NP-MRD: Showing NP-Card for Sorafenib (NP0136935)

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Record Information

Version

2.0

Created at

2022-05-30 16:28:54 UTC

Updated at

2022-05-30 16:28:54 UTC

NP-MRD ID

NP0136935

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sorafenib

Description

Sorafenib, also known as nexavar or sorafenib N-oxide, belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. Sorafenib is a moderately basic compound (based on its pKa). Within humans, sorafenib participates in a number of enzymatic reactions. In particular, sorafenib and uridine diphosphate glucuronic acid can be converted into sorafenib β-D-glucuronide and uridine 5'-diphosphate; which is mediated by the enzyme UDP-glucuronosyltransferase 1-9. In addition, sorafenib can be converted into sorafenib N-oxide through its interaction with the enzyme cytochrome P450 3A4. In humans, sorafenib is involved in sorafenib metabolism pathway. Sorafenib is a potentially toxic compound. Desmoid tumor (aggressive fibromatosis) A study performed in 2011 showed that Sorafenib is active against aggressive fibromatosis. In a randomized, double-blind, phase II trial combining sorafenib with doxorubicin, the median time to progression was not significantly delayed compared with doxorubicin alone in patients with advanced hepatocellular carcinoma. At the current time sorafenib is indicated as a treatment for advanced renal cell carcinoma (RCC), unresectable hepatocellular carcinomas (HCC) and thyroid cancer. In Scotland the drug had already been refused authorization by the Scottish Medicines Consortium for use within NHS Scotland, for the same reason.

Structure

MOL 3D MOL SDF PDB SMILES InChI

398
  Mrv0541 02231214392D          

 32 34  0  0  0  0            999 V2000
    1.6500    3.0938    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2540    3.9188    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    3.9188    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    4.7439    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -4.3313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -3.5063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -4.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 25  1  0  0  0  0
  3 25  1  0  0  0  0
  4 25  1  0  0  0  0
  5 17  1  0  0  0  0
  5 26  1  0  0  0  0
  6 24  2  0  0  0  0
  7 31  2  0  0  0  0
  8 12  1  0  0  0  0
  8 24  1  0  0  0  0
  9 15  1  0  0  0  0
  9 24  1  0  0  0  0
 10 28  2  0  0  0  0
 10 30  1  0  0  0  0
 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 12 14  2  0  0  0  0
 12 16  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  2  0  0  0  0
 13 25  1  0  0  0  0
 15 19  2  0  0  0  0
 15 20  1  0  0  0  0
 16 21  2  0  0  0  0
 17 22  2  0  0  0  0
 17 23  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 23  2  0  0  0  0
 26 27  2  0  0  0  0
 26 29  1  0  0  0  0
 27 28  1  0  0  0  0
 28 31  1  0  0  0  0
 29 30  2  0  0  0  0
M  END

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
    9.5046    1.7592    0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1307    1.2558    0.1581 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7393    0.2514   -0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5812   -0.2095   -1.5603 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3686   -0.2416   -0.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3840    0.2126    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0738   -0.2614    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1563    0.2657    0.9453 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8478   -0.1207    1.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8781    0.4966    0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4721    0.1143    0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8719   -0.8977    1.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1989   -1.3171    1.2625 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3230   -0.6708    0.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2115    0.3649    0.0573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6325   -1.2089    0.8973 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7802   -0.6019    0.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9327   -1.4056    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1239   -0.9461   -0.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2304    0.3438   -0.6619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7398    0.9405   -1.3068 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.1234    1.1503   -0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2075    2.5353   -1.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1831    3.1954   -0.3413 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0112    3.2041   -0.9102 F   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5064    2.6207   -2.4419 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9196    0.6745   -0.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -1.5382    1.9090 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4381   -1.1508    1.8365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526   -1.2328   -0.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7332   -1.6925   -1.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9955   -1.2111   -1.6667 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1698    1.1273   -0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4893    2.8176   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8194    1.7631    1.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5014    1.7003    0.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6199    0.9797    0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1652    1.2963   -0.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1193    0.6809   -0.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3772   -2.2092    1.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6931   -2.1117    1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8881   -2.4339    0.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0162   -1.5557   -0.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0949    1.3596   -0.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1993   -2.3525    2.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2004   -1.6523    2.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7522   -1.6246   -0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4363   -2.4636   -2.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5 32  2  0
 32 31  1  0
 31 30  2  0
 30  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 27  2  0
 27 22  1  0
 22 20  2  0
 20 21  1  0
 20 19  1  0
 19 18  2  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 12 28  1  0
 28 29  2  0
  7  6  2  0
  6  5  1  0
 29  9  1  0
 18 17  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
 31 48  1  0
 30 47  1  0
 10 38  1  0
 11 39  1  0
 13 40  1  0
 16 41  1  0
 27 44  1  0
 19 43  1  0
 18 42  1  0
 28 45  1  0
 29 46  1  0
  6 37  1  0
M  END

