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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9)transporters (2) Show 11 proteins XML

enzymes (9)transporters (2) Show 11 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:42 UTC

HMDB ID

HMDB0014671

Secondary Accession Numbers

HMDB14671

Metabolite Identification

Common Name

Erlotinib

Description

Erlotinib hydrochloride (trade name Tarceva, Genentech/OSIP, originally coded as OSI-774) is a drug used to treat non-small cell lung cancer, pancreatic cancer and several other types of cancer. Similar to gefitinib, erlotinib specifically targets the epidermal growth factor receptor (EGFR) tyrosine kinase. It binds in a reversible fashion to the adenosine triphosphate (ATP) binding site of the receptor. Erlotinib has recently been shown to be a potent inhibitor of JAK2V617F activity. JAK2V617F is a mutant of tyrosine kinase JAK2, is found in most patients with polycythemia vera (PV) and a substantial proportion of patients with idiopathic myelofibrosis or essential thrombocythemia. The study suggests that erlotinib may be used for treatment of JAK2V617F-positive PV and other myeloproliferative disorders.

Structure

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

530
  Mrv0541 02231214452D          

 29 31  0  0  0  0            999 V2000
    4.5080    0.2782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.9282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.6907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.9908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3795   -0.5754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3889    1.9568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1365    0.6735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3889    0.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0891   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1365    1.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0796   -1.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8083   -0.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7892   -2.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5180   -1.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5084   -1.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    4.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7797   -3.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7701   -3.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 15  1  0  0  0  0
  2 11  1  0  0  0  0
  2 17  1  0  0  0  0
  3 19  1  0  0  0  0
  3 26  1  0  0  0  0
  4 20  1  0  0  0  0
  4 27  1  0  0  0  0
  5 13  1  0  0  0  0
  5 16  1  0  0  0  0
  6  9  1  0  0  0  0
  6 18  2  0  0  0  0
  7 13  2  0  0  0  0
  7 18  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  2  0  0  0  0
  8 13  1  0  0  0  0
  9 14  2  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 14  1  0  0  0  0
 15 19  1  0  0  0  0
 16 21  1  0  0  0  0
 16 22  2  0  0  0  0
 17 20  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 28  1  0  0  0  0
 24 25  2  0  0  0  0
 28 29  3  0  0  0  0
M  END

HMDB0014671
     RDKit          3D
Erlotinib
 52 54  0  0  0  0  0  0  0  0999 V2000
    7.7761    1.8513   -1.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9569    0.9644   -1.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9904   -0.1196   -1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3473   -1.4270   -1.4317 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4300   -2.4471   -1.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1105   -2.1596   -0.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7122   -0.8765   -0.6890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3939   -0.5102   -0.2723 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584   -1.3962    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7982   -2.6655    0.5249 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0007   -3.5610    1.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2409   -3.1612    1.4371 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6636   -1.9232    1.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9623   -1.5814    1.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4015   -0.3149    1.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6262    0.1241    1.7709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7586   -0.3852    2.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3950   -1.4473    1.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7167   -0.8659    0.2107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3103   -1.8974   -0.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5553    0.6453    0.8430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051    1.8953    0.6472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5748    3.0578    0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2206    3.0494   -1.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948    4.2874   -1.8117 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161    4.7968   -1.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2758    0.2781    0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1799   -0.9986    0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6941    0.1028   -0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5000    2.6259   -1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3710   -1.6566   -1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7068   -3.4764   -1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4452   -3.0003   -0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450    0.5106   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3096   -4.5833    1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5974   -2.3271    2.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6339   -0.8275    3.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5156    0.4450    2.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7240   -2.2877    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3499   -1.8025    1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5963   -1.5224   -1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1600   -2.2722    0.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5259   -2.6774   -0.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6473    3.4372    0.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3381    3.8616    0.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5968    2.2233   -1.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2197    2.8848   -1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2084    4.1360   -1.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829    5.0910   -0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6510    5.7609   -1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3976    1.0025    0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4244    1.1396   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 15 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 21 27  1  0
 27 28  2  0
  7 29  2  0
 29  3  1  0
 28  9  1  0
 28 13  1  0
  1 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  8 34  1  0
 11 35  1  0
 14 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
 23 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
 26 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 29 52  1  0
M  END

