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Year of first isolation: |
1982 |
| Formula: | C28H42O9 |
| Molecular weight: | 522 |
| 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)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](O)C[C@@H]1COC(=O)[C@H]1C)O)O)C)O)C » 
| | IUPAC Name | (3S,4S)-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-methyloxolan-2-one | | CAS-RN | | | PubChem CID | 14693881 | InChiKey
[ ChemIDPlus: search ] | AJPNSKWVBMZHRH-HDWGAXEUSA-N | | InChI | InChI=1S/C28H42O9/c1-14-15(13-37-23(14)33)9-21(31)26(4,34)20-6-8-27(35)17-10-22(32)28(36)12-19(30)18(29)11-25(28,3)16(17)5-7-24(20,27)2/h10,14-16,18-21,29-31,34-36H,5-9,11-13H2,1-4H3/t14-,15+,16-,18-,19+,20-,21+,24+,25+,26+,27+,28+/m0/s1 |
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| CI-MS (NH3) m/z | 540 (M+NH4)+, 523 (MH)+, 505, 487, 469, 451, 378, 361, 343, 325, 267, 245, 229, 204, 187, 171, 160, 143 | | EI-MS m/z (relative intensity %) | 504 (M-18)+, 361, 343, 325, 187, 169, 143 | | HR-MS | |
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| CDCl3 | | 01 | 34.7 (t ) | | 02 | 67.9 (d ) | | 03 | 69.8 (d ) | | 04 | 35.9 (t ) | | 05 | 79.8 (s ) | | 06 | 201.0 (s ) | | 07 | 120.0 (d ) | | 08 | 166.7 (s ) | | 09 | 38.2 (d ) | | 10 | 44.8 (s ) | | 11 | 22.0 (t )$ | | 12 | 31.7 (t )* | | 13 | 48.2 (s ) | | 14 | 84.0 (s ) | | 15 | 32.1 (t )* | | 16 | 21.3 (t )$ | | 17 | 50.0 (d ) | | 18 | 17.9 (q ) | | 19 | 17.1 (q ) | | 20 | 76.7 (s ) | | 21 | 21.3 (q ) | | 22 | 76.0 (d ) | | 23 | 34.7 (t ) | | 24 | 40.7 (d ) | | 25 | 43.3 (d ) | | 26 | 179.8 (s ) | | 27 | 14.5 (q ) | | 28 | 72.9 (t ) |
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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 | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.13 (s ) | | 19-Me | 1.13 (s ) | | 21-Me | 1.53 (s ) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | ? | | 27-Me | 1.18 (d, 7) |
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| M.P. | | | [α]D20 | + 51.0 ° (c 4.7 ; MeOH) | | IR (KBr) ν max (cm-1) | 1755 (lactone), 1670 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 238 (3.954) |
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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 7.0 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 11.7 min (20E 19.8 min). |
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Drosophila melanogaster BII cell assay: EC50 = 1.3 x 10-7M |
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Permanent link to this datasheet: 29-NORSENGOSTERONE
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