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Year of first isolation: |
1995 |
| Formula: | C29H42O10 |
| Molecular weight: | 550 |
| 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(=O)C(C)(C2CCC3(C2(C(CC4C3=CC(=O)C5(C4(CC(C(C5)O)O)C)O)O)C)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]2C[C@H]([C@]2([C@]1(CC[C@@H]2[C@](C)(C(=O)C[C@@H]1[C@H](OC(=O)[C@H]1C)C)O)O)C)O)O)C » 
| | IUPAC Name | (3S,4S,5R)-4-[(3R)-3-hydroxy-2-oxo-3-[(2S,3R,5S,9R,10R,12R,13S,14R,17S)-2,3,5,12,14-pentahydroxy-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 | 163090292 | InChiKey
[ ChemIDPlus: search ] | VVTNIYVMFHJMNV-LOMBWDJFSA-N | | InChI | InChI=1S/C29H42O10/c1-13-15(14(2)39-24(13)35)8-22(33)27(5,36)20-6-7-28(37)17-10-23(34)29(38)12-19(31)18(30)11-25(29,3)16(17)9-21(32)26(20,28)4/h10,13-16,18-21,30-32,36-38H,6-9,11-12H2,1-5H3/t13-,14+,15-,16-,18-,19+,20-,21+,25+,26-,27+,28+,29+/m0/s1 |
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| MS (thermospray) m/z (positive ions) | 551 (M+H)+, 533 (M+H-H2O)+, 515 (M+H-2H2O)+, 497 (M+H-3H2O)+, 479 (M+H-4H2O)+, 461 (M+H-5H2O)+ | | HR-MS | |
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| C5D5N | | 01 | 34.8 | | 02 | 67.8 | | 03 | 69.7 | | 04 | 35.8 | | 05 | 79.8 | | 06 | 200.7 | | 07 | 120.8 | | 08 | 163.6 | | 09 | 38.1 | | 10 | 45.1 | | 11 | 30.7 | | 12 | 70.8 | | 13 | 51.9 | | 14 | 85.8 | | 15 | 31.6 | | 16 | 23.0 | | 17 | 59.2 | | 18 | 12.1 | | 19 | 17.2 | | 20 | 79.0 | | 21 | 28.9 | | 22 | 218.5 | | 23 | 42.0 | | 24 | 45.8 | | 25 | 42.2 | | 26 | 178.7 | | 27 | 14.7 | | 28 | 79.8 | | 29 | 20.3 |
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| C5D5N | | 01-Ha | 2.22 | | 01-He | 2.05 | | 02-Ha | 4.25 | | 03-He | 4.17 m, w1/2=12) | | 04-Ha | 1.98 | | 04-He | 1.98 | | 05-H | ? | | 07-H | 6.33 (d, 2.5) | | 09-H | 3.81 (m, w1/2=24) | | 11-Ha | 2.50 | | 11-He | 2.00 | | 12-He | 5.02 | | 15-Ha | 2.13 | | 15-Hb | 1.96 | | 16-Ha | 2.81 (m) | | 16-Hb | 2.25 | | 17-H | 3.39 (t, 10) | | 18-Me | 0.83 (s) | | 19-Me | 1.18 (s) | | 21-Me | 1.57 (s) | | 22-H | ? | | 23-Ha | 3.56 (dd, 19.0, 5.0) | | 23-Hb | 3.32 (dd, 19.0, 6.0) | | 24-Ha | 2.41 | | 25-H | 2.54 (dq, 11.0, 7.0) | | 27-Me | 1.31 (d, 7) | | 28-H | 4.25 (dq 8.5, 6.0) | | 29-Me | 1.41 (d, 6) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3405, 1755, 1706, 1674 | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | | | GLC | | | HPLC | RP-HPLC, column Spherisorb ODS-2, 10 ?m, 300 x 7.8 mm, flow-rate 3 ml.min-1, solvent iPrOH-H2O 1:5.6, temp. 23°C, Ret. 51.5 min (20E 17.2 min). |
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Drosophila melanogaster BII cell assay: EC50 = 2.7 x 10-6M |
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Permanent link to this datasheet: 22-DEHYDRO-12-HYDROXY-SENGOSTERONE
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