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Year of first isolation: |
1970 |
| Formula: | C29H40O8 |
| Molecular weight: | 516 |
| Occurence in plants: |
Ajuga decumbens [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Ajuga decumbens [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
Ajuga reptans [Lamiaceae (alt. Labiatae)] »
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| Occurence in animals: |
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| Canonical SMILES | CCC1=C(C(=O)OC(C1)C(C)(C2CCC3(C2(C(=O)CC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)C | 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(=O)[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H]1OC(=O)C(=C(C1)CC)C)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14R,17S)-17-[(1R)-1-[(2R)-4-ethyl-5-methyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,11,15,16,17-decahydrocyclopenta[a]phenanthrene-6,12-dione | | CAS-RN | 42975-12-2 | | PubChem CID | 181744 | InChiKey
[ ChemIDPlus: search ] | LLPOMLNTBDOEOC-LYUHEGIFSA-N | | InChI | InChI=1S/C29H40O8/c1-6-15-9-24(37-25(34)14(15)2)28(5,35)22-7-8-29(36)17-10-19(30)18-11-20(31)21(32)13-26(18,3)16(17)12-23(33)27(22,29)4/h10,16,18,20-22,24,31-32,35-36H,6-9,11-13H2,1-5H3/t16-,18-,20+,21-,22-,24+,26+,27-,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 516 (M)+ (5), 377 (M-C22-C29) (75), 359 (100), 341 (15), 183 (C20-C29) (71), 139 (C22-C29) (60), 111 (24) | | HR-MS | |
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| CDCl3 | | 01 | 37.9 (t ) | | 02 | 67.9 (d ) | | 03 | 68.2 (d ) | | 04 | 32.3 (t )* | | 05 | 51.5 (d ) | | 06 | 202.7 (s ) | | 07 | 124.3 (d ) | | 08 | 162.4 (s ) | | 09 | 37.1 (d ) | | 10 | 40.1 (s ) | | 11 | 37.1 (t ) | | 12 | 210.1 (s ) | | 13 | 61.9 (s ) | | 14 | 89.5 (s ) | | 15 | 32.2 (t )* | | 16 | 21.3 (t ) | | 17 | 44.1 (d ) | | 18 | 17.7 (q ) | | 19 | 24.0 (q ) | | 20 | 75.3 (s ) | | 21 | 22.5 (q ) | | 22 | 83.4 (d ) | | 23 | 27.4 (t )' | | 24 | 121.4 (s ) | | 25 | 154.9 (s ) | | 26 | 167.3 (s ) | | 27 | 11.8 (q )" | | 28 | 20.4 (t )' | | 29 | 12.5 (q )" |
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| CD3OD | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.00 (m, w1/2 = 20) | | 03-He | 4.16 (m, w1/2 = 7) | | 04-Ha | | | 04-He | | | 05-H | 3.00 (dd, 4, 14) | | 07-H | 6.33 (d, 2.5) | | 09-Ha | 3.45 (ddd, 2.5,9.5,9.5) | | 11-Ha | | | 11-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.49 (s ) | | 19-Me | 1.12 (s ) | | 21-Me | 1.65 (s ) | | 22-H | 4.42 (dd, 5.5, 12) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.87 (s ) | | 27-Me | -- | | 28-Me | 0.74 |
| Acetone (2,3-di-OAc) | | 01-Ha | | | 01-Hb | | | 02-Ha | 5.03 (ddd, 3, 5, 12) | | 03-He | 5.30 (m, w1/2 = 6) | | 04-Ha | | | 04-He | | | 05-H | 2.34 (dd ) | | 07-H | 5.97 | | 09-Ha | 3.67 (ddd ) | | 11-Ha | | | 11-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.26 | | 19-Me | 1.17 | | 21-Me | 1.27 | | 22-H | 4.18 (dd, 6,11) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.83 | | 27-Me | | | 28-Me | | | Acetoxy | 1.93, 2.09 (s) |
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| M.P. | 225-235 °C | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3440 (OH), 1718 (CO), 1696 (lactone), 1654 (cyclohexenone) | | UV (MeOH) λ max (log ε) | 233 (broad) (4.20) |
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Drosophila melanogaster BII cell assay: EC50 = 1.6 x 10-7M |
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Permanent link to this datasheet: AJUGALACTONE
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