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5-HYDROXYPODECDYSONE B

Year of first isolation: 2020
Formula:C27H42O7
Molecular weight:478
Occurence in plants:
Niedenzuella multiglandulosa [Malpighiaceae] » Images of Niedenzuella multiglandulosa Wikipedia: Niedenzuella multiglandulosa [Malpighiaceae]
Occurence in animals:
 
5-HYDROXYPODECDYSONE B

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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[ ChemSpider: search ]
C[C@@]12[C@@](C(CC3=C2CC[C@@]4(C)C3=CC[C@@H]4[C@]([C@H](O)CCC(C)(O)C)(O)C)=O)(O)C[C@@H](O)[C@@H](O)C1 » JSMol: View in 3D
IUPAC Name(2S,3R,5S,10R,13R,17S)-2,3,5-trihydroxy-10,13-dimethyl-17-((2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl)-1,2,3,4,5,7,10,11,12,13,16,17-dodecahydro-6H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
VFLXLHJYUDMQAA-VBQMQKFESA-N
InChIInChI=1S/C27H42O7/c1-23(2,32)10-9-21(30)26(5,33)20-7-6-16-15-12-22(31)27(34)14-19(29)18(28)13-25(27,4)17(15)8-11-24(16,20)3/h6,18-21,28-30,32-34H,7-14H2,1-5H3/t18-,19+,20-,21+,24-,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z  
EI-MS m/z (relative intensity %)
HR-ESIMS479.3002 [M+H]+, calc. for C27H42O7 478.2931 (∆ ppm = -1.5)

CARBON NMR

PROTON NMR

DMSO-d6
0134.0
0267.8
0368.3
0435.4
0579.9
06208.6
0739.2
08121.3
09136.9
1048.2
1122.2
1236.5
1345.4
14147.8
15119.3
1630.4
1755.8
1817.9
1923.6
2075.1
2120.0
2276.5
2326.0
2441.4
2568.7
2629.8
2729.0
DMSO-d6
01-Ha1.73 (dd, 14.2, 3.1) 1.66 (m)
01-He1.66 (m)
02-Ha3.29
03-He3.80 (dq, 6.3, 3.3)
04-Ha1.98 (dd, 14.4, 3.3)
04-He1.62 (dd, 14.3, 3.3)
05-H-
07-H3.42 's, 21.1), 2.69 (d, 21.1)
09-H-
11-H2.24 (m)
12-Ha2.14 (dt, 12.4; 4.0)
12-He1.46 (m)
15-H5.40 (t, 3.0, 2.1)
15-Ha1.86 (m)
16-Ha2.55 (ddd, 16.5, 10.7, 2.1)
16-Hb2.04 (ddd, 16.5, 7.6, 3.0)
17-H1.89 (dd, 10.7, 7.6)
18-Me0.96 (s)
19-Me0.84 (s)
21-Me1.11 (s)
22-H3.15 (dd, 11.5, 4.0)
23-Ha1.12 (m)
23-Hb1.45 (m)
24-Ha1.65 (m)
24-Hb1.24 (m)
25-H-
26-Me1.07 (s)
27-Me1.04 (s)
[other] 02-OHn.o.
[other] 03-OH4.73 (d, 6.3)
[other] 05-OH5.44 (s)
[other] 20-OH3.66 (s)
[other] 22-OH4.36 (d, 4.0)
[other] 25-OH4.07 (s)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D26+7 ° (c = 1 ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)224 (-) ;

CHROMATOGRAPHY

HPTLC
HPLC
GLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationMANOCCHIO RUSSO, H. et al. (2020) Phytochemistry Letters 37, 10-16 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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