530
  Mrv0541 02231214452D          

 29 31  0  0  0  0            999 V2000
    4.5080    0.2782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.9282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.6907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.9908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3795   -0.5754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3889    1.9568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1365    0.6735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3889    0.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0891   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1365    1.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0796   -1.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8083   -0.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7892   -2.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5180   -1.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5084   -1.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    4.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7797   -3.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7701   -3.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 15  1  0  0  0  0
  2 11  1  0  0  0  0
  2 17  1  0  0  0  0
  3 19  1  0  0  0  0
  3 26  1  0  0  0  0
  4 20  1  0  0  0  0
  4 27  1  0  0  0  0
  5 13  1  0  0  0  0
  5 16  1  0  0  0  0
  6  9  1  0  0  0  0
  6 18  2  0  0  0  0
  7 13  2  0  0  0  0
  7 18  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  2  0  0  0  0
  8 13  1  0  0  0  0
  9 14  2  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 14  1  0  0  0  0
 15 19  1  0  0  0  0
 16 21  1  0  0  0  0
 16 22  2  0  0  0  0
 17 20  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 28  1  0  0  0  0
 24 25  2  0  0  0  0
 28 29  3  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014671

> <DATABASE_NAME>
hmdb

> <SMILES>
COCCOC1=C(OCCOC)C=C2C(NC3=CC=CC(=C3)C#C)=NC=NC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H23N3O4/c1-4-16-6-5-7-17(12-16)25-22-18-13-20(28-10-8-26-2)21(29-11-9-27-3)14-19(18)23-15-24-22/h1,5-7,12-15H,8-11H2,2-3H3,(H,23,24,25)

> <INCHI_KEY>
AAKJLRGGTJKAMG-UHFFFAOYSA-N

> <FORMULA>
C22H23N3O4

> <MOLECULAR_WEIGHT>
393.4357

> <EXACT_MASS>
393.168856239

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
43.481984980674554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine

> <ALOGPS_LOGP>
3.13

> <JCHEM_LOGP>
3.2009875863333344

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.143808891275707

> <JCHEM_PKA_STRONGEST_BASIC>
4.5874862488003805

> <JCHEM_POLAR_SURFACE_AREA>
74.73

> <JCHEM_REFRACTIVITY>
107.78590000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.91e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
erlotinib

