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Year of first isolation: |
1990 |
| Formula: | C27H44O7 |
| Molecular weight: | 480 |
| Occurence in plants: |
Silene otites [Caryophyllaceae] »  ![Wikipedia: Silene otites [Caryophyllaceae]](/images/wikipedia.png)
Silene italica ssp. nemoralis [Caryophyllaceae] »
Silene viridiflora [Caryophyllaceae] »
Aerva javanica [Amaranthaceae] »
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(C(CC(C4)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | [C@@H]1([C@]2([C@@H](C[C@H](C1)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)C)O » 
| | IUPAC Name | (1R,3R,5R,9R,10R,13R,14S,17S)-1,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 101142458 | InChiKey
[ ChemIDPlus: search ] | YLEGNIQHVUHHFM-MVXUZTRZSA-N | | InChI | InChI=1S/C27H44O7/c1-23(2,32)9-8-21(30)26(5,33)20-7-11-27(34)17-14-19(29)18-12-15(28)13-22(31)25(18,4)16(17)6-10-24(20,27)3/h14-16,18,20-22,28,30-34H,6-13H2,1-5H3/t15-,16+,18+,20+,21-,22-,24-,25-,26-,27-/m1/s1 |
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| CI-MS (NH3) m/z | 498 (M+H+NH3)+, 481 (MH)+, 463, 445, 427, 380, 363, 347, 345. | | EI-MS m/z (relative intensity %) | 480 [M]+, 438 (2), 363 (75), 345 (100), 319 (70), 301 (11), 283 (6), 161 (5), 117 (4), 99 (6), 81 (12) | | HR-MS | 480.3082 |
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| CD3OD | | 01 | 72.6 | | 02 | | | 03 | 68.7 | | 04 | | | 05 | 47.8 | | 06 | | | 07 | 122.3 | | 08 | 168.0 | | 09 | | | 10 | 42.3 | | 11 | 21.7 | | 12 | 32.5 | | 13 | 49.1 | | 14 | 85.5 | | 15 | | | 16 | 21.7 | | 17 | 50.7 | | 18 | 18.2 | | 19 | 20.0 | | 20 | 78.1 | | 21 | 21.1 | | 22 | 78.6 | | 23 | 27.5 | | 24 | 42.5 | | 25 | 71.5 | | 26 | 29.1 | | 27 | 29.8 |
| DMSO | | 01 | 66.9 | | 02 | 37.0 | | 03 | 66.0 | | 04 | 32.0 | | 05 | 49.1 | | 06 | 203.6 | | 07 | 121.7 | | 08 | 166.0 | | 09 | 34.9 | | 10 | 38.0 | | 11 | 22.1 | | 12 | 31.2 | | 13 | 47.0 | | 14 | 83.6 | | 15 | 30.8 | | 16 | 20.5 | | 17 | 49.5 | | 18 | 18.5 | | 19 | 23.2 | | 20 | 76.4 | | 21 | 21.0 | | 22 | 77.0 | | 23 | 26.3 | | 24 | 42.3 | | 25 | 69.0 | | 26 | 30.2 | | 27 | 29.9 |
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| D2O | | 01-He | 3.68 (m br, 20°C; dd, 4, 8, 80°C) | | 02-Ha | | | 03-He | 3.70 (m br, 20°C); 3.87 (m, br, 80°C) | | 04-Ha | | | 04-He | | | 05-H | 2.76 (m br, 20°C; dd, 4, 8, 80°C) | | 07-H | 5.94 (d, 2.5, 80°C) | | 09-Ha | 3.23 (m br, 20°C; 3.19, m, w1/2=22, 80°C) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.36 (br, 20°C), 2.34 (t, 8.5, 80°C) | | 18-Me | 0.85 (s ) | | 19-Me | 1.10 (s ) | | 21-Me | 1.22 (s ) | | 22-H | 3.43 (dd, 11, 2, 80°C) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.23 (s ) | | 27-Me | 1.24 (s ) |
| DMSO | | 01-He | 3.64 | | 02-Ha | 1.50 (m), 1.31 (m) | | 03-He | 3.68 | | 04-Ha | 1.58 (m) | | 04-He | 1.49 (m) | | 05-H | 2.17 (dd, 3.6, 13.2) | | 07-H | 5.63 (m) | | 09-Ha | 2.96 (t, 9.2) | | 11-Ha | 1.49 (m) | | 11-He | 1.66 (m) | | 12-Ha | 2.03 (m) | | 12-He | 1.70 (m) | | 15-Ha | 1.84 (m) | | 15-Hb | 1.56 (m) | | 16-Ha | 1.90 (m) | | 16-Hb | 1.55 (m) | | 17-H | 2.25 (t, 9.2) | | 18-Me | 0.74 (s) | | 19-Me | 0.86 (s) | | 20-H | | | 21-Me | 1.05 (s) | | 22-H | 3.12 (t, 8.2) | | 23-Ha | 1.44 (m) | | 23-Hb | 1.00 (m) | | 24-Ha | 1.61 (m) | | 24-Hb | 1.30 (m) | | 26-Me | 1.05 (s) | | 27-Me | 1.02 (s) |
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| M.P. | | | [α]D20 | +20,1° (c 0.02, CHCl3) | | IR (KBr) ν max (cm-1) | 3460, 1645, 1620, | | UV (EtOH) λ max (log ε) | MeOH; 242 (4.06) |
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| HPTLC | | | TLC | | | GLC | | | HPLC | NP-HPLC, Retention time 13.5 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); Retention time 32.1 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 = 7.0 x 10-6M |
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| First isolation | GIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 |
 | | General | MENG, Y. et al. (2001) J. Chromatogr. A 935, 309-319 |
| | General | BÁTHORI, M. et al. (2002) Biomed. Chromatogr. 16, 373-378 |
| | Bioactivities | DINAN, L. et al. (2005) In: Comprehensive Molecular Insect Science (eds. L. I. Gilbert, C. Iatrou, S. Gill), Elsevier, Oxford, III, 197-242 |
| | General | SIMON, A. et al. (2008) Helv. Chim. Acta 91, 1640-1645 |
| | Identification | SALEEM, M. et al. (2013) Steroids 120, 1098-1102 |
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Permanent link to this datasheet: 2-DEOXYINTEGRISTERONE A
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