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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3)transporters (2) Show 5 proteins XML

enzymes (3)transporters (2) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:38 UTC

HMDB ID

HMDB0014462

Secondary Accession Numbers

HMDB14462

Metabolite Identification

Common Name

Gefitinib

Description

Gefitinib, also known as iressa or ZD 1839, belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups. This leads to inappropriate activation of the anti-apoptotic Ras signalling cascade, eventually leading to uncontrolled cell proliferation. Gefitinib is a drug which is used for the continued treatment of patients with locally advanced or metastatic non-small cell lung cancer after failure of either platinum-based or docetaxel chemotherapies. Adverse drug reactions (ADRs) are acceptable for a potentially fatal disease. Gefitinib is a very strong basic compound (based on its pKa). In humans, gefitinib is involved in gefitinib action pathway. IPASS (IRESSA Pan-Asia Study) was a randomized, large-scale, double-blinded study which compared gefitinib vs. carboplatin/ paclitaxel as a first-line treatment in advanced NSCLC.IPASS studied 1,217 patients with confirmed adenocarcinoma histology who were former or never smokers.

Structure

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

317
  Mrv0541 02231214352D          

 31 34  0  0  0  0            999 V2000
   10.2087   -2.9100    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.6471   -2.1016    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.3901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.0850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8084   -0.4186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8180    2.1136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5654    0.8303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    1.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8180    0.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5181   -0.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5654    1.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5085   -1.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2372   -0.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2182   -2.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9469   -0.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9374   -1.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 29  1  0  0  0  0
  2 31  1  0  0  0  0
  3 14  1  0  0  0  0
  3 15  1  0  0  0  0
  4 16  1  0  0  0  0
  4 17  1  0  0  0  0
  5 20  1  0  0  0  0
  5 26  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 23  1  0  0  0  0
  7 24  1  0  0  0  0
  8 21  1  0  0  0  0
  8 25  2  0  0  0  0
  9 23  2  0  0  0  0
  9 25  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  2  0  0  0  0
 18 19  2  0  0  0  0
 18 21  1  0  0  0  0
 18 23  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  2  0  0  0  0
 24 27  2  0  0  0  0
 24 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 30  2  0  0  0  0
 29 31  2  0  0  0  0
 30 31  1  0  0  0  0
M  END

HMDB0014462
     RDKit          3D
Gefitinib
 55 58  0  0  0  0  0  0  0  0999 V2000
   -0.0851   -6.0340    0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2899   -4.6925    0.0383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6398   -3.6835    0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9826   -4.0049    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9831   -3.0480    0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2729   -3.3973    0.2455 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2611   -2.5008    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9104   -1.2212    0.2227 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6592   -0.7546    0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3515    0.6122    0.0769 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2819    1.6887    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8064    2.9706   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5785    4.0955   -0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9207    3.9655    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7108    5.0822    0.1565 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4310    2.7268    0.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1117    2.5246    0.8209 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.6083    1.5946    0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6535   -1.7021    0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3091   -1.3907    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3021   -2.3519    0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0120   -1.9534   -0.0717 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3317   -0.5987   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8488   -0.3798   -0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0669    1.0900   -0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4376    1.4991   -0.3456 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6310    2.9082   -0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0903    3.1907   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8320    2.2404   -0.7975 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7682    1.0378   -0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3619    0.7867    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7566   -6.1839    0.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6293   -6.3110   -0.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917   -6.6920    0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3008   -5.0325    0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2730   -2.8659    0.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3177    0.8736   -0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7540    3.1123   -0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2128    5.0806   -0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0349    0.6312    0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0107   -0.3502   -0.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9791   -0.0221    0.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8724   -0.1365   -1.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1770   -0.8693   -1.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3032   -0.8822    0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6189    1.6017    0.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5121    1.4821   -1.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4164    3.3536   -1.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0064    3.3728    0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3773    4.2249   -0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2493    3.0135    0.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0689    0.2323   -0.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5000    1.1139    0.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3707    1.2455    1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2362   -0.2923    0.4824 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
  9 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 21  3  1  0
 31 26  1  0
 19  5  1  0
 18 11  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  7 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 18 40  1  0
 20 41  1  0
 23 42  1  0
 23 43  1  0
 24 44  1  0
 24 45  1  0
 25 46  1  0
 25 47  1  0
 27 48  1  0
 27 49  1  0
 28 50  1  0
 28 51  1  0
 30 52  1  0
 30 53  1  0
 31 54  1  0
 31 55  1  0
M  END

