N-(5-((4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)pyrimidin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxyphenyl)acrylamide

ID: ALA4104658

PubChem CID: 118514811

Max Phase: Preclinical

Molecular Formula: C30H35N7O2

Molecular Weight: 525.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)Nc1cc(Nc2nccc(-c3cn4c5c(cccc35)CCC4)n2)c(OC)cc1N(C)CCN(C)C

Standard InChI:  InChI=1S/C30H35N7O2/c1-6-28(38)32-24-17-25(27(39-5)18-26(24)36(4)16-15-35(2)3)34-30-31-13-12-23(33-30)22-19-37-14-8-10-20-9-7-11-21(22)29(20)37/h6-7,9,11-13,17-19H,1,8,10,14-16H2,2-5H3,(H,32,38)(H,31,33,34)

Standard InChI Key:  CLXOEYRLLVMPJB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   25.7694   -1.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2804   -2.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0842   -2.0529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3802   -1.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8722   -0.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8355   -4.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8344   -5.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5424   -5.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2521   -5.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2493   -4.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5406   -4.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5422   -6.6723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2498   -7.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1264   -5.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5382   -3.4005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8293   -2.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8268   -2.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1228   -3.4048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5333   -1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9554   -4.2117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6647   -4.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9523   -3.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3708   -4.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0801   -4.6123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7862   -4.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0832   -5.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4190   -5.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4242   -4.6279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7176   -4.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0086   -4.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0106   -5.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7177   -5.8537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7186   -3.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3797   -2.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0575   -2.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9700   -1.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7171   -2.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2626   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  9 13  1  0
 13 14  1  0
  8 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  2  0
 11 21  1  0
 21 22  1  0
 21 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 15 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 30 34  1  0
 34 35  2  0
 35  4  1  0
 36 34  1  0
 36  3  2  0
  2 37  2  0
 37 38  1  0
 38 39  2  0
 39 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4104658

   N-[5-[[4-(1-azatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraen-3-yl)pyrimidin-2-yl]amino]-2-[2-(dimethylamino)ethyl-methylamino]-4-methoxyphenyl]prop-2-enamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 525.66

Molecular Weight (Monoisotopic): 525.2852

AlogP: 4.92

#Rotatable Bonds: 10

Polar Surface Area: 87.55

Molecular Species: BASE

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.65

CX Basic pKa: 8.87

CX LogP: 4.97

CX LogD: 3.49

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.28

Np Likeness Score: -1.03

References

1. Zhang H, Wu W, Feng C, Liu Z, Bai E, Wang X, Lei M, Cheng H, Feng H, Shi J, Wang J, Zhang Z, Jin T, Chen S, Hu S, Zhu Y..  (2017)  Design, synthesis, SAR discussion, in vitro and in vivo evaluation of novel selective EGFR modulator to inhibit L858R/T790M double mutants.,  135  [PMID:28426996] [10.1016/j.ejmech.2017.04.036]

2. Huang WS, Li F, Gong Y, Zhang Y, Youngsaye W, Xu Y, Zhu X, Greenfield MT, Kohlmann A, Taslimi PM, Toms A, Zech SG, Zhou T, Das B, Jang HG, Tugnait M, Ye YE, Gonzalvez F, Baker TE, Nadworny S, Ning Y, Wardwell SD, Zhang S, Gould AE, Hu Y, Lane W, Skene RJ, Zou H, Clackson T, Narasimhan NI, Rivera VM, Dalgarno DC, Shakespeare WC..  (2023)  Discovery of mobocertinib, a potent, oral inhibitor of EGFR exon 20 insertion mutations in non-small cell lung cancer.,  80  [PMID:36423823] [10.1016/j.bmcl.2022.129084]

Source

Source(1):

• Scientific Literature