33:
270:
24:
137:
293:
InChI=1S/C17H22ClN9O2/c18-10-6(4-19)7-5-27-11(28)8-2-1-3-26(8)12-17(27,25-14(20)22-12)9(7)16(10)13(29)23-15(21)24-16/h1-3,6-7,9-10,12-13,29H,4-5,19H2,(H3,20,22,25)(H3,21,23,24)/t6-,7-,9+,10+,12+,13+,16+,17-/m1/s1
571:
Kinnel, Robin B.; Gehrken, Henning Peter; Scheuer, Paul J. (1993). "Palau'amine: a cytotoxic and immunosuppressive hexacyclic bisguanidine antibiotic from the sponge
Stylotella agminata".
534:
Rohde S, Gochfeld DJ, Ankisetty S, Avula B, Schupp PJ, Slattery M (May 2012). "Spatial variability in secondary metabolites of the indo-pacific sponge
Stylissa massa".
446:
atoms, the molecule is considered highly complex. The precise atomic structure was pinned down in 2007, and two years later, the molecule was synthesized in the lab of
309:
879:
815:
Lansdell, T. A; Hewlett, N. M; Skoumbourdis, A. P; Fodor, M. D; Seiple, I. B; Su, S; Baran, P. S; Feldman, K. S; Tepe, J. J (2012).
284:
904:
899:
451:
390:
884:
227:
817:"Palau'amine and Related Oroidin-alkaloids Dibromophakellin and Dibromophakellstatin Inhibit the Human 20S Proteasome"
536:
248:
23:
32:
894:
874:
188:
495:
157:
194:
683:
515:
455:
45:
265:
499:
487:
103:
869:
846:
797:
748:
730:
664:
553:
177:
836:
828:
787:
779:
738:
720:
654:
646:
611:
580:
545:
332:
113:
458:. Early efforts towards its synthesis were directed at a misassigned structure featuring a
236:
889:
482:
Based on the hypothesized biosynthesis of palau'amine, a proposed pathway to this dimeric
269:
82:)-2,2′-Diamino-11-(aminomethyl)-12-chloro-5′-hydroxy-1,1′,3a,5′,10a,11,12,13a-octahydro-8
841:
816:
792:
767:
743:
708:
659:
634:
427:
414:
384:
863:
709:"Recent Synthetic Studies Leading to Structural Revisions of Marine Natural Products"
630:
599:
439:
216:
629:
Seiple, Ian B.; Su, Shun; Young, Ian S.; Lewis, Chad A.; Yamaguchi, Junichiro;
615:
768:"Revisiting the Kinnel–Scheuer hypothesis for the biosynthesis of palau'amine"
549:
503:
447:
410:
369:
168:
734:
491:
850:
801:
752:
668:
650:
557:
443:
406:
584:
783:
483:
203:
832:
725:
148:
383:
Except where otherwise noted, data are given for materials in their
425:, is found. It has since been isolated in other sponges, including
418:
136:
126:
421:, near where the first sponge species discovered to produce it,
253:
684:"Bizarre Sea Sponge Compound Finally Synthesized by Humans"
470:-5/5 ring system is some 6 kcal/mol less stable than the
90:-spiropyrroloimidazopyrrolopyrazine-13,4′-imidazol]-8-one
409:
compound synthesized naturally by certain species of
466:
5/5 ring fusion, an error that was made because the
317:
Cl41(NC(=N/1O)\N)326/N=C(\N6n5c(C(=O)N2C34CN)ccc5)N
215:
112:
8:
600:"Sponge Alkaloids: Palau'amine Reconsidered"
413:. The name of the molecule derives from the
766:Ma Z, Lu J, Wang X, Chen C (Jan 7, 2011).
268:
176:
15:
840:
791:
742:
724:
658:
442:, and described in 1993. Containing nine
235:
573:Journal of the American Chemical Society
639:Angewandte Chemie International Edition
526:
314:
289:
264:
193:
434:The substance was first isolated from
296:Key: VYOQBYCIIJYKJA-VORKOXQSSA-N
156:
7:
206:
438:, a sponge found in the southwest
14:
635:"Total Synthesis of Palau'amine"
490:includes a key oxidation of a β-
353:
350:
344:
31:
22:
707:Usami, Yoshihide (2009-07-13).