398
  Mrv0541 02231214392D          

 32 34  0  0  0  0            999 V2000
    1.6500    3.0938    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2540    3.9188    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    3.9188    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    4.7439    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -4.3313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -3.5063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -4.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 25  1  0  0  0  0
  3 25  1  0  0  0  0
  4 25  1  0  0  0  0
  5 17  1  0  0  0  0
  5 26  1  0  0  0  0
  6 24  2  0  0  0  0
  7 31  2  0  0  0  0
  8 12  1  0  0  0  0
  8 24  1  0  0  0  0
  9 15  1  0  0  0  0
  9 24  1  0  0  0  0
 10 28  2  0  0  0  0
 10 30  1  0  0  0  0
 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 12 14  2  0  0  0  0
 12 16  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  2  0  0  0  0
 13 25  1  0  0  0  0
 15 19  2  0  0  0  0
 15 20  1  0  0  0  0
 16 21  2  0  0  0  0
 17 22  2  0  0  0  0
 17 23  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 23  2  0  0  0  0
 26 27  2  0  0  0  0
 26 29  1  0  0  0  0
 27 28  1  0  0  0  0
 28 31  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136935

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC(=O)C1=NC=CC(OC2=CC=C(NC(=O)NC3=CC(=C(Cl)C=C3)C(F)(F)F)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H16ClF3N4O3/c1-26-19(30)18-11-15(8-9-27-18)32-14-5-2-12(3-6-14)28-20(31)29-13-4-7-17(22)16(10-13)21(23,24)25/h2-11H,1H3,(H,26,30)(H2,28,29,31)

> <INCHI_KEY>
MLDQJTXFUGDVEO-UHFFFAOYSA-N

> <FORMULA>
C21H16ClF3N4O3

> <MOLECULAR_WEIGHT>
464.825

> <EXACT_MASS>
464.08630272

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
41.10586489713454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[4-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

> <ALOGPS_LOGP>
4.12

> <JCHEM_LOGP>
4.343329760666666

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.992074435078546

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.54979758623275

> <JCHEM_PKA_STRONGEST_BASIC>
2.0299195999719735

> <JCHEM_POLAR_SURFACE_AREA>
92.35000000000001

> <JCHEM_REFRACTIVITY>
114.51830000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sorafenib

