tyrphostin AG 1478 (CHEBI:75404)

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CHEBI:75404 - tyrphostin AG 1478

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ChEBI Name	tyrphostin AG 1478

ChEBI ID	CHEBI:75404

Definition	A member of the class of quinazolines that is quinazoline substituted by methoxy groups at positions 6 and 7 and a (3-chlorophenyl)nitrilo group at position 4. It acts as an epidermal growth factor receptor antagonist.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB4728982, ChemicalBook:CB8751920, eMolecules:594850, Selleckchem:ag-1478-tyrphostin-ag-1478, ZINC000000116937

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

0TO - Ideal conformer

Mrv1927 10272115403D

starting HoverWatcher_5

Time for openFile(0TO - Ideal conformer

Mrv1927 10272115403D

36 38 0 0 0 0 999 V2000

5.0640 1.0210 0.2930 C 0 0 0 0 0 0 0 0 0 0 0 0

4.3740 -0.0430 -0.2640 C 0 0 0 0 0 0 0 0 0 0 0 0

5.2460 -1.3920 -0.9230 Cl 0 0 0 0 0 0 0 0 0 0 0 0

2.9930 -0.0310 -0.2940 C 0 0 0 0 0 0 0 0 0 0 0 0

4.3740 2.0970 0.8190 C 0 0 0 0 0 0 0 0 0 0 0 0

2.9930 2.1170 0.7850 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2970 1.0490 0.2340 C 0 0 0 0 0 0 0 0 0 0 0 0

0.9000 1.0640 0.2040 N 0 0 0 0 0 0 0 0 0 0 0 0

0.1940 -0.1180 0.3120 C 0 0 0 0 0 0 0 0 0 0 0 0

0.8170 -1.2630 0.5600 N 0 0 0 0 0 0 0 0 0 0 0 0

0.1530 -2.4020 0.6670 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.1500 -2.4830 0.5370 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.2130 -0.1390 0.1680 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.8780 -1.3850 0.2850 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.9490 1.0240 -0.0890 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.3060 0.9510 -0.2200 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.0200 2.0810 -0.4690 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.2850 3.3010 -0.5810 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.9720 -0.2780 -0.1000 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.2700 -1.4380 0.1410 C 0 0 0 0 0 0 0 0 0 0 0 0

-5.3230 -0.3250 -0.2340 O 0 0 0 0 0 0 0 0 0 0 0 0

-5.9440 -1.6060 -0.1010 C 0 0 0 0 0 0 0 0 0 0 0 0

6.1440 1.0080 0.3200 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4550 -0.8610 -0.7280 H 0 0 0 0 0 0 0 0 0 0 0 0

4.9150 2.9230 1.2570 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4540 2.9580 1.1960 H 0 0 0 0 0 0 0 0 0 0 0 0

0.4260 1.9050 0.1070 H 0 0 0 0 0 0 0 0 0 0 0 0

0.7090 -3.3060 0.8690 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4460 1.9750 -0.1830 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.9730 4.1230 -0.7800 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7520 3.4910 0.3500 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.5690 3.2200 -1.3990 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.7910 -2.3800 0.2310 H 0 0 0 0 0 0 0 0 0 0 0 0

-7.0210 -1.5030 -0.2290 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.5500 -2.2810 -0.8610 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.7330 -2.0110 0.8890 H 0 0 0 0 0 0 0 0 0 0 0 0

3 2 1 0 0 0 0

2 4 1 0 0 0 0

2 1 2 0 0 0 0

11 10 2 0 0 0 0

11 12 1 0 0 0 0

4 7 2 0 0 0 0

1 5 1 0 0 0 0

10 9 1 0 0 0 0

12 14 2 0 0 0 0

7 8 1 0 0 0 0

7 6 1 0 0 0 0

5 6 2 0 0 0 0

9 8 1 0 0 0 0

9 13 2 0 0 0 0

14 13 1 0 0 0 0

14 20 1 0 0 0 0

13 15 1 0 0 0 0

20 19 2 0 0 0 0

15 16 2 0 0 0 0

19 16 1 0 0 0 0

19 21 1 0 0 0 0

16 17 1 0 0 0 0

22 21 1 0 0 0 0

18 17 1 0 0 0 0

1 23 1 0 0 0 0

4 24 1 0 0 0 0

5 25 1 0 0 0 0

6 26 1 0 0 0 0

8 27 1 0 0 0 0

11 28 1 0 0 0 0

15 29 1 0 0 0 0

18 30 1 0 0 0 0

18 31 1 0 0 0 0

18 32 1 0 0 0 0

20 33 1 0 0 0 0

22 34 1 0 0 0 0

22 35 1 0 0 0 0

22 36 1 0 0 0 0

M END): 17 ms

reading 36 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

36 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Molfile

Formula

C16H14ClN3O2

Net Charge

Average Mass

315.760

Monoisotopic Mass

315.07745

InChI

InChI=1S/C16H14ClN3O2/c1-21-14-7-12-13(8-15(14)22-2)18-9-19-16(12)20-11-5-3-4-10(17)6-11/h3-9H,1-2H3,(H,18,19,20)

