Äîêóìåíò âçÿò èç êýøà ïîèñêîâîé ìàøèíû. Àäðåñ îðèãèíàëüíîãî äîêóìåíòà : http://polly.phys.msu.ru/~baskin/chemoinformatics_group_1.pdf Äàòà èçìåíåíèÿ: Thu Nov 28 16:30:55 2013 Äàòà èíäåêñèðîâàíèÿ: Thu Feb 27 23:13:12 2014 Êîäèðîâêà:

( )

..., ..-.. ..., ...



( )



( )


QSAR/QSPR: - -
A
T r a i n i n g Te s t N e w


N
Cl



­
­ ­

­
­ ­ ­
N

­
­ ­ ­ ­ ­ ­ ­

­
­ ­ ­ ­ ­ ­ ­

­
­ ­ ­ ­ ­ ­ ­



N

F: A=F(S)


N

­ ­
N Cl

­ ­
N
Br N

­ ? ?

A


­ ­

N






«» QSPR


( )
( )





/ , HF, MO, DFT >>


> , -, FEP >

()












( )




· · · · · · · · · «» QSPR «-» QSPR

QSPR
· · -


· · NASAWIN ­ FRAGMENT ­

8


( )

the most accessed in 2011

the most accessed in 2012 J. Chem. Inf. Comput. Model. 2012, 52, 1413-1437

,., .., .. « »

9










Fr1 Fr2 .... Fri ....

N1 N2 ... Ni ...





:
10



:
· (1993) · (1993) · (2003) · (2007)

· « » (2009)


« »




NASAWIN: 60

11


( )

, . ., /3 , . ., lg() , 25 oC, lg() , 1 ., oC


0.043


0.046


Katritzky et al., 2000 Katritzky et al., 2000 Jurs et al, 1999

0.177

0.22

0.158

0.209

16.9

19.4

Tetteh et al, 1999



(: NASAWIN, LibSVM, WEKA)


, µ0 (·-1)


79
52


, 2005 , 2007

-

-,
- Na+ K+ c -, logK , H0f (/) , E

218 (2, 25 )
223

. , 2007
, 2007

163

Colorado, 2008

73

Pardubice, 2008



R
2

R2

R1 R2 N N+ R3
N

R1

R1
R2

N R

+

N

+

R4

N+ R2
R3

Br-

Br-

Br-

N+ BrR3

Br-

1

R1

PYR
26.2 34.8

IMZ
32.4 36.2

QUAT
30.3 36.1

FULL
31.5 33.7


SVR
, /

60 50 40 30 20 10 0 0 10 20 30 40 50 60 70 , /

­ ( ) . ­ ( ); ; . ­ 104 n

C : (10- ) Q2 = 0.801 , RMSE = 3.33 / SVR: Nu = 0.72, Log2(c) = 12.6, Log2(g)= -18.7

PRESS q2 1 1 SS


i 1

( yi y

p r ed 2 i

)


i 1

n

( yi y )

2


SVR
300
,

200 100 0 -100 -100
,

­
0 100 200 300

­ 515

C : (10- ) Q2 = 0.907 , RMSE = 15.82, 0

PRESS q2 1 1 SS


i 1

n

( yi y

p r ed 2 i

)


i 1

n

( yi y )

2




Q2 n T
g DCV

RMSEDCV 0.033 45.0 0.159 MAEDCV 0.021 32.0 0.096

Q2
DCV

RMSEDCV 0.026 42.7 0.066

MAEDCV 0.015 28.0 0.043

0.782 0.849 0.474

0.872 0.864 0.910



: n ­ 298K; Tg ­ ( K); ­ (/3, 298).

..., .. . // , 2010, . 430, 5, . 635-638.


/ (2009-2012)

1.
QSAR/QSPR ( " /-)

2.
,


1. QSAR/QSPR
( " ")



: : Q2=(SS-PSS)/SS, RMSEDCV , MAEDCV , : PSS - , SS - : (), ()
BaskinI.I., Zhokhova N.I.,etc./Conf.,Italy,2006




, .






2 1-1

...

1-N



.., , 427,.335-339,2009 .., . / Baskin, I.I., Zhokhova, etc./Conf.,Germany,2008



C60 log P A, B, E S, ,

.