317
  Mrv0541 02231214352D          

 31 34  0  0  0  0            999 V2000
   10.2087   -2.9100    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.6471   -2.1016    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.3901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.0850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8084   -0.4186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8180    2.1136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5654    0.8303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    0.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    1.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8180    0.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5181   -0.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5654    1.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5085   -1.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2372   -0.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2182   -2.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9469   -0.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9374   -1.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 29  1  0  0  0  0
  2 31  1  0  0  0  0
  3 14  1  0  0  0  0
  3 15  1  0  0  0  0
  4 16  1  0  0  0  0
  4 17  1  0  0  0  0
  5 20  1  0  0  0  0
  5 26  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 23  1  0  0  0  0
  7 24  1  0  0  0  0
  8 21  1  0  0  0  0
  8 25  2  0  0  0  0
  9 23  2  0  0  0  0
  9 25  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  2  0  0  0  0
 18 19  2  0  0  0  0
 18 21  1  0  0  0  0
 18 23  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  2  0  0  0  0
 24 27  2  0  0  0  0
 24 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 30  2  0  0  0  0
 29 31  2  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014462

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OCCCN2CCOCC2)C=C2C(NC3=CC(Cl)=C(F)C=C3)=NC=NC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H24ClFN4O3/c1-29-20-13-19-16(12-21(20)31-8-2-5-28-6-9-30-10-7-28)22(26-14-25-19)27-15-3-4-18(24)17(23)11-15/h3-4,11-14H,2,5-10H2,1H3,(H,25,26,27)

> <INCHI_KEY>
XGALLCVXEZPNRQ-UHFFFAOYSA-N

> <FORMULA>
C22H24ClFN4O3

> <MOLECULAR_WEIGHT>
446.902

> <EXACT_MASS>
446.152096566

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
46.1136503263008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(morpholin-4-yl)propoxy]quinazolin-4-amine

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
3.750953734666667

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.10506416809685

> <JCHEM_PKA_STRONGEST_BASIC>
6.846602821831034

> <JCHEM_POLAR_SURFACE_AREA>
68.74000000000001

> <JCHEM_REFRACTIVITY>
117.50680000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gefitinib

