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ASPERHIRATINE

Year of first isolation: 2022
Formula:C35H46O9
Molecular weight:610
Occurence in plants:
Aspergillus hiratsukae [Fungi] » Images of Aspergillus hiratsukae
Occurence in animals:
 
ASPERHIRATINE

STRUCTURE DESCRIPTORS

Isomeric SMILES
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C[C@@]12[C@@](C(C=C3C2CC[C@@]4(C)[C@@]3(O)CC[C@]4([H])[C@](C)([C@H](OC(C5=CC=CC=C5)=O)CC6[C@H](C)C(OC6)=O)O)=O)([H])C[C@@H](O)[C@@H](O)C1 » JSMol: View in 3D
IUPAC Name(2R,3R)-3-hydroxy-1-((4S)-4-methyl-5-oxotetrahydrofuran-3-yl)-3-((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)butan-2-yl benzoate
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
RCAUUNRRNQNDHA-JPMQESPRSA-N
InChIInChI=1S/C35H46O9/c1-19-21(18-43-30(19)39)14-29(44-31(40)20-8-6-5-7-9-20)34(4,41)28-11-13-35(42)23-15-25(36)24-16-26(37)27(38)17-32(24,2)22(23)10-12-33(28,35)3/h5-9,15,19,21-22,24,26-29,37-38,41-42H,10-14,16-18H2,1-4H3/t19-,21?,22?,24-,26+,27-,28-,29+,32+,33+,34+,35+/m0/s1

MASS SPECTRUM

HRESIMS (negative ion mode) m/z611.3227 [M+H]+, calculated 611.3215 for C35H47O9
CI-MS (NH3) m/z  
EI-MS m/z (relative intensity %)

CARBON NMR

PROTON NMR

CDCl3
0137.3
0268.7
0368.5
0434.2
0551.8
06206.3
07122.3
08167.5
0935.1
1039.3
1121.5
1231.7
1350.9
1485.3
1532.6
1621.6
1750.9
1818.0
1924.4.
2077.7
2121.7
2279.4
2334.1
2443.2
2514.5
26181.8
2773.5
2841.6
Benz 1'  168.0
Benz 2'131.7
Benz 3' 130.8
Benz 4' 129.7
Benz 5' 134.4
Benz 6' 129.7
Benz 7'130.8
CDCl3
01-Ha1.80 (m)
01-Hb1.45 (d, 12.6)
02-Ha3.84 (m)
03-He3.96 (s)
04-Ha2.10 (m)
04-Hb2.13 (m)
05-H2.40 (m)
07-H5.83 (d, 2.4)
09-H1.83 (dd, 7.4, 3.2)
11-Ha1.80 (m)
11-Hb2.14 (m)
12-Ha1.68 (m)
12-Hb2.03 (m)
15-Ha1.67 (m)
15-Hb2.16 (m)
16-Ha2.14 (m)
16-Hb1.68 (m)
17-H2.43 (t, 9.2)
18-Me0.89 (s)
19-Me0.97 (s)
21-Me1.42 (s)
22-H5.27 (dd, 10.9, 2.1)
23-Ha0.97 (dd, 8.2, 4.1)
23-Hb1.37 (m)
24-H2.20 (m)
25-H2.38 dd (7.1, 2.7)
27-Me1.27 d (7.1)
28-H4.25 (dd, 9.0, 7.7), 3.89 (t, 9.0)
Benz 3'8.10 (dd, 8.3, 1.2)
Benz 4'7.51 (dd, 11.0, 4.6)
Benz 5'7.63 (m)
Benz 6'7.51 (dd, 11.0, 4.6)
Benz 7'8.10 (dd, 8.3, 1.2)

PHYSICAL PROPERTIES

M.P.202.5 - 204.9 °C ;
[α]D25+26.3° (c 1.0 ; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)201.6 nm (1.39) ; 2320 (1.58), 315.4

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationZENG, Q. et al. (2022) Mar. Drugs 20, 150 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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