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Year of first isolation: |
2001 |
| Formula: | C27H44O7 |
| Molecular weight: | 480 |
| Occurence in plants: |
Silene pseudotites [Caryophyllaceae] »  ![Wikipedia: Silene pseudotites [Caryophyllaceae]](/images/wikipedia.png)
Silene italica ssp. nemoralis [Caryophyllaceae] »
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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,5S,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 | 70686925 | InChiKey
[ ChemIDPlus: search ] | YLEGNIQHVUHHFM-ZLQPYAMRSA-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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| HR-MS | | | EI-MS m/z (relative intensity %) | | | CI-MS (NH3) m/z | |
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| CD3OD | | 01 | 78.3 | | 02 | 41.8 | | 03 | 68.4 | | 04 | 30.8 | | 05 | 52.3 | | 06 | 202.8 | | 07 | 123.0 | | 08 | 166.9 | | 09 | 48.1 | | 10 | 44.5 | | 11 | 25.1 | | 12 | 33.3 | | 13 | 48.8 | | 14 | 85.6 | | 15 | 32.3 | | 16 | 21.4 | | 17 | 50.8 | | 18 | 18.4 | | 19 | 7.9 | | 20 | 78.1 | | 21 | 21.1 | | 22 | 78.6 | | 23 | 27.5 | | 24 | 42.6 | | 25 | 71.5 | | 26 | 29.1 | | 27 | 29.8 |
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| D2O | | 01-Ha | 3.744 (dd, 11.9, 4.3) | | 02-Ha | | | 02-He | | | 03-He | 3.744 (tt, 11.6, 4.7) | | 04-Ha | | | 04-He | | | 05-H | 2.543 (dd, 12.5, 3.1) | | 07-H | 5.99 (d, 2.3) | | 09-H | 2.95 (s, br, w1/2 = 23) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.31 (t, 9.9) | | 18-Me | 0.863 (s) | | 19-Me | 0.844 (s) | | 21-Me | 1.224 (s) | | 22-H | 3.427 (d, 10.6) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.224 (s) | | 27-Me | 1.233 (s) |
| CD3OD | | 01-Ha | 3.655 (dd, 11.8, 4.3) | | 02-Ha | 1.94 | | 02-He | 1.46 | | 03-He | 3.59 (tt, 11.5, 4.6) | | 04-Ha | 2.055 (dm) | | 04-He | 1.34 (q, 12.5) | | 05-H | 2.31 (dd, 12.5, 3.35) | | 07-H | 5.84 (d, 2.7) | | 09-H | 2.955 (ddd, 11.7, 7.0, 2.6) | | 11-Ha | 2.42 (dm) | | 11-He | 1.69 | | 12-Ha | 2.115 (td, 13.1, 4.8) | | 12-He | 1.77 | | 15-Ha | 1.535 (dd, 10.5, 9.6) | | 15-Hb | 1.97 | | 16-Ha | 1.771 | | 16-Hb | 1.96 | | 17-H | 2.38 (dd, 9.9, 8.1) | | 18-Me | 0.895 (s) | | 19-Me | 0.84 (s) | | 21-Me | 1.184 (s) | | 22-H | 3.325 (dd, >8, 1.7) | | 23-Ha | 1.29 | | 23-Hb | 1.67 | | 24-Ha | 1.42 | | 24-Hb | 1.80 (td, 12.0, 4.8) | | 26-Me | 1.19 (s) | | 27-Me | 1.204 (s) |
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| M.P. | - °C ; | | [α]D26 | +4 ° (c 0.1 ; MeOH) | | IR (KBr) ν max (cm-1) | 3400, 1650 | | UV (EtOH) λ max (log ε) | 242 (4.13) ; |
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| HPLC | NP-HPLC, column Zorbax(r)-SIL 250 x 9.4 mm, solvent CH2Cl2-iPrOH-H2O (125:40:3, v/v/v), flow-rate 4 ml.min-1, Ret. 22.5 min (20E 18.5 min). | | GLC | | | HPTLC | | | TLC | |
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Permanent link to this datasheet: (5α)-2-DEOXYINTEGRISTERONE A
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