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Year of first isolation: |
1990 |
| Formula: | C21H32O5 |
| Molecular weight: | 364 |
| 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 | CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)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]2C(C)O)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]2C(C)O)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]2C(C)O)O)C)C »
| | IUPAC Name | (2S,3R,5R,10R,13R,14S,17S)-2,3,14-trihydroxy-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 138453982 | InChiKey
[ ChemIDPlus: search ] | OIUWMPRXGZDPKO-ZDCYWFNZSA-N | | InChI | InChI=1S/C21H32O5/c1-11(22)12-5-7-21(26)14-8-16(23)15-9-17(24)18(25)10-19(15,2)13(14)4-6-20(12,21)3/h8,11-13,15,17-18,22,24-26H,4-7,9-10H2,1-3H3/t11?,12-,13+,15+,17-,18+,19-,20-,21-/m1/s1 |
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| CI-MS (NH3) m/z | 382 (MH+NH3)+, 365 (MH)+, 347, 345 | | 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 | | | 20 | | | 21 | |
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| CD3OD | | 01-Ha | 1.42 (dd, 13, 12) | | 01-Hb | | | 02-Ha | 3.84 (m ) | | 03-He | 3.95 (m, w1/2 = 8) | | 04-Ha | | | 04-He | | | 05-H | 2.38 (dd, 12, 5) | | 07-H | 5.82 (d, 2.5) | | 09-Ha | 3.14 (m, w1/2 = 22) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.69 (s ) | | 19-Me | 0.96 (s ) | | 20-CH-OH | ~ 3.65 (m ) | | 21-Me | 1.22 (d, 6.5) |
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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 | 1- Retention time 14.7 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 : 16.8 min); 2-Retention time 26.8 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 37.4 min) |
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Drosophila melanogaster BII cell assay: EC50 = 7.4 x 10-4M and 1.2 x 10--4M (two epimers) |
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Permanent link to this datasheet: DIHYDROPOSTSTERONE
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