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InChI=1S/C35H58O11/c1-4-5-11-16-31(42)34-33(44)22-29(40)20-27(38)18-25(36)17-26(37)19-28(39)21-32(43)23(2)14-12-9-7-6-8-10-13-15-30(41)24(3)46-35(34)45/h6-10,12-15,24-34,36-44H,4-5,11,16-22H2,1-3H3/b7-6+,10-8+,12-9+,15-13+,23-14+/t24-,25+,26-,27+,28-,29+,30+,31+,32+,33+,34-/m1/s1
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InChI=1/C35H58O11/c1-4-5-11-16-31(42)34-33(44)22-29(40)20-27(38)18-25(36)17-26(37)19-28(39)21-32(43)23(2)14-12-9-7-6-8-10-13-15-30(41)24(3)46-35(34)45/h6-10,12-15,24-34,36-44H,4-5,11,16-22H2,1-3H3/b7-6+,10-8+,12-9+,15-13+,23-14+/t24-,25+,26-,27+,28-,29+,30+,31+,32+,33+,34-/m1/s1
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Filipin IV is isomeric to filipin III. Their NMR spectra are nearly identical with the major difference being the splitting pattern of the proton at C2. This indicates that filipin IV is probably epimeric to filipin III at either C1' or
490:, it has found widespread use as a histochemical stain for cholesterol. This method of detecting cholesterol in cell membranes is used clinically in the study and diagnosis of Type C
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Filipin I, which has been difficult to characterize, is probably a mixture of several components each having two hydroxyl groups fewer than filipin III.
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It is also used in cellular biology as an inhibitor of the raft/caveolae endocytosis pathway on mammalian cells (at concentrations around 3 μg/mL)
450:, hence the name filipin. The isolate possessed potent antifungal activity. It was identified as a polyene macrolide based on its characteristic
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Filipin is a mixture of four components - filipin I (4%), II (25%), III (53%), and IV (18%) - and should be referred to as the filipin complex.
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The major component, filipin III, has the structure which was proposed by Ceder and Ryhage for the filipin complex.
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exhibit potent antifungal activity, most are too toxic for therapeutic applications, with the exceptions of
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108:)-4,6,8,10,12,14,16,27-Octahydroxy-3--17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
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Rychnovsky, S. D.; Richardson, T. I. (1995). "Relative and
Absolute Configuration of Filipin III".
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company in 1955 from the mycelium and culture filtrates of a previously unknown
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CCCCC(O)1C(=O)O(C)(O)\C=C\C=C\C=C\C=C\C=C(/C)(O)C(O)C(O)C(O)C(O)C(O)C1O
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478:. Unlike amphotericin B and nystatin A1 which form sterol-dependent
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is a mixture of chemical compounds first isolated by chemists at the
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Except where otherwise noted, data are given for materials in their
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data indicate that
Filipin II is 1'-deoxy-filipin III.
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Bergy, M. E.; Eble, T. E. (1968). "Filipin
Complex".
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695:at the U.S. National Library of Medicine
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299:Key: IMQSIXYSKPIGPD-NKYUYKLDSA-N
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309:Key: IMQSIXYSKPIGPD-NKYUYKLDBD
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534:of filipin III was determined by
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613:10.3891/acta.chem.scand.18-0558
391:(at 25 °C , 100 kPa).
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468:polyene macrolide antibiotics
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664:Angew. Chem. Int. Ed. Engl
596:"The Structure of Filipin"
536:13C NMR acetonide analysis
530:The relative and absolute
486:and binds specifically to
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443:Streptomyces filipinensis
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697:Medical Subject Headings
16:Not to be confused with
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492:Niemann-Pick disease
44:Preferred IUPAC name
641:10.1021/bi00842a021
573:10.1021/ja01623a032
381: g·mol
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555:Whitfield, G. B.;
448:Philippine Islands
418:Infobox references
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670:(11): 1227–1230.
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516:Mass spectrometry
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24:Filipin III
718:Antifungals
606:: 558–561.
488:cholesterol
484:fluorescent
476:nystatin A1
339:Properties
194:100.164.904
713:Macrolides
707:Categories
542:References
374:Molar mass
274:87Z59R7D14
167:ChemSpider
143:3D model (
122:CAS Number
581:101457395
462:Functions
458:spectra.
18:Filipinos
723:Polyenes
176:21106312
132:480-49-9
693:Filipin
649:4296188
430:Filipin
411:what is
409: (
379:654.838
254:6433194
241:PubChem
232:Filipin
699:(MeSH)
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452:UV-Vis
434:Upjohn
406:verify
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323:SMILES
215:D04186
38:Names
577:S2CID
501:Types
288:InChI
145:JSmol
645:PMID
518:and
474:and
454:and
265:UNII
226:MeSH
206:KEGG
672:doi
637:doi
608:doi
569:doi
526:C3.
520:NMR
244:CID
104:,28
100:,27
96:,25
92:,23
88:,21
84:,19
80:,17
76:,16
72:,14
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401:Y
364:O
358:H
352:C
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106:R
102:S
98:E
94:E
90:E
86:E
82:E
78:S
74:R
70:R
66:R
62:S
58:S
54:S
50:R
20:.
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