Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA015500
PROPERTIES
| NPAID | NPA015500 |
|---|---|
| CLUSTER ID | 5395 |
| NODE ID | 3837 |
| NAME | Glucolipsin A |
| FORMULA | C50H92O14 |
| MOLECULAR WEIGHT (Da) | 917.2720 |
| ACCURATE MASS (Da) | 916.6487 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | purpurogeniscleroticus |
| InChIKey | TURVNPRDJNOSQM-NURLJSJFSA-N |
| InChI | InChI=1S/C50H92O14/c1-33(2)27-23-19-15-11-7-9-13-17-21-25-29-37-35(5)47(57)59-31-40-42(52)44(54)46(56)50(64-40)62-38(30-26-22-18-14-10-8-12-16-20-24-28-34(3)4)36(6)48(58)60-32-39-41(51)43(53)45(55)49(61-37)63-39/h33-46,49-56H,7-32H2,1-6H3/t35?,36?,37-,38-,39?,40?,41?,42?,43?,44?,45?,46?,49?,50?/m1/s1 |
| SMILES | CC(C)CCCCCCCCCCCC[C@H]1OC2OC(COC(=O)C(C)[C@@H](CCCCCCCCCCCCC(C)C)OC3OC(COC(=O)C1C)C(O)C(O)C3O)C(O)C(O)C2O |
ORIGINAL ISOLATION REFERENCE
| CITATION | QIAN-CUTRONE, JINGFANG; UEKI, T.; HUANG, STELLA; MOOKHTIAR, KASIM A.; EZEKIEL, REGINA; KALINOWSKI, STEVEN S.; BROWN, KAREN S.; GOLIK, JERZY; LOWE, SUSAN; PIRNIK, DOLORES M.; HUGILL, ROBERT; VEITCH, JUDY A.; KLOHR, STEVEN E.; WHITNEY, JEFFREY L.; MANLY, SUSAN P. Glucolipsin A and B, Two New Glucokinase Activators Produced by Streptomyces purpurogeniscleroticus and Nocardia vaccinii Journal of Antibiotics 1999 52 (3) 245-255. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.52.245 | PMID | 10348039 |
SYNTHESES
| CITATION 1 | Fürstner A; Ruiz-Caro J; Prinz H; Waldmann H Structure assignment, total synthesis, and evaluation of the phosphatase modulating activity of glucolipsin A. Journal of Organic Chemistry 2004 69 (2) 459-67. DOI: 10.1021/jo035079f PMID: 14725460 | ||
|---|---|---|---|
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CC1C(OC2C(C(C(C(O2)COC(=O)C(C(OC3C(C(C(C(O3)COC1=O)O)O)O)CCCCCCCCCCCCC(C)C)C)O)O)O)CCCCCCCCCCCCC(C)C | QIAN-CUTRONE, JINGFANG; UEKI, T.; HUANG, STELLA; MOOKHTIAR, KASIM A.; EZEKIEL, REGINA; KALINOWSKI, STEVEN S.; BROWN, KAREN S.; GOLIK, JERZY; LOWE, SUSAN; PIRNIK, DOLORES M.; HUGILL, ROBERT; VEITCH, JUDY A.; KLOHR, STEVEN E.; WHITNEY, JEFFREY L.; MANLY, SUSAN P. Glucolipsin A and B, Two New Glucokinase Activators Produced by Streptomyces purpurogeniscleroticus and Nocardia vaccinii Journal of Antibiotics 1999 52 (3) 245-255. DOI: 10.7164/antibiotics.52.245 PMID: 10348039 | ||
| 2 | CC(C)CCCCCCCCCCCC[C@H]1OC2OC(COC(=O)C(C)[C@@H](CCCCCCCCCCCCC(C)C)OC3OC(COC(=O)C1C)C(O)C(O)C3O)C(O)C(O)C2O | Fürstner, Alois; Albert, Martin; Mlynarski, Jacek; Matheu, Maribel A concise synthesis of the fully functional lactide core of cycloviracin B with implications for the structural assignment of related glycolipids. Journal of the American Chemical Society 2002 124 (7) 1168-9. DOI: 10.1021/ja0175791 PMID: 11841275 | ||
