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Year of first isolation: |
2005 |
| Formula: | C31H46O9 |
| Molecular weight: | 562 |
| Occurence in plants: |
Ajuga taiwanensis [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Ajuga taiwanensis [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
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| Occurence in animals: |
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![AJUGALIDE E [cf. 2-EPI-CYASTERONE 22-ACETATE]](images/ecdy/389.gif)
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| Canonical SMILES | CC1C(C(OC1=O)C)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)OC(=O)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@@H]1O)O)C(=O)C=C1C2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CC1[C@@H](C(=O)O[C@@H]1C)C)OC(=O)C)O)O)C)C » 
| | IUPAC Name | [(2R,3R)-1-[(2R,3S,4S)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxy-3-[(2R,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]butan-2-yl] acetate | | CAS-RN | | | PubChem CID | 11272992 | InChiKey
[ ChemIDPlus: search ] | GFPSWBAAJFSDOH-JWIXMYEHSA-N | | InChI | InChI=1S/C31H46O9/c1-15-18(16(2)39-27(15)36)11-26(40-17(3)32)30(6,37)25-8-10-31(38)20-12-22(33)21-13-23(34)24(35)14-28(21,4)19(20)7-9-29(25,31)5/h12,15-16,18-19,21,23-26,34-35,37-38H,7-11,13-14H2,1-6H3/t15-,16+,18-,19-,21-,23+,24+,25-,26+,28+,29+,30+,31+/m0/s1 |
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| HR-FAB-MS m/z | 563.3221 (calculated for C31H46O9 563.3220) | | EI-MS m/z (relative intensity %) | | | HAB-MS m/z (relative intensity %) | 563 [M+H]+ (1), 562v(1), 544 (1), 526 (1), 516 (1), 508 (3), 498 (2), 484 (1), 466 (1), 451 (1), 448 (2), 433 (2), 377 (2), 371 (13), 363 (3), 360 (2), 353 (3), 345 (2), 327 (3), 301 (4), 300 (3), 299 (3), 250 (3), 249 (5), 183 (8), 149 (100), 139 (20) |
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| C5D5N | | 01 | 33.7 | | 02 | 75.2 | | 03 | 71.8 | | 04 | 43.1 | | 05 | 57.1 | | 06 | 201.6 | | 07 | 121.7 | | 08 | 165.6 | | 09 | 35.2 | | 10 | 39.0 | | 11 | 21.0 | | 12 | 31.9 | | 13 | 48.1 | | 14 | 84.0 | | 15 | 31.8 | | 16 | 21.5 | | 17 | 50.2 | | 18 | 17.8 | | 19 | 23.9 | | 20 | 76.2 | | 21 | 21.7 | | 22 | 76.9 | | 23 | 33.1 | | 24 | 48.2 | | 25 | 42.7 | | 26 | 178.6 | | 27 | 15.6 | | 28 | 79.2 | | 29 | 19.0 | | OAc | 170.9, 21.2 |
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| C5D5N | | 01-H | 2.20-2.00 (m), 2.00-1.60 (m) | | 02-H | 3.81 (ddd, 7.6, 7.6, 4.0) | | 03-H | 4.18 (ddd, 7.6, 7.6, 4.0) | | 04-H | 2.43-2.38 (m), 1.45-1.38 (m) | | 05-H | 2.43-2.38 (m) | | 07-H | 6.21 (br, s) | | 09-H | 3.67 (t, 9.0) | | 11-H | 2.00-1.60 (m) | | 12-H | 2.59-2.53 (m), 2.00-1.60 (m) | | 15-H | 2.20-2.00 (m), 2.00-1.60 (m) | | 16-H | 2.59-2.53 (m), 2.20-2.00 (m) | | 17-H | 2.79 (t, 8.8) | | 18-Me | 1.14 (s) | | 19-Me | 1.01 (s) | | 21-Me | 1.53 (s) | | 22-H | 5.43 (d, 10.0) | | 23-H | 2.00-1.60 (m) | | 24-H | 2.00-1.60 (m) | | 25-H | 2.25 (dq, 6.8, 6.8) | | 27-Me | 1.41 (d, 6.8) | | 28-H | 3.95 (dq, 6.8, 6.8) | | 29-Me | 1.29 (d, 6.8) | | OAc | 2.01 (s) | | OH | 6.53 (s), 5.53 (s) |
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| M.P. | 210-212 °C ; | | [α]D25 | + 111.7 ° (c 0.01 ; CHCl3) | | IR (KBr) ν max (cm-1) | 3382, 1730, 1654, 1248, 1197, 1063, 1038 | | UV (MeOH) λ max (log ε) | 240 (4.10) ; |
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Permanent link to this datasheet: AJUGALIDE E [cf. 2-EPI-CYASTERONE 22-ACETATE]
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