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014671
     RDKit          3D
Erlotinib
 52 54  0  0  0  0  0  0  0  0999 V2000
    7.7761    1.8513   -1.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9569    0.9644   -1.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9904   -0.1196   -1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3473   -1.4270   -1.4317 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4300   -2.4471   -1.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1105   -2.1596   -0.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7122   -0.8765   -0.6890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3939   -0.5102   -0.2723 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584   -1.3962    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7982   -2.6655    0.5249 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0007   -3.5610    1.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2409   -3.1612    1.4371 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6636   -1.9232    1.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9623   -1.5814    1.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4015   -0.3149    1.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6262    0.1241    1.7709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7586   -0.3852    2.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3950   -1.4473    1.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7167   -0.8659    0.2107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3103   -1.8974   -0.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5553    0.6453    0.8430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051    1.8953    0.6472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5748    3.0578    0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2206    3.0494   -1.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948    4.2874   -1.8117 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161    4.7968   -1.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2758    0.2781    0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1799   -0.9986    0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6941    0.1028   -0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5000    2.6259   -1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3710   -1.6566   -1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7068   -3.4764   -1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4452   -3.0003   -0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450    0.5106   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3096   -4.5833    1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5974   -2.3271    2.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6339   -0.8275    3.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5156    0.4450    2.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7240   -2.2877    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3499   -1.8025    1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5963   -1.5224   -1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1600   -2.2722    0.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5259   -2.6774   -0.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6473    3.4372    0.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3381    3.8616    0.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5968    2.2233   -1.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2197    2.8848   -1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2084    4.1360   -1.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829    5.0910   -0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6510    5.7609   -1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3976    1.0025    0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4244    1.1396   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 15 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 21 27  1  0
 27 28  2  0
  7 29  2  0
 29  3  1  0
 28  9  1  0
 28 13  1  0
  1 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  8 34  1  0
 11 35  1  0
 14 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
 23 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
 26 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 29 52  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 530                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.415   0.519   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   3.599   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.414   1.289   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.081   7.449   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      13.775  -1.074   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      13.793   3.653   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      15.188   1.257   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      12.416   1.289   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.416   2.829   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748   1.289   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.748   2.829   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.082   0.519   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.793   0.466   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.082   3.599   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   1.289   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.100  -1.859   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415   5.139   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.188   2.861   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.748   0.519   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.081   5.909   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.082  -3.399   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.442  -1.105   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.407  -4.185   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.767  -1.890   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.749  -3.430   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.080   0.519   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.748   8.219   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.389  -5.725   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.371  -7.265   0.000  0.00  0.00           C+0
CONECT    1   10   15                                                       
CONECT    2   11   17                                                       
CONECT    3   19   26                                                       
CONECT    4   20   27                                                       
CONECT    5   13   16                                                       
CONECT    6    9   18                                                       
CONECT    7   13   18                                                       
CONECT    8    9   12   13                                                  
CONECT    9    6    8   14                                                  
CONECT   10    1   11   12                                                  
CONECT   11    2   10   14                                                  
CONECT   12    8   10                                                       
CONECT   13    5    7    8                                                  
CONECT   14    9   11                                                       
CONECT   15    1   19                                                       
CONECT   16    5   21   22                                                  
CONECT   17    2   20                                                       
CONECT   18    6    7                                                       
CONECT   19    3   15                                                       
CONECT   20    4   17                                                       
CONECT   21   16   23                                                       
CONECT   22   16   24                                                       
CONECT   23   21   25   28                                                  
CONECT   24   22   25                                                       
CONECT   25   23   24                                                       
CONECT   26    3                                                            
CONECT   27    4                                                            
CONECT   28   23   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

