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Year of first isolation: |
1996 |
| Formula: | C29H44O8 |
| Molecular weight: | 520 |
| 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 | | 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@H](O)C[C@@H]1CCOC(=O)C1C)O)O)C)C » 
| | IUPAC Name | (4S)-4-((2R,3R)-2,3-dihydroxy-3-((2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)butyl)-3-methyltetrahydro-2H-pyran-2-one | | CAS-RN | | | PubChem CID | | InChiKey
[ ChemIDPlus: search ] | RIEJYAPWEYTGAC-NFVVRSECSA-N | | InChI | InChI=1S/C29H44O8/c1-15-16(7-10-37-25(15)34)11-24(33)28(4,35)23-6-9-29(36)18-12-20(30)19-13-21(31)22(32)14-26(19,2)17(18)5-8-27(23,29)3/h12,15-17,19,21-24,31-33,35-36H,5-11,13-14H2,1-4H3/t15?,16-,17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z | MS (Thermospray) m/z (relative intensity %) | | EI-MS m/z (relative intensity %) | | | MS (thermospray) m/z (relat. intensity %) | 521 (M+H)+ (38), 503 (M+H-H2O)+ (100) | | MS (thermospray) m/z (negative ions) | 565 M+HCOO)- (100), 547 M+HCOO-H2O) (55) |
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| C5D5N | | 01 | 37.9 | | 02 | 68.1 | | 03 | 68.0 | | 04 | 32.4 | | 05 | 51.4 | | 06 | 203.5 | | 07 | 121.6 | | 08 | 166.0 | | 09 | 34.4 | | 10 | 38.6 | | 11 | 21.0 | | 12 | 32.0 | | 13 | 48.1 | | 14 | 84.0 | | 15 | 31.6 | | 16 | 21.3 | | 17 | 49.8 | | 18 | 17.8 | | 19 | 24.4 | | 20 | 76.8 | | 21 | 21.1 | | 22 | 75.7 | | 23 | 36.9 | | 24 | 37.8 | | 25 | 41.2 | | 26 | 174.8 | | 27 | 16.5 | | 28 | 29.6 | | 29 | 67.2 |
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| C5D5N | | 01-Ha | 2.13 | | 01-He | 1.93 | | 02-Ha | 4.19 | | 03-He | 4.25 | | 04-Ha | 2.05 | | 04-He | 1.81 | | 05-H | 3.03 (m, w1/2=23) | | 07-H | 6.27 (d, 2.1) | | 09-H | 3.60 (m, w1/2=22) | | 11-Ha | 1.89 | | 11-He | 1.74 | | 12-Ha | 2.61 | | 12-He | 2.04 | | 15-Ha | | | 15-Hb | | | 16-Ha | 2.40 (m) | | 16-Hb | 1.98 | | 17-H | 2.86 (t, 9.1) | | 18-Me | 1.22 (s) | | 19-Me | 1.06 (s) | | 21-Me | 1.56 | | 22-H | 3.89 (m, w1/2=18) | | 23-Ha | 1.88 | | 23-Hb | 1.57 | | 24-H | 1.94 | | 25-H | 2.56 | | 27-Me | 1.39 (d, 6.9) | | 28-Ha | 2.04 | | 28-Hb | 1.82 | | 29-Ha | 4.26 | | 29-Hb | 4.14 |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3416 (OH), 1718 (delta-lactone), 1654 (cyclohexenone) | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | silicagel, successive elution with AcOEt:MeOH 100:8 and 8:1.2 | | GLC | | | HPLC | RP-HPLC, column Tracer 15x1 cm packed with Spherisorb-ODS2 5?m, solvent iPrOH-H2O (10:90), flow-rate 3 mL.min-1, 35°C, Ret 25.21 min. |
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Permanent link to this datasheet: REPTANSTERONE
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