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 398                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080   5.775   0.000  0.00  0.00          Cl+0
HETATM    2  F   UNK     0       4.207   7.315   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       7.288   7.315   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0       5.748   8.855   0.000  0.00  0.00           F+0
HETATM    5  O   UNK     0       9.748  -5.775   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       7.081   0.385   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      15.083  -4.235   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       8.415   2.695   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       9.748   0.385   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      13.750  -8.085   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      16.417  -6.545   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       7.081   3.465   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748   5.775   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081   5.005   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748  -1.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748   2.695   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748  -4.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414   5.005   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.082  -1.925   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415  -1.925   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414   3.465   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.082  -3.465   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.415  -3.465   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.415   1.155   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.748   7.315   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.082  -6.545   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.416  -5.775   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.750  -6.545   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.082  -8.085   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.416  -8.855   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.083  -5.775   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.751  -5.775   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2   25                                                            
CONECT    3   25                                                            
CONECT    4   25                                                            
CONECT    5   17   26                                                       
CONECT    6   24                                                            
CONECT    7   31                                                            
CONECT    8   12   24                                                       
CONECT    9   15   24                                                       
CONECT   10   28   30                                                       
CONECT   11   31   32                                                       
CONECT   12    8   14   16                                                  
CONECT   13   14   18   25                                                  
CONECT   14   12   13                                                       
CONECT   15    9   19   20                                                  
CONECT   16   12   21                                                       
CONECT   17    5   22   23                                                  
CONECT   18    1   13   21                                                  
CONECT   19   15   22                                                       
CONECT   20   15   23                                                       
CONECT   21   16   18                                                       
CONECT   22   17   19                                                       
CONECT   23   17   20                                                       
CONECT   24    6    8    9                                                  
CONECT   25    2    3    4   13                                             
CONECT   26    5   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   10   27   31                                                  
CONECT   29   26   30                                                       
CONECT   30   10   29                                                       
CONECT   31    7   11   28                                                  
CONECT   32   11                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
4-(4-((((4-Chloro-3-(trifluoromethyl)phenyl)amino)carbonyl)amino)phenoxy)-N-methyl-2-pyridinecarboxamide	ChEBI
N-(4-Chloro-3-(trifluoromethyl)phenyl)-n'-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl)urea	ChEBI
Sorafenibum	ChEBI
Sorafenib tosylate	HMDB
4-(4-(3-(4-Chloro-3-trifluoromethylphenyl)ureido)phenoxy)pyridine-2-carboxyllic acid methyamide-4-methylbenzenesulfonate	HMDB
Nexavar	HMDB
Sorafenib N-oxide	HMDB
Sorafenib N oxide	HMDB
4-(4-(3-(4-Chloro-3-trifluoromethylphenyl)ureido)phenoxy)pyridine-2-carboxylic acid methyamide-4-methylbenzenesulfonate	HMDB

Chemical Formula

C₂₁H₁₆ClF₃N₄O₃

Average Mass

464.8250 Da

Monoisotopic Mass

464.08630 Da

IUPAC Name

4-[4-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

Traditional Name

sorafenib

CAS Registry Number

Not Available

SMILES

CNC(=O)C1=NC=CC(OC2=CC=C(NC(=O)NC3=CC(=C(Cl)C=C3)C(F)(F)F)C=C2)=C1

InChI Identifier

InChI=1S/C21H16ClF3N4O3/c1-26-19(30)18-11-15(8-9-27-18)32-14-5-2-12(3-6-14)28-20(31)29-13-4-7-17(22)16(10-13)21(23,24)25/h2-11H,1H3,(H,26,30)(H2,28,29,31)

InChI Key

MLDQJTXFUGDVEO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Diarylethers

Alternative Parents

Substituents

Diaryl ether
Trifluoromethylbenzene
N-phenylurea
Pyridine carboxylic acid or derivatives
Pyridinecarboxamide
2-heteroaryl carboxamide
Phenoxy compound
Phenol ether
Halobenzene
Chlorobenzene
Benzenoid
Pyridine
Monocyclic benzene moiety
Aryl halide
Aryl chloride
Heteroaromatic compound
Urea
Secondary carboxylic acid amide
Carbonic acid derivative
Carboxamide group
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organofluoride
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl fluoride
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:50924 )
ureas (CHEBI:50924 )
monochlorobenzenes (CHEBI:50924 )
(trifluoromethyl)benzenes (CHEBI:50924 )
pyridinecarboxamide (CHEBI:50924 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.12	ALOGPS
logP	4.34	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	11.55	ChemAxon
pKa (Strongest Basic)	2.03	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.35 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	114.52 m³·mol⁻¹	ChemAxon
Polarizability	41.11 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0014542

DrugBank ID

DB00398

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

187440

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sorafenib

METLIN ID

Not Available

PubChem Compound

216239

PDB ID

Not Available

ChEBI ID

50924

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Sorafenib (NP0136935)

MOL for NP0136935 (Sorafenib)

3D MOL for NP0136935 (Sorafenib)

3D SDF for NP0136935 (Sorafenib)

3D-SDF for NP0136935 (Sorafenib)

PDB for NP0136935 (Sorafenib)

3D PDB for NP0136935 (Sorafenib)

SMILES for NP0136935 (Sorafenib)

INCHI for NP0136935 (Sorafenib)

Structure for NP0136935 (Sorafenib)

3D Structure for NP0136935 (Sorafenib)