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16α-HYDROXYTAXISTERONE

Year of first isolation: 2021
Formula:C27H44O7
Molecular weight:480
Occurence in plants:
Helleborus niger [Ranunculaceae] » Images of Helleborus niger Wikipedia: Helleborus niger [Ranunculaceae]
Occurence in animals:
 
16α-HYDROXYTAXISTERONE

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CC(C2C(C)(CCCC(C)(C)O)O)O)O
Isomeric SMILES
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C[C@]34CC[C@H]1C(=CC(=O)[C@H]2[C@@]1(C[C@@H]([C@@H](C2)O[H])O[H])C)[C@@]3(C[C@H]([C@@H]4[C@](C)(CCCC(C)(C)O[H])O[H])O[H])O[H] » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,13R,14S,16R,17R)-17-((S)-2,6-dihydroxy-6-methylheptan-2-yl)-2,3,14,16-tetrahydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID155387997
InChiKey
[ ChemIDPlus: search ]
JLGSDRXEKUKFKR-PRSWSNRVSA-N
InChIInChI=1S/C27H44O7/c1-23(2,32)8-6-9-26(5,33)22-21(31)14-27(34)16-11-18(28)17-12-19(29)20(30)13-24(17,3)15(16)7-10-25(22,27)4/h11,15,17,19-22,29-34H,6-10,12-14H2,1-5H3/t15-,17-,19+,20-,21+,22-,24+,25+,26-,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z  
EI-MS m/z (relative intensity %)
HRESIMS (negative ion mode) m/z 

CARBON NMR

PROTON NMR

CD3OD
0137.3
0268.5
0368.7
0432.8
0551.8
06206.3
07122.2
08166.9
0934.9
1039.3
1121.1
1232.4
1350.3
1484.7
1543.0
1672.6
1759.2
1819.0
1924.4
2075.9
2126.6
2245.7
2319.9
2445.3
2571.6
2629.2
2729.4
CD3OD
01-Ha1.43 (m)
01-Hb1.79 (m)
02-Ha3.84 (m)
03-He3.95 (m)
04-Ha1.77
04-Hb1.74
05-H2.38 (dd, 9.4, 4.4)
07-H5.77 (s)
09-H3.16 (dd)
11-Ha1.80 (m)
11-Hb1.68 (m)
12-Ha1.80 (m)
12-Hb2.29 (m)
15-Ha2.42 (dd, 14.1, 8.3)
15-Hb1.66 (d, 14.1)
16-H4.49 (dd, 8.3, 6.1)
17-H2.33 (d, 6.1)
18-Me0.86 (s)
19-Me0.96 (s)
21-Me1.30 (s)
22-Ha1.72 (m)
22-Hb1.53 (m)
23-Ha1.53 (m)
23-Hb1.45 (m)
24-Ha1.53 (m)
24-Hb1.45 (m)
26-Me1.19 (s)
27-Me1.19 (s)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D20- (c - ; MeOH)
IR (KBr) ν max (cm-1)3417, 1652
UV (?) λ max (log ε)242.1 nm (-) ;

CHROMATOGRAPHY

GLC
TLC
HPLC
HPTLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationYOKOSUKA, A. et al. (2021) J. Nat. Med. 75, 393-402 Search more

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© Université Pierre & Marie Curie, Paris 6, France
© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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