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Year of first isolation: |
1980 |
| Formula: | C27H42O7 |
| Molecular weight: | 478 |
| Occurence in plants: |
Ajuga nipponensis [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Ajuga nipponensis [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
Polypodium vulgare [Polypodiaceae] »
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| Occurence in animals: |
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| Canonical SMILES | CC1(CCC(O1)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5(C4(CC(C(C5)O)O)C)O)C)O)O)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)(C1CCC(O1)(C)C)O)O)C)O)C » 
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H]1CCC(O1)(C)C)O)O)C)C »
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H]1CCC(O1)(C)C)O)O)C)C »
| | IUPAC Name | (2S,3R,5S,9R,10R,13R,14S,17S)-17-[(1R)-1-(5,5-dimethyloxolan-2-yl)-1-hydroxyethyl]-2,3,5,14-tetrahydroxy-10,13-dimethyl-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 21123579 | InChiKey
[ ChemIDPlus: search ] | UVQAWEDRKUWQCJ-DJLNXEJJSA-N | | InChI | InChI=1S/C27H42O7/c1-22(2)9-8-21(34-22)25(5,31)19-7-11-26(32)16-12-20(30)27(33)14-18(29)17(28)13-24(27,4)15(16)6-10-23(19,26)3/h12,15,17-19,21,28-29,31-33H,6-11,13-14H2,1-5H3/t15-,17-,18+,19-,21?,23+,24+,25+,26+,27+/m0/s1 |
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| EI-MS m/z (relative intensity %) | 479 (MH)+, 443, 379 (M-C22-C27), 361, 343, 325, 143 (C20-C27), 125, 99 (C22-C27), 81 | | HR-MS | |
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| CD3OD | | 01 | 34.4 | | 02 | 68.6 | | 03 | 70.4 | | 04 | 36.3 | | 05 | 80.4 | | 06 | 202.5 | | 07 | 120.7 | | 08 | 167.7 | | 09 | 39.2 | | 10 | 45.5 | | 11 | 22.6 | | 12 | 32.5 | | 13 | 48.4 | | 14 | 85.2 | | 15 | 31.8 | | 16 | 21.9 | | 17 | 51.9 | | 18 | 18.3 | | 19 | 17.1 | | 20 | 77.1 | | 21 | 20.8 | | 22 | 85.7 | | 23 | 28.6 | | 24 | 39.8 | | 25 | 81.8 | | 26 | 28.5 | | 27 | 29.1 |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 07-H | | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.94 (s ) | | 19-Me | 1.04 (s ) | | 21-Me | 1.28 (s ) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.10 (s ) | | 27-Me | 1.10 (s ) |
| CD3OD | | 01-Ha | 1.73 | | 01-Hb | 1.73 | | 02-Ha | 3.94 | | 03-He | 3.99 | | 04-Ha | 2.07 | | 04-He | 1.77 | | 05-H | | | 07-H | 5.85 | | 09-Ha | 3.19 | | 11-Ha | 1.75 | | 11-He | 1.81 | | 12-Ha | 2.15 | | 12-He | 1.86 | | 15-Ha | 1.60 | | 15-Hb | 1.96 | | 16-Ha | 1.81 | | 16-Hb | 2.00 | | 17-H | 2.36 | | 18-Me | 0.85 | | 19-Me | 0.91 | | 20-H | | | 21-Me | 1.21 | | 22-H | 3.91 | | 23-Ha | 1.75 | | 23-Hb | 1.89 | | 24-Ha | 1.75 | | 24-Hb | 1.75 | | 26-Me | 1.24 | | 27-Me | 1.25 |
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| M.P. | 234-237 °C | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3400, 1690 | | UV (EtOH) λ max (log ε) | 244-246 (4.07) |
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| HPTLC | | | TLC | Rf 0.71 NP-TLC on silica (CHCl3-EtOH 5:1) (20E 0.32); Rf 0.32 NP-TLC on silica (CHCl3-EtOH 4:1) | | GLC | | | HPLC | |
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Permanent link to this datasheet: AJUGASTERONE D
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