COMPND    HMDB0014671
HETATM    1  C1  UNL     1       7.776   1.851  -1.284  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.957   0.964  -1.227  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.990  -0.120  -1.150  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.347  -1.427  -1.432  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.430  -2.447  -1.351  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.110  -2.160  -0.978  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.712  -0.876  -0.689  1.00  0.00           C  
HETATM    8  N1  UNL     1       2.394  -0.510  -0.272  1.00  0.00           N  
HETATM    9  C8  UNL     1       1.458  -1.396   0.292  1.00  0.00           C  
HETATM   10  N2  UNL     1       1.798  -2.666   0.525  1.00  0.00           N  
HETATM   11  C9  UNL     1       1.001  -3.561   1.082  1.00  0.00           C  
HETATM   12  N3  UNL     1      -0.241  -3.161   1.437  1.00  0.00           N  
HETATM   13  C10 UNL     1      -0.664  -1.923   1.244  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.962  -1.581   1.637  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.401  -0.315   1.438  1.00  0.00           C  
HETATM   16  O1  UNL     1      -3.626   0.124   1.771  1.00  0.00           O  
HETATM   17  C13 UNL     1      -4.759  -0.385   2.311  1.00  0.00           C  
HETATM   18  C14 UNL     1      -5.395  -1.447   1.459  1.00  0.00           C  
HETATM   19  O2  UNL     1      -5.717  -0.866   0.211  1.00  0.00           O  
HETATM   20  C15 UNL     1      -6.310  -1.897  -0.551  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.555   0.645   0.843  1.00  0.00           C  
HETATM   22  O3  UNL     1      -2.005   1.895   0.647  1.00  0.00           O  
HETATM   23  C17 UNL     1      -1.575   3.058   0.111  1.00  0.00           C  
HETATM   24  C18 UNL     1      -1.221   3.049  -1.357  1.00  0.00           C  
HETATM   25  O4  UNL     1      -0.795   4.287  -1.812  1.00  0.00           O  
HETATM   26  C19 UNL     1       0.316   4.797  -1.197  1.00  0.00           C  
HETATM   27  C20 UNL     1      -0.276   0.278   0.467  1.00  0.00           C  
HETATM   28  C21 UNL     1       0.180  -0.999   0.661  1.00  0.00           C  
HETATM   29  C22 UNL     1       4.694   0.103  -0.792  1.00  0.00           C  
HETATM   30  H1  UNL     1       8.500   2.626  -1.317  1.00  0.00           H  
HETATM   31  H2  UNL     1       7.371  -1.657  -1.721  1.00  0.00           H  
HETATM   32  H3  UNL     1       5.707  -3.476  -1.572  1.00  0.00           H  
HETATM   33  H4  UNL     1       3.445  -3.000  -0.948  1.00  0.00           H  
HETATM   34  H5  UNL     1       2.145   0.511  -0.417  1.00  0.00           H  
HETATM   35  H6  UNL     1       1.310  -4.583   1.257  1.00  0.00           H  
HETATM   36  H7  UNL     1      -2.597  -2.327   2.108  1.00  0.00           H  
HETATM   37  H8  UNL     1      -4.634  -0.828   3.338  1.00  0.00           H  
HETATM   38  H9  UNL     1      -5.516   0.445   2.497  1.00  0.00           H  
HETATM   39  H10 UNL     1      -4.724  -2.288   1.314  1.00  0.00           H  
HETATM   40  H11 UNL     1      -6.350  -1.802   1.919  1.00  0.00           H  
HETATM   41  H12 UNL     1      -6.596  -1.522  -1.545  1.00  0.00           H  
HETATM   42  H13 UNL     1      -7.160  -2.272   0.035  1.00  0.00           H  
HETATM   43  H14 UNL     1      -5.526  -2.677  -0.694  1.00  0.00           H  
HETATM   44  H15 UNL     1      -0.647   3.437   0.644  1.00  0.00           H  
HETATM   45  H16 UNL     1      -2.338   3.862   0.321  1.00  0.00           H  
HETATM   46  H17 UNL     1      -0.597   2.223  -1.680  1.00  0.00           H  
HETATM   47  H18 UNL     1      -2.220   2.885  -1.889  1.00  0.00           H  
HETATM   48  H19 UNL     1       1.208   4.136  -1.286  1.00  0.00           H  
HETATM   49  H20 UNL     1       0.083   5.091  -0.157  1.00  0.00           H  
HETATM   50  H21 UNL     1       0.651   5.761  -1.696  1.00  0.00           H  
HETATM   51  H22 UNL     1       0.398   1.002   0.018  1.00  0.00           H  
HETATM   52  H23 UNL     1       4.424   1.140  -0.572  1.00  0.00           H  
CONECT    1    2    2    2   30
CONECT    2    3
CONECT    3    4    4   29
CONECT    4    5   31
CONECT    5    6    6   32
CONECT    6    7   33
CONECT    7    8   29   29
CONECT    8    9   34
CONECT    9   10   10   28
CONECT   10   11
CONECT   11   12   12   35
CONECT   12   13
CONECT   13   14   14   28
CONECT   14   15   36
CONECT   15   16   21   21
CONECT   16   17
CONECT   17   18   37   38
CONECT   18   19   39   40
CONECT   19   20
CONECT   20   41   42   43
CONECT   21   22   27
CONECT   22   23
CONECT   23   24   44   45
CONECT   24   25   46   47
CONECT   25   26
CONECT   26   48   49   50
CONECT   27   28   28   51
CONECT   29   52
END