InChIKey

GFNNBHLJANVSQV-UHFFFAOYSA-N

SMILES

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

Roles Classification
Biological Role(s):	epidermal growth factor receptor antagonist An antagonist at the epidermal growth factor receptor. antiviral agent A substance that destroys or inhibits replication of viruses.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	tyrphostin AG 1478 (CHEBI:75404) has role antineoplastic agent (CHEBI:35610) tyrphostin AG 1478 (CHEBI:75404) has role antiviral agent (CHEBI:22587) tyrphostin AG 1478 (CHEBI:75404) has role epidermal growth factor receptor antagonist (CHEBI:74440) tyrphostin AG 1478 (CHEBI:75404) has role geroprotector (CHEBI:176497) tyrphostin AG 1478 (CHEBI:75404) is a aromatic ether (CHEBI:35618) tyrphostin AG 1478 (CHEBI:75404) is a monochlorobenzenes (CHEBI:83403) tyrphostin AG 1478 (CHEBI:75404) is a quinazolines (CHEBI:38530)

IUPAC Name

N-(3-chlorophenyl)-6,7-dimethoxy-quinazolin-4-amine

Synonyms	Sources
AG 1478	ChemIDplus
AG-1478	ChemIDplus
tyrphostin AG-1478	ChEBI

Manual Xrefs	Databases
0TO	PDBeChem
LSM-1224	LINCS
View more database links

Registry Numbers	Types	Sources
170449-18-0	CAS Registry Number	ChemIDplus
7437034	Reaxys Registry Number	Reaxys

Citations

Ye X, Linton JM, Schork NJ, Buck LB, Petrascheck M (2014)
A pharmacological network for lifespan extension in Caenorhabditis elegans.
Aging cell 13, 206-215 [PubMed:24134630]
[show Abstract]

Stogios PJ, Spanogiannopoulos P, Evdokimova E, Egorova O, Shakya T, Todorovic N, Capretta A, Wright GD, Savchenko A (2013)
Structure-guided optimization of protein kinase inhibitors reverses aminoglycoside antibiotic resistance.
The Biochemical journal 454, 191-200 [PubMed:23758273]
[show Abstract]

Weglicki WB, Kramer JH, Spurney CF, Chmielinska JJ, Mak IT (2012)
The EGFR tyrosine kinase inhibitor tyrphostin AG-1478 causes hypomagnesemia and cardiac dysfunction.
Canadian journal of physiology and pharmacology 90, 1145-1149 [PubMed:22646904]
[show Abstract]

Spindler SR, Li R, Dhahbi JM, Yamakawa A, Sauer F (2012)
Novel protein kinase signaling systems regulating lifespan identified by small molecule library screening using Drosophila.
PloS one 7, e29782 [PubMed:22363408]
[show Abstract]

Hamdi MM, Mutungi G (2010)
Dihydrotestosterone activates the MAPK pathway and modulates maximum isometric force through the EGF receptor in isolated intact mouse skeletal muscle fibres.
The Journal of physiology 588, 511-525 [PubMed:20008468]
[show Abstract]

Choi BH, Choi JS, Rhie DJ, Yoon SH, Min DS, Jo YH, Kim MS, Hahn SJ (2002)
Direct inhibition of the cloned Kv1.5 channel by AG-1478, a tyrosine kinase inhibitor.
American journal of physiology. Cell physiology 282, C1461-8 [PubMed:11997261]
[show Abstract]

Han Y, Caday CG, Nanda A, Cavenee WK, Huang HJ (1996)
Tyrphostin AG 1478 preferentially inhibits human glioma cells expressing truncated rather than wild-type epidermal growth factor receptors.
Cancer research 56, 3859-3861 [PubMed:8752145]
[show Abstract]

Last Modified

27 October 2021

CHEBI:75404 - tyrphostin AG 1478

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