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22-OXO-DACRYHAINANSTERONE

Year of first isolation: 2021
Formula:C27H40O6
Molecular weight:460
Occurence in plants:
Cyanotis arachnoidea [Commelinaceae] » Images of Cyanotis arachnoidea Wikipedia: <br />
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Occurence in animals:
 
22-OXO-DACRYHAINANSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
CC(C)CCC([C@@](C)([C@H]1CC[C@@]2([C@@]1(CC=C3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O[H])O[H])C)C)O[H])O[H])=O » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10S,13R,14S,17S)-2,3,14-trihydroxy-17-((R)-2-hydroxy-6-methyl-3-oxoheptan-2-yl)-10,13-dimethyl-1,2,3,4,5,10,12,13,14,15,16,17-dodecahydro-6H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
FGVSLGUJXWEAGT-GDQRBCJQSA-N
InChIInChI=1S/C27H40O6/c1-15(2)6-7-23(31)26(5,32)22-9-11-27(33)17-12-19(28)18-13-20(29)21(30)14-24(18,3)16(17)8-10-25(22,27)4/h8,12,15,18,20-22,29-30,32-33H,6-7,9-11,13-14H2,1-5H3/t18-,20+,21-,22-,24+,25+,26+,27+/m0/s

MASS SPECTRUM

HRESIMS (positive ion mode) m/z 461.28981 [M+H]+, calculated for C27H41O6 461.28977

CARBON NMR

PROTON NMR

MeOH-d4
0137.3
0268.8
0368.4
0435.8
0551.7
06206.9
07119.4
08156.2
09136.3
1040.7
11133.7
1239.0
1348.2
1484.5
1531.5
1622.0
1751.8
1818.1
1931.7
2081.8
2125.2
22217.4
2335.5
2433.9.
2528.9
2622.9
2722.9
MeOH-d4
01-Hɑ2.09
01-Hβ1.71 (t, 12.5)
02-Hɑ3.73
03-Hɑ3.85
04-Hɑ1.59
04-Hβ1.77
05-Hɑ2.45 (dd, 12.5, 4.0)
05-Hβ2.45 (dd, 12.5, 4.0)
07-H5.74
09-H-
11-Hɑ-
11-Hβ6.30
12-Hɑ2.83
12-Hβ2.43
14-Hɑ-
15-Hɑ1.79
15-Hβ1.95
16-Hɑ1.55
16-Hβ1.79
17-Hɑ2.76 (t, 9.5)
18-Me0.88 (s)
19-Me1.11 (s)
20-H-
21-Me1.40 (s)
22-H-
23-H2.67
24-H1.46
25-H1.56
26-Me0.92 (d, 6.5)
27-Me0.92 (d, 6.5)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D25+51.3° (c 0.170 ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)245 nm (-) ;

CHROMATOGRAPHY

HPTLC
HPLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationTÓTH G., HERKE et al. (2021) J. Nat. Prod. 84, 1870–1881 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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