HMDB0014671
     RDKit          3D
Erlotinib
 52 54  0  0  0  0  0  0  0  0999 V2000
    7.7761    1.8513   -1.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9569    0.9644   -1.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9904   -0.1196   -1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3473   -1.4270   -1.4317 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4300   -2.4471   -1.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1105   -2.1596   -0.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7122   -0.8765   -0.6890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3939   -0.5102   -0.2723 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584   -1.3962    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7982   -2.6655    0.5249 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0007   -3.5610    1.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2409   -3.1612    1.4371 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6636   -1.9232    1.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9623   -1.5814    1.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4015   -0.3149    1.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6262    0.1241    1.7709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7586   -0.3852    2.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3950   -1.4473    1.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7167   -0.8659    0.2107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3103   -1.8974   -0.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5553    0.6453    0.8430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051    1.8953    0.6472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5748    3.0578    0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2206    3.0494   -1.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948    4.2874   -1.8117 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161    4.7968   -1.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2758    0.2781    0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1799   -0.9986    0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6941    0.1028   -0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5000    2.6259   -1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3710   -1.6566   -1.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7068   -3.4764   -1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4452   -3.0003   -0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450    0.5106   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3096   -4.5833    1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5974   -2.3271    2.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6339   -0.8275    3.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5156    0.4450    2.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7240   -2.2877    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3499   -1.8025    1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5963   -1.5224   -1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1600   -2.2722    0.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5259   -2.6774   -0.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6473    3.4372    0.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3381    3.8616    0.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5968    2.2233   -1.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2197    2.8848   -1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2084    4.1360   -1.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829    5.0910   -0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6510    5.7609   -1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3976    1.0025    0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4244    1.1396   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 15 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 21 27  1  0
 27 28  2  0
  7 29  2  0
 29  3  1  0
 28  9  1  0
 28 13  1  0
  1 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  8 34  1  0
 11 35  1  0
 14 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
 23 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
 26 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
 29 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[6,7-Bis(2-methoxy-ethoxy)quinazoline-4-yl]-(3-ethynylphenyl)amine	ChEBI
[6,7-Bis-(2-methoxy-ethoxy)-quinazolin-4-yl]-(3-ethynyl-phenyl)-amine	ChEBI
Erlotinibum	ChEBI
OSI-774	HMDB
11C Erlotinib	HMDB
HCL, Erlotinib	HMDB
Hydrochloride, erlotinib	HMDB
N-(3-Ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine	HMDB
OSI 774	HMDB
Erlotinib hydrochloride	HMDB
11C-Erlotinib	HMDB
Tarceva	HMDB
Erlotinib HCL	HMDB

Chemical Formula

C₂₂H₂₃N₃O₄

Average Molecular Weight

393.4357

Monoisotopic Molecular Weight

393.168856239

IUPAC Name

N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine

Traditional Name

erlotinib

CAS Registry Number

183321-74-6

SMILES

COCCOC1=C(OCCOC)C=C2C(NC3=CC=CC(=C3)C#C)=NC=NC2=C1

InChI Identifier

InChI=1S/C22H23N3O4/c1-4-16-6-5-7-17(12-16)25-22-18-13-20(28-10-8-26-2)21(29-11-9-27-3)14-19(18)23-15-24-22/h1,5-7,12-15H,8-11H2,2-3H3,(H,23,24,25)

InChI Key

AAKJLRGGTJKAMG-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
Aniline or substituted anilines
Alkyl aryl ether
Aminopyrimidine
Monocyclic benzene moiety
Pyrimidine
Benzenoid
Imidolactam
Heteroaromatic compound
Dialkyl ether
Ether
Acetylide
Secondary amine
Azacycle
Organonitrogen compound
Amine
Organic nitrogen compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:114785 )
quinazolines (CHEBI:114785 )

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

Source

Exogenous

Exogenous (HMDB: HMDB0014671)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Erlotinib Action Pathway (PathBank: SMP0000472)

