Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA017832
PROPERTIES
| NPAID | NPA017832 |
|---|---|
| CLUSTER ID | 1057 |
| NODE ID | 910 |
| NAME | Citrinadin B |
| FORMULA | C28H39N3O4 |
| MOLECULAR WEIGHT (Da) | 481.6370 |
| ACCURATE MASS (Da) | 481.2941 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Penicillium |
| ORIGIN SPECIES | citrinum |
| InChIKey | FMXABKNHBZJYPO-ASWVUWAYSA-N |
| InChI | InChI=1S/C28H39N3O4/c1-16-9-7-10-17-13-28(34)25(4,5)27(14-26(28,29-6)15-31(16)17)19-12-8-11-18(20(19)30-23(27)33)21(32)22-24(2,3)35-22/h8,11-12,16-17,22,29,34H,7,9-10,13-15H2,1-6H3,(H,30,33)/t16-,17+,22+,26+,27-,28-/m0/s1 |
| SMILES | CN[C@]12CN3[C@H](CCC[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 | Mugishima, Takao; Tsuda, Masashi; Kasai, Yuu; Ishiyama, Haruaki; Fukushi, Eri; Kawabata, Jun; Watanabe, Masayuki; Akao, Kenichi; Kobayashi, Jun'ichi Absolute stereochemistry of citrinadins A and B from marine-derived fungus Journal of Organic Chemistry 2005 70 (23) 9430-9435. | ||
|---|---|---|---|
| DOI | 10.1021/jo051499o | PMID | 16268618 |
SYNTHESES
| CITATION 1 | Kong K; Enquist JA; McCallum ME; Smith GM; Matsumaru T; Menhaji-Klotz E; Wood JL An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B. Journal of the American Chemical Society 2013 135 (30) 10890-10893. DOI: 10.1021/ja405548b PMID: 23837485 | ||
|---|---|---|---|
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | C[C@@H]1CCC[C@@H]2N1C[C@]3(C[C@]4(C5=CC=CC(=C5NC4=O)C(=O)[C@@H]6C(O6)(C)C)C([C@@]3(C2)O)(C)C)NC | Mugishima, Takao; Tsuda, Masashi; Kasai, Yuu; Ishiyama, Haruaki; Fukushi, Eri; Kawabata, Jun; Watanabe, Masayuki; Akao, Kenichi; Kobayashi, Jun'ichi Absolute stereochemistry of citrinadins A and B from marine-derived fungus Journal of Organic Chemistry 2005 70 (23) 9430-9435. DOI: 10.1021/jo051499o PMID: 16268618 | ||
| 2 | CN[C@]12CN3[C@H](CCC[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 | Kong K; Enquist JA; McCallum ME; Smith GM; Matsumaru T; Menhaji-Klotz E; Wood JL An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B. Journal of the American Chemical Society 2013 135 (30) 10890-10893. DOI: 10.1021/ja405548b PMID: 23837485 | ||
