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Year of first isolation: |
1990 |
| Formula: | C27H44O7 |
| Molecular weight: | 480 |
| Occurence in plants: |
Silene nutans [Caryophyllaceae] »  ![Wikipedia: Silene nutans [Caryophyllaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | [C@@H]1([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)(CCCC(C)(C)O)O)O)C)C)O » 
| | IUPAC Name | (1S,2R,3R,5S,9R,10R,13R,14S,17S)-17-((S)-2,6-dihydroxy-6-methylheptan-2-yl)-1,2,3,14-tetrahydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | | InChiKey
[ ChemIDPlus: search ] | MXVMNRFIIZOGBE-CWQJGELWSA-N | | InChI | InChI=1S/C27H44O7/c1-23(2,32)9-6-10-25(4,33)20-8-12-27(34)16-13-18(28)17-14-19(29)21(30)22(31)26(17,5)15(16)7-11-24(20,27)3/h13,15,17,19-22,29-34H,6-12,14H2,1-5H3/t15-,17+,19+,20-,21+,22+,24+,25-,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | 498, 491 (MH)+, 463, 445, 427, 409, 380, 363, 347 | | 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 | | | 22 | | | 23 | | | 24 | | | 25 | | | 26 | | | 27 | | | 28 | | | 29 | |
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| D2O | | 01-Ha | 3.73 (d, 3.5) | | 01-He | -- | | 02-He | 3.94 (m, w1/2=8) | | 03-He | 3.71 (m, w1/2=18) | | 04-Ha | 1.65 | | 04-He | 1.86 | | 05-H | 2.56 (dd, 11, 7.2) | | 07-H | 6.00 (d, 2.5) | | 09-Ha | 2.91 (m, w1/2=21) | | 11-Ha | 1.78 | | 11-He | 2.28 (m ) | | 12-Ha | 2.26 | | 12-He | 1.88 | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.28 (m ) | | 18-Me | 0.81 (s ) | | 19-Me | 0.93 (s ) | | 21-Me | 1.29 (s ) | | 22-Ha | | | 22-Hb | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.22 (s ) | | 27-Me | 1.22 (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 | 1- Retention time 17.6 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 40.4 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 = 8.0 x 10-8M |
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Permanent link to this datasheet: (5α)-22-DEOXYINTEGRISTERONE A
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