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	0.0089 g/L	Not Available
LogP	2.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0089 g/L	ALOGPS
logP	3.13	ALOGPS
logP	3.2	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	16.14	ChemAxon
pKa (Strongest Basic)	4.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.73 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	107.79 m³·mol⁻¹	ChemAxon
Polarizability	43.48 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
DarkChem	[M+H]+	191.742	31661259
DarkChem	[M-H]-	191.008	31661259
DeepCCS	[M+H]+	197.83	30932474
DeepCCS	[M-H]-	194.28	30932474
DeepCCS	[M-2H]-	230.354	30932474
DeepCCS	[M+Na]+	206.645	30932474
AllCCS	[M+H]+	194.7	32859911
AllCCS	[M+H-H2O]+	192.1	32859911
AllCCS	[M+NH4]+	197.2	32859911
AllCCS	[M+Na]+	197.9	32859911
AllCCS	[M-H]-	196.2	32859911
AllCCS	[M+Na-2H]-	196.1	32859911
AllCCS	[M+HCOO]-	196.1	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.	5.27 minutes	32390414
Predicted by Siyang on May 30, 2022	11.6152 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.35 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2522.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	199.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	165.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	152.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	73.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	469.1 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	449.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	77.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	980.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	437.2 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	1196.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	316.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	191.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	157.4 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	10.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Erlotinib	COCCOC1=C(OCCOC)C=C2C(NC3=CC=CC(=C3)C#C)=NC=NC2=C1	4702.1	Standard polar	33892256
Erlotinib	COCCOC1=C(OCCOC)C=C2C(NC3=CC=CC(=C3)C#C)=NC=NC2=C1	3215.0	Standard non polar	33892256
Erlotinib	COCCOC1=C(OCCOC)C=C2C(NC3=CC=CC(=C3)C#C)=NC=NC2=C1	3557.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Erlotinib,1TMS,isomer #1	C#CC1=CC=CC(N(C2=NC=NC3=CC(OCCOC)=C(OCCOC)C=C23)[Si](C)(C)C)=C1	3174.5	Semi standard non polar	33892256
Erlotinib,1TMS,isomer #1	C#CC1=CC=CC(N(C2=NC=NC3=CC(OCCOC)=C(OCCOC)C=C23)[Si](C)(C)C)=C1	3168.7	Standard non polar	33892256
Erlotinib,1TMS,isomer #1	C#CC1=CC=CC(N(C2=NC=NC3=CC(OCCOC)=C(OCCOC)C=C23)[Si](C)(C)C)=C1	4627.6	Standard polar	33892256
Erlotinib,1TBDMS,isomer #1	C#CC1=CC=CC(N(C2=NC=NC3=CC(OCCOC)=C(OCCOC)C=C23)[Si](C)(C)C(C)(C)C)=C1	3375.0	Semi standard non polar	33892256
Erlotinib,1TBDMS,isomer #1	C#CC1=CC=CC(N(C2=NC=NC3=CC(OCCOC)=C(OCCOC)C=C23)[Si](C)(C)C(C)(C)C)=C1	3338.4	Standard non polar	33892256
Erlotinib,1TBDMS,isomer #1	C#CC1=CC=CC(N(C2=NC=NC3=CC(OCCOC)=C(OCCOC)C=C23)[Si](C)(C)C(C)(C)C)=C1	4639.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Erlotinib GC-MS (Non-derivatized) - 70eV, Positive	splash10-002k-2129000000-90a20b25b74b231ffec1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erlotinib GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erlotinib 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 - Erlotinib 10V, Positive-QTOF	splash10-0006-0009000000-0faffd4c59a79313872f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erlotinib 20V, Positive-QTOF	splash10-0a4l-4019000000-3b47513e20a5bfacb8f4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erlotinib 40V, Positive-QTOF	splash10-07fr-3092000000-09a2b2602ea3efd921bc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erlotinib 10V, Negative-QTOF	splash10-000x-0009000000-0e3a84b624af3648dfc4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erlotinib 20V, Negative-QTOF	splash10-0089-0049000000-7d705f21b90db0f6f3ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erlotinib 40V, Negative-QTOF	splash10-00di-1192000000-6d6a8f8831beb774d61c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erlotinib 10V, Negative-QTOF	splash10-0f7o-0019000000-98c0248bef3527a16545	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erlotinib 20V, Negative-QTOF	splash10-0fkc-0095000000-b346f0645c009b0dbd23	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erlotinib 40V, Negative-QTOF	splash10-0uk9-2098000000-c15ff6cb37269237da44	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erlotinib 10V, Positive-QTOF	splash10-0006-0009000000-cab9b4eadff55f06446d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erlotinib 20V, Positive-QTOF	splash10-01ox-0009000000-576d45602f85d8bf2186	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erlotinib 40V, Positive-QTOF	splash10-004i-1079000000-e0507c536b38d89e26b1	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Erlotinib 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 DB00530	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00530	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00530

