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Year of first isolation: |
1992 |
| Formula: | C29H42O8 |
| Molecular weight: | 518 |
| Occurence in plants: |
Ajuga iva [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Ajuga iva [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(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)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]2CC[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)C » 
| | IUPAC Name | (3S,4S,5R)-4-[(3R)-3-hydroxy-2-oxo-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]-3,5-dimethyloxolan-2-one | | CAS-RN | | | PubChem CID | 44566366 | InChiKey
[ ChemIDPlus: search ] | RTGDGVVYWQUBLM-ROUKFCEHSA-N | | InChI | InChI=1S/C29H42O8/c1-14-16(15(2)37-25(14)34)10-24(33)28(5,35)23-7-9-29(36)18-11-20(30)19-12-21(31)22(32)13-26(19,3)17(18)6-8-27(23,29)4/h11,14-17,19,21-23,31-32,35-36H,6-10,12-13H2,1-5H3/t14-,15+,16-,17-,19-,21+,22-,23-,26+,27+,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z | 536 (M+H+NH3)+, 519 (M+H)+, 501 (M+H-18)+, 380 (M+H+NH3-C22--C29)+, 363 (M+H-C22--C29)+, 345 (M+H-C22--C29-18)+ | | EI-MS m/z (relative intensity %) | |
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| C5D5N | | 01 | | | 02 | | | 03 | | | 04 | | | 05 | | | 06 | | | 07 | | | 08 | | | 09 | | | 10 | | | 11 | | | 12 | | | 13 | | | 14 | | | 15 | | | 16 | | | 17 | | | 18 | | | 19 | | | 20 | | | 21 | | | 22 | | | 23 | | | 24 | | | 25 | | | 26 | | | 27 | | | 28 | | | 29 | |
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| CD3OD | | 01-Ha | | | 01-Hb | | | 02-Ha | 3.83 (m, w1/2=22) | | 03-He | 3.95 (m, w1/2=8) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.8 (d, 2.5) | | 09-Ha | 3.16 (m, w1/2=22) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.64 (7,9) | | 18-Me | 0.87 (s) | | 19-Me | 0.96 (s) | | 21-Me | 1.39 (s) | | 23-Ha | 2.9 (dd, 18, 6) | | 23-Hb | 2.98 (dd, 18, 5.6) | | 24-H | | | 25-H | 2.5 (m) | | 26-Me | 1.19 (d, 7) | | 28-H | 4.22 (dq, 9, 6) | | 29-Me | 1.42 (d, 6) |
| D2O | | 01-Ha | 1.4 | | 01-Hb | 1.85 | | 02-Ha | 3.99 (m, w1/2=22) | | 03-He | 4.07 (m, w1/2=8) | | 04-Ha | 1.75 | | 04-He | 1.75 | | 05-H | 2.36 | | 07-H | 5.96 (d, 2.5) | | 09-Ha | 3.12 (m, w1/2=22) | | 11-Ha | 1.7 | | 11-He | 1.8 | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.87 (s) | | 19-Me | 1.00 (s) | | 21-Me | 1.49 (s) | | 23-Ha | 2.95 | | 23-Hb | 2.95 | | 24-H | 2.35 | | 25-H | 2.6 (m) | | 26-Me | 1.20 (d, 7) | | 28-H | 4.39 (dq, 9, 6) | | 29-Me | 1.42 (d, 6) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 1750 (gama-lactone), 1702 (CO), 1652 (cyclohexenone) ; | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | | | GLC | | | HPLC | 1-Retention time 13.6 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O, 125:25:2 v/v/v, flow-rate 1 ml.min-1] (20E : 45.6 min); 2-Retention time 8.2 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:40:3 v/v/v, flow-rate 1 ml.min-1] (20E : 16.9 min); 3-Retention time 35.4 min [Waters Novapak C18, 100 mm x 8 mm i.d., solvent CH3CN-1? trifluoroacetic acid in H2O 23:77 v/v, flow-rate 1 ml.min-1] (20E : 5.7 min) |
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Permanent link to this datasheet: 22-OXOCYASTERONE
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