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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (11)transporters (4) Show 15 proteins XML

enzymes (11)transporters (4) Show 15 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015397

Secondary Accession Numbers

HMDB15397

Metabolite Identification

Common Name

Sunitinib

Description

Sunitinib is an oral, small-molecule, multi-targeted receptor tyrosine kinase (RTK) inhibitor that was approved by the FDA for the treatment of renal cell carcinoma (RCC) and imatinib-resistant gastrointestinal stromal tumor (GIST) on January 26, 2006. Sunitinib inhibits cellular signaling by targeting multiple RTKs. These include all platelet-derived growth factor receptors (PDGF-R) and vascular endothelial growth factor receptors (VEGF-R). Sunitinib also inhibits KIT (CD117), the RTK that drives the majority of GISTs. In addition, sunitinib inhibits other RTKs including RET, CSF-1R, and flt3.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

1268
  Mrv0541 02231215222D          

 29 31  0  0  0  0            999 V2000
    1.6500   -1.1857    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    1.6702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8806   -2.0107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0675    1.7635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2498   -0.9455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1546    0.7122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -2.6746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5144    1.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7949    0.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9746    0.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6377   -0.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7077    1.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9650   -0.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8742    1.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8140    2.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3480    0.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -1.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8304   -0.5626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5633    1.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7181   -0.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556   -2.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4273    2.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3671    3.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 28  1  0  0  0  0
  2 16  2  0  0  0  0
  3 23  2  0  0  0  0
  4  8  1  0  0  0  0
  4 14  1  0  0  0  0
  4 15  1  0  0  0  0
  5 11  1  0  0  0  0
  5 13  1  0  0  0  0
  6 12  1  0  0  0  0
  6 16  1  0  0  0  0
  7 21  1  0  0  0  0
  7 23  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  2  0  0  0  0
  9 16  1  0  0  0  0
 10 11  2  0  0  0  0
 10 20  1  0  0  0  0
 11 18  1  0  0  0  0
 13 22  1  0  0  0  0
 14 24  1  0  0  0  0
 15 25  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 17 23  1  0  0  0  0
 19 21  2  0  0  0  0
 19 26  1  0  0  0  0
 21 27  1  0  0  0  0
 26 28  2  0  0  0  0
 27 29  2  0  0  0  0
 28 29  1  0  0  0  0
M  END

HMDB0015397
     RDKit          3D
Sunitinib
 56 58  0  0  0  0  0  0  0  0999 V2000
    6.2307    1.6429    0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4171    0.3403   -0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6849   -0.7247    0.2129 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1803   -1.9498   -0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7202   -3.2226    0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2827   -0.7009   -0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    0.4636    0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718    0.3123   -0.0420 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1991    1.3539    0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6920    2.3627    0.9117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187    1.3973    0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0234    2.5265    0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5648    3.9059    0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2765    2.1666   -0.0776 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3530    0.8737   -0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5684    0.1162   -0.7119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6280    0.0610    0.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7800    0.7080    1.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9244    1.4334    1.9426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0865    0.3715    1.8246 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7669   -0.4664    0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0109   -1.0608    0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4530   -1.8555   -0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5741   -2.0404   -1.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9514   -2.8201   -2.2699 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3262   -1.4479   -1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8900   -0.6527   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0569    0.3784   -0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7590   -1.0451   -0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6639    1.5706    1.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8584    2.4467   -0.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2459    2.0443    0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4923    0.0626   -0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1240    0.3789   -1.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3073   -1.9425   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9296   -1.9292   -1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9645   -4.0238   -0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770   -3.3110    0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3142   -3.5590    1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2497   -0.7572   -1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8066   -1.6144    0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4890    0.6779    1.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042    1.3701   -0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8113   -0.5373   -0.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    4.0912    0.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4978    3.9218    1.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3444    4.6222    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0763    2.8742   -0.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6219   -0.4379   -1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5075    0.6867    2.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7130   -0.9201    1.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4333   -2.3177   -0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6254   -1.5917   -2.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7160   -1.6167   -0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1561   -1.4824    0.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1814   -1.1340   -1.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 15 28  2  0
 28 29  1  0
 28 11  1  0
 27 17  1  0
 27 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
 13 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 16 49  1  0
 20 50  1  0
 22 51  1  0
 23 52  1  0
 26 53  1  0
 29 54  1  0
 29 55  1  0
 29 56  1  0
M  END

1268
  Mrv0541 02231215222D          

 29 31  0  0  0  0            999 V2000
    1.6500   -1.1857    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    1.6702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8806   -2.0107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0675    1.7635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2498   -0.9455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1546    0.7122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -2.6746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5144    1.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7949    0.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9746    0.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6377   -0.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7077    1.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9650   -0.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8742    1.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8140    2.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3480    0.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -1.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8304   -0.5626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5633    1.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7181   -0.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556   -2.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4273    2.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3671    3.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 28  1  0  0  0  0
  2 16  2  0  0  0  0
  3 23  2  0  0  0  0
  4  8  1  0  0  0  0
  4 14  1  0  0  0  0
  4 15  1  0  0  0  0
  5 11  1  0  0  0  0
  5 13  1  0  0  0  0
  6 12  1  0  0  0  0
  6 16  1  0  0  0  0
  7 21  1  0  0  0  0
  7 23  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  2  0  0  0  0
  9 16  1  0  0  0  0
 10 11  2  0  0  0  0
 10 20  1  0  0  0  0
 11 18  1  0  0  0  0
 13 22  1  0  0  0  0
 14 24  1  0  0  0  0
 15 25  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 17 23  1  0  0  0  0
 19 21  2  0  0  0  0
 19 26  1  0  0  0  0
 21 27  1  0  0  0  0
 26 28  2  0  0  0  0
 27 29  2  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015397

