NP-MRD: Showing NP-Card for Canertinib (NP0137208)

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Record Information

Version

2.0

Created at

2022-05-30 16:45:15 UTC

Updated at

2022-05-30 16:45:15 UTC

NP-MRD ID

NP0137208

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Canertinib

Description

Canertinib, also known as CI-1033, 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. A quinazoline compound having a 3-chloro-4-fluoroanilino group at the 4-position, a propenamido group at the 6-position, and a 3-morpholinopropoxy group at the 7-position. Canertinib was first documented in 2001 (PMID: 11706399). Canertinib is a very strong basic compound (based on its pKa) (PMID: 15534081).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231218112D          

 34 37  0  0  0  0            999 V2000
    8.7797   -4.3538    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.2181   -3.5454    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.9413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    3.1163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3795   -1.8624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3889    0.6698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1365   -0.6135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    3.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    4.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3645   -0.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv0541 02231218112D          

 34 37  0  0  0  0            999 V2000
    8.7797   -4.3538    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.2181   -3.5454    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.9413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    3.1163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0137208

> <DATABASE_NAME>
NP-MRD

> <SMILES>
FC1=C(Cl)C=C(NC2=NC=NC3=CC(OCCCN4CCOCC4)=C(NC(=O)C=C)C=C23)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H25ClFN5O3/c1-2-23(32)30-21-13-17-20(14-22(21)34-9-3-6-31-7-10-33-11-8-31)27-15-28-24(17)29-16-4-5-19(26)18(25)12-16/h2,4-5,12-15H,1,3,6-11H2,(H,30,32)(H,27,28,29)

> <INCHI_KEY>
OMZCMEYTWSXEPZ-UHFFFAOYSA-N

> <FORMULA>
C24H25ClFN5O3

> <MOLECULAR_WEIGHT>
485.938

> <EXACT_MASS>
485.162995603

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
50.36363708123799

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[3-(morpholin-4-yl)propoxy]quinazolin-6-yl}prop-2-enamide

> <ALOGPS_LOGP>
4.09

> <JCHEM_LOGP>
3.902628374666667

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.115008026555433

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.538746987896001

> <JCHEM_PKA_STRONGEST_BASIC>
6.868894857342122

> <JCHEM_POLAR_SURFACE_AREA>
88.61

> <JCHEM_REFRACTIVITY>
130.5543

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
canertinib

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      16.389  -8.127   0.000  0.00  0.00          Cl+0
HETATM    2  F   UNK     0      19.074  -6.618   0.000  0.00  0.00           F+0
HETATM    3  O   UNK     0       3.080   7.357   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.415   1.197   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.081   0.427   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       5.748   5.817   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       8.415  -1.883   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      13.775  -3.476   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      13.793   1.250   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      15.188  -1.145   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       7.081   5.047   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   5.047   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748   7.357   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081   3.507   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080   5.817   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414   8.127   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415   2.737   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748   0.427   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748  -1.113   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.416  -1.113   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.082   1.197   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.416   0.427   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.082  -1.883   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.793  -1.937   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.100  -4.262   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.188   0.459   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.081  -1.113   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.082  -5.802   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.442  -3.507   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.407  -6.587   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.767  -4.293   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.748  -1.883   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.749  -5.833   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.414  -1.113   0.000  0.00  0.00           C+0
CONECT    1   30                                                            
CONECT    2   33                                                            
CONECT    3   15   16                                                       
CONECT    4   17   18                                                       
CONECT    5   27                                                            
CONECT    6   11   12   13                                                  
CONECT    7   19   27                                                       
CONECT    8   24   25                                                       
CONECT    9   22   26                                                       
CONECT   10   24   26                                                       
CONECT   11    6   14                                                       
CONECT   12    6   15                                                       
CONECT   13    6   16                                                       
CONECT   14   11   17                                                       
CONECT   15    3   12                                                       
CONECT   16    3   13                                                       
CONECT   17    4   14                                                       
CONECT   18    4   19   21                                                  
CONECT   19    7   18   23                                                  
CONECT   20   22   23   24                                                  
CONECT   21   18   22                                                       
CONECT   22    9   20   21                                                  
CONECT   23   19   20                                                       
CONECT   24    8   10   20                                                  
CONECT   25    8   28   29                                                  
CONECT   26    9   10                                                       
CONECT   27    5    7   32                                                  
CONECT   28   25   30                                                       
CONECT   29   25   31                                                       
CONECT   30    1   28   33                                                  
CONECT   31   29   33                                                       
CONECT   32   27   34                                                       
CONECT   33    2   30   31                                                  
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
CI-1033	ChEBI
Canertinib	MeSH