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014462
     RDKit          3D
Gefitinib
 55 58  0  0  0  0  0  0  0  0999 V2000
   -0.0851   -6.0340    0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2899   -4.6925    0.0383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6398   -3.6835    0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9826   -4.0049    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9831   -3.0480    0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2729   -3.3973    0.2455 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2611   -2.5008    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9104   -1.2212    0.2227 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6592   -0.7546    0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3515    0.6122    0.0769 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2819    1.6887    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8064    2.9706   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5785    4.0955   -0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9207    3.9655    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7108    5.0822    0.1565 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4310    2.7268    0.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1117    2.5246    0.8209 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.6083    1.5946    0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6535   -1.7021    0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3091   -1.3907    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3021   -2.3519    0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0120   -1.9534   -0.0717 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3317   -0.5987   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8488   -0.3798   -0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0669    1.0900   -0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4376    1.4991   -0.3456 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6310    2.9082   -0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0903    3.1907   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8320    2.2404   -0.7975 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7682    1.0378   -0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3619    0.7867    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7566   -6.1839    0.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6293   -6.3110   -0.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917   -6.6920    0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3008   -5.0325    0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2730   -2.8659    0.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3177    0.8736   -0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7540    3.1123   -0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2128    5.0806   -0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0349    0.6312    0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0107   -0.3502   -0.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9791   -0.0221    0.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8724   -0.1365   -1.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1770   -0.8693   -1.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3032   -0.8822    0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6189    1.6017    0.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5121    1.4821   -1.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4164    3.3536   -1.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0064    3.3728    0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3773    4.2249   -0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2493    3.0135    0.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0689    0.2323   -0.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5000    1.1139    0.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3707    1.2455    1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2362   -0.2923    0.4824 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
  9 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 21  3  1  0
 31 26  1  0
 19  5  1  0
 18 11  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  7 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 18 40  1  0
 20 41  1  0
 23 42  1  0
 23 43  1  0
 24 44  1  0
 24 45  1  0
 25 46  1  0
 25 47  1  0
 27 48  1  0
 27 49  1  0
 28 50  1  0
 28 51  1  0
 30 52  1  0
 30 53  1  0
 31 54  1  0
 31 55  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 317                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      19.056  -5.432   0.000  0.00  0.00          Cl+0
HETATM    2  F   UNK     0      21.741  -3.923   0.000  0.00  0.00           F+0
HETATM    3  O   UNK     0       3.080  -0.728   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.082   0.812   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.082   3.892   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       5.748   0.812   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      16.442  -0.781   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      16.460   3.945   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      17.855   1.550   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.081   1.582   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   1.582   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -0.728   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415   0.812   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   0.812   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -1.498   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748   1.582   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.416   1.582   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.083   1.582   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.750   0.812   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.416   3.122   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.083   3.122   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.750   3.892   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.460   0.758   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.767  -1.567   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.855   3.154   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.082   5.432   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.749  -3.107   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      19.109  -0.812   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      19.074  -3.892   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.434  -1.598   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.416  -3.137   0.000  0.00  0.00           C+0
CONECT    1   29                                                            
CONECT    2   31                                                            
CONECT    3   14   15                                                       
CONECT    4   16   17                                                       
