|
|
|
|
Year of first isolation: |
1969 |
| Formula: | C29H46O7 |
| Molecular weight: | 506 |
| Occurence in plants: |
Ajuga incisa [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Ajuga incisa [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
|
| Occurence in animals: |
|
|
|
| |
| Canonical SMILES | CCC(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)C(=C)CO | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CCC2[C@](C)([C@@H](C[C@H](C(=C)CO)CC)O)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R,5R)-5-ethyl-2,3-dihydroxy-6-(hydroxymethyl)hept-6-en-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 21490-21-1 | | PubChem CID | 15813982 | InChiKey
[ ChemIDPlus: search ] | ODENAQIZHMFEAO-BQBPTSSQSA-N | | InChI | InChI=1S/C29H46O7/c1-6-17(16(2)15-30)11-25(34)28(5,35)24-8-10-29(36)19-12-21(31)20-13-22(32)23(33)14-26(20,3)18(19)7-9-27(24,29)4/h12,17-18,20,22-25,30,32-36H,2,6-11,13-15H2,1,3-5H3/t17-,18+,20+,22-,23+,24+,25-,26-,27-,28-,29-/m1/s1 |
| |
| CI-MS (NH3) m/z | | | EI-MS m/z | 506 (M)+, 363, 345, 327, 143 (M-C22-C27), 125, 107. | | HR-MS | |
|
|
| C5D5N | | 01 | | | 02 | | | 03 | | | 04 | | | 05 | | | 06 | | | 07 | | | 08 | | | 09 | | | 10 | | | 11 | | | 12 | | | 13 | | | 14 | | | 15 | | | 16 | | | 17 | | | 18 | | | 19 | | | 20 | | | 21 | | | 22 | | | 23 | | | 24 | | | 25 | | | 26 | | | 27 | | | 28 | | | 29 | |
|
| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.05 (w1/2 20) | | 03-He | 4.14 (w1/2 8) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 6.18 | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.16 | | 19-Me | 1.05 | | 21-Me | 1.54 | | 22-H | 3.85 (dd ) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 29-Me | 0.86 ( t, 7) | | CH2-OH | 4.36 | | CH2= | 5.03, 5.33 |
| CDCl3 (tetra-OAc) | | 01-Ha | | | 01-Hb | | | 02-Ha | 5.07 (w1/2 22) | | 03-He | 5.35 (w1/2 9) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.82 (d ) | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.82 | | 19-Me | 1.01 | | 21-Me | 1.21 | | 22-H | 4.85 (dd ) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 29-Me | 0.86 (t, 7) | | CH2-OH | | | CH2= | 4.91, 5.09 | | CH2O-Ac | 4.28, 4.69 (q, 14) |
|
| |
| M.P. | 240 °C (decomp.) | | [α]D20 | + 54.7 ° (c ; MeOH) (n --> pi*) | | IR (KBr) ν max (cm-1) | 3400, 1650 | | UV (EtOH) λ max (log ε) | 244 (4.028) |
| |
| |
Drosophila melanogaster BII cell assay: EC50 = 3.3 x 10-7M | Chilo dipping assay: highly active |
| |
| First isolation | IMAI, S. et al. (1969) Chem. Commun., 82-83 |
 | | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | Bioactivities | DINAN, L. et al. (2003) In: Studies in Natural Products Chemisty (ed. Atta-ur-Rahman), Elsevier, Amsterdam, 29, 3-71 |
|
| |
Permanent link to this datasheet: AJUGASTERONE B
|
|