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)CCNC(=O)C1=C(C)NC(\C=C2/C(=O)NC3=C2C=C(F)C=C3)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C22H27FN4O2/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25-14(20)4)12-17-16-11-15(23)7-8-18(16)26-21(17)28/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28)/b17-12-

> <INCHI_KEY>
WINHZLLDWRZWRT-ATVHPVEESA-N

> <FORMULA>
C22H27FN4O2

> <MOLECULAR_WEIGHT>
398.4738

> <EXACT_MASS>
398.211804333

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
44.319045037443416

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[2-(diethylamino)ethyl]-5-{[(3Z)-5-fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene]methyl}-2,4-dimethyl-1H-pyrrole-3-carboxamide

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
2.9273768136666662

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.237659583379774

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.462899232702135

> <JCHEM_PKA_STRONGEST_BASIC>
9.0426929039079

> <JCHEM_POLAR_SURFACE_AREA>
77.23

> <JCHEM_REFRACTIVITY>
116.26629999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sunitinib

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015397
     RDKit          3D
Sunitinib
 56 58  0  0  0  0  0  0  0  0999 V2000
    6.2307    1.6429    0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4171    0.3403   -0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6849   -0.7247    0.2129 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1803   -1.9498   -0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7202   -3.2226    0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2827   -0.7009   -0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    0.4636    0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718    0.3123   -0.0420 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1991    1.3539    0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6920    2.3627    0.9117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187    1.3973    0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0234    2.5265    0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5648    3.9059    0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2765    2.1666   -0.0776 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3530    0.8737   -0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5684    0.1162   -0.7119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6280    0.0610    0.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7800    0.7080    1.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9244    1.4334    1.9426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0865    0.3715    1.8246 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7669   -0.4664    0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0109   -1.0608    0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4530   -1.8555   -0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5741   -2.0404   -1.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9514   -2.8201   -2.2699 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3262   -1.4479   -1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8900   -0.6527   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0569    0.3784   -0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7590   -1.0451   -0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6639    1.5706    1.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8584    2.4467   -0.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2459    2.0443    0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4923    0.0626   -0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1240    0.3789   -1.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3073   -1.9425   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9296   -1.9292   -1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9645   -4.0238   -0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770   -3.3110    0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3142   -3.5590    1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2497   -0.7572   -1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8066   -1.6144    0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4890    0.6779    1.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042    1.3701   -0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8113   -0.5373   -0.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    4.0912    0.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4978    3.9218    1.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3444    4.6222    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0763    2.8742   -0.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6219   -0.4379   -1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5075    0.6867    2.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7130   -0.9201    1.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4333   -2.3177   -0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6254   -1.5917   -2.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7160   -1.6167   -0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1561   -1.4824    0.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1814   -1.1340   -1.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 15 28  2  0
 28 29  1  0
 28 11  1  0
 27 17  1  0
 27 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
 13 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 16 49  1  0
 20 50  1  0
 22 51  1  0
 23 52  1  0
 26 53  1  0
 29 54  1  0
 29 55  1  0
 29 56  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1268                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       3.080  -2.213   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0      13.243   3.118   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      10.977  -3.753   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      18.793   3.292   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      11.666  -1.765   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      15.222   1.329   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       8.538  -4.993   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      17.760   2.149   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.684   0.510   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.153   0.673   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.524  -0.733   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.254   2.472   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.001  -0.997   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.299   2.969   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.319   4.757   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.716   1.652   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.538  -2.514   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.017  -1.050   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.081  -2.983   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.385   2.008   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.081  -4.523   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.407  -1.626   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.437  -3.753   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.331   4.112   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.352   5.900   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.747  -2.213   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.747  -5.293   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.414  -2.983   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.414  -4.523   0.000  0.00  0.00           C+0
CONECT    1   28                                                            
CONECT    2   16                                                            
CONECT    3   23                                                            
CONECT    4    8   14   15                                                  
CONECT    5   11   13                                                       
CONECT    6   12   16                                                       
CONECT    7   21   23                                                       
CONECT    8    4   12                                                       
CONECT    9   10   13   16                                                  
CONECT   10    9   11   20                                                  
CONECT   11    5   10   18                                                  
CONECT   12    6    8                                                       
CONECT   13    5    9   22                                                  
CONECT   14    4   24                                                       
CONECT   15    4   25                                                       
CONECT   16    2    6    9                                                  
CONECT   17   18   19   23                                                  
CONECT   18   11   17                                                       
CONECT   19   17   21   26                                                  
CONECT   20   10                                                            
CONECT   21    7   19   27                                                  
CONECT   22   13                                                            
CONECT   23    3    7   17                                                  
CONECT   24   14                                                            
CONECT   25   15                                                            
CONECT   26   19   28                                                       
CONECT   27   21   29                                                       
CONECT   28    1   26   29                                                  
CONECT   29   27   28                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