CONECT    5   20   26                                                       
CONECT    6   10   11   12                                                  
CONECT    7   23   24                                                       
CONECT    8   21   25                                                       
CONECT    9   23   25                                                       
CONECT   10    6   13                                                       
CONECT   11    6   14                                                       
CONECT   12    6   15                                                       
CONECT   13   10   16                                                       
CONECT   14    3   11                                                       
CONECT   15    3   12                                                       
CONECT   16    4   13                                                       
CONECT   17    4   19   20                                                  
CONECT   18   19   21   23                                                  
CONECT   19   17   18                                                       
CONECT   20    5   17   22                                                  
CONECT   21    8   18   22                                                  
CONECT   22   20   21                                                       
CONECT   23    7    9   18                                                  
CONECT   24    7   27   28                                                  
CONECT   25    8    9                                                       
CONECT   26    5                                                            
CONECT   27   24   29                                                       
CONECT   28   24   30                                                       
CONECT   29    1   27   31                                                  
CONECT   30   28   31                                                       
CONECT   31    2   29   30                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0014462
HETATM    1  C1  UNL     1      -0.085  -6.034   0.093  1.00  0.00           C  
HETATM    2  O1  UNL     1       0.290  -4.693   0.038  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.640  -3.683   0.061  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.983  -4.005   0.140  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.983  -3.048   0.167  1.00  0.00           C  
HETATM    6  N1  UNL     1      -4.273  -3.397   0.246  1.00  0.00           N  
HETATM    7  C5  UNL     1      -5.261  -2.501   0.275  1.00  0.00           C  
HETATM    8  N2  UNL     1      -4.910  -1.221   0.223  1.00  0.00           N  
HETATM    9  C6  UNL     1      -3.659  -0.755   0.143  1.00  0.00           C  
HETATM   10  N3  UNL     1      -3.352   0.612   0.077  1.00  0.00           N  
HETATM   11  C7  UNL     1      -4.282   1.689   0.112  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.806   2.971  -0.172  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.578   4.095  -0.164  1.00  0.00           C  
HETATM   14  C10 UNL     1      -5.921   3.965   0.144  1.00  0.00           C  
HETATM   15  F1  UNL     1      -6.711   5.082   0.157  1.00  0.00           F  
HETATM   16  C11 UNL     1      -6.431   2.727   0.430  1.00  0.00           C  
HETATM   17 CL1  UNL     1      -8.112   2.525   0.821  1.00  0.00          CL  
HETATM   18  C12 UNL     1      -5.608   1.595   0.412  1.00  0.00           C  
HETATM   19  C13 UNL     1      -2.654  -1.702   0.114  1.00  0.00           C  
HETATM   20  C14 UNL     1      -1.309  -1.391   0.036  1.00  0.00           C  
HETATM   21  C15 UNL     1      -0.302  -2.352   0.008  1.00  0.00           C  
HETATM   22  O2  UNL     1       1.012  -1.953  -0.072  1.00  0.00           O  
HETATM   23  C16 UNL     1       1.332  -0.599  -0.124  1.00  0.00           C  
HETATM   24  C17 UNL     1       2.849  -0.380  -0.210  1.00  0.00           C  
HETATM   25  C18 UNL     1       3.067   1.090  -0.260  1.00  0.00           C  
HETATM   26  N4  UNL     1       4.438   1.499  -0.346  1.00  0.00           N  
HETATM   27  C19 UNL     1       4.631   2.908  -0.391  1.00  0.00           C  
HETATM   28  C20 UNL     1       6.090   3.191  -0.104  1.00  0.00           C  
HETATM   29  O3  UNL     1       6.832   2.240  -0.797  1.00  0.00           O  
HETATM   30  C21 UNL     1       6.768   1.038  -0.101  1.00  0.00           C  
HETATM   31  C22 UNL     1       5.362   0.787   0.462  1.00  0.00           C  
HETATM   32  H1  UNL     1      -0.757  -6.184   0.982  1.00  0.00           H  
HETATM   33  H2  UNL     1      -0.629  -6.311  -0.839  1.00  0.00           H  
HETATM   34  H3  UNL     1       0.792  -6.692   0.263  1.00  0.00           H  
HETATM   35  H4  UNL     1      -2.301  -5.033   0.184  1.00  0.00           H  
HETATM   36  H5  UNL     1      -6.273  -2.866   0.339  1.00  0.00           H  
HETATM   37  H6  UNL     1      -2.318   0.874  -0.008  1.00  0.00           H  
HETATM   38  H7  UNL     1      -2.754   3.112  -0.419  1.00  0.00           H  
HETATM   39  H8  UNL     1      -4.213   5.081  -0.382  1.00  0.00           H  
HETATM   40  H9  UNL     1      -6.035   0.631   0.648  1.00  0.00           H  
HETATM   41  H10 UNL     1      -1.011  -0.350  -0.006  1.00  0.00           H  
HETATM   42  H11 UNL     1       0.979  -0.022   0.754  1.00  0.00           H  
HETATM   43  H12 UNL     1       0.872  -0.136  -1.038  1.00  0.00           H  
HETATM   44  H13 UNL     1       3.177  -0.869  -1.148  1.00  0.00           H  
HETATM   45  H14 UNL     1       3.303  -0.882   0.665  1.00  0.00           H  
HETATM   46  H15 UNL     1       2.619   1.602   0.617  1.00  0.00           H  
HETATM   47  H16 UNL     1       2.512   1.482  -1.147  1.00  0.00           H  
HETATM   48  H17 UNL     1       4.416   3.354  -1.388  1.00  0.00           H  
HETATM   49  H18 UNL     1       4.006   3.373   0.409  1.00  0.00           H  
HETATM   50  H19 UNL     1       6.377   4.225  -0.375  1.00  0.00           H  
HETATM   51  H20 UNL     1       6.249   3.014   0.976  1.00  0.00           H  
HETATM   52  H21 UNL     1       7.069   0.232  -0.794  1.00  0.00           H  
HETATM   53  H22 UNL     1       7.500   1.114   0.754  1.00  0.00           H  
HETATM   54  H23 UNL     1       5.371   1.246   1.488  1.00  0.00           H  
HETATM   55  H24 UNL     1       5.236  -0.292   0.482  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   35
CONECT    5    6    6   19
CONECT    6    7
CONECT    7    8    8   36
CONECT    8    9
CONECT    9   10   19   19
CONECT   10   11   37
CONECT   11   12   12   18
CONECT   12   13   38
CONECT   13   14   14   39
CONECT   14   15   16
CONECT   16   17   18   18
CONECT   18   40
CONECT   19   20
CONECT   20   21   21   41
CONECT   21   22
CONECT   22   23
CONECT   23   24   42   43
CONECT   24   25   44   45
CONECT   25   26   46   47
CONECT   26   27   31
CONECT   27   28   48   49
CONECT   28   29   50   51
CONECT   29   30
CONECT   30   31   52   53
CONECT   31   54   55
END

