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14β,14,15-DIHYDROCALONYSTERONE

Year of first isolation: 2021
Formula:C27H42O7
Molecular weight:478
Occurence in plants:
Cyanotis arachnoidea [Commelinaceae] » Images of Cyanotis arachnoidea Wikipedia: Cyanotis arachnoidea [Commelinaceae]
Occurence in animals:
 
14β,14,15-DIHYDROCALONYSTERONE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
C[C@]12CCC3=C([C@H]1CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O[H])O[H])O[H])C(=O)C(=C4[C@@]3(C[C@@H]([C@@H](C4)O[H])O[H])C)O[H] » JSMol: View in 3D
IUPAC Name(2S,3R,10R,13R,17S)-2,3,6-trihydroxy-10,13-dimethyl-17-((2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl)-1,2,3,4,10,11,12,13,16,17-decahydro-7H-cyclopenta[a]phenanthren-7-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
BGWQNGDNVIJHPA-QCUJNDDWSA-N
InChIInChI=1S/C27H42O7/c1-24(2,33)10-9-20(30)27(5,34)19-7-6-14-21-15(8-11-25(14,19)3)26(4)13-18(29)17(28)12-16(26)22(31)23(21)32/h14,17-20,28-31,33-34H,6-13H2,1-5H3/t14-,17-,18+,19+,20-,25+,26-,27-/m1/s1

MASS SPECTRUM

HRESIMS (positive ion mode) m/z 479.30065 [M+H]+, calculated for C27H43O7 479.30033

CARBON NMR

PROTON NMR

DMSO-d6
0140.3
0268.0
0371.7
0426.8
05133.2
06142.6
07180.2
08131.5
09164.7
1040.5
1122.4
1235.0
1340.4
1446.4
1530.2
1625.2
1750.8
1823.8
1926.5
2075.6
2119.9
2276.4
2326.0
2441.3
2568.7
2629.0
2729.9
DMSO-d6
01-Hɑ1.14
01-Hβ2.17 (dd, 14.0, 2.7)
02-Hɑ3.80
03-Hɑ3.31
04-Hɑ2.89 (dd, 12.2, 4.5)
04-Hβ2.35 (t, 12.2)
05-H-
07-H-
09-H-
11-Hɑ2.22
11-Hβ2.32
12-Hɑ1.37
12-Hβ1.72
14-Hɑ2.43 (t, 8.1)
14-Hβ2.43 (t, 8.1)
15-Hɑ0.92
15-Hβ2.08
16-Hɑ1.50
16-Hβ1.70
17-Hɑ1.68
18-Me1.10 (s)
19-Me1.36 (s)
20-H-
21-Me1.13 (s)
22-H3.20
23-H1.42, 1.13
24-H1.64, 1.23
25-H-
26-Me1.03 (s)
27-Me1.05 (s)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D25+123.7° (c 0.130 ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)245 nm (-) ;

CHROMATOGRAPHY

HPLC
HPTLC
GLC
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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