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Compounds

COMPOUND NPA033504

STRUCTURE
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PROPERTIES
NPAID NPA033504
CLUSTER ID 1057
NODE ID 910
NAME 21R-citrinadin A
FORMULA C35H52N4O6
MOLECULAR WEIGHT (Da) 624.8230
ACCURATE MASS (Da) 624.3887
ORIGIN ORGANISM TYPE Fungus
ORIGIN GENUS Penicillium
ORIGIN SPECIES citrinum ATCC 9849
InChIKey BERMVHWKOOMCMF-AVGRWZFCSA-N
InChI InChI=1S/C35H52N4O6/c1-19(2)26(38(9)10)29(41)44-22-14-20(3)39-18-33(36-8)17-34(32(6,7)35(33,43)16-21(39)15-22)24-13-11-12-23(25(24)37-30(34)42)27(40)28-31(4,5)45-28/h11-13,19-22,26,28,36,43H,14-18H2,1-10H3,(H,37,42)/t20-,21+,22+,26-,28+,33+,34-,35-/m0/s1
SMILES CN[C@]12CN3[C@H](C[C@H](OC(=O)[C@H](C(C)C)N(C)C)C[C@@H]3C)C[C@]1(O)C(C)(C)[C@]1(C2)C(=O)NC2=C(C(=O)[C@H]3OC3(C)C)C=CC=C21
ORIGINAL ISOLATION REFERENCE
CITATION Liu, Zhiwen; Zhao, Fanglong; Zhao, Boyang; Yang, Jie; Ferrara, Joseph; Sankaran, Banumathi; Venkataram Prasad; Kundu, Biki Bapi; Phillips, George N.; Gao, Yang; Hu, Liya; Zhu, Tong; Gao, Xue Structural basis of the stereoselective formation of the spirooxindole ring in the biosynthesis of citrinadins Nature Communications 2021 12 (1) 4158.
DOI 10.1038/s41467-021-24421-0 PMID 34230497
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Eukarya - 2759
Kingdom Fungi MycoBank 4751
Phylum Ascomycota MycoBank 4890
Class Eurotiomycetes MycoBank 147545
Order Eurotiales MycoBank 5042
Family Aspergillaceae MycoBank 1131492
Genus Penicillium MycoBank 5073
REVISIONS
VERSION SMILES CITATION
Original Isolation CN[C@]12CN3[C@@H](C)C[C@@H](OC(=O)[C@@H](C(C)C)N(C)C)C[C@@H]3C[C@]1(O)C(C)(C)[C@]1(C2)C(=O)NC2=C(C(=O)[C@@H]3OC3(C)C)C=CC=C21 Liu, Zhiwen; Zhao, Fanglong; Zhao, Boyang; Yang, Jie; Ferrara, Joseph; Sankaran, Banumathi; Venkataram Prasad; Kundu, Biki Bapi; Phillips, George N.; Gao, Yang; Hu, Liya; Zhu, Tong; Gao, Xue Structural basis of the stereoselective formation of the spirooxindole ring in the biosynthesis of citrinadins Nature Communications 2021 12 (1) 4158. DOI: 10.1038/s41467-021-24421-0 PMID: 34230497
2 CN[C@]12CN3[C@H](C[C@H](OC(=O)[C@H](C(C)C)N(C)C)C[C@@H]3C)C[C@]1(O)C(C)(C)[C@]1(C2)C(=O)NC2=C(C(=O)[C@H]3OC3(C)C)C=CC=C21 Bian Z; Marvin CC; Martin SF Enantioselective total synthesis of (-)-citrinadin A and revision of its stereochemical structure. Journal of the American Chemical Society 2013 135 (30) 10886-9. DOI: 10.1021/ja405547f PMID: 23837457
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