact mass spectrometry. IC50 of WF-3681 was 2.5 X 10(-7) M for partially purified aldose reductase of rabbit lens.
3. Studies on WF-3681, a novel aldose reductase inhibitor. II. Structure determination and synthesis
M Hashimoto, I Uchida, T Namiki, M Nishikawa, Y Itoh J Antibiot (Tokyo) . 1987 Oct;40(10):1400-7. doi: 10.7164/antibiotics.40.1400.
The structure of WF-3681, a novel aldose reductase inhibitor produced by Chaetomella raphigera Swift No. 3681, was deduced to be 1 on the basis of its spectroscopic and chemical evidences and confirmed by a total synthesis starting from (E)-5-phenyl-4-pentenol.
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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 ╳