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

154044

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Erlotinib

METLIN ID

Not Available

PubChem Compound

176870

PDB ID

AQ4

ChEBI ID

114785

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

Blum G, Gazit A, Levitzki A: Substrate competitive inhibitors of IGF-1 receptor kinase. Biochemistry. 2000 Dec 26;39(51):15705-12. [PubMed:11123895 ]
Raymond E, Faivre S, Armand JP: Epidermal growth factor receptor tyrosine kinase as a target for anticancer therapy. Drugs. 2000;60 Suppl 1:15-23; discussion 41-2. [PubMed:11129168 ]
Jones HE, Goddard L, Gee JM, Hiscox S, Rubini M, Barrow D, Knowlden JM, Williams S, Wakeling AE, Nicholson RI: Insulin-like growth factor-I receptor signalling and acquired resistance to gefitinib (ZD1839; Iressa) in human breast and prostate cancer cells. Endocr Relat Cancer. 2004 Dec;11(4):793-814. [PubMed:15613453 ]
Dudek AZ, Kmak KL, Koopmeiners J, Keshtgarpour M: Skin rash and bronchoalveolar histology correlates with clinical benefit in patients treated with gefitinib as a therapy for previously treated advanced or metastatic non-small cell lung cancer. Lung Cancer. 2006 Jan;51(1):89-96. Epub 2005 Nov 14. [PubMed:16290256 ]
Li Z, Xu M, Xing S, Ho WT, Ishii T, Li Q, Fu X, Zhao ZJ: Erlotinib effectively inhibits JAK2V617F activity and polycythemia vera cell growth. J Biol Chem. 2007 Feb 9;282(6):3428-32. Epub 2006 Dec 18. [PubMed:17178722 ]
Lansiaux A, Bailly C: [Perspectives on the oncologist pharmacopoeia]. Bull Cancer. 2003 Jan;90(1):25-30. [PubMed:12609801 ]

Only showing the first 10 proteins. There are 11 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

References

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

Enzyme Details

3. Cytochrome P450 1B1

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. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:: CYP1B1
Uniprot ID:: Q16678
Molecular weight:: 60845.33

References

Enzyme Details

4. 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

Enzyme Details

5. 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

References

Enzyme Details

6. Cytochrome P450 1A1

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:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

Enzyme Details

7. Cytochrome P450 1A2

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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Enzyme Details

8. Cytochrome P450 2C8

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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Enzyme Details

9. Nuclear receptor subfamily 1 group I member 2

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes
Gene Name:: NR1I2
Uniprot ID:: O75469
Molecular weight:: 49761.2

References

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

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

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for Erlotinib (HMDB0014671)

MOL for HMDB0014671 (Erlotinib)

3D MOL for HMDB0014671 (Erlotinib)

3D SDF for HMDB0014671 (Erlotinib)

3D-SDF for HMDB0014671 (Erlotinib)

PDB for HMDB0014671 (Erlotinib)

3D PDB for HMDB0014671 (Erlotinib)

SMILES for HMDB0014671 (Erlotinib)

INCHI for HMDB0014671 (Erlotinib)

Structure for HMDB0014671 (Erlotinib)

3D Structure for HMDB0014671 (Erlotinib)

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

References

Transporters

References

References