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Year of first isolation: |
1982 |
| Formula: | C28H42O8 |
| Molecular weight: | 506 |
| Occurence in plants: |
Ajuga reptans [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Ajuga reptans [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC1C(COC1=O)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)O | 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(CC[C@@H]2[C@](C)([C@H](O)C[C@@H]1COC(=O)[C@H]1C)O)O)C)C » 
| | IUPAC Name | (3S,4S)-4-[(2R,3R)-2,3-dihydroxy-3-[(2S,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]butyl]-3-methyloxolan-2-one | | CAS-RN | | | PubChem CID | 14693886 | InChiKey
[ ChemIDPlus: search ] | KIUYPOUMVLICAJ-KNKPZWPBSA-N | | InChI | InChI=1S/C28H42O8/c1-14-15(13-36-24(14)33)9-23(32)27(4,34)22-6-8-28(35)17-10-19(29)18-11-20(30)21(31)12-25(18,2)16(17)5-7-26(22,28)3/h10,14-16,18,20-23,30-32,34-35H,5-9,11-13H2,1-4H3/t14-,15+,16-,18-,20+,21-,22-,23+,25+,26+,27+,28+/m0/s1 |
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| CI-MS (NH3) m/z | 524 (M+NH4)+, 507 (M+H)+, 489, 471, 453, ?, 363, 345, 329, ? | | EI-MS m/z (relative intensity %) | 488 (M-18)+, 363, 345, 327, 309, 187, 169, 143, | | HR-MS | |
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| CDCl3 | | 01 | 38.0 (t ) | | 02 | 68.2 (d ) | | 03 | 68.2 (d ) | | 04 | 32.6 * | | 05 | 51.5 (d ) | | 06 | 203.9 (s ) | | 07 | 121.9 (d ) | | 08 | 166.2 (s ) | | 09 | 34.6 (d ) | | 10 | 38.8 (s ) | | 11 | 21.6 $ | | 12 | 31.9 * | | 13 | 48.3 (s ) | | 14 | 84.3 (s ) | | 15 | 31.2 * | | 16 | 21.7 $ | | 17 | 50.3 (d ) | | 18 | 18.0 (q ) | | 19 | 24.6 (q ) | | 20 | 76.9 (s ) | | 21 | 21.4 $ | | 22 | 76.2 (d ) | | 23 | 34.8 (t ) | | 24 | 40.5 (d ) | | 25 | 43.5 (d ) | | 26 | 181.1 (s ) | | 27 | 14.6 (q ) | | 28 | 73.1 (t ) |
| C5D5N | | 01 | 37.96 | | 02 | 68.09 | | 03 | 68.02 | | 04 | 32.44 | | 05 | 51.38 | | 06 | 203.43 | | 07 | 121.76 | | 08 | 165.90 | | 09 | 34.39 | | 10 | 38.67 | | 11 | 21.09 | | 12 | 32.02 | | 13 | 48.17 | | 14 | 84.09 | | 15 | 31.83 | | 16 | 21.36 | | 17 | 50.12 | | 18 | 17.89 | | 19 | 24.45 | | 20 | 76.66 | | 21 | 21.24 | | 22 | 75.97 | | 23 | 34.74 | | 24 | 40.67* | | 25 | 43.31* | | 26 | 179.78 | | 27 | 14.44 | | 28 | 72.90 |
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| CDCl3 | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 6.25 (d, 2) | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.20 (s ) | | 19-Me | 1.04 (s ) | | 21-Me | 1.55 (s ) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-H | | | 25-H | | | 26-Me | ? | | 27-Me | 1.18 (d, 7) | | 28-Ha | | | 28-Hb | |
| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | 4.17 (m, w1/2= 21.0) | | 03-He | 4.22 (m, w1/2= 8.5) | | 04-Ha | | | 04-He | | | 05-H | 3.01 (dd, 12.9, 3.6) | | 07-H | 6.27 (d, 2.2) | | 09-Ha | 3.60 | | 11-Ha | | | 11-He | | | 12-Ha | 2.63 | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.87 (brt, 8.5) | | 18-Me | 1.23 (s ) | | 19-Me | 1.07 (s ) | | 21-Me | 1.57 (s ) | | 22-H | 3.89 | | 23-Ha | | | 23-Hb | | | 24-H | | | 25-H | 2.22 (dq, 10.5, 7.2) | | 26-Me | ? | | 27-Me | 1.16 (d, 6.9) | | 28-Ha | 4.65 (dd, 9.0, 7.8) | | 28-Hb | 3.96 (dd, ca. 10.4, 8.8) |
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| M.P. | 152-155 °C | | [α]D20 | + 32.4 ° (c 6.25; MeOH) | | IR (KBr) ν max (cm-1) | 1750 (lactone), 1650 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 241 (3.991) |
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| NP-HPLC | column Zorbax-SIL (25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1), solvent cyclohexane-iPrOH-H2O (100:40:3), Ret 21.6 min (20E 19.2 min); solvent CH2Cl2-iPrOH-H2O (125:40:3) Ret 9.2 min (20E 19.5 min). | | TLC | | | GLC | | | RP-HPLC | column Spherisorb-5ODS2 (25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1) solvent iPrOH-H2O (7:93), 35°C, Ret 15.8 min (20E 19.8 min). |
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Drosophila melanogaster BII cell assay: EC50 = 1.2 x 10-8M |
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Permanent link to this datasheet: 29-NORCYASTERONE
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