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Year of first isolation: |
2013 |
| Formula: | C27H42O6 |
| Molecular weight: | 462 |
| Occurence in plants: |
Vitex doniana [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Vitex doniana [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(C1CCC2(C1(CC(C3C2=CC(=O)C4C3(CC(C(C4)O)O)C)O)C)O)C5CCC(O5)(C)C | 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]2[C@H](C[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@H]1CCC(O1)(C)C)O)C)O)C » 
| | IUPAC Name | (2S,3R,5R,10R,11S,13R,14S,17R)-17-[(1S)-1-[(2S)-5,5-dimethyloxolan-2-yl]ethyl]-2,3,11,14-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 71533239 | InChiKey
[ ChemIDPlus: search ] | JNZGVPFIDQLKCF-AADHXZMHSA-N | | InChI | InChI=1S/C27H42O6/c1-14(22-7-8-24(2,3)33-22)15-6-9-27(32)17-11-18(28)16-10-19(29)20(30)12-25(16,4)23(17)21(31)13-26(15,27)5/h11,14-16,19-23,29-32H,6-10,12-13H2,1-5H3/t14-,15+,16-,19+,20-,21-,22-,23?,25-,26+,27+/m0/s1 |
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| HRESI-MS (ToF) | m/z 463.3591 (calc. 453.3454 [M+H]+, 485.2652 (calc. 485.2636 [M+Na]+) | | ESI-MS m/z (relative intensity %) | 463 [M+H]+ (60), 445 [M+H-H2O]+ (100), 427 [M+H-2H2O]+ (30), 409 [M+H-3H2O]+ (60) |
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| CD3OD | | 01 | 39.4 | | 02 | 71.4 | | 03 | 68.8 | | 04 | 33.1 | | 05 | 51.9 | | 06 | 206.9 | | 07 | 121.7 | | 08 | 168.6 | | 09 | 42.5 | | 10 | | | 11 | 76.3 | | 12 | 43.5 | | 13 | | | 14 | 85.3 | | 15 | 32.4 | | 16 | 21.7 | | 17 | 50.6 | | 18 | 18.2 | | 19 | 24.5 | | 20 | 35.2 | | 21 | 21.2 | | 22 | 85.0 | | 23 | 29.7 | | 24 | 37.3 | | 25 | 79.5 | | 26 | 27.5 | | 27 | 27.3 |
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| CD3OD | | 01-Ha | 1.25-1.34 (m) | | 01-He | 2.49 (m) | | 02-Ha | 4.44 (m, w1/2=5.5) | | 03-He | 4.35 (m, w1/2=2.5) | | 04-Ha | 1.70-1.72 (m) | | 04-He | 1.70-1.72 (m) | | 05-H | 2.26 (dd, 13.1, 3.5) | | 07-H | 5.62 (d, 1.5) | | 09-H | 3.14 (m, w1/2=10) | | 11-Ha | 4.32 (m, w1/2=2.5) | | 12-H | 2.25 (dd, 12.5, 10.4), 2.23 (dd, 12.4, 6.0) | | 15-Ha | 1.47-1.49 (m) | | 15-Hb | 1.90-2.00 (m) | | 16-Ha | 1.58-1.60 (m) | | 16-Hb | 1.49-1.50 (m) | | 17-H | 2.52 (dd, 9.6, 8.5) | | 18-Me | 0.80 (s) | | 19-Me | 0.83 (s) | | 20-H | 2.44 (m) | | 21-Me | 0.92 (d, 6.5) | | 22-H | 3.75 (m) | | 23-Ha | 1.70-1.72 (m) | | 23-Hb | 1.97-2.00 (m) | | 24-Ha | 1.72-1.74 (m) | | 24-Hb | 1.72-1.74 (m) | | 26-Me | 1.05 (s) | | 27-Me | 1.01 (s) |
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| M.P. | 258-262 °C ; | | [α]D20 | ° (c ; MeOH) | | IR (KBr) ν max (cm-1) | 3427, 2832, 1654, 1059 | | UV (MeOH) λ max (log ε) | 241 (3.54) ; |
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Permanent link to this datasheet: 11β-HYDROXY-20-DEOXYSHIDASTERONE
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