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AJUGACUMLACTONE

Year of first isolation: 2022
Formula:C30H44O7
Molecular weight:516
Occurence in plants:
Ajuga decumbens [Lamiaceae (alt. Labiatae)] » Images of Ajuga decumbens Wikipedia: Ajuga decumbens [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
AJUGACUMLACTONE

STRUCTURE DESCRIPTORS

Canonical SMILESC[C@@]12[C@@](C(C=C3C2CC[C@@]4(C)[C@@]3(O)CC[C@@H]4[C@@](C)(O)[C@H](O5)CC(CCC)=C(C)C5=O)=O)([H])C[C@@H](O)[C@@H](O)C1
Isomeric SMILES
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[ ChemSpider: search ]
O=C1C(C)=C(CCC)C[C@H]([C@@]([C@H]2CC[C@@]3(O)C4=CC([C@]5([H])C[C@@H](O)[C@@H](O)C[C@]5(C)C4CC[C@]23C)=O)(O)C)O1 » JSMol: View in 3D
IUPAC Name(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)-3-methyl-4-propyl-5,6-dihydro-2H-pyran-2-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
YGKDUZQAZYIXBO-WRXGHIAKSA-N
InChIInChI=1S/C30H44O7/c1-6-7-17-12-25(37-26(34)16(17)2)29(5,35)24-9-11-30(36)19-13-21(31)20-14-22(32)23(33)15-27(20,3)18(19)8-10-28(24,30)4/h13,18,20,22-25,32-33,35-36H,6-12,14-15H2,1-5H3/t18?,20-,22+,23-,24-,25+,27+,28+,29+,30+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z  
EI-MS m/z (relative intensity %)
HRESIMS (positive ion mode) m/z 539.2979 [M+Na]+, calc. 539.2979

CARBON NMR

PROTON NMR

CD3OD
0136.0
0267.4
0367.2
0431.5
0550.5
06205.3
07121.0
08166.2
0933.7
1038.0
1120.1
1230.4
1347.6
1483.9
1531.1
1620.2
1749.0
1816.8
1923.1
2075.0
2120.0
2282.0
2328.8
24156.1
25120.3
26167.9
2710.7
28-H229.5
29-H226.7
30-Me10.5
CD3OD
01-Ha1.43 (m)
01-Hb1.77 (m)
02-Ha3.84 (m)
03-He3.96 (d, 3.0)
04-Ha1.74 (m)
04-Hb1.70 (m)
05-H2.35 (m)
07-H5.82 (d, 2.6)
09-H3.16 (m)
11-Ha3.87 (m)
11-Hb1.76 (m)
12-Ha1.97 (m)
12-Hb1.61 (m)
15-Ha2.16 (m)
15-Hb 
16-Ha2.00 (m)
16-Hb1.99 (m)
17-H2.40 (m)
18-Me0.89 (s)
19-Me0.97 (s)
21-Me1.31 (s)
22-H4.17 (d, 3.8)
23-Ha2.46 (m)
23-Hb2.34 (m)
27-Me1.86 (m)
28-H21.25 (m)
29-H22.32 (m)
30-Me1.12 (t, 7.6)

PHYSICAL PROPERTIES

M.P.146-147 °C;
[α]D20– (c ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)nm (-) ; –

CHROMATOGRAPHY

GLC
HPLC
TLC
HPTLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationOLATUNDE, O.Z. et al. (2022) Steroids 186, article 109089 Search more

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