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Year of first isolation: |
1994 |
| Formula: | C27H44O9 |
| Molecular weight: | 512 |
| Occurence in plants: |
Polypodium vulgare [Polypodiaceae] »  ![Wikipedia: Polypodium vulgare [Polypodiaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4(C3(CC(C(C4)O)O)C)O)C1(CCC2C(C)(C(CC(C(C)(C)O)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](C[C@@H](C(C)(C)O)O)O)O)O)C)O)C » 
| | IUPAC Name | (2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R,5S)-2,3,5,6-tetrahydroxy-6-methylheptan-2-yl]-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 102004055 | InChiKey
[ ChemIDPlus: search ] | VTQDNMCNLAYGSH-PFENJZEKSA-N | | InChI | InChI=1S/C27H44O9/c1-22(2,33)19(30)11-20(31)25(5,34)18-7-9-26(35)15-10-21(32)27(36)13-17(29)16(28)12-24(27,4)14(15)6-8-23(18,26)3/h10,14,16-20,28-31,33-36H,6-9,11-13H2,1-5H3/t14-,16-,17+,18-,19-,20+,23+,24+,25+,26+,27+/m0/s1 |
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| MS (thermospray) m/z (positive ions) | 530 (M+NH4)+, 513 (M+H)+, 495 (M+H-H2O)+, 477 (M+H-2H2O)+, 459 (M+H-3H2O)+ | | HR-MS | |
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| C5D5N | | 01 | 34.85 | | 02 | 67.99 | | 03 | 69.90 | | 04 | 35.99 | | 05 | 79.93 | | 06 | 201.01 | | 07 | 119.92 | | 08 | 166.85 | | 09 | 38.29 | | 10 | 44.77 | | 11 | 22.01 | | 12 | 32.02 | | 13 | 48.12 | | 14 | 83.96 | | 15 | 31.65 | | 16 | 21.44 | | 17 | 49.92 | | 18 | 17.91 | | 19 | 17.23 | | 20 | 76.74 | | 21 | 21.79 | | 22 | 78.33 | | 23 | 32.95 | | 24 | 80.37 | | 25 | 72.27 | | 26 | 27.00 * | | 27 | 25.27 * |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.26 | | 03-He | 4.17 | | 04-Ha | | | 04-He | | | 07-H | 6.26 (d, 2.4) | | 09-Ha | 3.61 (d, 9.6) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.98 (t, 8.4) | | 18-Me | 1.19 (s ) | | 19-Me | 1.15 (s ) | | 21-Me | 1.61 (s ) | | 22-H | 4.25 (d, 10.5) | | 23-Ha | | | 23-Hb | | | 24-H | 4.09 (d, 9.3) | | 26-Me | 1.47 (s )* | | 27-Me | 1.52 (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 | RP-HPLC, Retention time 7.02 min [column ODS2, 5 ?m, 15 cm long, 4.6 mm i.d., eluted with ACN-iPrOH-H2O 3:4:53 at 55°C and 1.2 ml.min-1) (E 30.72 min, 20E 10.98 min) |
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Drosophila melanogaster BII cell assay: EC50 = 2.3 x 10-8M |
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Permanent link to this datasheet: 5-HYDROXYABUTASTERONE
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