Q2
DCV

Q2
DCV

RMSEDCV 0.76

RMSE
V

DC

568 0.598 , lg Ko (
2/ )

0.800

0.53

C60 165 , lg S

0.448

0.91

0.637

0.74


«- »
Log P A ( ) B ( ) E ( ) S (/ ) 7805 457 R 0.980 0.983 RMSE 0.345 0.051 RMSE 0.395 0.058

t

v

457

0.971

0.066

0.081

457

0.997

0.040

0.074

457

0.987

0.072

0.137


2. "" QSAR/QSPR
,





. : . ( , ) ,


. "" ,



31

P .

-- - . , . - , ­ , ­ - .
a P a C P a C P C

:
100 50

CH3
Prediction, ppm

0 -50 -100 -150

a

P H

C CH

a

P

C C F

: PH

3-n

­ Rn

-200 -200

-150

-100

-50

0

50

100

Experi ment, ppm

(PH2-R, PH-R2, P-R3) n=291

Q2DCV = 0.9560, RMSEDCV=9.1 ppm, MAEDCV=6.1 ppm
.., ..,etc.//,417,c.639-641,2007


.
.

1-[(2-)-]­6() (HEPT) -1 (log (1/ E50)

:
Predi cti on , log 1/EC 50

1
O d N C X a b N R3 c C C R2 R1 d

Csp3 Csp
3

in

d

R1

9 7 5 3

2
c S

in

c

R2

3

d C

C C H2 C O CH3

3

5

7

9

in

d

R1

Experiment, lo g 1/EC50

: n=101 .

4
b

H2 C

in

b

R3

Q

2

DCV

= 0.856, RMSE MAEDCV=0.4

DCV

=0.5,

.., ..,etc.//,417,c.639-641,2007


.

«» , . . - , ­ , , ­ . , . :
1
C a O C O C H2O H+ C a O C OH

8
OH C

7 6
Prediction, -log k
C HO d

2

O C O C O d

H2O H+

O C OH HO d C O

5 4 3 2

3

O C O d C

H2O H+ O

OH

1 0 0 1 2 3 4 5 6 7 8 Experi ment, -l og k

: n=2092 T 0-154oC H2O/.0-98%

Q2

DCV

= 0.9162, RMSE

DCV

=0.31, MAE

DCV

=0.19

..., .., etc. // , 2007,


3. ,
"-" .

LIBSVM (


KEGG DRUG (6000 , 120 )
1. 2. 0-1 3. 42 . 3. 5. (, 6. : = / ( + ) = / ( + ) = (. + .) / 2

42

100
, %

90 80 70 60 50 40 30 20 10 0 1 3 5 7 9 11 13 15 17 19 21 23 25 27 29 31 33 35 37 39 41






( )





- : , , ,





http://sites.google.com/site/conmolfields/home

10-07-00201 13-07-00511


() t(r) r , t
X f (r )

CMF:


i

w fi e

( r ri )

2

wfi ­ i f (., ­ )

, wfi (. , , Tripos)
X f (r )


t

c ftt (r )

t (r )


i



t ,T ( i )

e

( r ri )

2



t ,T ( i )

1

i T(i)


Am+3/Eu
SF - Am+3/Eu Am (5f77s2) 0.097 * Eu (4f76s2) 0.100
+3

+3

Am+3/Eu+3

SF (Am+3, Eu+3) 1,1,2,2- , -

48 : = 2 : 1
**
** Varnek A. et al. // Solvent Extr. Ion. Exch. 2007. V.25. P.1­26

* . . . .. . .: . 1982




Am+3/Eu+3

5,6--3-1,2,4- Eu

+3



3D ChemAxon






, 3D QSPR 2D QSPR

q2 0.73 RMSEcv 0.22 R2p
red

Am+3/Eu+3

3D QSPR (CMF)
RMSE

pred

0.76

0.20






C (sp2) C (sp3)
logSF = 1.57 logSF = -0.22

Am+3/Eu+3

­

C (sp2)

C (sp2)

­
C (sp3)
C (sp3)




­ , , ,






. «» (.. ) , . , , .






( )








: - - QSPR -

: , , , , ,




. « » - ( )