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27-HYDROXY-PRECYASTERONE

Year of first isolation: 2022
Formula:C29H44O9
Molecular weight:536
Occurence in plants:
Ajuga multiflora [Lamiaceae (alt. Labiatae)] » Images of Ajuga multiflora Wikipedia: Ajuga multiflora [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
27-HYDROXY-PRECYASTERONE

STRUCTURE DESCRIPTORS

Isomeric SMILES
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C[C@@]12[C@@](C(C=C3C2CC[C@@]4(C)[C@@]3(O)CC[C@@H]4[C@@](C)(O)[C@H](O5)C[C@H]([C@@H](O)C)[C@H](CO)C5=O)=O)([H])C[C@@H](O)[C@@H](O)C1 » JSMol: View in 3D
IUPAC Name(3R,4S,6R)-6-((1R)-1-hydroxy-1-((2S,3R,5R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl)-4-((S)-1-hydroxyethyl)-3-(hydroxymethyl)tetrahydro-2H-pyran-2-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
PPIUTJKDCXSNNX-RJRZVDSCSA-N
InChIInChI=1S/C29H44O9/c1-14(31)15-9-24(38-25(35)16(15)13-30)28(4,36)23-6-8-29(37)18-10-20(32)19-11-21(33)22(34)12-26(19,2)17(18)5-7-27(23,29)3/h10,14-17,19,21-24,30-31,33-34,36-37H,5-9,11-13H2,1-4H3/t14-,15+,16-,17?,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z  
EI-MS m/z (relative intensity %)
HRESIMS (positive ion mode) m/z 537.3065 [M+H]+ calculated 537.3058 for C29H45O9

CARBON NMR

PROTON NMR

DMSO-d6
0136.6
0266.8
0366.6
0431.5
0550.1
06202.6
07120.5
08165.1
0933.1
1037.6
1120.1
1230.8
1346.9
1483.0
1530.4
1620.2
1748.6
1817.2
1923.9
2075.7
2120.8
2273.6
2334.0
2441.0
2549.8
26177.0
2758.9
2879.7
2919.7
DMSO-d6
01-Ha 
01-Hb 
02-Ha 
03-He 
04-Ha 
04-Hb 
05-H 
07-H5.63 (s)
09-H3.0 (m)
11-Ha 
11-Hb 
12-Ha2.02 (td, 13.0, 4.6)
12-Hb2.02 (td, 13.0, 4.6)
15-Ha 
15-Hb 
16-Ha1.85 (m)
16-Hb1.85 (m)
17-H 
18-Me0.76 (s)
19-Me0.83 (s)
21-Me1.06 (s)
22-H3.31 (d, 11.0)
23-Ha 
23-Hb 
24-H2.28 (m)
25-H2.46 (d, 3.3)
26-Me
27-Me 
28-H4.21 (dq, 12.2, 6.0)
29-Me1.33 (d, 6.1)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D20– (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)247 nm (-) ;

CHROMATOGRAPHY

TLC
HPTLC
HPLC
GLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationLEE, Y. et al. (2022) Nat. Prod. Res. 1-8 Search more

see Important notice
© 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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