COMPND    HMDB0015397
HETATM    1  C1  UNL     1       6.231   1.643   0.224  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.417   0.340  -0.484  1.00  0.00           C  
HETATM    3  N1  UNL     1       5.685  -0.725   0.213  1.00  0.00           N  
HETATM    4  C3  UNL     1       6.180  -1.950  -0.445  1.00  0.00           C  
HETATM    5  C4  UNL     1       5.720  -3.223   0.138  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.283  -0.701  -0.123  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.492   0.464   0.334  1.00  0.00           C  
HETATM    8  N2  UNL     1       2.072   0.312  -0.042  1.00  0.00           N  
HETATM    9  C7  UNL     1       1.199   1.354   0.311  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.692   2.363   0.912  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.219   1.397   0.056  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.023   2.527   0.203  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.565   3.906   0.604  1.00  0.00           C  
HETATM   14  N3  UNL     1      -2.276   2.167  -0.078  1.00  0.00           N  
HETATM   15  C11 UNL     1      -2.353   0.874  -0.399  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.568   0.116  -0.712  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.628   0.061   0.078  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.780   0.708   1.352  1.00  0.00           C  
HETATM   19  O2  UNL     1      -3.924   1.433   1.943  1.00  0.00           O  
HETATM   20  N4  UNL     1      -6.086   0.372   1.825  1.00  0.00           N  
HETATM   21  C15 UNL     1      -6.767  -0.466   0.897  1.00  0.00           C  
HETATM   22  C16 UNL     1      -8.011  -1.061   0.872  1.00  0.00           C  
HETATM   23  C17 UNL     1      -8.453  -1.856  -0.164  1.00  0.00           C  
HETATM   24  C18 UNL     1      -7.574  -2.040  -1.212  1.00  0.00           C  
HETATM   25  F1  UNL     1      -7.951  -2.820  -2.270  1.00  0.00           F  
HETATM   26  C19 UNL     1      -6.326  -1.448  -1.194  1.00  0.00           C  
HETATM   27  C20 UNL     1      -5.890  -0.653  -0.153  1.00  0.00           C  
HETATM   28  C21 UNL     1      -1.057   0.378  -0.319  1.00  0.00           C  
HETATM   29  C22 UNL     1      -0.759  -1.045  -0.614  1.00  0.00           C  
HETATM   30  H1  UNL     1       5.664   1.571   1.169  1.00  0.00           H  
HETATM   31  H2  UNL     1       5.858   2.447  -0.448  1.00  0.00           H  
HETATM   32  H3  UNL     1       7.246   2.044   0.585  1.00  0.00           H  
HETATM   33  H4  UNL     1       7.492   0.063  -0.466  1.00  0.00           H  
HETATM   34  H5  UNL     1       6.124   0.379  -1.555  1.00  0.00           H  
HETATM   35  H6  UNL     1       7.307  -1.942  -0.433  1.00  0.00           H  
HETATM   36  H7  UNL     1       5.930  -1.929  -1.533  1.00  0.00           H  
HETATM   37  H8  UNL     1       5.965  -4.024  -0.636  1.00  0.00           H  
HETATM   38  H9  UNL     1       4.677  -3.311   0.434  1.00  0.00           H  
HETATM   39  H10 UNL     1       6.314  -3.559   1.024  1.00  0.00           H  
HETATM   40  H11 UNL     1       4.250  -0.757  -1.255  1.00  0.00           H  
HETATM   41  H12 UNL     1       3.807  -1.614   0.289  1.00  0.00           H  
HETATM   42  H13 UNL     1       3.489   0.678   1.393  1.00  0.00           H  
HETATM   43  H14 UNL     1       3.804   1.370  -0.221  1.00  0.00           H  
HETATM   44  H15 UNL     1       1.811  -0.537  -0.544  1.00  0.00           H  
HETATM   45  H16 UNL     1       0.377   4.091   0.058  1.00  0.00           H  
HETATM   46  H17 UNL     1      -0.498   3.922   1.691  1.00  0.00           H  
HETATM   47  H18 UNL     1      -1.344   4.622   0.212  1.00  0.00           H  
HETATM   48  H19 UNL     1      -3.076   2.874  -0.054  1.00  0.00           H  
HETATM   49  H20 UNL     1      -3.622  -0.438  -1.643  1.00  0.00           H  
HETATM   50  H21 UNL     1      -6.507   0.687   2.724  1.00  0.00           H  
HETATM   51  H22 UNL     1      -8.713  -0.920   1.701  1.00  0.00           H  
HETATM   52  H23 UNL     1      -9.433  -2.318  -0.172  1.00  0.00           H  
HETATM   53  H24 UNL     1      -5.625  -1.592  -2.024  1.00  0.00           H  
HETATM   54  H25 UNL     1      -1.716  -1.617  -0.691  1.00  0.00           H  
HETATM   55  H26 UNL     1      -0.156  -1.482   0.207  1.00  0.00           H  
HETATM   56  H27 UNL     1      -0.181  -1.134  -1.563  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   33   34
CONECT    3    4    6
CONECT    4    5   35   36
CONECT    5   37   38   39
CONECT    6    7   40   41
CONECT    7    8   42   43
CONECT    8    9   44
CONECT    9   10   10   11
CONECT   11   12   12   28
CONECT   12   13   14
CONECT   13   45   46   47
CONECT   14   15   48
CONECT   15   16   28   28
CONECT   16   17   17   49
CONECT   17   18   27
CONECT   18   19   19   20
CONECT   20   21   50
CONECT   21   22   22   27
CONECT   22   23   51
CONECT   23   24   24   52
CONECT   24   25   26
CONECT   26   27   27   53
CONECT   28   29
CONECT   29   54   55   56
END

HMDB0015397
     RDKit          3D
Sunitinib
 56 58  0  0  0  0  0  0  0  0999 V2000
    6.2307    1.6429    0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4171    0.3403   -0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6849   -0.7247    0.2129 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1803   -1.9498   -0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7202   -3.2226    0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2827   -0.7009   -0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    0.4636    0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718    0.3123   -0.0420 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1991    1.3539    0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6920    2.3627    0.9117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187    1.3973    0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0234    2.5265    0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5648    3.9059    0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2765    2.1666   -0.0776 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3530    0.8737   -0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5684    0.1162   -0.7119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6280    0.0610    0.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7800    0.7080    1.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9244    1.4334    1.9426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0865    0.3715    1.8246 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7669   -0.4664    0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0109   -1.0608    0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4530   -1.8555   -0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5741   -2.0404   -1.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9514   -2.8201   -2.2699 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3262   -1.4479   -1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8900   -0.6527   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0569    0.3784   -0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7590   -1.0451   -0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6639    1.5706    1.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8584    2.4467   -0.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2459    2.0443    0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4923    0.0626   -0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1240    0.3789   -1.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3073   -1.9425   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9296   -1.9292   -1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9645   -4.0238   -0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770   -3.3110    0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3142   -3.5590    1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2497   -0.7572   -1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8066   -1.6144    0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4890    0.6779    1.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042    1.3701   -0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8113   -0.5373   -0.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    4.0912    0.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4978    3.9218    1.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3444    4.6222    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0763    2.8742   -0.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6219   -0.4379   -1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5075    0.6867    2.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7130   -0.9201    1.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4333   -2.3177   -0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6254   -1.5917   -2.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7160   -1.6167   -0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1561   -1.4824    0.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1814   -1.1340   -1.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 15 28  2  0
 28 29  1  0
 28 11  1  0
 27 17  1  0
 27 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
 13 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 16 49  1  0
 20 50  1  0
 22 51  1  0
 23 52  1  0
 26 53  1  0
 29 54  1  0
 29 55  1  0
 29 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
SU-11248	ChEBI
Sunitinibum	ChEBI
Sutent	ChEBI
SU11248	HMDB
Sunitinib malate	HMDB
5-(5-Fluoro-2-oxo-1,2-dihydroindolylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide	HMDB

