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Year of first isolation: |
1995 |
| Formula: | C28H46O8 |
| Molecular weight: | 510 |
| Occurence in plants: |
Paxillus atrotomentosus [Fungi] »  ![Wikipedia: Paxillus atrotomentosus [Fungi]](/images/wikipedia.png)
Ajuga turkestanica [Lamiaceae (alt. Labiatae)] »
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| Occurence in animals: |
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| Canonical SMILES | CC(CC(C(C)(C1CCC2(C1(CC(C3C2=CC(=O)C4C3(CC(C(C4)O)O)C)O)C)O)O)O)C(C)(C)O | 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@](C)([C@@H](CC(C(C)(C)O)C)O)O)O)C)O)C » 
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@](C)([C@@H](C[C@H](C(C)(C)O)C)O)O)O)C)O)C »
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@](C)([C@@H](C[C@@H](C(C)(C)O)C)O)O)O)C)O)C »
| | IUPAC Name | (2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R,5S)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 15839570 | InChiKey
[ ChemIDPlus: search ] | FSNRQNKYLJDXMZ-APCZMLFGSA-N | | InChI | InChI=1S/C28H46O8/c1-14(24(2,3)34)9-22(33)27(6,35)21-7-8-28(36)16-11-17(29)15-10-18(30)19(31)12-25(15,4)23(16)20(32)13-26(21,28)5/h11,14-15,18-23,30-36H,7-10,12-13H2,1-6H3/t14-,15-,18+,19-,20+,21-,22+,23+,25-,26+,27+,28+/m0/s1 |
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| FAB-MS m/z | 533 (M+Na)+ (2), 511 (M+H)+ (4), 493 (12), 475 (13), 457 (11), 439 (3), 387 (2), 379 (2), 373 (2), 362 (4), 345 (5), 317 (6), 299 (9), 281 (5), 249 (7), 225 (8), 213 (10), 197 (12), 181 (23), 157 (25), 113 (75), 93 (100), 83 (71), 69 (70), 57 (95) | | HRESI-MS | 533.30800 [M+Na], expected 533.30849 for C28H46O8Na | | ESI-MS m/z | 511 [M+H], 493 [MH-H2O], 475 [MH-2H2O], 457 [MH-3H2O], 439 [MH-4H2O] |
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| CD3OD | | 01 | 39.07 | | 02 | 68.94 | | 03 | 68.56 | | 04 | 33.28 | | 05 | 52.78 | | 06 | 206.72 | | 07 | 122.78 | | 08 | 165.70 | | 09 | 42.93 | | 10 | 39.90 | | 11 | 69.50 | | 12 | 43.75 | | 13 | a | | 14 | 84.95 | | 15 | 31.83 | | 16 | 21.61 | | 17 | 50.20 | | 18 | 18.85 | | 19 | 24.60 | | 20 | 77.96 | | 21 | 20.66 | | 22 | 77.88 | | 23 | 35.12 | | 24 | 44.42 | | 25 | 74.07 | | 26 | 28.19 | | 27 | 25.86 | | 28 | 16.89 |
| D2O | | 01 | 39.1 | | 02 | 69.3 | | 03 | 69.3 | | 04 | 33.7 | | 05 | 53.4 | | 06 | 210.4 | | 07 | 123.9 | | 08 | 167.6 | | 09 | 43.4 | | 10 | 40.7 | | 11 | 70.3 | | 12 | 43.9 | | 13 | 49.4 | | 14 | 86.6 | | 15 | 32.4 | | 16 | 22.0 | | 17 | 50.8 | | 18 | 19.7 | | 19 | 25.3 | | 20 | 80.2 | | 21 | 21.5 | | 22 | 76.1 | | 23 | 35.2 | | 24 | 42.0 | | 25 | 76.4 | | 26 | 27.3 | | 27 | 27.7 | | 28 | 15.1 |
