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ZOANTHONE A

Year of first isolation: 2016
Formula:C29H46O9
Molecular weight:538
Occurence in plants:
 
Occurence in animals:
Zoanthus sp. [Zoanthidae] » Images of Zoanthus sp. Wikipedia: Zoanthus sp. [Zoanthidae]
ZOANTHONE A

STRUCTURE DESCRIPTORS

Canonical SMILESCC(=O)OC(C)(C)CCC(C(C)(C1CCC2(C1(CC(C3C2=CC(=O)C4C3(CC(C(C4)O)O)C)O)C)O)O)O
Isomeric SMILES
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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](CCC(C)(C)OC(=O)C)O)O)O)C)O)C » JSMol: View in 3D
IUPAC Name[(5R,6R)-5,6-dihydroxy-2-methyl-6-[(2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptan-2-yl] acetate
CAS-RN 
PubChem CID127053212
InChiKey
[ ChemIDPlus: search ]
CSIOSPOYAIWNMK-MWPSDTLYSA-N
InChIInChI=1S/C29H46O9/c1-15(30)38-25(2,3)9-8-23(35)28(6,36)22-7-10-29(37)17-12-18(31)16-11-19(32)20(33)13-26(16,4)24(17)21(34)14-27(22,29)5/h12,16,19-24,32-37H,7-11,13-14H2,1-6H3/t16-,19+,20-,21+,22-,23+,24+,26-,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z  
EI-MS m/z (relative intensity %)
HR-ESIMS561.3034 [M+Na]+

CARBON NMR

PROTON NMR

C5D5N
0139.9
0268.4
0368.2
0432.9
0552.5
06203.9
07122.3
08164.2
0942.8
1039.5
1168.9
1244.2
1348.1
1484.2
1531.9
1621.5
1750.0
1818.9
1924.9
2076.8
2121.5
2277.4
2326.9
2439.3
2582.3
25-OAc170.2, 20.2
2626.3
2726.1
C5D5N
01-Ha2.01 (t, 7.8)
01-He3.49 (dd, 12.5, 4.1)
02-Ha4.59 (m)
03-He4.25 (br, s)
04-Ha1.78 (m)
04-He2.08 (dt, 9.1, 2.1)
05-H3.08 (t, 8.5)
07-H6.32 (d, 2.3)
09-H3.90 (dd, 8.6, 2.4)
11-Ha4.61 (m)
12-Ha2.72 (dd, 12.4, 6.3)
12-He3.07 (d, 14.2)
15-Ha2.23 (m)
15-Hb1.83 (m)
16-Ha2.47 (m)
16-Hb2.18 (m)
17-H3.09 (t, 9.8)
18-Me1.29 (s)
19-Me1.34 (s)
21-Me1.63 (s)
22-H3.85 (dd, 10.2, 5.5)
23-Ha1.59 (m)
23-Hb1.86 (m)
24-Ha2.14 (m)
24-Hb2.41 (dd, 12.0, 5.0)
25-OAc 1.95 (s)
26-Me26.3 (s)
27-Me26.1 (s)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D2547 ° (c 0.05; MeOH)
IR (KBr) ν max (cm-1)3382 (OH), 1654 (ketone), 1026
UV (EtOH) λ max (log ε)239, 215 () ;

CHROMATOGRAPHY

HPLC
GLC
TLC
HPTLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationCHENG, Y.B. et al. (2016) Bioorg. Med. Chem. Lett. 26, 2344-2348 Search more

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