Chemical Formula

C₂₂H₂₇FN₄O₂

Average Molecular Weight

398.4738

Monoisotopic Molecular Weight

398.211804333

IUPAC Name

N-[2-(diethylamino)ethyl]-5-{[(3Z)-5-fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene]methyl}-2,4-dimethyl-1H-pyrrole-3-carboxamide

Traditional Name

sunitinib

CAS Registry Number

557795-19-4

SMILES

CCN(CC)CCNC(=O)C1=C(C)NC(\C=C2/C(=O)NC3=C2C=C(F)C=C3)=C1C

InChI Identifier

InChI=1S/C22H27FN4O2/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25-14(20)4)12-17-16-11-15(23)7-8-18(16)26-21(17)28/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28)/b17-12-

InChI Key

WINHZLLDWRZWRT-ATVHPVEESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolines

Direct Parent

Indolines

Alternative Parents

Substituents

Dihydroindole
Pyrrole-3-carboxamide
Pyrrole-3-carboxylic acid or derivatives
Aryl fluoride
Aryl halide
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Vinylogous amide
Tertiary amine
Amino acid or derivatives
Secondary carboxylic acid amide
Tertiary aliphatic amine
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Amine
Organofluoride
Organohalogen compound
Organonitrogen compound
Organopnictogen compound
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:38940 )
pyrroles (CHEBI:38940 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015397)
Membrane (HMDB: HMDB0015397)