HMDB0014462
     RDKit          3D
Gefitinib
 55 58  0  0  0  0  0  0  0  0999 V2000
   -0.0851   -6.0340    0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2899   -4.6925    0.0383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6398   -3.6835    0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9826   -4.0049    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9831   -3.0480    0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2729   -3.3973    0.2455 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2611   -2.5008    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9104   -1.2212    0.2227 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6592   -0.7546    0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3515    0.6122    0.0769 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2819    1.6887    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8064    2.9706   -0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5785    4.0955   -0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9207    3.9655    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7108    5.0822    0.1565 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4310    2.7268    0.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1117    2.5246    0.8209 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.6083    1.5946    0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6535   -1.7021    0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3091   -1.3907    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3021   -2.3519    0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0120   -1.9534   -0.0717 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3317   -0.5987   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8488   -0.3798   -0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0669    1.0900   -0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4376    1.4991   -0.3456 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6310    2.9082   -0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0903    3.1907   -0.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8320    2.2404   -0.7975 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7682    1.0378   -0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3619    0.7867    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7566   -6.1839    0.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6293   -6.3110   -0.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917   -6.6920    0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3008   -5.0325    0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2730   -2.8659    0.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3177    0.8736   -0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7540    3.1123   -0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2128    5.0806   -0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0349    0.6312    0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0107   -0.3502   -0.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9791   -0.0221    0.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8724   -0.1365   -1.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1770   -0.8693   -1.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3032   -0.8822    0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6189    1.6017    0.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5121    1.4821   -1.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4164    3.3536   -1.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0064    3.3728    0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3773    4.2249   -0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2493    3.0135    0.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0689    0.2323   -0.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5000    1.1139    0.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3707    1.2455    1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2362   -0.2923    0.4824 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
  9 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 21  3  1  0
 31 26  1  0
 19  5  1  0
 18 11  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  7 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 18 40  1  0
 20 41  1  0
 23 42  1  0
 23 43  1  0
 24 44  1  0
 24 45  1  0
 25 46  1  0
 25 47  1  0
 27 48  1  0
 27 49  1  0
 28 50  1  0
 28 51  1  0
 30 52  1  0
 30 53  1  0
 31 54  1  0
 31 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(3'-Chloro-4'-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline	ChEBI
Gefitinibum	ChEBI
Iressa	ChEBI
Irressat	ChEBI
N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-4-quinazolinamine	ChEBI
ZD 1839	ChEBI
ZD-1839	ChEBI
ZD1839	ChEBI
N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-4-quinazolinamide	HMDB

