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Year of first isolation: |
1996 |
| Formula: | C29H44O9 |
| Molecular weight: | 536 |
| Occurence in plants: |
Ajuga reptans var. atropurpurea [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Ajuga reptans var. atropurpurea [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC1C(C(OC1=O)C)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5(C4(CC(C(C5)O)O)C)O)C)O)O)O | 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)([C@@H](C[C@H]1[C@@H](C(=O)O[C@H]1C)C)O)O)O)C)O)C » 
| | IUPAC Name | (3S,4S,5S)-4-[(2R,3R)-2,3-dihydroxy-3-[(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-6-oxo-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]butyl]-3,5-dimethyloxolan-2-one | | CAS-RN | | | PubChem CID | 101355230 | InChiKey
[ ChemIDPlus: search ] | YQCOGGGDJXBMBU-ZHDQNANASA-N | | InChI | InChI=1S/C29H44O9/c1-14-16(15(2)38-24(14)34)10-22(32)27(5,35)21-7-9-28(36)18-11-23(33)29(37)13-20(31)19(30)12-26(29,4)17(18)6-8-25(21,28)3/h11,14-17,19-22,30-32,35-37H,6-10,12-13H2,1-5H3/t14-,15-,16-,17-,19-,20+,21-,22+,25+,26+,27+,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | | | MS (thermospray) m/z (relat. intensity %) | 554 (M+NH4)+ (25), 537 (M+H) (100), 536 (M)+ (82), 519 (M+H-H20) (34), 501 (M+H-2H2O) (21) |
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| C5D5N | | 01 | 34.8 | | 02 | 67.9 | | 03 | 69.8 | | 04 | 35.9 | | 05 | 79.8 | | 06 | 200.9 | | 07 | 120.0 | | 08 | 166.6 | | 09 | 38.2 | | 10 | 44.8 | | 11 | 22.0 | | 12 | 32.1 | | 13 | 48.2 | | 14 | 83.9 | | 15 | 31.6 | | 16 | 21.3 | | 17 | 50.0 | | 18 | 17.9 | | 19 | 17.1 | | 20 | 76.7 | | 21 | 21.1 | | 22 | 76.4 | | 23 | 30.8 | | 24 | 46.0 | | 25 | 38.7 | | 26 | 179.1 | | 27 | 16.3 | | 28 | 78.7 | | 29 | 14.3 |
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| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | 4.27 (m, w1/2=24) | | 03-He | 4.18 (m, w1/2=15) | | 04-Ha | | | 04-He | | | 05-H | ? | | 07-H | 6.27 (d, 2.1) | | 09-H | 3.66 (m, w1/2=24) | | 11-Ha | | | 11-He | | | 12-Ha | 2.62 | | 12-He | 2.08 | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.88 (t, 8.4) | | 18-Me | 1.24 (s) | | 19-Me | 1.18 (s) | | 21-Me | 1.61 (s) | | 22-H | 3.90 (m, w1/2=20) | | 23-Ha | 1.81 | | 23-Hb | 1.69 | | 24-H | 2.48 | | 25-H | 2.33 (dq, 11.4, 6.9) | | 27-Me | 1.17 (d, 7) | | 28-H | 5.01 | | 29-Me | 1.31 (d, 6) | | H-2 OH | 5.56 (w1/2=15) | | H-22 OH | 5.56 W1/2=8) | | H-3 OH | 5.88 (d, 8.1) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3416 (OH), 1749 (?-lactone), 1670 (cyclohexenone) | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | | | GLC | | | HPLC | RP-HPLC, column Tracer 30x0.78 cm packed with Spherisorb-ODS2 10?m, solvent iPrOH-H2O (13:87), flow-rate 3 mL.min-1, 23°C, Ret 22.5 min. |
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Permanent link to this datasheet: 28-EPI-SENGOSTERONE
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