Source

Exogenous

Exogenous (HMDB: HMDB0015397)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.031 g/L	Not Available
LogP	2.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.031 g/L	ALOGPS
logP	3.24	ALOGPS
logP	2.93	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	11.46	ChemAxon
pKa (Strongest Basic)	9.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.23 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	116.27 m³·mol⁻¹	ChemAxon
Polarizability	44.32 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	207.26	30932474
DeepCCS	[M-H]-	204.902	30932474
DeepCCS	[M-2H]-	238.836	30932474
DeepCCS	[M+Na]+	214.065	30932474
AllCCS	[M+H]+	196.9	32859911
AllCCS	[M+H-H2O]+	194.2	32859911
AllCCS	[M+NH4]+	199.3	32859911
AllCCS	[M+Na]+	200.0	32859911
AllCCS	[M-H]-	200.4	32859911
AllCCS	[M+Na-2H]-	200.9	32859911
AllCCS	[M+HCOO]-	201.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.24 minutes	32390414
Predicted by Siyang on May 30, 2022	10.256 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.58 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	118.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1043.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	174.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	157.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	67.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	306.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	398.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	421.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	733.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	292.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1007.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	221.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	287.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	315.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	393.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	69.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sunitinib	CCN(CC)CCNC(=O)C1=C(C)NC(\C=C2/C(=O)NC3=C2C=C(F)C=C3)=C1C	4771.5	Standard polar	33892256
Sunitinib	CCN(CC)CCNC(=O)C1=C(C)NC(\C=C2/C(=O)NC3=C2C=C(F)C=C3)=C1C	3561.4	Standard non polar	33892256
Sunitinib	CCN(CC)CCNC(=O)C1=C(C)NC(\C=C2/C(=O)NC3=C2C=C(F)C=C3)=C1C	3713.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sunitinib,1TMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C	3452.8	Semi standard non polar	33892256
Sunitinib,1TMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C	3335.7	Standard non polar	33892256
Sunitinib,1TMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C	4546.5	Standard polar	33892256
Sunitinib,1TMS,isomer #2	CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C	3544.6	Semi standard non polar	33892256
Sunitinib,1TMS,isomer #2	CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C	3429.0	Standard non polar	33892256
Sunitinib,1TMS,isomer #2	CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C	4484.6	Standard polar	33892256
Sunitinib,1TMS,isomer #3	CCN(CC)CCNC(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C	3447.4	Semi standard non polar	33892256
Sunitinib,1TMS,isomer #3	CCN(CC)CCNC(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C	3083.4	Standard non polar	33892256
Sunitinib,1TMS,isomer #3	CCN(CC)CCNC(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C	4051.5	Standard polar	33892256
Sunitinib,2TMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C	3438.2	Semi standard non polar	33892256
Sunitinib,2TMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C	3457.2	Standard non polar	33892256
Sunitinib,2TMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C	4261.0	Standard polar	33892256
Sunitinib,2TMS,isomer #2	CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C	3323.0	Semi standard non polar	33892256
Sunitinib,2TMS,isomer #2	CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C	3166.5	Standard non polar	33892256
Sunitinib,2TMS,isomer #2	CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C	3820.4	Standard polar	33892256
Sunitinib,2TMS,isomer #3	CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C	3448.6	Semi standard non polar	33892256
Sunitinib,2TMS,isomer #3	CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C	3240.2	Standard non polar	33892256
Sunitinib,2TMS,isomer #3	CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C	3777.5	Standard polar	33892256
Sunitinib,3TMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C	3378.1	Semi standard non polar	33892256
Sunitinib,3TMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C	3306.8	Standard non polar	33892256
Sunitinib,3TMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C	3587.9	Standard polar	33892256
Sunitinib,1TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C	3666.9	Semi standard non polar	33892256
Sunitinib,1TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C	3519.3	Standard non polar	33892256
Sunitinib,1TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C	4552.0	Standard polar	33892256
Sunitinib,1TBDMS,isomer #2	CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C	3710.1	Semi standard non polar	33892256
Sunitinib,1TBDMS,isomer #2	CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C	3629.0	Standard non polar	33892256
Sunitinib,1TBDMS,isomer #2	CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C	4483.1	Standard polar	33892256
Sunitinib,1TBDMS,isomer #3	CCN(CC)CCNC(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C	3654.3	Semi standard non polar	33892256
Sunitinib,1TBDMS,isomer #3	CCN(CC)CCNC(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C	3298.9	Standard non polar	33892256
Sunitinib,1TBDMS,isomer #3	CCN(CC)CCNC(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C	4064.5	Standard polar	33892256
Sunitinib,2TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C	3787.9	Semi standard non polar	33892256
Sunitinib,2TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C	3818.4	Standard non polar	33892256
Sunitinib,2TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)NC3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C	4325.8	Standard polar	33892256
Sunitinib,2TBDMS,isomer #2	CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C	3713.6	Semi standard non polar	33892256
Sunitinib,2TBDMS,isomer #2	CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C	3553.0	Standard non polar	33892256
Sunitinib,2TBDMS,isomer #2	CCN(CC)CCN(C(=O)C1=C(C)[NH]C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C	3918.9	Standard polar	33892256
Sunitinib,2TBDMS,isomer #3	CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C	3819.6	Semi standard non polar	33892256
Sunitinib,2TBDMS,isomer #3	CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C	3624.3	Standard non polar	33892256
Sunitinib,2TBDMS,isomer #3	CCN(CC)CCNC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C	3866.0	Standard polar	33892256
Sunitinib,3TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C	3903.1	Semi standard non polar	33892256
Sunitinib,3TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C	3840.7	Standard non polar	33892256
Sunitinib,3TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(/C=C2\C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C23)=C1C)[Si](C)(C)C(C)(C)C	3779.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sunitinib GC-MS (Non-derivatized) - 70eV, Positive	splash10-001r-9043000000-f9288d8cb7c447b10d86	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sunitinib GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sunitinib GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sunitinib 10V, Positive-QTOF	splash10-0002-0419000000-d91569989d4c1e438a58	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sunitinib 20V, Positive-QTOF	splash10-1039-4964000000-32cdbd9b3679f4b806d9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sunitinib 40V, Positive-QTOF	splash10-00di-9740000000-14530852543a6132d98b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sunitinib 10V, Negative-QTOF	splash10-0002-0019000000-716107e6148bcb3af14c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sunitinib 20V, Negative-QTOF	splash10-052b-5398000000-e20fbe1cd3f11ad37acb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sunitinib 40V, Negative-QTOF	splash10-0006-9230000000-0d8caf257003c837c3d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sunitinib 10V, Positive-QTOF	splash10-0002-0009000000-c7521df282758983a81b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sunitinib 20V, Positive-QTOF	splash10-003r-0197000000-fc31f5a3f60673e3fb48	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sunitinib 40V, Positive-QTOF	splash10-0a4i-0293000000-c9aae10759016725c932	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sunitinib 10V, Negative-QTOF	splash10-0002-0009000000-f6f1dd2f48935333770c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sunitinib 20V, Negative-QTOF	splash10-0002-2049000000-fe9e71e910a9eddb2023	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sunitinib 40V, Negative-QTOF	splash10-052g-6194000000-ce0d447fabdb293e1813	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01268	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01268	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01268

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4486264

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sunitinib

METLIN ID

Not Available

PubChem Compound

5329102

PDB ID

B49

ChEBI ID

38940

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Demetri GD, van Oosterom AT, Garrett CR, Blackstein ME, Shah MH, Verweij J, McArthur G, Judson IR, Heinrich MC, Morgan JA, Desai J, Fletcher CD, George S, Bello CL, Huang X, Baum CM, Casali PG: Efficacy and safety of sunitinib in patients with advanced gastrointestinal stromal tumour after failure of imatinib: a randomised controlled trial. Lancet. 2006 Oct 14;368(9544):1329-38. [PubMed:17046465 ]
Motzer RJ, Hutson TE, Tomczak P, Michaelson MD, Bukowski RM, Rixe O, Oudard S, Negrier S, Szczylik C, Kim ST, Chen I, Bycott PW, Baum CM, Figlin RA: Sunitinib versus interferon alfa in metastatic renal-cell carcinoma. N Engl J Med. 2007 Jan 11;356(2):115-24. [PubMed:17215529 ]
(). FDA label . .

