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Compounds

COMPOUND NPA000074

STRUCTURE
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PROPERTIES
NPAID NPA000074
CLUSTER ID 26
NODE ID 25
NAME Laxaphycin B
FORMULA C65H114N14O19
MOLECULAR WEIGHT (Da) 1395.7060
ACCURATE MASS (Da) 1394.8385
ORIGIN ORGANISM TYPE Bacterium
ORIGIN GENUS Lyngbya
ORIGIN SPECIES majuscula
InChIKey URYPPVMQQUERGK-KGUUYBSXSA-N
InChI InChI=1S/C65H114N14O19/c1-16-18-19-20-21-23-38-29-43(83)72-44(31(5)6)58(91)76-47(51(84)32(7)8)60(93)68-35(12)55(88)75-48(52(85)33(9)10)61(94)70-39(25-26-42(66)82)64(97)78(15)50(34(11)17-2)63(96)77-49(53(86)54(67)87)62(95)74-46(37(14)81)65(98)79-27-22-24-41(79)57(90)71-40(28-30(3)4)56(89)73-45(36(13)80)59(92)69-38/h30-41,44-53,80-81,84-86H,16-29H2,1-15H3,(H2,66,82)(H2,67,87)(H,68,93)(H,69,92)(H,70,94)(H,71,90)(H,72,83)(H,73,89)(H,74,95)(H,75,88)(H,76,91)(H,77,96)/t34-,35+,36-,37-,38-,39?,40-,41+,44+,45+,46-,47-,48-,49-,50+,51+,52-,53-/m1/s1
SMILES CCCCCCC[C@@H]1CC(=O)N[C@@H](C(C)C)C(=O)N[C@H]([C@@H](O)C(C)C)C(=O)N[C@@H](C)C(=O)N[C@H]([C@H](O)C(C)C)C(=O)NC(CCC(N)=O)C(=O)N(C)[C@@H]([C@H](C)CC)C(=O)N[C@H]([C@@H](O)C(N)=O)C(=O)N[C@H]([C@@H](C)O)C(=O)N2CCC[C@H]2C(=O)N[C@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1
ORIGINAL ISOLATION REFERENCE
CITATION Bonnard, Isabelle; Rolland, Marc; Salmon, Jean-Marie; Debiton, Eric; Barthomeuf, Chantal; Banaigs, Bernard Total structure and inhibition of tumor cell proliferation of laxaphycins Journal of Medicinal Chemistry 2007 50 (6) 1266-1279.
DOI 10.1021/jm061307x PMID 17323939
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Bacteria LPSN 2
Phylum Cyanobacteria LPSN 1117
Class Cyanophyceae LPSN -
Order Oscillatoriales LPSN 1150
Family Oscillatoriaceae LPSN 1892254
Genus Lyngbya LPSN 28073
SYNTHESES
CITATION 1 Boyaud F; Mahiout Z; Lenoir C; Tang S; Wdzieczak-Bakala J; Witczak A; Bonnard I; Banaigs B; Ye T; Inguimbert N First total synthesis and stereochemical revision of laxaphycin B and its extension to lyngbyacyclamide A. Organic Letters 2013 15 (15) 3898-3901. DOI: 10.1021/ol401645m PMID: 23855751
REVISIONS
VERSION SMILES CITATION
Original Isolation CCCCCCC[C@@H]1CC(=O)N[C@H](C(=O)N[C@H](C(=O)NC(C(=O)N[C@@H](C(=O)NC(C(=O)N(C(C(=O)N[C@@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)NC(C(=O)N[C@H](C(=O)N1)C(C)O)CC(C)C)[C@@H](C)O)[C@H](C(=O)N)O)[C@@H](C)CC)C)CCC(=O)N)C(C(C)C)O)C)[C@H](C(C)C)O)C(C)C Bonnard, Isabelle; Rolland, Marc; Salmon, Jean-Marie; Debiton, Eric; Barthomeuf, Chantal; Banaigs, Bernard Total structure and inhibition of tumor cell proliferation of laxaphycins Journal of Medicinal Chemistry 2007 50 (6) 1266-1279. DOI: 10.1021/jm061307x PMID: 17323939
2 CCCCCCC[C@@H]1CC(=O)N[C@@H](C(C)C)C(=O)N[C@H]([C@@H](O)C(C)C)C(=O)N[C@@H](C)C(=O)N[C@H]([C@H](O)C(C)C)C(=O)NC(CCC(N)=O)C(=O)N(C)[C@@H]([C@H](C)CC)C(=O)N[C@H]([C@@H](O)C(N)=O)C(=O)N[C@H]([C@@H](C)O)C(=O)N2CCC[C@H]2C(=O)N[C@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 Boyaud F; Mahiout Z; Lenoir C; Tang S; Wdzieczak-Bakala J; Witczak A; Bonnard I; Banaigs B; Ye T; Inguimbert N First total synthesis and stereochemical revision of laxaphycin B and its extension to lyngbyacyclamide A. Organic Letters 2013 15 (15) 3898-3901. DOI: 10.1021/ol401645m PMID: 23855751
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