|
|
|
|
Year of first isolation: |
1995 |
| Formula: | C28H40O10 |
| Molecular weight: | 536 |
| Occurence in plants: |
Ajuga reptans var. atropurpurea [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Ajuga reptans var. atropurpurea [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
|
| Occurence in animals: |
|
|
|
| |
| Canonical SMILES | CC1C(COC1=O)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]1COC(=O)[C@H]1C)O)O)C)O)O)C » 
| | IUPAC Name | (4S)-4-[(3R)-3-hydroxy-2-oxo-3-[(9R,10R,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-methyloxolan-2-one | | CAS-RN | | | PubChem CID | 129681967 | InChiKey
[ ChemIDPlus: search ] | ZYFVAVXYLVLPRL-MNVOMPJFSA-N | | InChI | InChI=1S/C28H40O10/c1-13-14(12-38-23(13)34)7-21(32)26(4,35)19-5-6-27(36)16-9-22(33)28(37)11-18(30)17(29)10-24(28,2)15(16)8-20(31)25(19,27)3/h9,13-15,17-20,29-31,35-37H,5-8,10-12H2,1-4H3/t13?,14-,15+,17?,18?,19+,20?,24-,25+,26-,27-,28?/m1/s1 |
| |
| MS (thermospray) m/z (positive ions) | 537 (M+H)+, 519 (M+H-H2O)+, 501 (M+H-2H2O)+, 483 (M+H-3H2O)+, 465 (M+H-4H2O)+ | | HR-MS | |
|
|
| C5D5N | | 01 | 34.8 | | 02 | 67.7 | | 03 | 69.7 | | 04 | 35.8 | | 05 | 79.8 | | 06 | 200.7 | | 07 | 120.8 | | 08 | 163.6 | | 09 | 38.1 | | 10 | 45.2 | | 11 | 30.7 | | 12 | 70.8 | | 13 | 51.9 | | 14 | 85.7 | | 15 | 31.6 | | 16 | 22.9 | | 17 | 59.2 | | 18 | 12.3 | | 19 | 17.2 | | 20 | 78.9 | | 21 | 28.8 | | 22 | 219.0 | | 23 | 42.8 | | 24 | 39.7 | | 25 | 39.2 | | 26 | 179.4 | | 27 | 13.8 | | 28 | 71.4 |
|
| C5D5N | | 01-Ha | 2.25 | | 01-He | 2.10 | | 02-Ha | 4.25 (m, w1/2=25) | | 03-He | 4.19 (m, w1/2=16) | | 04-Ha | 2.00 | | 04-He | 2.00 | | 05-H | ? | | 07-H | 6.33 (d, 3.5) | | 09-H | 3.82 (m, w1/2=16) | | 11-Ha | 2.49 (m) | | 11-He | 1.99 | | 12-He | 5.02 | | 15-Ha | 2.11 | | 15-Hb | 1.94 | | 16-Ha | 2.81 (m) | | 16-Hb | 2.25 | | 17-H | 3.37 (t, 9.5) | | 18-Me | 0.76 (s) | | 19-Me | 1.20 (s) | | 21-Me | 1.56 (s) | | 22-H | ? | | 23-Ha | 3.64 (dd, 19.0, 3.5) | | 23-Hb | 3.30 (dd, 19.0, 10.0) | | 24-Ha | 2.64 (m) | | 25-H | 2.34 (dq, 7) | | 27-Me | 1.19 (d, 7) | | 28-Ha | 4.78 (t, 8.5) | | 28-Hb | 3.85 (t, 8.5) |
|
| |
| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3416, 1759, 1709, 1674 | | UV (EtOH) λ max (log ε) | |
| |
| 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. 23.1 min (20E 17.2 min). |
| |
Drosophila melanogaster BII cell assay: EC50 = 1.3 x 10-5M |
| |
| |
Permanent link to this datasheet: 22-DEHYDRO-12-HYDROXY-29-NOR-SENGOSTERONE
|
|
