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Year of first isolation: |
2008 |
| Formula: | C29H44O8 |
| Molecular weight: | 520 |
| Occurence in plants: |
Ajuga reptans var. reptans [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Ajuga reptans var. reptans [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
Ajuga macrosperma var. breviflora [Lamiaceae (alt. Labiatae)] »
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| Canonical SMILES | CCC1C(C(=O)OC1C(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)O)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]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H]([C@H]1[C@@H]([C@H](C)C(=O)O1)CC)O)O)O)C)C » 
| | IUPAC Name | (3S,4R,5R)-5-[(1R,2R)-1,2-dihydroxy-2-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]propyl]-4-ethyl-3-methyloxolan-2-one | | CAS-RN | | | PubChem CID | 102394044 | InChiKey
[ ChemIDPlus: search ] | QHMFBDXCUNQLMU-SMJKJTOCSA-N | | InChI | InChI=1S/C29H44O8/c1-6-15-14(2)25(34)37-23(15)24(33)28(5,35)22-8-10-29(36)17-11-19(30)18-12-20(31)21(32)13-26(18,3)16(17)7-9-27(22,29)4/h11,14-16,18,20-24,31-33,35-36H,6-10,12-13H2,1-5H3/t14-,15+,16-,18-,20+,21-,22-,23+,24+,26+,27+,28+,29+/m0/s1 |
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| | | HR-ESI-MS m/z | 521.3140 [M+H], calc for C29H45O8 521.3114 |
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| C5D5N | | 01 | 37.9 | | 02 | 68.1 | | 03 | 68.0 | | 04 | 32.5 | | 05 | 51.4 | | 06 | 203.5 | | 07 | 121.6 | | 08 | 166.0 | | 09 | 34.4 | | 10 | 38.6 | | 11 | 21.4 | | 12 | 31.9 | | 13 | 48.1 | | 14 | 84.0 | | 15 | 31.6 | | 16 | 21.0 | | 17 | 50.7 | | 18 | 18.0 | | 19 | 24.4 | | 20 | 75.8 | | 21 | 22.5 | | 22 | 77.8 | | 23 | 82.9 | | 24 | 40.9 | | 25 | 38.1 | | 26 | 180.4 | | 27 | 10.6 | | 28 | 22.0 | | 29 | 12.0 |
| CD3OD | | 01 | 37.5 | | 02 | 68.8 | | 03 | 68.6 | | 04 | 33.0 | | 05 | 51.9 | | 06 | 206.6 | | 07 | 122.2 | | 08 | 168.1 | | 09 | 35.2 | | 10 | 39.4 | | 11 | 21.6 | | 12 | 32.6 | | 13 | 49.2 | | 14 | 85.3 | | 15 | 31.8 | | 16 | 21.6 | | 17 | 51.2 | | 18 | 18.3 | | 19 | 24.5 | | 20 | 77.1 | | 21 | 22.0 | | 22 | 78.1 | | 23 | 84.4 | | 24 | 42.3 | | 25 | 38.8 | | 26 | 182.9 | | 27 | 10.6 | | 28 | 22.7 | | 29 | 12.0 |
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| C5D5N | | 01-Ha | 1.93 (dd, 13.4, 12.0) | | 01-He | 2.14 | | 02-Ha | 4.20 (brd) | | 03-He | 4.27 (m, w1/2 = 8.4) | | 04-Ha | 1.83 (brt, 13.4) | | 04-He | 2.07 (dd, 13.7, 3.7) | | 05-H | 3.02 (dd, 13.5, 3.5) | | 07-H | 6.24 (d, 2.2) | | 09-H | 3.60 (m) | | 11-Ha | 1.72 (qd, 12.0, 4.4) | | 11-Hb | 1.87 | | 12-Ha | 2.60 (td, 12.4, 4.6) | | 12-He | 2.00 (brd, 12.4) | | 15-Ha | 1.89 | | 15-Hb | 2.15 | | 16-Ha | 2.15 | | 16-Hb | 2.44 (m) | | 17-H | 3.06 (dt, 9.0) | | 18-Me | 1.19 (s) | | 19-Me | 1.07 (s) | | 21-Me | 1.65 (s) | | 22-H | 4.19 (brs) | | 23-Ha | 4.62 (brd, 2.4) | | 24-H | 2.81 (td, 9.0, 4.5) | | 25-H | 3.45 (q, 7.7) | | 27-Me | 1.14 (d, 7.6) | | 28-Ha | 1.22 (m) | | 28-Hb | 1.48 (m) | | 29-Me | 0.98 (t, 7.3) | | OH | 6.40 (br), 7.35 (br) |
| CD3OD | | 01-Ha | 1.43 | | 01-He | 1.81 | | 02-Ha | 3.84 | | 03-He | 3.95 | | 04-Ha | 1.71 | | 04-He | 1.78 | | 05-H | 2.38 | | 07-H | 5.81 | | 09-H | 3.16 | | 11-Ha | 1.70 | | 11-Hb | 1.82 | | 12-Ha | 2.16 | | 12-He | 1.87 | | 15-Ha | 1.63 | | 15-Hb | 1.98 | | 16-Ha | 1.81 | | 16-Hb | 2.00 | | 17-H | 2.57 | | 18-Me | 0.88 | | 19-Me | 0.97 | | 21-Me | 1.30 (s) | | 22-H | 3.62 (d, 4.3) | | 23-Ha | 4.34 (dd, 4.3, 2.0) | | 24-H | 2.62 (tdd, 8.7, 5.1, 2.1) | | 25-H | 3.10 (dq, 8.2, 7.6) | | 27-Me | 1.13 (d, 7.6) | | 28-Ha | 1.35 (14.2, 8.9, 7.3) | | 28-Hb | 1.59 | | 29-Me | 1.00 (t, 7.3) |
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| M.P. | 268-270 °C ; | | [α]D22 | - 159.3 ° (c 0.23; MeOH) | | [α]D25 | +15 ° (c 0.1; MeOH) | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | 242 (3.9459) ; |
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Permanent link to this datasheet: BREVIFLORASTERONE
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