|
|
|
|
Year of first isolation: |
1986 |
| Formula: | C27H44O8 |
| Molecular weight: | 496 |
| Occurence in plants: |
Tapinella panuoides [Fungi] »  ![Wikipedia: Tapinella panuoides [Fungi]](/images/wikipedia.png)
|
| Occurence in animals: |
Cepaea nemoralis [Helicidae] »
|
|
| |
| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CC(C2C(C)(C(CCC(C)(C)O)O)O)O)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]2CC[C@]2([C@]1(C[C@@H]([C@@H]2[C@](C)([C@H](O)CCC(C)(C)O)O)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,16S,17R)-2,3,14,16-tetrahydroxy-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 | 100953174 | InChiKey
[ ChemIDPlus: search ] | ZOKOAVXGNRAXRR-BZYHFBBWSA-N | | InChI | InChI=1S/C27H44O8/c1-23(2,33)8-7-21(32)26(5,34)22-20(31)13-27(35)15-10-17(28)16-11-18(29)19(30)12-24(16,3)14(15)6-9-25(22,27)4/h10,14,16,18-22,29-35H,6-9,11-13H2,1-5H3/t14-,16-,18+,19-,20-,21+,22-,24+,25+,26-,27+/m0/s1 |
| |
| CI-MS (NH3) m/z | 497 (M+H)+, 479, 461, 443, 425, 407, 379, 363, 361, 345, 343 | | EI-MS m/z (relative intensity %) | | | HR-MS | |
|
|
| CD3OD | | 01 | 37.32 | | 02 | 68.70 | | 03 | 68.50 | | 04 | 32.86 | | 05 | 51.81 | | 06 | 206.36 | | 07 | 122.09 | | 08 | 167.00 | | 09 | 34.90 | | 10 | 39.29 | | 11 | 21.39 | | 12 | 32.42 | | 13 | * | | 14 | 83.27 | | 15 | 44.95 | | 16 | 73.34 | | 17 | 51.66 | | 18 | 16.41 | | 19 | 24.42 | | 20 | 80.82 | | 21 | 20.64 | | 22 | 77.79 | | 23 | 27.77 | | 24 | 42.57 | | 25 | 71.29 | | 26 | 29.79 | | 27 | 28.89 |
|
| D2O | | 01-Ha | | | 01-He | | | 02-Ha | 3.97 (m, w1/2=22) | | 03-He | 4.07 (m, w1/2=8) | | 04-Ha | | | 04-He | | | 05-H | 2.36 | | 07-H | 5.96 (d, 2.5) | | 09-Ha | 3.11 (m, w1/2=22) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | 2.36 (m ) | | 15-Hb | 2.14 (m ) | | 16-Ha | 4.73 (m, w1/2=22) | | 17-H | 2.34 (d, 7.8) | | 18-Me | 1.11 (s ) | | 19-Me | 1.02 (s ) | | 21-Me | 1.24 (s ) | | 22-H | 3.86 (d ) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.23 (s ) | | 27-Me | 1.23 (s ) |
| CD3OD | | 01-Ha | 1.79 (dd, 13,0, 4.5) | | 01-He | 1.43 (dd, 8.0, 12.3) | | 02-Ha | 3.82 (ddd, 12.0, 4.0, 3.5) | | 03-He | 3.94 (q 3.0) | | 04-Ha | 1.72 | | 04-He | 1.68 | | 05-H | 2.40 (dd, 12.6, 4.8) | | 07-H | 5.81 (d, 2.5) | | 09-Ha | 3.16 (ddd 10.5, 7.0, 2.5) | | 11-Ha | 1.70 | | 11-He | 1.82 | | 12-Ha | 2.14 (dt, 12.5, 12.5, 5.2) | | 12-He | 1.93 (ddd) | | 15-Ha | 2.25 (dd, 13.6, 7.6) | | 15-Hb | 2.08 (dd, 13.6, 4.7) | | 16-Ha | 4.68 (dt, 7.6, 7.6, 4.7) | | 17-H | 2.44 (d, 7.6) | | 18-Me | 1.136 (s ) | | 19-Me | 0.990 (s ) | | 21-Me | 1.197 (s ) | | 22-H | 3.88 (dd, 10.6, 1.5) | | 23-Ha | 1.67 | | 23-Hb | 1.36 | | 24-Ha | 1.86 (ddd 13.3 12.0, 5.0) | | 24-Hb | 1.50 (ddd 13.3 11.5, 4.0) | | 26-Me | 1.197 (s ) | | 27-Me | 1.213 (s ) |
|
| |
| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | |
| |
| HPTLC | | | TLC | | | NP-HPLC | column Zorbax-Sil 250x4.6 mm, solvent CH2Cl2-iPrOH-H20 (125:25:2), flow-rate gradient 0.5 to 1 ml.min-1 in 80 min, Ret 64.6 min (20E 49.4 min). | | RP-HPLC | column Ultrasphere ODS 250x4.6 mm, solvent linear gradient (60 min) from 8 to 40% CH3CN in 20 mM Tris-HClO4, pH 7.5, flow-rate 1 ml.min-1, Ret 26.6 min (20E 29.2 min). |
| |
Drosophila melanogaster BII cell assay: EC50 = 9.0 x 10-6M |
| |
| |
Permanent link to this datasheet: MALACOSTERONE
|
|