Only showing the first 10 proteins. There are 15 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

2. Vascular endothelial growth factor receptor 3

General function:: Involved in protein kinase activity
Specific function:: Receptor for VEGFC. Has a tyrosine-protein kinase activity
Gene Name:: FLT4
Uniprot ID:: P35916
Molecular weight:: 145597.3

References

Roskoski R Jr: Sunitinib: a VEGF and PDGF receptor protein kinase and angiogenesis inhibitor. Biochem Biophys Res Commun. 2007 May 4;356(2):323-8. Epub 2007 Mar 7. [PubMed:17367763 ]
Deprimo SE, Bello CL, Smeraglia J, Baum CM, Spinella D, Rini BI, Michaelson MD, Motzer RJ: Circulating protein biomarkers of pharmacodynamic activity of sunitinib in patients with metastatic renal cell carcinoma: modulation of VEGF and VEGF-related proteins. J Transl Med. 2007 Jul 2;5:32. [PubMed:17605814 ]
Katoh Y, Katoh M: Comparative integromics on VEGF family members. Int J Oncol. 2006 Jun;28(6):1585-9. [PubMed:16685460 ]
Gridelli C, Maione P, Del Gaizo F, Colantuoni G, Guerriero C, Ferrara C, Nicolella D, Comunale D, De Vita A, Rossi A: Sorafenib and sunitinib in the treatment of advanced non-small cell lung cancer. Oncologist. 2007 Feb;12(2):191-200. [PubMed:17296815 ]
Ahmed SI, Thomas AL, Steward WP: Vascular endothelial growth factor (VEGF) inhibition by small molecules. J Chemother. 2004 Nov;16 Suppl 4:59-63. [PubMed:15688612 ]

Enzyme Details

3. FL cytokine receptor

General function:: Involved in protein kinase activity
Specific function:: Receptor for the FL cytokine. Has a tyrosine-protein kinase activity
Gene Name:: FLT3
Uniprot ID:: P36888
Molecular weight:: 112902.5

References

O'Farrell AM, Abrams TJ, Yuen HA, Ngai TJ, Louie SG, Yee KW, Wong LM, Hong W, Lee LB, Town A, Smolich BD, Manning WC, Murray LJ, Heinrich MC, Cherrington JM: SU11248 is a novel FLT3 tyrosine kinase inhibitor with potent activity in vitro and in vivo. Blood. 2003 May 1;101(9):3597-605. Epub 2003 Jan 16. [PubMed:12531805 ]
O'Farrell AM, Foran JM, Fiedler W, Serve H, Paquette RL, Cooper MA, Yuen HA, Louie SG, Kim H, Nicholas S, Heinrich MC, Berdel WE, Bello C, Jacobs M, Scigalla P, Manning WC, Kelsey S, Cherrington JM: An innovative phase I clinical study demonstrates inhibition of FLT3 phosphorylation by SU11248 in acute myeloid leukemia patients. Clin Cancer Res. 2003 Nov 15;9(15):5465-76. [PubMed:14654525 ]
Baratte S, Sarati S, Frigerio E, James CA, Ye C, Zhang Q: Quantitation of SU1 1248, an oral multi-target tyrosine kinase inhibitor, and its metabolite in monkey tissues by liquid chromatograph with tandem mass spectrometry following semi-automated liquid-liquid extraction. J Chromatogr A. 2004 Jan 23;1024(1-2):87-94. [PubMed:14753710 ]
Schmidt-Arras D, Schwable J, Bohmer FD, Serve H: Flt3 receptor tyrosine kinase as a drug target in leukemia. Curr Pharm Des. 2004;10(16):1867-83. [PubMed:15180525 ]
Yee KW, Schittenhelm M, O'Farrell AM, Town AR, McGreevey L, Bainbridge T, Cherrington JM, Heinrich MC: Synergistic effect of SU11248 with cytarabine or daunorubicin on FLT3 ITD-positive leukemic cells. Blood. 2004 Dec 15;104(13):4202-9. Epub 2004 Aug 10. [PubMed:15304385 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

4. Vascular endothelial growth factor receptor 2

General function:: Involved in protein kinase activity
Specific function:: Receptor for VEGF or VEGFC. Has a tyrosine-protein kinase activity. The VEGF-kinase ligand/receptor signaling system plays a key role in vascular development and regulation of vascular permeability. In case of HIV-1 infection, the interaction with extracellular viral Tat protein seems to enhance angiogenesis in Kaposi's sarcoma lesions
Gene Name:: KDR
Uniprot ID:: P35968
Molecular weight:: 151525.6

References

Mendel DB, Laird AD, Xin X, Louie SG, Christensen JG, Li G, Schreck RE, Abrams TJ, Ngai TJ, Lee LB, Murray LJ, Carver J, Chan E, Moss KG, Haznedar JO, Sukbuntherng J, Blake RA, Sun L, Tang C, Miller T, Shirazian S, McMahon G, Cherrington JM: In vivo antitumor activity of SU11248, a novel tyrosine kinase inhibitor targeting vascular endothelial growth factor and platelet-derived growth factor receptors: determination of a pharmacokinetic/pharmacodynamic relationship. Clin Cancer Res. 2003 Jan;9(1):327-37. [PubMed:12538485 ]
Schueneman AJ, Himmelfarb E, Geng L, Tan J, Donnelly E, Mendel D, McMahon G, Hallahan DE: SU11248 maintenance therapy prevents tumor regrowth after fractionated irradiation of murine tumor models. Cancer Res. 2003 Jul 15;63(14):4009-16. [PubMed:12873999 ]
Baratte S, Sarati S, Frigerio E, James CA, Ye C, Zhang Q: Quantitation of SU1 1248, an oral multi-target tyrosine kinase inhibitor, and its metabolite in monkey tissues by liquid chromatograph with tandem mass spectrometry following semi-automated liquid-liquid extraction. J Chromatogr A. 2004 Jan 23;1024(1-2):87-94. [PubMed:14753710 ]
Schoffski P, Dumez H, Clement P, Hoeben A, Prenen H, Wolter P, Joniau S, Roskams T, Van Poppel H: Emerging role of tyrosine kinase inhibitors in the treatment of advanced renal cell cancer: a review. Ann Oncol. 2006 Aug;17(8):1185-96. Epub 2006 Jan 17. [PubMed:16418310 ]
Amino N, Ideyama Y, Yamano M, Kuromitsu S, Tajinda K, Samizu K, Hisamichi H, Matsuhisa A, Shirasuna K, Kudoh M, Shibasaki M: YM-359445, an orally bioavailable vascular endothelial growth factor receptor-2 tyrosine kinase inhibitor, has highly potent antitumor activity against established tumors. Clin Cancer Res. 2006 Mar 1;12(5):1630-8. [PubMed:16533791 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

