NMRanalyst Sample Application: Dihydrotestosterone

Dihydrotestosterone
NMRanalyst Sample Application

NMRanalyst

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Sample Description:

Molecular Formula: C₁₉H₃₀O₂
Molecular Weight: 290.440

InChI=

1/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-
8-16(14)18/h12,14-17,21H,3-11H2,1-2H3

IUPAC Name:

17-Hydroxyandrostan-3-one

CAS Number: 521-18-6
PubChem: 15
NMRShiftDB: 20059206
Spectrometer: Bruker AP 600 MHz
Probe: 1mm MicroProbe
Solvent: DMSO-d₆ (some H₂O)
Sample Concentration: ca. 200 µg

Provided by:

Dr. Till Kühn, Bruker BioSpin

Directory	npF2	NS	swF2	spF2	npF1	swF1	spF1	time

proton (1)	32768	1	12376.24	-2482.69				4 s
gHSQC (5)	512	16	4595.59	-123.29	256	25000.00	-1188.44	2 h 33 m
gHMBC (6)	2048	32	5387.93	-519.46	512	37735.85	-2271.10	10 h 17 m
gDQF-COSY (7)	1024	2	4595.59	-123.29	512	4595.59	-123.29	1 h 23 m

Original 1D Proton Spectrum:

1D Proton Spectrum (Water Subtracted):

Top 10 FindIt Molecular Structures Consistent With Molecular Formula and Proton Resonances:

The correct structure is at position 1.


 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.952514 (      15)    2: 0.951895 (   10634)    3: 0.951509 (  352069)
    4: 0.951213 (  136297)    5: 0.951195 (   19274)    6: 0.951104 ( 5061847)
    7: 0.950559 ( 6431162)    8: 0.950308 (  225744)    9: 0.950046 (  234464)
   10: 0.949857 (  446692)

2D Multiplicity-Edited HSQC Spectrum:

Determined HSQC Correlations:

Top 10 FindIt Molecular Structures Consistent With Proton and Protonated Carbon (HSQC) Resonances:

The correct structure is at position 5.


 Best 10 structures in decreasing rating (structure ID shown in parentheses):
    1: 0.961909 ( 2754185)    2: 0.952877 ( 5934064)    3: 0.941439 (  281595)
    4: 0.935020 (  841323)    5: 0.925680 (      15)    6: 0.922834 (  134100)
    7: 0.922596 (  239756)    8: 0.920055 (  635979)    9: 0.918443 ( 2748110)
   10: 0.917488 (    1843)

Automated VerifyIt Proton Assignments:

Automated VerifyIt Carbon Assignments:

2D DQF-COSY Spectrum:

AssembleIt HSQC & DQF-COSY Derived Carbon-Carbon Correlations:

AssembleIt HSQC & DQF-COSY Derived Correlations

2D HMBC Spectrum:

AssembleIt HSQC, HMBC & DQF-COSY Derived Correlations:

AssembleIt Derived Structure With NMRgraph Added Likely Oxygen Atoms:

only one possible structure

Comments:

Essential androgen for the virilization of the male embryo and for subsequent growth of tissues such as the prostate.

The water resonance in the proton spectrum is two orders of magnitude larger than component resonances. Till supplied a 1D NOESY dataset with presaturation solving this challenge experimentally. But NMRanalyst can solve this water resonance challenge in the 1D proton spectrum directly as shown.

The 1D Analysis workwindow allows specification of resonance parameters. If the table [Remove] switch for a resonance is selected, the software subtracts the selected resonance and proceeds with a regular spectral analysis. Water related resonances can be collected manually in this table for subtraction. This takes several iterations of analyzing the spectrum and copying resonances to be deleted. But its advantage is resonance integrals remain correct and the spectrum remains phase sensitive.

When no carbon spectrum is available, HSQC correlations are another option. The shown carbon assignments do not contain quarternary carbons, as they have no attached proton for their detection.

From the HSQC and HMBC analysis results, all carbon resonance information can be assembled with the software. It is equivalent to the analysis result of a carbon spectrum. FindIt identifies this structure from the molecular formula and the proton results as the most likely structure.

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