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| CD3OD | | 01-Ha | 1.38 (dd, 13.0, 12.0) | | 01-He | 2.59 (dd, 13.0, 4.2) | | 02-Ha | 4.01 (ddd, 12.0, 4.2, 3.5) | | 03-He | 3.96 (q ) | | 04-Ha | 1.78 (dt, 14.0, 13.2, 2.5) | | 04-He | 1.68 (dt, 14.0, 4.0, 2.5) | | 05-H | 2.34 (dd, 13.2, 4.0) | | 07-H | 5.80 (dd, 2.7, 0.8) | | 09-H | 3.14 (dd, 8.8, 2.7) | | 11-Ha | 4.10 (ddd, 10.5, 8.8, 6.0) | | 12-Ha | 2.21 (dd, 12.2, 10.5) | | 12-He | 2.15 (dd, 12.2, 6.0) | | 15-Ha | 1.95 | | 15-Hb | 1.57 | | 16-Ha | 2.00 | | 16-Hb | 1.79 | | 17-H | 2.42 (dd, 9.6, 8.6) | | 18-Me | 0.874 (s ) | | 19-Me | 1.056 (s ) | | 21-Me | 1.195 (s ) | | 22-H | 3.47 (dd, 9.4, 2.0) | | 23-Ha | 1.86 (ddd, 14.4, 4.2, 2.0) | | 23-Hb | 1.05 | | 24-H | 1.65 (dp, 4.2, 7.0, 7.0, 7.0, 7.0) | | 26-Me | 1.142 (s ) | | 27-Me | 1.211 (s ) | | 28-Me | 1.034 (d, 7.0) |
| D2O | | 01-Ha | 1.39 (t, 13) | | 01-He | 2.48 (dd, 13, 3.7) | | 02-Ha | 4.09 (m, w1/2 =11) | | 03-He | 4.09 (m, w1/2 =11) | | 04-Ha | 1.74 | | 04-He | 1.79 | | 05-H | 2.31 | | 07-H | 5.98 (d, 2.6) | | 09-Ha | 3.13 (dd, 8.8, 3.6) | | 11-Ha | 4.23 (m, w1/2 =27, ddd, 10.8, 9, 6.1) | | 12-Ha | 2.05 | | 12-He | 2.28 (dd, 12.7, 6) | | 15-Ha | 2.06 | | 15-Hb | 1.65 | | 16-Ha | 1.90* | | 16-Hb | 1.84* | | 17-H | 2.32 (m) | | 18-Me | 0.87 (s) | | 19-Me | 1.09 (s) | | 20-H | | | 21-Me | 1.26 (s) | | 22-H | 3.55 (d, 11) | | 23-Ha | 1.25 | | 23-Hb | 1.52 | | 24-Ha | 1.73 | | 26-Me | 1.18 (s) | | 27-Me | 1.20 (s) | | 28-Me | 0.96 (d, 6.8) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3404 (OH), 1657 (cyclohexenone), 1054, 1072 (C-O) | | UV (EtOH) λ max (log ε) | |
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| NP-HPLC | column Silasorb 600 (4 x 250 mm), flow-rate 0.8 ml.min-1, solvent Et2O-CH3CN-H2O (780:190: 30), Ret 50.5 min (20E 31.7 min) | | HPTLC | | | TLC | | | GLC | | | HPLC | RP-HPLC : column Separon SIX C18 (4 x 250 mm), solvent MeOH-H2O, linear gradient 10 to 70 % MeOH in 50 min, flow-rate 0.6 ml.min-1, Ret 41.1 min (20E 42.7 min). |
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Drosophila melanogaster BII cell assay: EC50 = 1.0 x 10-5M |
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| First isolation | VOKÁČ, K. et al. (1995) 16th Conference on Isoprenoids, Prague, Abstracts, pp. 77-78 |
 | | Bioactivities | HARMATHA, J. et al. (1997) Arch. Insect Biochem. Physiol. 35, 219-225 |
| | Identification | VOKÁČ, K. et al. (1998) Tetrahedron 54, 1657-1666 |
| | General | GUIBOUT, L. et al. (2015) Phytochemical Analysis 26, 293-300 |
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Permanent link to this datasheet: 25-HYDROXYATROTOSTERONE A
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