5. Macrophage colony-stimulating factor 1 receptor

General function:: Involved in protein kinase activity
Specific function:: Protein tyrosine-kinase transmembrane receptor for CSF1 and IL34
Gene Name:: CSF1R
Uniprot ID:: P07333
Molecular weight:: 107983.0

References

Guo J, Marcotte PA, McCall JO, Dai Y, Pease LJ, Michaelides MR, Davidsen SK, Glaser KB: Inhibition of phosphorylation of the colony-stimulating factor-1 receptor (c-Fms) tyrosine kinase in transfected cells by ABT-869 and other tyrosine kinase inhibitors. Mol Cancer Ther. 2006 Apr;5(4):1007-13. [PubMed:16648572 ]
Roskoski R Jr: Sunitinib: a VEGF and PDGF receptor protein kinase and angiogenesis inhibitor. Biochem Biophys Res Commun. 2007 May 4;356(2):323-8. Epub 2007 Mar 7. [PubMed:17367763 ]

Enzyme Details

6. Alpha-type platelet-derived growth factor receptor

General function:: Involved in protein kinase activity
Specific function:: Receptor that binds both PDGFA and PDGFB and has a tyrosine-protein kinase activity
Gene Name:: PDGFRA
Uniprot ID:: P16234
Molecular weight:: 122668.5

References

Prenen H, Cools J, Mentens N, Folens C, Sciot R, Schoffski P, Van Oosterom A, Marynen P, Debiec-Rychter M: Efficacy of the kinase inhibitor SU11248 against gastrointestinal stromal tumor mutants refractory to imatinib mesylate. Clin Cancer Res. 2006 Apr 15;12(8):2622-7. [PubMed:16638875 ]

Enzyme Details

7. Beta-type platelet-derived growth factor receptor

General function:: Involved in protein kinase activity
Specific function:: Receptor that binds specifically to PDGFB and PDGFD and has a tyrosine-protein kinase activity. Phosphorylates Tyr residues at the C-terminus of PTPN11 creating a binding site for the SH2 domain of GRB2
Gene Name:: PDGFRB
Uniprot ID:: P09619
Molecular weight:: 123966.9

References

Mendel DB, Laird AD, Xin X, Louie SG, Christensen JG, Li G, Schreck RE, Abrams TJ, Ngai TJ, Lee LB, Murray LJ, Carver J, Chan E, Moss KG, Haznedar JO, Sukbuntherng J, Blake RA, Sun L, Tang C, Miller T, Shirazian S, McMahon G, Cherrington JM: In vivo antitumor activity of SU11248, a novel tyrosine kinase inhibitor targeting vascular endothelial growth factor and platelet-derived growth factor receptors: determination of a pharmacokinetic/pharmacodynamic relationship. Clin Cancer Res. 2003 Jan;9(1):327-37. [PubMed:12538485 ]
Abrams TJ, Lee LB, Murray LJ, Pryer NK, Cherrington JM: SU11248 inhibits KIT and platelet-derived growth factor receptor beta in preclinical models of human small cell lung cancer. Mol Cancer Ther. 2003 May;2(5):471-8. [PubMed:12748309 ]
Baratte S, Sarati S, Frigerio E, James CA, Ye C, Zhang Q: Quantitation of SU1 1248, an oral multi-target tyrosine kinase inhibitor, and its metabolite in monkey tissues by liquid chromatograph with tandem mass spectrometry following semi-automated liquid-liquid extraction. J Chromatogr A. 2004 Jan 23;1024(1-2):87-94. [PubMed:14753710 ]
Pietras K, Hanahan D: A multitargeted, metronomic, and maximum-tolerated dose "chemo-switch" regimen is antiangiogenic, producing objective responses and survival benefit in a mouse model of cancer. J Clin Oncol. 2005 Feb 10;23(5):939-52. Epub 2004 Nov 22. [PubMed:15557593 ]
Gollob JA: Sorafenib: scientific rationales for single-agent and combination therapy in clear-cell renal cell carcinoma. Clin Genitourin Cancer. 2005 Dec;4(3):167-74. [PubMed:16425993 ]

Enzyme Details

8. Vascular endothelial growth factor receptor 1

General function:: Involved in protein kinase activity
Specific function:: Receptor for VEGF, VEGFB and PGF. Has a tyrosine-protein kinase activity. The VEGF-kinase ligand/receptor signaling system plays a key role in vascular development and regulation of vascular permeability. Isoform SFlt1 may have an inhibitory role in angiogenesis
Gene Name:: FLT1
Uniprot ID:: P17948
Molecular weight:: 150767.2

References

O'Farrell AM, Foran JM, Fiedler W, Serve H, Paquette RL, Cooper MA, Yuen HA, Louie SG, Kim H, Nicholas S, Heinrich MC, Berdel WE, Bello C, Jacobs M, Scigalla P, Manning WC, Kelsey S, Cherrington JM: An innovative phase I clinical study demonstrates inhibition of FLT3 phosphorylation by SU11248 in acute myeloid leukemia patients. Clin Cancer Res. 2003 Nov 15;9(15):5465-76. [PubMed:14654525 ]
Roskoski R Jr: Sunitinib: a VEGF and PDGF receptor protein kinase and angiogenesis inhibitor. Biochem Biophys Res Commun. 2007 May 4;356(2):323-8. Epub 2007 Mar 7. [PubMed:17367763 ]

Enzyme Details

9. Mast/stem cell growth factor receptor

General function:: Involved in protein kinase activity
Specific function:: This is the receptor for stem cell factor (mast cell growth factor). It has a tyrosine-protein kinase activity. Binding of the ligands leads to the autophosphorylation of KIT and its association with substrates such as phosphatidylinositol 3-kinase (Pi3K)
Gene Name:: KIT
Uniprot ID:: P10721
Molecular weight:: 109863.7