Chemical Formula

C₂₂H₂₄ClFN₄O₃

Average Molecular Weight

446.902

Monoisotopic Molecular Weight

446.152096566

IUPAC Name

N-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(morpholin-4-yl)propoxy]quinazolin-4-amine

Traditional Name

gefitinib

CAS Registry Number

184475-35-2

SMILES

COC1=C(OCCCN2CCOCC2)C=C2C(NC3=CC(Cl)=C(F)C=C3)=NC=NC2=C1

InChI Identifier

InChI=1S/C22H24ClFN4O3/c1-29-20-13-19-16(12-21(20)31-8-2-5-28-6-9-30-10-7-28)22(26-14-25-19)27-15-3-4-18(24)17(23)11-15/h3-4,11-14H,2,5-10H2,1H3,(H,25,26,27)

InChI Key

XGALLCVXEZPNRQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinazolinamines

Alternative Parents

Substituents

Quinazolinamine
Anisole
Aniline or substituted anilines
Alkyl aryl ether
Aminopyrimidine
Chlorobenzene
Fluorobenzene
Halobenzene
Aryl chloride
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Morpholine
Oxazinane
Pyrimidine
Benzenoid
Imidolactam
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Secondary amine
Azacycle
Dialkyl ether
Ether
Oxacycle
Organonitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organic nitrogen compound
Amine
Organic oxygen compound
Organofluoride
Organochloride
Organopnictogen compound
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinazolines (CHEBI:49668 )
morpholines (CHEBI:49668 )

Ontology

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	0.027 g/L	Not Available
LogP	3.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.027 g/L	ALOGPS
logP	4.02	ALOGPS
logP	3.75	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	16.11	ChemAxon
pKa (Strongest Basic)	6.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.74 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	117.51 m³·mol⁻¹	ChemAxon
Polarizability	46.11 Å³	ChemAxon
Number of Rings	4	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]+	203.549	30932474
DeepCCS	[M-H]-	201.191	30932474
DeepCCS	[M-2H]-	235.183	30932474
DeepCCS	[M+Na]+	210.932	30932474
AllCCS	[M+H]+	202.9	32859911
AllCCS	[M+H-H2O]+	200.7	32859911
AllCCS	[M+NH4]+	205.0	32859911
AllCCS	[M+Na]+	205.6	32859911
AllCCS	[M-H]-	198.8	32859911
AllCCS	[M+Na-2H]-	198.8	32859911
AllCCS	[M+HCOO]-	198.9	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.	4.39 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6028 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.9 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	40.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1898.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	178.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	173.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	114.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	426.9 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	402.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	333.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	787.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	348.3 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	1224.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	283.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	270.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	242.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	155.2 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	9.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gefitinib	COC1=C(OCCCN2CCOCC2)C=C2C(NC3=CC(Cl)=C(F)C=C3)=NC=NC2=C1	4951.1	Standard polar	33892256
