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Year of first isolation: |
1996 |
| Formula: | C19H28O5 |
| Molecular weight: | 336 |
| Occurence in plants: |
Silene otites [Caryophyllaceae] »  ![Wikipedia: Silene otites [Caryophyllaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2O)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(CCC2O)O)C)C » 
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]2O)O)C)C »
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]2O)O)C)C »
| | IUPAC Name | (2S,3R,5S,9R,10R,13R,14R,17S)-2,3,14,17-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one (NB: for 17b-OH) | | CAS-RN | 19892-42-3 | | PubChem CID | 22213160 | InChiKey
[ ChemIDPlus: search ] | IHVPTRBJWKUCFE-IBKDVBTPSA-N | | InChI | InChI=1S/C19H28O5/c1-17-9-15(22)14(21)8-12(17)13(20)7-11-10(17)3-5-18(2)16(23)4-6-19(11,18)24/h7,10,12,14-16,21-24H,3-6,8-9H2,1-2H3/t10-,12+,14+,15-,16?,17+,18+,19+/m0/s1 |
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| CI-MS (NH3) m/z | 354 (MH+NH3)+, 337 (MH)+, 319, 308, 249, 231, 213 | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| C5D5N | | 01 | | | 02 | | | 03 | | | 04 | | | 05 | | | 06 | | | 07 | | | 08 | | | 09 | | | 10 | | | 11 | | | 12 | | | 13 | | | 14 | | | 15 | | | 16 | | | 17 | | | 18 | | | 19 | |
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| CD3OD | | 01-Ha | | | 01-He | | | 02-He | 3.96 (m, w1/2 = 8) | | 03-Ha | 3.57 (m, w1/2 = 22) | | 04-Ha | | | 04-He | | | 05-H | 2.38 (dd ) | | 07-H | 5.82 (d, 2.5) | | 09-Ha | 2.74 (m, w1/2 = 22) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 4.29 (dd, 8.8, 6.4) | | 18-Me | 0.71 (s ) | | 19-Me | 1.03 (s ) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | | | GLC | | | HPLC | NP-HPLC, column Zorbax-SIL (25 cm long, 4.6 mm i.d.), flow-rate 1 ml.min-1, solvent CH2Cl2-iPrOH-H2O (125:50:4), Ret 8.8 min (9.6 min for the 5beta isomer); solvent cyclohexane-iPrOH-H2O (100:40:3), Ret 23.1 min (20.6 min for the 5beta isomer). |
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Drosophila melanogaster BII cell assay: EC50 = 5.6 x 10-6M |
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Permanent link to this datasheet: (5α)-DIHYDRORUBROSTERONE
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