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Year of first isolation: |
1995 |
| Formula: | C28H40O9 |
| Molecular weight: | 520 |
| 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(COC1=O)CC(=O)C(C)(C2CCC3(C2(C(CC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)O)C)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]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)C » 
| | IUPAC Name | (4S)-4-[(3R)-3-hydroxy-2-oxo-3-[(9R,10R,13S,14R,17S)-2,3,12,14-tetrahydroxy-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 | 129681947 | InChiKey
[ ChemIDPlus: search ] | UYTJADWYDZXNQA-WUOSKBNASA-N | | InChI | InChI=1S/C28H40O9/c1-13-14(12-37-24(13)34)7-23(33)27(4,35)21-5-6-28(36)16-8-18(29)17-9-19(30)20(31)11-25(17,2)15(16)10-22(32)26(21,28)3/h8,13-15,17,19-22,30-32,35-36H,5-7,9-12H2,1-4H3/t13?,14-,15+,17?,19?,20?,21+,22?,25-,26+,27-,28-/m1/s1 |
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| EI-MS m/z (relative intensity %) | | | HR-MS | | | MS (thermospray) m/z (negative ions) | 565 (M+HCOO)-, 547 M+HCOO-H2O). |
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| C5D5N | | 01 | 37.9 | | 02 | 67.9 | | 03 | 67.8 | | 04 | 32.3 | | 05 | 51.2 | | 06 | 203.3 | | 07 | 122.3 | | 08 | 163.1 | | 09 | 34.5 | | 10 | 38.8 | | 11 | 29.7 | | 12 | 70.9 | | 13 | 51.9 | | 14 | 85.9 | | 15 | 31.6 | | 16 | 22.9 | | 17 | 59.3 | | 18 | 12.2 | | 19 | 24.3 | | 20 | 78.9 | | 21 | 28.7 | | 22 | 219.0 | | 23 | 42.8 | | 24 | 39.7 | | 25 | 39.2 | | 26 | 179.4 | | 27 | 13.8 | | 28 | 71.4 |
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| C5D5N | | 01-Ha | 2.13 | | 01-He | 1.98 | | 02-Ha | 4.15 (m, w1/2=26) | | 03-He | 4.23 (m, w1/2=12) | | 04-Ha | 2.01 | | 04-He | 1.74 (t, 15.0) | | 05-H | 3.05 (dd, 13.0, 3.5) | | 07-H | 6.30 (d, 2.0) | | 09-H | 3.75 (m, w1/2=16) | | 11-Ha | 2.46 (m) | | 11-He | 1.92 | | 12-He | 5.04 | | 15-Ha | 2.16 | | 15-Hb | 1.94 | | 16-Ha | 2.81 (m) | | 16-Hb | 2.25 | | 17-H | 3.39 (t, 9.5) | | 18-Me | 0.77 (s) | | 19-Me | 1.10 (s) | | 21-Me | 1.56 (s) | | 22-H | ? | | 23-Ha | 3.63 (dd, 19.0, 3.5) | | 23-Hb | 3.30 (dd, 19.0, 10.0) | | 24-Ha | 2.65 (m) | | 25-H | 2.33 (dq, 11.0, 7.0) | | 27-Me | 1.18 (d, 7.0) | | 28-Ha | 4.78 (t, 8.5) | | 28-Hb | 3.84 (t, 8.5) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3394, 1754, 1705, 1652 | | 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. 29.3 min (20E 17.2 min). |
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Permanent link to this datasheet: 22-DEHYDRO-12-HYDROXY-29-NOR-CYASTERONE
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