Gefitinib	COC1=C(OCCCN2CCOCC2)C=C2C(NC3=CC(Cl)=C(F)C=C3)=NC=NC2=C1	3340.0	Standard non polar	33892256
Gefitinib	COC1=C(OCCCN2CCOCC2)C=C2C(NC3=CC(Cl)=C(F)C=C3)=NC=NC2=C1	3909.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gefitinib,1TMS,isomer #1	COC1=CC2=NC=NC(N(C3=CC=C(F)C(Cl)=C3)[Si](C)(C)C)=C2C=C1OCCCN1CCOCC1	3453.5	Semi standard non polar	33892256
Gefitinib,1TMS,isomer #1	COC1=CC2=NC=NC(N(C3=CC=C(F)C(Cl)=C3)[Si](C)(C)C)=C2C=C1OCCCN1CCOCC1	3391.4	Standard non polar	33892256
Gefitinib,1TMS,isomer #1	COC1=CC2=NC=NC(N(C3=CC=C(F)C(Cl)=C3)[Si](C)(C)C)=C2C=C1OCCCN1CCOCC1	4893.7	Standard polar	33892256
Gefitinib,1TBDMS,isomer #1	COC1=CC2=NC=NC(N(C3=CC=C(F)C(Cl)=C3)[Si](C)(C)C(C)(C)C)=C2C=C1OCCCN1CCOCC1	3644.1	Semi standard non polar	33892256
Gefitinib,1TBDMS,isomer #1	COC1=CC2=NC=NC(N(C3=CC=C(F)C(Cl)=C3)[Si](C)(C)C(C)(C)C)=C2C=C1OCCCN1CCOCC1	3566.6	Standard non polar	33892256
Gefitinib,1TBDMS,isomer #1	COC1=CC2=NC=NC(N(C3=CC=C(F)C(Cl)=C3)[Si](C)(C)C(C)(C)C)=C2C=C1OCCCN1CCOCC1	4869.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Gefitinib GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uxr-9424700000-182dba69c82bee61cbe2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gefitinib 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gefitinib LC-ESI-qTof , Positive-QTOF	splash10-0002-1511900000-d0570bedf59699989575	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gefitinib , positive-QTOF	splash10-00di-0193000000-38bb088cc8af6a0e12a4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gefitinib , positive-QTOF	splash10-0002-1511900000-d0570bedf59699989575	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gefitinib 10V, Positive-QTOF	splash10-0002-0201900000-dafa6866c6b59a71a89e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gefitinib 20V, Positive-QTOF	splash10-0udi-2904200000-011d82a75223a5017b87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gefitinib 40V, Positive-QTOF	splash10-009l-9402000000-d87048e0478c6d231bfe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gefitinib 10V, Negative-QTOF	splash10-0002-0004900000-bb4c9a2e360df1c7e52e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gefitinib 20V, Negative-QTOF	splash10-014s-3019400000-c4f741a0f46f6e8edd9f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gefitinib 40V, Negative-QTOF	splash10-0uy0-3279000000-593bcb0bda5ac3068617	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gefitinib 10V, Negative-QTOF	splash10-0002-0000900000-f5b40d44879371ef81fb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gefitinib 20V, Negative-QTOF	splash10-0f6t-0005900000-a102859e7a71e3a4e883	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gefitinib 40V, Negative-QTOF	splash10-0udi-1029000000-4b9f808b7f687fe38a43	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gefitinib 10V, Positive-QTOF	splash10-0002-0000900000-fc203d826511c11b8cd1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gefitinib 20V, Positive-QTOF	splash10-0fba-1901400000-c8c0d48bbd64a7e7fa9a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gefitinib 40V, Positive-QTOF	splash10-0uk9-9515200000-6abbaa993868c8b744f4	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Gefitinib Action Pathway		Not Available

