Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA013130
PROPERTIES
| NPAID | NPA013130 |
|---|---|
| CLUSTER ID | 854 |
| NODE ID | 739 |
| NAME | Pacidamycin D |
| FORMULA | C32H41N9O10 |
| MOLECULAR WEIGHT (Da) | 711.7330 |
| ACCURATE MASS (Da) | 711.2976 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | coeruleorubidus |
| InChIKey | PBFVZISIBPPZNE-RRZBLPPNSA-N |
| InChI | InChI=1S/C32H41N9O10/c1-15(33)28(46)40(4)17(3)25(27(45)35-14-19-12-23(42)29(51-19)41-10-9-24(43)38-32(41)50)39-26(44)16(2)36-31(49)37-22(30(47)48)11-18-13-34-21-8-6-5-7-20(18)21/h5-10,13-17,22-23,25,29,34,42H,11-12,33H2,1-4H3,(H,35,45)(H,39,44)(H,47,48)(H2,36,37,49)(H,38,43,50)/t15-,16-,17-,22-,23+,25-,29+/m0/s1 |
| SMILES | C[C@H](N)C(=O)N(C)[C@@H](C)[C@H](NC(=O)[C@H](C)NC(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(=O)O)C(=O)NC=C1C[C@@H](O)[C@H](N2C=CC(=O)NC2=O)O1 |
ORIGINAL ISOLATION REFERENCE
| CITATION | FRONKO, R. M.; LEE, J. C.; GALAZZO, J. G.; CHAMBERLAND, S.; MALOUIN, F.; LEE, M. D. New Pacidamycins Produced by Streptomyces coeruleorubidus, NRRL 18370 Journal of Antibiotics 2000 53 (12) 1405-1410. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.53.1405 | PMID | 11217807 |
SYNTHESES
| CITATION 1 | Okamoto K; Sakagami M; Feng F; Togame H; Takemoto H; Ichikawa S; Matsuda A Total synthesis of pacidamycin D by Cu(I)-catalyzed oxy enamide formation. Organic Letters 2011 13 (19) 5240-3. DOI: 10.1021/ol202124b PMID: 21902200 | ||
|---|---|---|---|
| CITATION 2 | Okamoto K; Sakagami M; Feng F; Togame H; Takemoto H; Ichikawa S; Matsuda A Total synthesis and biological evaluation of pacidamycin D and its 3'-hydroxy analogue. Journal of Organic Chemistry 2012 77 (3) 1367-77. DOI: 10.1021/jo202159q PMID: 22196045 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CC(C(C(=O)N/C=C\1/CC(C(O1)N2C=CC(=O)NC2=O)O)NC(=O)C(C)NC(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)O)N(C)C(=O)C(C)N | FRONKO, R. M.; LEE, J. C.; GALAZZO, J. G.; CHAMBERLAND, S.; MALOUIN, F.; LEE, M. D. New Pacidamycins Produced by Streptomyces coeruleorubidus, NRRL 18370 Journal of Antibiotics 2000 53 (12) 1405-1410. DOI: 10.7164/antibiotics.53.1405 PMID: 11217807 | ||
| 2 | C[C@H](N)C(=O)N(C)[C@@H](C)[C@H](NC(=O)[C@H](C)NC(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(=O)O)C(=O)NC=C1C[C@@H](O)[C@H](N2C=CC(=O)NC2=O)O1 | Boojamra, C G; Lemoine, R C; Lee, J C; Léger, R; Stein, K A; Vernier, N G; Magon, A; Lomovskaya, O; Martin, P K; Chamberland, S; Lee, M D; Hecker, S J; Lee, V J Stereochemical elucidation and total synthesis of dihydropacidamycin D, a semisynthetic pacidamycin. Journal of the American Chemical Society 2001 123 (5) 870-4. DOI: 10.1021/ja003292c PMID: 11456620 | ||