Chemical Formula

C₂₄H₂₅ClFN₅O₃

Average Mass

485.9380 Da

Monoisotopic Mass

485.16300 Da

IUPAC Name

N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[3-(morpholin-4-yl)propoxy]quinazolin-6-yl}prop-2-enamide

Traditional Name

canertinib

CAS Registry Number

Not Available

SMILES

FC1=C(Cl)C=C(NC2=NC=NC3=CC(OCCCN4CCOCC4)=C(NC(=O)C=C)C=C23)C=C1

InChI Identifier

InChI=1S/C24H25ClFN5O3/c1-2-23(32)30-21-13-17-20(14-22(21)34-9-3-6-31-7-10-33-11-8-31)27-15-28-24(17)29-16-4-5-19(26)18(25)12-16/h2,4-5,12-15H,1,3,6-11H2,(H,30,32)(H,27,28,29)

InChI Key

OMZCMEYTWSXEPZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 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
N-arylamide
Aniline or substituted anilines
Alkyl aryl ether
Halobenzene
Fluorobenzene
Aminopyrimidine
Chlorobenzene
Pyrimidine
Aryl chloride
Imidolactam
Benzenoid
Morpholine
Oxazinane
Monocyclic benzene moiety
Aryl halide
Aryl fluoride
Heteroaromatic compound
Acrylic acid or derivatives
Amino acid or derivatives
Carboxamide group
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Secondary amine
Oxacycle
Carboxylic acid derivative
Azacycle
Ether
Dialkyl ether
Organohalogen compound
Organic nitrogen compound
Organic oxygen compound
Amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organochloride
Organofluoride
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:61399 )
monochlorobenzenes (CHEBI:61399 )
quinazolines (CHEBI:61399 )
morpholines (CHEBI:61399 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.09	ALOGPS
logP	3.9	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	12.54	ChemAxon
pKa (Strongest Basic)	6.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.61 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	130.55 m³·mol⁻¹	ChemAxon
Polarizability	50.36 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB05424

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Canertinib

METLIN ID

Not Available

PubChem Compound

156414

PDB ID

Not Available

ChEBI ID

61399

Good Scents ID

Not Available

References

General References

Slichenmyer WJ, Elliott WL, Fry DW: CI-1033, a pan-erbB tyrosine kinase inhibitor. Semin Oncol. 2001 Oct;28(5 Suppl 16):80-5. doi: 10.1016/s0093-7754(01)90285-4. [PubMed:11706399 ]
Calvo E, Tolcher AW, Hammond LA, Patnaik A, de Bono JS, Eiseman IA, Olson SC, Lenehan PF, McCreery H, Lorusso P, Rowinsky EK: Administration of CI-1033, an irreversible pan-erbB tyrosine kinase inhibitor, is feasible on a 7-day on, 7-day off schedule: a phase I pharmacokinetic and food effect study. Clin Cancer Res. 2004 Nov 1;10(21):7112-20. doi: 10.1158/1078-0432.CCR-04-1187. [PubMed:15534081 ]

Showing NP-Card for Canertinib (NP0137208)

MOL for NP0137208 (Canertinib)

3D MOL for NP0137208 (Canertinib)

3D SDF for NP0137208 (Canertinib)

3D-SDF for NP0137208 (Canertinib)

PDB for NP0137208 (Canertinib)

3D PDB for NP0137208 (Canertinib)

SMILES for NP0137208 (Canertinib)

INCHI for NP0137208 (Canertinib)

Structure for NP0137208 (Canertinib)

3D Structure for NP0137208 (Canertinib)