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 DB00317	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00317	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00317

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

110217

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gefitinib

METLIN ID

Not Available

PubChem Compound

123631

PDB ID

Not Available

ChEBI ID

49668

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

Sordella R, Bell DW, Haber DA, Settleman J: Gefitinib-sensitizing EGFR mutations in lung cancer activate anti-apoptotic pathways. Science. 2004 Aug 20;305(5687):1163-7. Epub 2004 Jul 29. [PubMed:15284455 ]
Pao W, Miller V, Zakowski M, Doherty J, Politi K, Sarkaria I, Singh B, Heelan R, Rusch V, Fulton L, Mardis E, Kupfer D, Wilson R, Kris M, Varmus H: EGF receptor gene mutations are common in lung cancers from "never smokers" and are associated with sensitivity of tumors to gefitinib and erlotinib. Proc Natl Acad Sci U S A. 2004 Sep 7;101(36):13306-11. Epub 2004 Aug 25. [PubMed:15329413 ]
(). FDA label . .

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

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Epidermal growth factor receptor

General function:: Involved in transmembrane receptor protein tyrosine kinase activity
Specific function:: Isoform 2 may act as an antagonist of EGF action
Gene Name:: EGFR
Uniprot ID:: P00533
Molecular weight:: 134276.2

References

Ciardiello F, Caputo R, Bianco R, Damiano V, Pomatico G, De Placido S, Bianco AR, Tortora G: Antitumor effect and potentiation of cytotoxic drugs activity in human cancer cells by ZD-1839 (Iressa), an epidermal growth factor receptor-selective tyrosine kinase inhibitor. Clin Cancer Res. 2000 May;6(5):2053-63. [PubMed:10815932 ]
Albanell J, Codony-Servat J, Rojo F, Del Campo JM, Sauleda S, Anido J, Raspall G, Giralt J, Rosello J, Nicholson RI, Mendelsohn J, Baselga J: Activated extracellular signal-regulated kinases: association with epidermal growth factor receptor/transforming growth factor alpha expression in head and neck squamous carcinoma and inhibition by anti-epidermal growth factor receptor treatments. Cancer Res. 2001 Sep 1;61(17):6500-10. [PubMed:11522647 ]
Nicholson RI, Hutcheson IR, Harper ME, Knowlden JM, Barrow D, McClelland RA, Jones HE, Wakeling AE, Gee JM: Modulation of epidermal growth factor receptor in endocrine-resistant, oestrogen receptor-positive breast cancer. Endocr Relat Cancer. 2001 Sep;8(3):175-82. [PubMed:11566608 ]
Moasser MM, Basso A, Averbuch SD, Rosen N: The tyrosine kinase inhibitor ZD1839 ("Iressa") inhibits HER2-driven signaling and suppresses the growth of HER2-overexpressing tumor cells. Cancer Res. 2001 Oct 1;61(19):7184-8. [PubMed:11585753 ]
Arteaga CL, Johnson DH: Tyrosine kinase inhibitors-ZD1839 (Iressa). Curr Opin Oncol. 2001 Nov;13(6):491-8. [PubMed:11673690 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. 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

Shen J, Carcaboso AM, Hubbard KE, Tagen M, Wynn HG, Panetta JC, Waters CM, Elmeliegy MA, Stewart CF: Compartment-specific roles of ATP-binding cassette transporters define differential topotecan distribution in brain parenchyma and cerebrospinal fluid. Cancer Res. 2009 Jul 15;69(14):5885-92. doi: 10.1158/0008-5472.CAN-09-0700. Epub 2009 Jun 30. [PubMed:19567673 ]

Enzyme Details

2. 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

Ozvegy-Laczka C, Hegedus T, Varady G, Ujhelly O, Schuetz JD, Varadi A, Keri G, Orfi L, Nemet K, Sarkadi B: High-affinity interaction of tyrosine kinase inhibitors with the ABCG2 multidrug transporter. Mol Pharmacol. 2004 Jun;65(6):1485-95. [PubMed:15155841 ]
An Y, Ongkeko WM: ABCG2: the key to chemoresistance in cancer stem cells? Expert Opin Drug Metab Toxicol. 2009 Dec;5(12):1529-42. doi: 10.1517/17425250903228834. [PubMed:19708828 ]
Shen J, Carcaboso AM, Hubbard KE, Tagen M, Wynn HG, Panetta JC, Waters CM, Elmeliegy MA, Stewart CF: Compartment-specific roles of ATP-binding cassette transporters define differential topotecan distribution in brain parenchyma and cerebrospinal fluid. Cancer Res. 2009 Jul 15;69(14):5885-92. doi: 10.1158/0008-5472.CAN-09-0700. Epub 2009 Jun 30. [PubMed:19567673 ]
Noguchi K, Kawahara H, Kaji A, Katayama K, Mitsuhashi J, Sugimoto Y: Substrate-dependent bidirectional modulation of P-glycoprotein-mediated drug resistance by erlotinib. Cancer Sci. 2009 Sep;100(9):1701-7. doi: 10.1111/j.1349-7006.2009.01213.x. Epub 2009 May 12. [PubMed:19493273 ]
Shi Z, Parmar S, Peng XX, Shen T, Robey RW, Bates SE, Fu LW, Shao Y, Chen YM, Zang F, Chen ZS: The epidermal growth factor tyrosine kinase inhibitor AG1478 and erlotinib reverse ABCG2-mediated drug resistance. Oncol Rep. 2009 Feb;21(2):483-9. [PubMed:19148526 ]

Showing metabocard for Gefitinib (HMDB0014462)

MOL for HMDB0014462 (Gefitinib)

3D MOL for HMDB0014462 (Gefitinib)

3D SDF for HMDB0014462 (Gefitinib)

3D-SDF for HMDB0014462 (Gefitinib)

PDB for HMDB0014462 (Gefitinib)

3D PDB for HMDB0014462 (Gefitinib)

SMILES for HMDB0014462 (Gefitinib)

INCHI for HMDB0014462 (Gefitinib)

Structure for HMDB0014462 (Gefitinib)

3D Structure for HMDB0014462 (Gefitinib)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

Transporters

References

References