References

Abrams TJ, Lee LB, Murray LJ, Pryer NK, Cherrington JM: SU11248 inhibits KIT and platelet-derived growth factor receptor beta in preclinical models of human small cell lung cancer. Mol Cancer Ther. 2003 May;2(5):471-8. [PubMed:12748309 ]
Schueneman AJ, Himmelfarb E, Geng L, Tan J, Donnelly E, Mendel D, McMahon G, Hallahan DE: SU11248 maintenance therapy prevents tumor regrowth after fractionated irradiation of murine tumor models. Cancer Res. 2003 Jul 15;63(14):4009-16. [PubMed:12873999 ]
Joensuu H: Second line therapies for the treatment of gastrointestinal stromal tumor. Curr Opin Oncol. 2007 Jul;19(4):353-8. [PubMed:17545799 ]
Baratte S, Sarati S, Frigerio E, James CA, Ye C, Zhang Q: Quantitation of SU1 1248, an oral multi-target tyrosine kinase inhibitor, and its metabolite in monkey tissues by liquid chromatograph with tandem mass spectrometry following semi-automated liquid-liquid extraction. J Chromatogr A. 2004 Jan 23;1024(1-2):87-94. [PubMed:14753710 ]
Roskoski R Jr: Sunitinib: a VEGF and PDGF receptor protein kinase and angiogenesis inhibitor. Biochem Biophys Res Commun. 2007 May 4;356(2):323-8. Epub 2007 Mar 7. [PubMed:17367763 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

10. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

Transporters

Enzyme Details

1. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Hu S, Chen Z, Franke R, Orwick S, Zhao M, Rudek MA, Sparreboom A, Baker SD: Interaction of the multikinase inhibitors sorafenib and sunitinib with solute carriers and ATP-binding cassette transporters. Clin Cancer Res. 2009 Oct 1;15(19):6062-9. doi: 10.1158/1078-0432.CCR-09-0048. Epub 2009 Sep 22. [PubMed:19773380 ]

Enzyme Details

2. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Hu S, Chen Z, Franke R, Orwick S, Zhao M, Rudek MA, Sparreboom A, Baker SD: Interaction of the multikinase inhibitors sorafenib and sunitinib with solute carriers and ATP-binding cassette transporters. Clin Cancer Res. 2009 Oct 1;15(19):6062-9. doi: 10.1158/1078-0432.CCR-09-0048. Epub 2009 Sep 22. [PubMed:19773380 ]
Shukla S, Robey RW, Bates SE, Ambudkar SV: Sunitinib (Sutent, SU11248), a small-molecule receptor tyrosine kinase inhibitor, blocks function of the ATP-binding cassette (ABC) transporters P-glycoprotein (ABCB1) and ABCG2. Drug Metab Dispos. 2009 Feb;37(2):359-65. doi: 10.1124/dmd.108.024612. Epub 2008 Oct 29. [PubMed:18971320 ]

Enzyme Details

3. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Hu S, Chen Z, Franke R, Orwick S, Zhao M, Rudek MA, Sparreboom A, Baker SD: Interaction of the multikinase inhibitors sorafenib and sunitinib with solute carriers and ATP-binding cassette transporters. Clin Cancer Res. 2009 Oct 1;15(19):6062-9. doi: 10.1158/1078-0432.CCR-09-0048. Epub 2009 Sep 22. [PubMed:19773380 ]
Dai CL, Liang YJ, Wang YS, Tiwari AK, Yan YY, Wang F, Chen ZS, Tong XZ, Fu LW: Sensitization of ABCG2-overexpressing cells to conventional chemotherapeutic agent by sunitinib was associated with inhibiting the function of ABCG2. Cancer Lett. 2009 Jun 28;279(1):74-83. doi: 10.1016/j.canlet.2009.01.027. Epub 2009 Feb 18. [PubMed:19232821 ]
Shukla S, Robey RW, Bates SE, Ambudkar SV: Sunitinib (Sutent, SU11248), a small-molecule receptor tyrosine kinase inhibitor, blocks function of the ATP-binding cassette (ABC) transporters P-glycoprotein (ABCB1) and ABCG2. Drug Metab Dispos. 2009 Feb;37(2):359-65. doi: 10.1124/dmd.108.024612. Epub 2008 Oct 29. [PubMed:18971320 ]

Enzyme Details

4. Multidrug resistance-associated protein 4

General function:: Involved in ATP binding
Specific function:: May be an organic anion pump relevant to cellular detoxification
Gene Name:: ABCC4
Uniprot ID:: O15439
Molecular weight:: 149525.3

References

Hu S, Chen Z, Franke R, Orwick S, Zhao M, Rudek MA, Sparreboom A, Baker SD: Interaction of the multikinase inhibitors sorafenib and sunitinib with solute carriers and ATP-binding cassette transporters. Clin Cancer Res. 2009 Oct 1;15(19):6062-9. doi: 10.1158/1078-0432.CCR-09-0048. Epub 2009 Sep 22. [PubMed:19773380 ]

Only showing the first 10 proteins. There are 15 proteins in total.

Show all enzymes and transporters

Showing metabocard for Sunitinib (HMDB0015397)

MOL for HMDB0015397 (Sunitinib)

3D MOL for HMDB0015397 (Sunitinib)

3D SDF for HMDB0015397 (Sunitinib)

3D-SDF for HMDB0015397 (Sunitinib)

PDB for HMDB0015397 (Sunitinib)

3D PDB for HMDB0015397 (Sunitinib)

SMILES for HMDB0015397 (Sunitinib)

INCHI for HMDB0015397 (Sunitinib)

Structure for HMDB0015397 (Sunitinib)

3D Structure for HMDB0015397 (Sunitinib)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

Transporters

References

References

References

References