682:Madrigal, Alexis (2010-01-14).
604:Chemical & Engineering News
387:(at 25 °C , 100 kPa).
359:
338:
1:
880:Halogen-containing alkaloids
821:Journal of Natural Products
537:Journal of Chemical Ecology
921:
616:10.1021/cen-v085n010.p012a
452:Scripps Research Institute
598:Halford, Bethany (2007).
550:10.1007/s10886-012-0124-8
381:
325:
305:
280:
96:
44:
39:
30:
21:
405:is a toxic chlorinated
651:10.1002/anie.200907112
498:to initiate a cascade
496:manganese(III) acetate
905:Proteasome inhibitors
900:Nitrogen heterocycles
516:proteasome inhibitor
478:Biomimetic synthesis
474:-configured system.
456:La Jolla, California
46:Preferred IUPAC name
885:Guanidine alkaloids
585:10.1021/ja00061a065
500:radical cyclization
436:Stylotella agminata
423:Stylotella agminata
377: g·mol
18:
784:10.1039/c0cc02214d
510:Biological effects
488:imidazole alkaloid
391:Infobox references
16:
833:10.1021/np300231f
726:10.3390/md7030314
514:Palau'amine is a
399:Chemical compound
397:
396:
249:CompTox Dashboard
138:Interactive image
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579:(8): 3376–3377.
568:
562:
561:
531:
376:
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355:
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333:Chemical formula
273:
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140:
116:
35:
26:
19:
17:Palau'amine
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895:Spiro compounds
875:Organochlorides
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5:
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719:(3): 314–330.
699:
674:
631:Baran, Phil S.
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428:Stylissa massa
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385:standard state
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645:(6): 1095–8.
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544:(5): 463–75.
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440:Pacific Ocean
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415:island nation
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25:
20:
827:(5): 980–5.
824:
820:
810:
778:(1): 427–9.
775:
771:
761:
716:
713:Marine Drugs
712:
702:
691:. Retrieved
687:
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624:
607:
603:
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576:
572:
566:
541:
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481:
471:
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463:
462:rather than
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97:Identifiers
87:
83:
79:
75:
71:
67:
63:
59:
55:
51:
772:Chem Commun
411:sea sponges
403:Palau'amine
326:Properties
114:148717-58-2
864:Categories
693:2010-01-15
610:(10): 12.
522:References
506:skeleton.
504:ageliferin
448:Phil Baran
370:Molar mass
237:53Z543U79T
169:ChemSpider
125:3D model (
104:CAS Number
870:Alkaloids
735:1660-3397
492:ketoester
851:22591513
802:20848010
753:19841716
669:20041464
633:(2010).
558:22569832
444:nitrogen
407:alkaloid
217:71308253
178:17279008
842:3367325
793:2999656
744:2763102
660:3367661
484:pyrrole
450:at the
204:PubChem
195:C438976
890:Amines
849:
839:
800:
790:
751:
741:
733:
667:
657:
556:
464:trans-
375:419.87
310:SMILES
149:ChEMBL
40:Names
688:Wired
494:with
468:trans
419:Palau
285:InChI
127:JSmol
847:PMID
798:PMID
749:PMID
731:ISSN
665:PMID
554:PMID
460:cis-
228:UNII
189:MeSH
78:,13b
74:,13a
62:,10a
837:PMC
829:doi
788:PMC
780:doi
739:PMC
721:doi
655:PMC
647:doi
612:doi
581:doi
577:115
546:doi
472:cis
454:in
417:of
254:EPA
207:CID
86:,10
70:,12
66:,11
58:,5′
54:,4′
50:(3a
866::
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835:.
825:75
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351:Cl
348:22
342:17
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486:-
363:2
360:O
357:9
354:N
345:H
339:C
256:)
252:(
129:)
88:H
84:H
80:R
76:S
72:S
68:S
64:S
60:S
56:R
52:R
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